Quinolin-2-one derivatives

Abstract

Compounds of the formula I ##STR00001##
in which X.sup.1, X.sup.2, X.sup.3, X.sup.4, R.sup.1, R.sup.2, R.sup.3, Q and Y have the meanings indicated in Claim 1,
are inhibitors of c-Kit kinase, and can be employed for the treatment of cancer.

Claims

1. Compounds of the formula I ##STR00494## in which X.sup.1, X.sup.2, X.sup.3, X.sup.4 each, independently of one another, denote CH or N, Y denotes N or CH, Q denotes H or CH.sub.3, R.sup.1 denotes H, F, Cl, Br, CN, CH.sub.3, CF.sub.3 or OCH.sub.3, R.sup.2 denotes H, F or Cl, R.sup.3 denotes phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, indolyl, indazolyl, thiophenyl, dihydroisoindolyl or benzimidazolyl, each of which is unsubstituted or mono-, di- or trisubstituted by Hal, CN, NO.sub.2, A, (CR.sup.4).sub.nOR.sup.4, (CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nS(O).sub.mR.sup.4, (CR.sup.4).sub.nCON(R.sup.4).sub.2, (CR.sup.4).sub.nCOHet, (CR.sup.4).sub.nSO.sub.2N(R.sup.4).sub.2, (CR.sup.4).sub.nSO.sub.2Het, (CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nHet, O(CR.sup.4).sub.nCOHet, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, (CR.sup.4).sub.nN(R.sup.4)(CR.sup.4).sub.nHet, (CR.sup.4).sub.nCON(R.sup.4)(CR.sup.4).sub.nHet, (CR.sup.4).sub.nCON(R.sup.4)(CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nN(R.sup.4)COA, (CR.sup.4).sub.nN(R.sup.4)COHet, (CR.sup.4).sub.nOCyc and/or (CR.sup.4).sub.nCOOR.sup.4, R.sup.4 denotes H or A, A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein two adjacent carbon atoms may form a double bond and/or one or two non-adjacent CH- and/or CH.sub.2-groups may be replaced by N-, O- and/or S-atoms and wherein 1-7 H-atoms may be replaced by R.sup.5, or cyclic alkyl having 3-7 C atoms, A denotes unbranched or branched alkyl with 1-6 C-atoms, wherein one or two non-adjacent CH- and/or CH.sub.2-groups may be replaced by O-atoms, Cyc denotes cyclobutyl, cyclopentyl or cyclohexyl, each of which is unsubstituted or mono- or disubstituted by A, Hal, OR.sup.4, N(R.sup.4).sub.2, Het, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, CON(R.sup.4).sub.2 and/or O, R.sup.5 denotes F, Cl or OH, Het denotes pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl, [1,4]-diazepanyl, oxazolidinyl, hexahydro-pyrrolo[3,4-c]pyrrolyl, 2-oxa-6-aza-spiro[3.4]octanyl, 2-oxa-6-aza-spiro[3.5]nonanyl, 2-oxa-7-aza-spiro[3.5]nonanyl, 2,5-dioxa-8-aza-spiro[3.5]nonanyl, oxetanyl, 2-oxa-5-aza-spiro[3.4]octanyl, 2-oxa-6-aza-spiro[3.3]heptanyl, 3-aza-bicyclo[3.1.0]hexanyl, 2-oxa-7-aza-spiro[3.5]nonanyl, isoxazolidinyl, azetidinyl, 2,6-diaza-spiro[3.4]octanyl, hexahydro-pyrrolo[3,4-b]pyrrolyl, tetrahydrofuranyl or isothiazolidinyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, Hal, OR.sup.4, OCOA, COA, (CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nHet, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, CON(R.sup.4).sub.2, COHet, (CR.sup.4).sub.nS(O).sub.mR.sup.4, and/or O, Het denotes pyrrolidinyl, morpholinyl, piperidinyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyridyl, pyrazolyl or piperazinyl, each of which is unsubstituted or mono- or disubstituted by A, Hal, OR.sup.4, N(R.sup.4).sub.2 and/or O, Hal denotes F, Cl, Br or I, n denotes 0, 1, 2 or 3, m denotes 0, 1 or 2, with the proviso that only one or two of X.sup.1, X.sup.2, X.sup.3, X.sup.4 denote N, and pharmaceutically acceptable solvates, salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

2. Compounds according to claim 1 in which R.sup.1 denotes H, F, Cl, Br, CN, CH.sub.3, CF.sub.3 or OCH.sub.3, R.sup.2 denotes H or F, and pharmaceutically acceptable solvates, salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

3. Compounds according to claim 1, in which R.sup.3 denotes phenyl, pyridyl, pyrimidinyl, indolyl, indazolyl, thiophenyl, dihydroisoindolyl or benzimidazolyl, each of which is unsubstituted or mono-, di- or trisubstituted by Hal, A, (CR.sup.4).sub.nOR.sup.4, (CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nS(O).sub.mR.sup.4, (CR.sup.4).sub.nCON(R.sup.4).sub.2, (CR.sup.4).sub.nCOHet, (CR.sup.4).sub.nSO.sub.2Het, (CR.sup.4).sub.nHet, O(CR.sup.4).sub.nCOHet, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, (CR.sup.4).sub.nN(R.sup.4)(CR.sup.4).sub.nHet, (CR.sup.4).sub.nCON(R.sup.4)(CR.sup.4).sub.nHet, (CR.sup.4).sub.nCON(R.sup.4)(CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nN(R.sup.4)COA, (CR.sup.4).sub.nN(R.sup.4)COHet, (CR.sup.4).sub.nOCyc and/or (CR.sup.4).sub.nCOOR.sup.4, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

4. Compounds according to claim 1, in which A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein two adjacent carbon atoms may form a double bond and/or one or two non-adjacent CH- and/or CH.sub.2-groups may be replaced by N- and/or O-atoms and wherein 1-7 H-atoms may be replaced by R.sup.5, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

5. Compounds according to claim 1, in which Het.sup.+ denotes pyrrolidinyl, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

6. Compounds according to claim 1, in which X.sup.1, X.sup.2, X.sup.3, X.sup.4 each, independently of one another, denote CH or N, Y denotes N or CH, Q denotes H or CH.sub.3, R.sup.1 denotes H, F, Cl, Br, CN, CH.sub.3, CF.sub.3 or OCH.sub.3, R.sup.2 denotes H or F, R.sup.3 denotes phenyl, pyridyl, pyrimidinyl, indolyl, indazolyl, thiophenyl, dihydroisoindolyl or benzimidazolyl, each of which is unsubstituted or mono-, di- or trisubstituted by Hal, A, (CR.sup.4).sub.nOR.sup.4, (CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nS(O).sub.mR.sup.4, (CR.sup.4).sub.nCON(R.sup.4).sub.2, (CR.sup.4).sub.nCOHet, (CR.sup.4).sub.nSO.sub.2Het, (CR.sup.4).sub.nHet, O(CR.sup.4).sub.nCOHet, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, (CR.sup.4).sub.nN(R.sup.4)(CR.sup.4).sub.nHet, (CR.sup.4).sub.nCON(R.sup.4)(CR.sup.4).sub.nHet, (CR.sup.4).sub.nCON(R.sup.4)(CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nN(R.sup.4)COA, (CR.sup.4).sub.nN(R.sup.4)COHet, (CR.sup.4).sub.nOCyc and/or (CR.sup.4).sub.nCOOR.sup.4, R.sup.4 denotes H or A, A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein two adjacent carbon atoms may form a double bond and/or one or two non-adjacent CH- and/or CH.sub.2-groups may be replaced by N- and/or O-atoms and wherein 1-7 H-atoms may be replaced by R.sup.5, Cyc denotes cyclobutyl, cyclopentyl or cyclohexyl, each of which is unsubstituted or mono- or disubstituted by A, Hal, OR.sup.4, N(R.sup.4).sub.2, Het, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, CON(R.sup.4).sub.2 and/or O, A denotes unbranched or branched alkyl with 1-6 C-atoms, wherein one or two non-adjacent CH- and/or CH.sub.2-groups may be replaced by O-atoms, R.sup.5 denotes F, Cl or OH, Het denotes pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl, [1,4]-diazepanyl, oxazolidinyl, hexahydro-pyrrolo[3,4-c]pyrrolyl, 2-oxa-6-aza-spiro[3.4]octanyl, 2-oxa-6-aza-spiro[3.5]nonanyl, 2-oxa-7-aza-spiro[3.5]nonanyl, 2,5-dioxa-8-aza-spiro[3.5]nonanyl, oxetanyl, 2-oxa-5-aza-spiro[3.4]octanyl, 2-oxa-6-aza-spiro[3.3]heptanyl, 3-aza-bicyclo[3.1.0]hexanyl, 2-oxa-7-aza-spiro[3.5]nonanyl, isoxazolidinyl, azetidinyl, 2,6-diaza-spiro[3.4]octanyl, hexahydro-pyrrolo[3,4-b]pyrrolyl, tetrahydrofuranyl or isothiazolidinyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, Hal, OR.sup.4, OCOA, COA, (CR.sup.4).sub.nN(R.sup.4).sub.2, (CR.sup.4).sub.nHet, (CR.sup.4).sub.nO(CR.sup.4).sub.nHet, CON(R.sup.4).sub.2, COHet, (CR.sup.4).sub.nS(O).sub.mR.sup.4, and/or O, Het denotes pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyridyl or pyrazolyl, Hal denotes F, Cl, Br or I, N denotes 0, 1, 2 or 3, m denotes 0, 1 or 2, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

7. Compounds according to claim 1, selected from the group consisting of 6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, N,N-dimethyl-4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, N,N-dimethyl-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 3-[1-(4-dimethylaminomethyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-[1,8]naphthyridin-2-one, 3-(1-phenyl-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one, 3-[1-(4-hydroxymethyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-[1,8]naphthyridin-2-one, N-(2-hydroxy-ethyl)-4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, N-(2-methoxy-ethyl)-4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 3-[1-(4-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 4-[4-(6-chloro-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-N,N-dimethyl-benzamide, 3-[1-(4-fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-[1-(2-fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-{1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, N-(1-methyl-piperidin-4-ylmethyl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 4-[4-(6-methoxy-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-N,N-dimethyl-benzamide, 4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-pyridine-2-carboxylic acid methyl ester, 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N,N-dimethyl-benzamide, N-(2-hydroxy-ethyl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 3-[1-(1H-indol-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, N-(2-morpholin-4-yl-ethyl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(1-methyl-piperidin-4-ylmethyl)-benzamide, 3-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid methyl ester, 3-[1-(3-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-{1-[4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-(1-phenyl-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 3-[1-(3H-benzimidazol-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,7]naphthyridin-2-one, 7-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 3-{1-[3-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[3-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[6-(3-oxo-morpholin-4-yl)-pyridin-3-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[2-methyl-4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[3-fluoro-4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-[1-(3,4,5-trimethoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 2-fluoro-N-methyl-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 3-{1-[3-methyl-4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridin-2-one, N,N-dimethyl-4-[4-(2-oxo-1,2-dihydro-[1,7]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 3-(1-phenyl-1H-pyrazol-4-yl)-1H-[1,8]naphthyridin-2-one, 3-(1-phenyl-1H-pyrazol-4-yl)-1H-[1,7]naphthyridin-2-one, 3-[1-(4-fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-[1,6]naphthyridin-2-one, 3-(1-phenyl-1H-pyrazol-4-yl)-1H-[1,6]naphthyridin-2-one, 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 5-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,7]naphthyridin-2-one, 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-N-piperidin-4-yl-benzamide, 3-[1-(4-piperazin-1-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-[1-(2-piperazin-1-yl-pyrimidin-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-[1-(4-[1,4]diazepan-1-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, N-(1-Methyl-piperidin-4-yl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, N-methyl-N-(1-methyl-piperidin-4-yl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 3-{1-[4-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(4-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridin-2-one, 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,7]naphthyridin-2-one, 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 7-methyl-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 3-{1-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 3-{1-[4-(4-methyl-2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(4-methyl-[1,4]diazepan-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 3-(1-phenyl-1H-pyrazol-4-yl)-1H-quinolin-2-one, 3-{1-[3-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 4-[4-(2-Oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid, 3-{1-[3-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[3-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-[1-(4-isopropenyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-{1-[4-(1-methanesulfonyl-1-methyl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-chloro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,5]naphthyridin-2-one, 6-fluoro-3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 5-fluoro-3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one, 3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one, 5,7-difluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one; 7-bromo-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-methoxy-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-{1-[4-(Morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-8H-pyrido[2,3-d]pyrimidin-7-one, 6-fluoro-3-{1-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 5,7-difluoro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-chloro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxo-oxazolidin-3-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(1,1-dioxo-116-isothiazolidin-2-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-(1-{4-[2-(4-acetyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-6-fluoro-1H-quinolin-2-one, 3-(1-{4-[2-(4-acetyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-6,7-difluoro-1H-quinolin-2-one; acetic acid 1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperidin-4-yl ester, acetic acid 1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperidin-3-yl ester, 3-{1-[4-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-5,7-difluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[3-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[3-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-5-oxo-[1,4]diazepane-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(2-dimethylamino-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-(2-diethylamino-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 7-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 5-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 8-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 6-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 6-chloro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-[1-(4-[1,4]diazepan-1-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-6-fluoro-1H-[1,8]naphthyridin-2-one, 6-fluoro-3-{1-[3-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-chloro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 5,6-difluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(piperazine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(2-piperazin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(3-piperazin-1-yl-propoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-piperidin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(2-piperidin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(3-piperazin-1-yl-propoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-methyl-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 5,7-difluoro-3-{1-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indol-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indol-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(2-oxo-2-piperazin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxo-2-piperazin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-trifluoromethyl-1H-quinolin-2-one, 3-{1-[4-(4-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-(4-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indazol-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-7-methoxy-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-7-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 5-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 8-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 5,7-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-Fluoro-3-{1-[3-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 7-chloro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-[1,4]diazepan-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one, 5,6-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(1-methyl-piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(1-methyl-piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-methyl-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-trifluoromethyl-1H-quinolin-2-one, 3-{1-[4-(4-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-(4-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6,7-difluoro-3-(1-{1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-indazol-5-yl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(4-methyl-2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-Fluoro-3-(1-{4-[4-(2-methoxy-ethyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one, 6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-2-oxo-1,2-dihydro-quinoline-7-carbonitrile, 6-fluoro-3-(1-{1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-indol-5-yl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, acetic acid (R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidin-3-yl ester, acetic acid (S)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidin-3-yl ester, 6-fluoro-3-{1-[4-((R)-3-hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-hydroxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(3-hydroxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 4-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-Difluoro-3-{1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, N-(2-diethylamino-ethyl)-4-[4-(6,7-difluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 4-[4-(7-chloro-6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(2-diethylamino-ethyl)-benzamide, 3-(1-{4-[4-(2-diethylamino-ethyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-6,7-difluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(4-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((R)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((S)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, N-(2-diethylamino-ethyl)-4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 6-fluoro-3-{1-[4-((S)-2-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-2-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((R)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((S)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-(1-{4-[3-(2-diethylamino-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-7-aza-spiro[4.4]nonane-7-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-6-aza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(3-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(3-dimethylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[3-(4-hydroxy-piperidin-1-yl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[3-(2-morpholin-4-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(2-methoxy-ethyl)-N-methyl-benzamide, 4-[4-(6,7-difluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(2-methoxy-ethyl)-N-methyl-benzamide, 6-fluoro-3-{1-[4-((R)-3-hydroxymethyl-morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-hydroxymethyl-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-hydroxymethyl-morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((2S,5S)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((2R,5R)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((2S,5S)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-((2R,5R)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[3-(2-morpholin-4-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-7-methyl-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[3-(2-pyrrolidin-1-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6,7-difluoro-3-(1-{4-[3-(2-pyrrolidin-1-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, (R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-3-carboxylic acid amide, 6-fluoro-3-{1-[4-((2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-6-aza-spiro[3.5]nonane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-7-aza-spiro[3.5]nonane-7-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-oxetan-3-yl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(2,5-dioxa-8-aza-spiro[3.5]nonane-8-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-oxetan-3-yl-benzamide, 6,7-difluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-5-aza-spiro[3.4]octane-5-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-6-aza-spiro[3.3]heptane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 3-{1-[4-((3R,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N,N-bis-(2-methoxy-ethyl)-benzamide, 3-{1-[4-(3-diethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, N-(3-acetyl-3-aza-bicyclo[3.1.0]hex-6-yl)-4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide, 6-fluoro-3-{1-[4-((2S,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, (S)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-2-carboxylic acid amide, (S)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-3-carboxylic acid amide, 6-fluoro-3-{1-[4-((2R,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-oxa-5-aza-spiro[3.5]nonane-5-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-2-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((2R,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((2S,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-(1-{4-[3-(4-hydroxy-piperidin-1-yl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-chloro-3-{1-[4-(4-oxetan-3-yl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(3-dimethylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(2-hydroxymethyl-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(2-oxa-7-aza-spiro[3.5]nonane-7-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(2-oxa-6-aza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(2-oxa-6-aza-spiro[3.3]heptane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-(1-{4-[(S)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-chloro-3-(1-{4-[(R)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-pyrazol-4-yl)-1H-quinolin-2-one, (R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-2-carboxylic acid amide, 3-{1-[4-((3R,4R)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((3S,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-chloro-3-{1-[4-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((R)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((3R,4R)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((3S,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((R)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(azetidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[2-(4-methyl-piperazine-1-carbonyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-methanesulfonyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methanesulfonyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(3-methanesulfonylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[2-(1-methyl-1H-pyrazol-4-yl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-pyridin-3-yl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-ylmethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(2-methyl-2,6-diaza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(2-methyl-2,6-diaza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((3aR,6aR)-5-methyl-hexahydro-pyrrolo[3,4-b]pyrrole-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(2,2-dimethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[3-(4-methyl-piperazine-1-carbonyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-pyrazol-4-yl)-1H-quinolin-2-one, 3-{1-[4-((3R,4R)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((2S,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((2R,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((3S,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((S)-3-amino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((cis)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((cis)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((R)-3-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 6-Fluoro-3-{1-[4-((R)-3-methylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((R)-3-amino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-hydroxymethyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-2-hydroxymethyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-2-hydroxymethyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-(6-amino-3-aza-bicyclo[3.1.0]hexane-3-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-chloro-3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((cis)-5-methyl-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 3-{1-[4-((R)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-(6-dimethylamino-3-aza-bicyclo[3.1.0]hexane-3-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-fluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-diethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((R)-3-diethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-(4-dimethylamino-3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((S)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one, 3-{1-[4-((trans)-3-dimethylamino-4-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-[1-(4-methylamino-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, (R)-tetrahydro-furan-2-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide, (S)-tetrahydro-furan-2-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide, tetrahydro-pyran-4-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide, (R)-N-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-2-methoxy-N-methyl-propionamide, (2S,4S)-4-methoxy-pyrrolidine-2-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide, (S)-N-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-2-methoxy-N-methyl-propionamide, 1-methyl-piperidine-4-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide, 6-fluoro-3-{1-[5-((S)-3-methoxy-pyrrolidine-1-carbonyl)-thiophen-3-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[5-((R)-3-methoxy-pyrrolidine-1-carbonyl)-thiophen-3-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, N-{4-[4-(6,7-difluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-N-methyl-acetamide, N-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-N-methyl-acetamide, 6-fluoro-3-[1-(2-methyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 6-Fluoro-3-{1-[4-((trans)-3-methoxy-cyclopentyloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((1S,3R)-3-methoxy-cyclopentyloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-[1-(4-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((1S,2S)-2-methoxy-cyclopentyloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-[1-(4-cyclopentyloxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, 3-[1-(4-cyclopentyloxy-phenyl)-1H-[1,2,3]triazol-4-yl]-6-fluoro-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(tetrahydro-furan-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(tetrahydro-furan-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6,7-difluoro-3-{1-[4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-fluoro-3-{1-[4-(1-methyl-piperidin-4-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, 6-chloro-3-{1-[4-(1-methyl-piperidin-4-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, and pharmaceutically acceptable solvates, salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

Description

SYNTHESIS OF INTERMEDIATES

Bromoquinolones and Bromonaphthyridones

Synthesis of 3-bromo-6-fluoro-1H-quinolin-2-one

(1) ##STR00007##

(2) A solution of 2-amino-5-fluoro-benzaldehyde (7.42 g, 53.3 mmol) in dimethyl malonate (45 ml) is heated to 140 C. and stirred at this temperature for 16 hours. The reaction mixture is allowed to reach room temperature. The resultant precipitate is filtered off, washed with tert-butyl methyl ether and dried under vacuum to afford 6-fluoro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester as light ochre solid; HPLC/MS 1.17 min (B), [M+H].sup.+ 222.

(3) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.11 (s, 1H), 8.49 (s, 1H), 7.70 (dd, J=9.0, 2.9 Hz, 1H), 7.52 (td, J=8.9, 2.9 Hz, 1H), 7.35 (dd, J=9.1, 4.7 Hz, 1H), 3.81 (s, 3H).

(4) To a slurry of 6-fluoro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid methyl ester (6.92 g, 31.3 mmol) in a mixture of THF (30 ml) and water (38 ml) is added lithium hydroxide (6.59 g, 275 mmol) and the mixture is stirred for 2 hours at 65 C. After cooling to room temperature, 1 N aqueous hydrochloric acid is added until a pH value of 1 is reached. The resultant precipitate is filtered off, washed with water and dried under vacuum to afford 6-fluoro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid as light yellow solid; HPLC/MS 1.18 min (B), [M+H].sup.+ 208.

(5) A suspension of 6-fluoro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (6.70 g, 32.3 mmol) in pyridine (108 ml) is cooled to 0 C. Under stirring and continuous external cooling, bromine (6.63 ml, 129 mmol) is added dropwise. The reaction mixture is heated to 65 C. and stirred at this temperature for 1 hour. After cooling to room temperature, the reaction mixture is poured into water (160 ml). 37% aqueous hydrochloric acid is added until a pH value of 4 is reached. The resultant precipitate is filtered off and washed with water. The filtrate is extracted three times with dichloromethane; the organic phases are combined, dried over sodium sulfate and evaporated. The residue is combined with the precipitate and chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 3-bromo-6-fluoro-1H-quinolin-2-one as light yellow solid; HPLC/MS 1.26 min (B), [M+H].sup.+ 242,244.

(6) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.31 (s, 1H), 8.49 (s, 1H), 7.54 (dd, J=9.1, 2.8 Hz, 1H), 7.46 (td, J=8.8, 2.8 Hz, 1H), 7.36 (dd, J=9.0, 4.8 Hz, 1H).

(7) The following compounds are prepared similarly

(8) ##STR00008##

(9) 3-Bromo-6-chloro-1H-[1,8]naphthyridin-2-one, light brown solid; HPLC/MS 1.24 min (B), [M+H].sup.+ 261.

(10) ##STR00009##

(11) 3-Bromo-6-methoxy-1H-[1,8]naphthyridin-2-one, brown solid; HPLC/MS 1.12 min (B), [M+H].sup.+ 255,257.

(12) .sup.1H NMR (400 MHz, DMSO-d6) 12.59 (s, 1H), 8.49 (s, 1H), 8.36 (d, J=3.0 Hz, 1H), 7.75 (d, J=3.0 Hz, 1H), 3.86 (s, 3H).

(13) ##STR00010##

(14) 3-Bromo-1H-[1,8]naphthyridin-2-one, brown solid; HPLC/MS 1.09 min (B), [M+H].sup.+ 225,227.

(15) .sup.1H NMR (400 MHz, DMSO-d6) 12.74 (s, 1H), 8.56 (m, 2H), 8.13 (d, 1H), 7.30 (dd, 1H).

(16) ##STR00011##

(17) 3-Bromo-1H-[1,7]naphthyridin-2-one, orange-brown solid; HPLC/MS 1.00 min (B), [M+H].sup.+ 225,227.

(18) ##STR00012##

(19) 3-Bromo-7-methyl-1H-[1,8]naphthyridin-2-one, light yellow solid; HPLC/MS 1.16 min (B), [M+H].sup.+ 239,241.

(20) ##STR00013##

(21) 3-Bromo-6-fluoro-1H-[1,8]naphthyridin-2-one, beige solid; HPLC/MS 1.15 min (B), [M+H].sup.+ 243,245.

(22) .sup.1H NMR (500 MHz, DMSO-d6) 12.80 (s, 1H), 8.62 (d, J=2.8 Hz, 1H), 8.52 (s, 1H), 8.08 (dd, J=8.5, 2.9 Hz, 1H).

Ethynyl-Quinolones and Ethynyl-Naphthyridones

Synthesis of 3-ethynyl-1H-quinolin-2-one

(23) ##STR00014##

(24) To a suspension of 3-bromo-1H-quinolin-2-one (2.24 g, 10.0 mmol) in dioxane (40 ml) are added triethylamine (3.67 ml, 26.5 mmol) and copper(I) iodide (1.90 g, 10.0 mmol). The reaction mixture is purged with nitrogen and bis(triphenylphosphine)palladium(II) chloride (286 mg, 0.40 mmol) and trimethylsilyl-acetylene (2.37 ml, 17.1 mmol) are added. The reaction mixture is flushed with nitrogen and stirred in a closed reaction vial for 16 hours at 80 C. The reaction mixture is allowed to reach room temperature and filtered through a plug of kieselguhr. The residue is washed with dichloromethane and the filtrate is evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 3-trimethylsilanylethynyl-1H-quinolin-2-one as light brown solid; HPLC/MS 1.52 min (B), [M+H].sup.+ 242.

(25) To a solution of 3-trimethylsilanylethynyl-1H-quinolin-2-one (2.16 g, 8.95 mmol) in methanol (18 ml) is added potassium fluoride on aluminium oxide (1.04 g, 5.7 mmol fluoride) and the reaction mixture is stirred at room temperature for 30 minutes. The reaction mixture is poured into ice water. The solids are filtered off, washed with water and dried under vacuum. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 3-ethynyl-1H-quinolin-2-one as light brown solid; HPLC/MS 1.18 min (B), [M+H].sup.+ 170.

(26) 1H NMR (400 MHz, DMSO-d.sub.6) 12.02 (s, 1H), 8.23 (s, 1H), 7.67 (dd, J=7.9, 1.4 Hz, 1H), 7.53 (ddd, J=8.5, 7.2, 1.5 Hz, 1H), 7.34-7.27 (m, 1H), 7.20 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 4.34 (s, 1H).

(27) The following compounds are prepared similarly:

(28) ##STR00015##

(29) 6-Chloro-3-ethynyl-1H-[1,8]naphthyridin-2-one, light beige solid; HPLC/MS 1.20 min (B), [M+H].sup.+ 205.

(30) ##STR00016##

(31) 3-Ethynyl-6-methoxy-1H-[1,8]naphthyridin-2-one, beige solid; HPLC/MS 1.11 min (B), [M+H].sup.+ 201.

(32) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 8.30 (d, J=3.0 Hz, 1H), 8.18 (s, 1H), 7.72 (d, J=3.0 Hz, 1H), 4.41 (s, 1H), 3.84 (s, 3H).

(33) ##STR00017##

(34) 3-Ethynyl-6-fluoro-1H-quinolin-2-one, beige solid; HPLC/MS 1.27 min (A), [M+H].sup.+ 188.

(35) ##STR00018##

(36) 3-Ethynyl-1H-[1,7]naphthyridin-2-one, beige powder; HPLC/MS 0.97 min (B), [M+H].sup.+ 171;

(37) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (bs, 1H) 8.60 (s, 1H), 8.22 (d, J=5.2 Hz, 1H), 8.14 (s, 1H), 7.51 (d, J=5.2 Hz, 1H), 4.41 (s, 1H).

(38) ##STR00019##

(39) 3-Ethynyl-7-methyl-1H-[1,8]naphthyridin-2-one, beige solid; HPLC/MS 1.13 min (B), [M+H].sup.+ 185;

(40) ##STR00020##

(41) 3-Ethynyl-6-fluoro-1H-[1,8]naphthyridin-2-one, orange-beige solid; HPLC/MS 1.11 min (B), [M+H].sup.+ 189;

(42) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.45 (s, 1H), 8.47 (d, J=2.8 Hz, 1H), 8.10 (s, 1H), 7.96 (dd, J=8.5, 3.0 Hz, 1H), 4.38 (s, 1H).

(43) Aromatic Azides

Synthesis of 4-(4-azido-phenyl)-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

(44) ##STR00021##

(45) To a stirred solution of 4-(4-amino-phenyl)-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (4.37 g, 15.0 mmol) in a mixture of ethanol (47 ml) and water (47 ml) is added aqueous hydrochloric acid (37%, 9.15 ml). The solution is cooled to 0 C. and a solution sodium nitrite (1.24 g, 18.0 mmol) in water (10 ml) is added slowly. The reaction mixture is stirred for 10 minutes at room temperature. Then sodium azide (1.46 g, 22.5 mmol) is added in portions and the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture is poured into water, the solids are filtered off, washed with water and dried under vacuum to afford 4-(4-azido-phenyl)-3-oxo-piperazine-1-carboxylic acid tert-butyl ester as beige solid; HPLC/MS 1.60 min (A), [M+H].sup.+ 318.

(46) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.39 (d, J=8.8 Hz, 2H), 7.14 (d, J=8.8 Hz, 2H), 4.06 (s, 2H), 3.76-3.62 (m, 4H), 1.44 (s, 9H).

(47) The following compounds are prepared similarly

(48) ##STR00022##

(49) (4-Azido-benzyl)-dimethyl-amine; .sup.1H NMR (400 MHz, CDCl.sub.3) 7.46 (d, 2H), 6.99 (d, 2H), 3.38 (s, 2H), 2.25 (s, 6H).

(50) ##STR00023##

(51) (4-Azido-phenyl)-methanol; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.36 (d, 2H), 7.07 (d, 2H), 5.25 t, 1H), 4.49 (d, 2H).

(52) ##STR00024##

(53) 1-[2-(4-Azido-phenoxy)-ethyl]-pyrrolidine, brown oil; HPLC/MS 1.07 min (B), [M+H].sup.+ 233.

(54) ##STR00025##

(55) 4-[2-(4-Azido-phenoxy)-ethyl]-morpholine, brown oil; HPLC/MS 1.05 min (B), [M+H].sup.+ 249.

(56) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.08-6.96 (m, 4H), 4.08 (t, J=5.8 Hz, 2H), 3.56-3.60 (m, 4H), 2.68 (t, J=5.8 Hz, 2H), 2.44-2.49 (m, 2H).

(57) ##STR00026##

(58) 4-(5-Azido-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester, brown solid; HPLC/MS 1.83 min (A), [M-.sup.tbu].sup.+ 250.

(59) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 8.29 (s, 2H), 3.72-3.65 (m, 4H), 3.46-3.36 (m, 4H), 1.42 (s, 9H).

(60) ##STR00027##

(61) 4-[2-(4-Azido-phenoxy)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester, beige powder; HPLC/MS 1.30 min (A), [M+H].sup.+ 348.

(62) ##STR00028##

(63) 4-(4-Azido-phenyl)-piperazine-1-carboxylic acid tert-butyl ester, brown solid; HPLC/MS 1.94 min (A), [M+H].sup.+ 304.

(64) ##STR00029##

(65) 4-(4-Azido-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester, brown oil; HPLC/MS 1.97 min (A), [M+H].sup.+ 318.

(66) ##STR00030##

(67) 4-(4-Azido-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester, brown oil; HPLC/MS 1.97 min (A), [M+H].sup.+ 318.

(68) ##STR00031##

(69) (4-Azido-3-methyl-phenyl)-morpholin-4-yl-methanone, yellow resin; HPLC/MS 1.42 min (A), [M+H].sup.+ 247.

(70) ##STR00032##

(71) 5-Azido-1,2,3-trimethoxy-benzene, beige solid; HPLC/MS 1.56 min (A), [M+H].sup.+ 210.

(72) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 6.42 (s, 2H), 3.80 (s, 6H), 3.64 (s, 3H).

(73) ##STR00033##

(74) (4-Azido-2-fluoro-phenyl)-morpholin-4-yl-methanone, light brown oil; HPLC/MS 1.31 min (A), [M+H].sup.+ 251.

(75) ##STR00034##

(76) 4-Azido-2-fluoro-N-methyl-benzamide, light brown oil; HPLC/MS 1.23 min (A), [M+H].sup.+ 195.

(77) ##STR00035##

(78) 4-[2-(3-Azido-phenoxy)-ethyl]-morpholine, brown oil; HPLC/MS 1.03 min (A), [M+H].sup.+ 249.

(79) ##STR00036##

(80) 3-(4-Azido-phenyl)-oxazolidin-2-one, pale brown powder; HPLC/MS 1.44 min (A), [M+H].sup.+ 205. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.60 (d, J=9.0 Hz, 2H), 7.15 (d, J=9.0 Hz, 2H), 4.59-4.33 (m, 2H), 4.10-4.00 (m, 2H).

(81) ##STR00037##

(82) 2-(4-Azido-phenyl)-isothiazolidine 1,1-dioxide, beige powder; HPLC/MS 1.47 min (A), [M+H].sup.+ 239.

(83) ##STR00038##

(84) 4-(4-Azido-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester, light yellow solid; UPLC/MS 0.90 min, [M+H].sup.+ 268.

(85) ##STR00039##

(86) 4-(4-Azido-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester, beige solid; HPLC/MS 1.93 min (A), [M+H].sup.+ 275.

(87) ##STR00040##

(88) 4-[2-(4-Azido-phenyl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester, light yellow solid; UPLC/MS 1.13 min, [M-.sup.tBu].sup.+290. .sup.1H NMR (400 MHz, DMSO-d.sub.6) b 7.31-7.25 (m, 2H), 7.15-7.04 (m, 2H), 3.72 (s, 2H), 3.50-3.42 (m, 4H), 3.30-3.23 (m, 4H), 1.41 (s, 9H).

(89) ##STR00041##

(90) [2-(4-Azido-phenyl)-ethyl]-dimethyl-amine, red-brown oil; UPLC/MS 0.77 min, [M+H].sup.+ 191. .sup.1H NMR (500 MHz, DMSO-d.sub.6) 7.27 (d, J=8.4 Hz, 2H), 7.07-6.99 (m, 2H), 2.75-2.66 (m, 2H), 2.47-2.38 (m, 2H), 2.17 (s, 6H).

(91) ##STR00042##

(92) 1-[2-(4-Azido-phenyl)-ethyl]-pyrrolidine, red-brown oil; UPLC/MS 0.78 min, [M+H].sup.+ 217. .sup.1H NMR (500 MHz, DMSO-d.sub.6) 7.30-7.26 (m, 1H), 7.06-7.01 (m, 1H), 2.73 (t, J=7.6 Hz, 1H), 2.60 (t, J=7.6 Hz, 1H), 2.49-2.43 (m, 3H), 1.71-1.63 (m, 4H).

(93) ##STR00043##

(94) [2-(4-Azido-phenoxy)-ethyl]-diethyl-amine, brown liquid; HPLC/MS 1.08 min (A), [M+H].sup.+ 235.

Synthesis of 4-(4-azido-phenyl)-morpholin-3-one

(95) ##STR00044##

(96) A suspension of 4-(4-amino-phenyl)-morpholin-3-one (3.00 g, 15.6 mmol) in acetonitrile (35 ml) is cooled to 0 C. Then butyl nitrite (2.43 g, 23.6 mmol) is added dropwise. The reaction mixture is stirred for 15 minutes at 0 C. Then trimethylsilyl azide is added dropwise. The reaction mixture is stirred for 20 hours at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 4-(4-azido-phenyl)-morpholin-3-one as beige solid; HPLC/MS 1.21 min (B), [M+H].sup.+ 219.

(97) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 7.45 (d, J=8.8 Hz, 2H), 7.16 (d, J=8.8 Hz, 2H), 4.20 (s, 2H), 4.04-3.92 (m, 2H), 3.81-3.66 (m, 2H).

(98) The following compounds are prepared similarly

(99) ##STR00045##

(100) 4-(4-Azido-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester, beige solid; HPLC/MS 1.85 min (B), [M-.sup.tbu].sup.+277.

(101) ##STR00046##

(102) 4-(4-Azido-2-fluoro-phenyl)-morpholin-3-one, yellow powder; HPLC/MS 1.27 min (A), [M+H].sup.+ 237.

(103) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.49 (t, J=8.4 Hz, 1H), 7.17 (dd, J=11.0, 2.5 Hz, 1H), 7.05 (ddd, J=8.6, 2.5, 1.0 Hz, 1H), 4.22 (s, 2H), 4.03-3.82 (m, 2H), 3.73-3.58 (m, 2H).

(104) ##STR00047##

(105) 4-(5-Azido-pyridin-2-yl)-morpholin-3-one, yellow solid; HPLC/MS 1.15 min (A), [M+H].sup.+ 220.

(106) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 8.27 (dd, J=2.9, 0.7 Hz, 1H), 8.05 (dd, J=8.9, 0.7 Hz, 1H), 7.69 (dd, J=8.9, 2.9 Hz, 1H), 4.27 (s, 2H), 4.05-3.90 (m, 4H).

Synthesis of 2-(4-azido-phenyl)-propan-2-ol

(107) ##STR00048##

(108) To a suspension of 2-(4-bromo-phenyl)-propan-2-ol (1.00 g, 4.65 mmol), copper(I) iodide (177 mg, 0.93 mmol) and sodium (2R)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxy-ethanolate hydrate (100 mg, 0.46 mmol in a mixture of DMF (4 ml) and water (5 ml) are added sodium azide (605 mg, 9.3 mmol) and N,N-dimethyl-ethane-1,2-diamine (123 mg, 1.39 mmol). The reaction mixture is stirred at room temperature for 19 hours. The reaction mixture is poured into 40 ml saturated aqueous sodium chloride solution. The mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 2-(4-azido-phenyl)-propan-2-ol as light brown oil; HPLC/MS 1.47 min (B), [M-N.sub.2OH].sup.+132.

(109) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.49 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.4 Hz, 2H), 5.01 (s, 1H), 1.41 (s, 6H).

(110) The following compounds are prepared similarly

(111) ##STR00049##

(112) 5-Azido-1H-indole, dark brown oil; HPLC/MS 1.46 min (B), [M+H].sup.+ 159.

(113) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 11.19 (s, 1H), 7.43 (dt, J=8.6, 0.8 Hz, 1H), 7.40 (t, J=2.8 Hz, 1H), 7.29 (dt, J=2.2, 0.7 Hz, 1H), 6.84 (dd, J=8.6, 2.2 Hz, 1H), 6.42 (ddd, J=3.0, 2.0, 0.9 Hz, 1H).

(114) ##STR00050##

(115) (5-Azido-indol-1-yl)-acetic acid methyl ester, black gum; HPLC/MS 1.72 min (A), [M+H].sup.+ 231.

(116) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.47 (d, J=8.7 Hz, 1H), 7.41 (d, J=3.2 Hz, 1H), 7.32 (d, J=2.1 Hz, 1H), 6.91 (d, J=2.2 Hz, 1H), 6.89 (d, J=2.2 Hz, 1H), 6.47 (dd, J=3.2, 0.8 Hz, 2H), 5.16 (s, 1H), 3.69 (s, 3H).

Synthesis of (4-azido-phenyl)-morpholin-4-yl-methanone

(117) ##STR00051##

(118) To a solution of 4-azidobenzoic acid (2.50 g, 15.3 mmol), morpholine (1.35 ml, 15.5 mmol) and [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (HATU; 5.85 g, 15.4 mmol) in DMF (30 ml) is added ethyl-diisopropyl-amine (7.90 ml, 46.5 mmol) and the reaction mixture is stirred for 16 hours at room temperature. To the reaction mixture is added ethyl acetate, saturated aqueous Na.sub.2CO.sub.3 solution and water. The organic phase is separated, washed with water, with 2 N aqueous HCl solution and saturated sodium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford (4-azido-phenyl)-morpholin-4-yl-methanone as colourless oil, which crystallizes on standing; HPLC/MS 1.27 min (A), [M+H].sup.+ 233.

(119) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.48 (d, J=8.5 Hz, 2H), 7.20 (d, J=8.5 Hz, 2H), 3.38-3-66 (m, 8H).

(120) The following compounds are prepared similarly:

(121) ##STR00052##

(122) 4-Azido-N,N-dimethylbenzamide, brown oil; HPLC/MS 2.24 min (A), [M+H].sup.+ 191.

(123) ##STR00053##

(124) 4-[(4-Azido-benzoyl)-methyl-amino]-piperidine-1-carboxylic acid tert-butyl ester, yellow oil; HPLC/MS 1.42 min (B), [M-.sup.tbu].sup.+304.

(125) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.44 (d, J=8.5 Hz, 2H), 7.24-7.08 (m, 1H), 4.41 (m, 1H), 4.02 (m, 4H), 2.79 (s, 3H), 1.73-1.51 (m, 4H), 1.41 (s, 9H).

(126) ##STR00054##

(127) 4-Azido-N-(2-hydroxy-ethyl)-benzamide, white crystals; HPLC/MS 1.10 min (B), [M+H].sup.+ 207.

(128) ##STR00055##

4-Azido-N-(2-methoxy-ethyl)-benzamide

(129) ##STR00056##

(130) [1-(4-Azido-benzoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester, light yellow glass; HPLC/MS 1.45 min (B), [M+H].sup.+ 346.

(131) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.40 (d, J=8.5 Hz, 1H), 7.17 (d, J=8.5 Hz, 1H), 6.84 (d, J=7.8 Hz, 1H), 4.10-4.40 (m, 1H), 3.45-3.60 (m, 2H), 2.85-3.15 (m, 2H), 1.65-1.85 (m, 2H), 1.38 (s, 9H), 1.20-1.40 (m, 2H).

(132) ##STR00057##

(133) 4-(4-Azido-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester, light yellow solid; HPLC/MS 1.49 min (B), [M-.sup.tbu].sup.+276.

(134) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 7.47 (d, J=8.5 Hz, 2H), 7.19 (d, J=8.5 Hz, 2H), 3.30-3.62 (m, 8H), 1.42 (s, 9H).

(135) ##STR00058##

(136) 4-Azido-N-(2-morpholin-4-yl-ethyl)-benzamide, brown glass; HPLC/MS 0.98 min (B), [M+H].sup.+ 276.

(137) ##STR00059##

(138) 4-(4-Azido-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester, light yellow solid; HPLC/MS 1.49 min (B), [M-.sup.tbu].sup.+290.

(139) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 8.26 (d, J=7.8 Hz, 1H), 7.90 (d, J=8.6 Hz, 2H), 7.20 (d, J=8.6 Hz, 2H), 3.90-4.03 (m, 3H), 2.77-2.94 (m, 2H), 1.75-1.82 (m, 2H), 1.42 (s, 9H), 1.36-1.48 (m, 2H).

(140) ##STR00060##

(141) 4-Azido-N-(1-methyl-piperidin-4-ylmethyl)-benzamide, light yellow oil; HPLC/MS 1.00 min (B), [M+H].sup.+ 274.

(142) ##STR00061##

(143) (4-Azido-2-methyl-phenyl)-morpholin-4-yl-methanone, brown resin; HPLC/MS 1.35 min (A), [M+H].sup.+ 247

(144) ##STR00062##

(145) (4-Azido-phenyl)-[4-(3-methoxy-propyl)-piperazin-1-yl]-methanone, brown oil; HPLC/MS 1.00 min (A), [M+H].sup.+ 304.

(146) ##STR00063##

(147) 4-(3-Azido-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester, beige solid; HPLC/MS 1.69 min (A), [M+H].sup.+ 232.

(148) ##STR00064##

(149) 4-(4-Azido-benzoyl)-1-methyl-piperazin-2-one, light yellow gum; HPLC/MS 1.18 min (A), [M+H].sup.+ 269.

(150) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.55-7.47 (m, 2H), 7.24-7.17 (m, 2H), 4.06 (s, 1H), 3.87-3.54 (m, 2H), 3.36 (t, J=5.5 Hz, 1H), 2.86 (s, 3H).

(151) ##STR00065##

(152) (4-Azido-phenyl)-((R)-3-hydroxy-pyrrolidin-1-yl)-methanone, pale brown oil; HPLC/MS 1.16 min (A), [M+H].sup.+ 233.

(153) ##STR00066##

(154) (4-Azido-phenyl)-((S)-3-hydroxy-pyrrolidin-1-yl)-methanone, pale brown oil; HPLC/MS 1.16 min (A), [M+H].sup.+ 233.

(155) ##STR00067##

(156) (4-Azido-phenyl)-[1,3]bipyrrolidinyl-1-methanone, brown gum; HPLC/MS 0.94 min (A), [M+H].sup.+ 286.

(157) ##STR00068##

(158) 1-(4-Azido-benzoyl)-4-methyl-[1,4]diazepan-5-one, yellow resin; UPLC/MS 0.51 min, [M+H].sup.+ 274.

(159) ##STR00069##

(160) Acetic acid 1-(4-azido-benzoyl)-piperidin-4-yl ester, yellow resin; HPLC/MS 1.48 min (A), [M+H].sup.+ 289.

(161) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.38 (d, J=8.5 Hz, 2H), 7.16-6.99 (m, 2H), 4.87 (tt, J=7.9, 3.8 Hz, 1H), 4.06-3.11 (m, 4H), 1.93 (s, 3H), 1.80 (bs, 2H), 1.53 (bs, 2H).

Synthesis of 4-[2-(5-azido-indol-1-yl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester

(162) ##STR00070##

(163) 4-[2-(5-azido-indol-1-yl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester, light beige solid; UPLC/MS 0.84 min, [M+H].sup.+ 329.

Synthesis of 4-[2-(4-azido-phenoxy)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester

(164) ##STR00071##

(165) 4-[2-(4-Azido-phenoxy)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester, yellow solid; UPLC/MS 0.84 min, [M+H].sup.+ 306.

Synthesis of 4-[2-(5-azido-indazol-1-yl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester

(166) ##STR00072##

(167) 4-[2-(5-Azido-indazol-1-yl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester, purple solid, UPLC/MS 1.04 min, [M+H].sup.+ 386.

Triazolyl-Acetic Acids

Synthesis of 4-[4-(4-carboxymethyl-[1,2,3]triazol-1-yl)-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester

(168) ##STR00073##

(169) To a suspension of copper(II) sulfate pentahydrate (86 mg, 0.54 mmol) and sodium (2R)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxy-ethanolate hydrate (116 mg, 0.54 mmol in a mixture of tert-butanol (10 ml) and water (10 ml) are added 3-butynoic acid (451 mg, 5.37 mmol) and 4-(4-azido-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (1.78 g, 5.37 mmol). The reaction mixture is stirred at 80 C. for 19 hours. The reaction mixture is allowed to reach room temperature and poured into water. The resultant precipitate is filtered off, washed with water and dried. The residue is triturated with tert-butyl methyl ether to afford 4-[4-(4-carboxymethyl-[1,2,3]triazol-1-yl)-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester as beige powder. A second crop can be obtained by extracting the filtrate with ethyl acetate. HPLC/MS 1.36 min (A), [M+H].sup.+ 416.

(170) .sup.1H NMR (400 MHz, DMSO-d.sub.6, d-TFA) 8.59 (s, 1H), 7.99 (d, J=8.5 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H), 3.84 (s, 2H), 3.35-3.75 (m, 8H), 1.45 (s, 9H).

(171) The following compounds are prepared similarly:

(172) ##STR00074##

(173) [1-(4-Fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-acetic acid, light brown solid; HPLC/MS 1.18 min (B), [M+H].sup.+ 222.

(174) .sup.1H NMR (400 MHz, DMSO-d.sub.6, d-TFA) 8.48 (s, 1H), 7.86 (dd, J=9.0, 4.6 Hz, 2H), 7.27 (t, J=8.7 Hz, 2H), 3.73 (s, 2H).

(175) ##STR00075##

(176) {1-[4-(Morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, beige solid; HPLC/MS 1.01 min (A), [M+H].sup.+ 317.

(177) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.58 (s, 1H), 8.73 (s, 1H), 8.35-7.83 (m, 2H), 7.86-7.52 (m, 2H), 3.80 (s, 2H), 3.48 (d, J=124.8 Hz, 9H).

(178) ##STR00076##

(179) 4-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester, grey solid; HPLC/MS 1.51 min (A), [M+H].sup.+ 388.

(180) .sup.1H NMR (400 MHz, DMSO-d.sub.6, d-TFA) 8.56 (s, 1H), 7.85 (d, J=8.7 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 3.81 (s, 2H), 3.58-3.64 (m, 4H), 3.33-3-39 (m, 4H), 1.46 (s, 9H).

(181) ##STR00077##

(182) {1-[4-(3-Oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, beige solid; HPLC/MS 1.06 min (A), [M+H].sup.+ 303.

(183) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d1) 8.58 (s, 1H), 7.90 (d, J=8.8 Hz, 2H), 7.60 (d, J=8.8 Hz, 2H), 4.21 (s, 2H), 3.99-3.95 (m, 2H), 3.82-3.71 (m, 4H).

(184) ##STR00078##

(185) (1-{4-[4-(3-Methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-acetic acid, beige solid; HPLC/MS 0.86 min (A), [M+H].sup.+ 388.

(186) ##STR00079##

(187) 4-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester, violet solid; HPLC/MS 1.52 min (A), [M+H].sup.+ 402.

(188) ##STR00080##

(189) 4-(3-Azido-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester, beige solid; HPLC/MS 1.38 min (A), [M+H].sup.+ 416.

(190) ##STR00081##

(191) {1-[4-(4-Methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, light yellow powder; UPLC/MS 0.40 min, [M+H].sup.+ 344.

(192) ##STR00082##

(193) {1-[3-(2-Morpholin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, beige solid; HPLC/MS 0.88 min (A), [M+H].sup.+ 333.

(194) ##STR00083##

(195) [1-(1-Methoxycarbonylmethyl-1H-indol-6-yl)-1H-[1,2,3]triazol-4-yl]-acetic acid, light brown solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 315. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.61 (bs, 1H), 8.56 (s, 1H), 8.03 (t, J=1.3 Hz, 1H), 7.63-7.61 (m, 2H), 7.51 (d, J=3.2 Hz, 1H), 6.62 (d, J=3.2 Hz, 1H), 5.24 (s, 2H), 3.78 (s, 2H), 3.71 (s, 3H).

(196) ##STR00084##

(197) {1-[4-((R)-3-Hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, dark brown oil; HPLC/MS 0.95 min (A), [M+H].sup.+ 317.

(198) ##STR00085##

(199) {1-[4-((S)-3-Hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, dark brown oil; HPLC/MS 0.95 min (A), [M+H].sup.+ 317.

(200) ##STR00086##

(201) {1-[4-(2-Oxo-oxazolidin-3-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown powder; HPLC/MS 1.08 min (A), [M+H].sup.+ 289. .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 8.63 (s, 1H), 8.19-7.87 (m, 2H), 7.87-7.70 (m, 2H), 4.50 (m, 2H), 4.16 (m, 2H), 3.80 (s, 2H).

(202) ##STR00087##

(203) {1-[4-(1,1-Dioxo-isothiazolidin-2-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown powder; HPLC/MS 1.11 min (A), [M+H].sup.+ 323.

(204) ##STR00088##

(205) {1-[4-(1,1-Dioxo-isothiazolidin-2-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown powder; HPLC/MS 1.11 min (A), [M+H].sup.+ 323.

(206) ##STR00089##

(207) {1-[4-([1,3]Bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown solid; HPLC/MS 0.84 min (A), [M+H].sup.+ 370.

(208) ##STR00090##

(209) {1-[4-(4-Methyl-5-oxo-[1,4]diazepane-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown solid; UPLC/MS 0.40 min, [M+H].sup.+ 358.

(210) ##STR00091##

(211) 4-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-benzoyl]-piperidine-1-carboxylic acid tert-butyl ester, beige solid; HPLC/MS 1.57 min (A), [M+H].sup.+ 415.

(212) ##STR00092##

(213) {1-[4-(4-Acetoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, beige solid; HPLC/MS 1.17 min (A), [M+H].sup.+ 373.

(214) ##STR00093##

(215) {1-[4-(3-Acetoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, light brown foam; HPLC/MS 1.18 min (A), [M+H].sup.+ 373.

(216) ##STR00094##

(217) 4-{2-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenoxy]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester, brown solid; HPLC/MS 1.10 min (A), [M+H].sup.+ 432.

(218) ##STR00095##

(219) 4-{3-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenoxy]-propyl}-piperazine-1-carboxylic acid tert-butyl ester, brown powder; HPLC/MS 1.12 min (A), [M+H].sup.+446.

(220) ##STR00096##

(221) {1-[4-(3-Methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown foam; HPLC/MS 1.13 min (A), [M+H].sup.+ 345.

(222) ##STR00097##

(223) {1-[3-([1,3]Bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, light brown solid; HPLC/MS 0.84 min (A), [M+H].sup.+ 370.

(224) ##STR00098##

(225) 4-{2-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester, brown oil, which crystallizes slowly; HPLC/MS 1.73 min (A), [M+H].sup.+ 431.

(226) ##STR00099##

(227) {1-[4-((R)-3-Methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, green resin; UPLC/MS 0.73 min, [M+H].sup.+ 331.

(228) ##STR00100##

(229) {1-[4-((S)-3-Methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, green resin; UPLC/MS 0.73 min, [M+H].sup.+ 331.

(230) ##STR00101##

(231) 4-{2-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenyl]-acetyl}-piperazine-1-carboxylic acid tert-butyl ester, beige solid; UPLC/MS 0.92 min [M+H].sup.+ 430.

(232) ##STR00102##

(233) {1-[4-(4-tert-Butoxycarbonylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, beige solid; UPLC/MS 0.90 min [M+H].sup.+ 430.

(234) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.59 (s, 1H), 8.72 (s, 1H), 8.12-7.73 (m, 2H), 7.58 (d, J=8.5 Hz, 2H), 6.88 (d, J=7.7 Hz, 1H), 4.33 (bs, 1H), 3.80 (s, 2H), 3.55 (bs, 2H), 3.14 (bs, 1H), 2.99 (bs, 1H), 1.77 (m, 2H), 1.40 (m, 11H).

(235) ##STR00103##

(236) 4-{2-[5-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-indol-1-yl]-acetyl}-piperazine-1-carboxylic acid tert-butyl ester, beige solid; UPLC/MS 0.92 min, [M+H].sup.+ 469.

(237) ##STR00104##

(238) 4-{2-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenoxy]-acetyl}-piperazine-1-carboxylic acid tert-butyl ester, off-white solid; UPLC/MS 0.92 min, [M+H].sup.+ 446.

(239) ##STR00105##

(240) {1-[4-(2-Dimethylamino-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, dark brown residue; UPLC/MS 0.63 min, [M+H].sup.+ 275.

(241) ##STR00106##

(242) {1-[4-(2-Pyrrolidin-1-yl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, dark brown solid; UPLC/MS 0.65 min, [M+H].sup.+ 301.

(243) ##STR00107##

(244) 4-[4-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester, beige solid; HPLC/MS 1.34 min (A), [M+H].sup.+ 402.

(245) ##STR00108##

(246) 4-{2-[5-(4-Carboxymethyl-[1,2,3]triazol-1-yl)-indazol-1-yl]-acetyl}-piperazine-1-carboxylic acid tert-butyl ester, gray powder; UPLC/MS 0.88 min, [M+H].sup.+ 470.

(247) ##STR00109##

(248) {1-[4-(2-Diethylamino-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown residue; HPLC/MS 0.91 min (A), [M+H].sup.+ 391.

(249) ##STR00110##

(250) {1-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid, brown solid foam; HPLC/MS 0.89 min (A), [M+H].sup.+ 317.

2-Aminobenzaldehydes

Synthesis of 6-amino-2,3-difluoro-benzaldehyde

(251) ##STR00111##

(252) A suspension of 2,3-difluoro-6-aminobenzoic acid (1.00 g, 5.78 mmol) in THF (30 ml) is cooled to 0 C. under nitrogen. Lithium aluminium hydride (1.0 M solution in THF, 8.7 ml, 8.7 mmol) is added dropwise within 30 minutes. The reaction mixture is stirred for 1 hour at 0 C. and for 18 hours at room temperature. The reaction mixture is quenched with water and filtered over kieselguhr. The filtrate is concentrated in vacuo and the residue is partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford (6-amino-2,3-difluoro-phenyl)-methanol as brown solid; HPLC/MS 0.99 min (A), [M+H].sup.+ 160.

(253) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 7.01 (dt, J=10.6, 9.0 Hz, 1H), 6.42 (ddd, J=8.9, 4.1, 1.9 Hz, 1H), 5.13 (s, 2H), 5.07 (t, J=5.5 Hz, 1H), 4.47 (dd, J=5.5, 2.3 Hz, 2H).

(254) To a solution of (6-amino-2,3-difluoro-phenyl)-methanol (565 mg, 3.56 mmol) in dichloromethane (8 ml) is added manganese dioxide (620 mg, 7.13 mmol) and the reaction mixture is stirred at 80 C. for 3 hours. The reaction mixture is allowed to reach room temperature and filtered over kieselguhr. The filtrate is evaporated to afford 6-amino-2,3-difluoro-benzaldehyde as brown solid; HPLC/MS 1.44 min (A), [M+H].sup.+ 158,

(255) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 10.16 (d, J=0.5 Hz, 1H), 7.44 (dt, J=10.5, 9.3 Hz, 1H), 7.34 (s, 2H), 6.57 (dddd, J=9.4, 3.8, 2.0, 0.7 Hz, 1H).

(256) The following compounds are prepared similarly

(257) ##STR00112##

(258) 2-Amino-4,6-difluoro-benzaldehyde, dark red solid; HPLC/MS 1.47 min (A), [M+H].sup.+ 158;

(259) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 10.08 (d, J=0.6 Hz, 1H), 7.73 (s, 2H), 6.42-6.34 (m, 2H).

(260) ##STR00113##

(261) 2-Amino-4,5-difluoro-benzaldehyde, dark brown residue; UPLC/MS 0.65 min, [M+H].sup.+ 158.

(262) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 9.73 (s, 1H), 7.66 (dd, J=11.0, 9.1 Hz, 1H), 7.23 (s, 2H), 6.70 (dd, J=13.2, 6.7 Hz, 1H).

(263) ##STR00114##

(264) 2-Amino-4-trifluoromethyl-benzaldehyde, light orange solid; UPLC/MS 1.05 min, [M+H].sup.+ 190.

(265) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 9.95 (d, J=0.6 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.40 (s, 2H), 7.13 (s, 1H), 6.90 (dd, J=8.1, 1.7 Hz, 1H).

(266) ##STR00115##

(267) 2-Amino-5-fluoro-4-methoxy-benzaldehyde, beige solid; HPLC/MS 1.31 min (A), [M+H].sup.+ 170.

Example 1

6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A1)

(268) ##STR00116##

(269) To a suspension of 3-ethynyl-6-fluoro-1H-quinolin-2-one (46.8 mg, 0.25 mmol), copper(II) sulfate pentahydrate (4.0 mg, 0.03 mmol) and sodium (2R)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxy-ethanolate hydrate (5.4 mg, 0.03 mmol) in DMF (0.5 ml) is added (4-azido-phenyl)-morpholin-4-yl-methanone (65.0 mg, 0.28 mmol). The reaction mixture is heated to 110 C. and stirred at this temperature for 22 hours. The reaction mixture is allowed to reach room temperature. Water is added and the resultant precipitate is filtered off, washed with water and dried. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as off-white powder; HPLC/MS 1.44 min (A), [M+H].sup.+ 420.

(270) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.80 (dd, J=9.3, 2.7 Hz, 1H), 7.65 (d, J=8.5 Hz, 2H), 7.47 (dd, J=9.0, 2.7 Hz, 1H), 7.45-7.39 (m, 1H), 3.75-3.35 (m, 8H).

(271) The following compounds are prepared similarly:

3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A2)

(272) ##STR00117##
beige solid, HPLC/MS 1.27 min (B), [M+H].sup.+ 402; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.11 (d, J=8.2 Hz, 2H), 7.92 (d, J=7.9 Hz, 1H), 7.67 (d, J=8.2 Hz, 2H), 7.57 (t, J=7.7 Hz, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.27 (t, J=7.5 Hz, 1H), 3.75-3.35 (m, 8H).

N,N-dimethyl-4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A3)

(273) ##STR00118##
beige powder; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.58 (s, 1H), 9.28 (s, 1H), 8.87 (s, 1H), 8.59 (s, 1H), 8.38 (d, J=7.8 Hz, 1H), 8.09 (d, J=8.1 Hz, 2H), 7.66 (d, J=8.1 Hz, 2H), 7.34 (t, J=6.3 Hz, 1H), 3.02 (s, 3H), 3.00 (s, 3H).

N,N-dimethyl-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A4)

(274) ##STR00119##
light yellow solid, HPLC/MS 1.28 min (B), [M+H].sup.+ 360; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.22 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.14-8.04 (m, 2H), 7.91 (dd, J=7.9, 1.4 Hz, 1H), 7.68-7.62 (m, 2H), 7.56 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.1 Hz, 1H), 7.26 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 3.02 (s, 4H), 2.97 (s, 3H).

3-[1-(4-dimethylaminomethyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-[1,8]naphthyridin-2-one (A5)

(275) ##STR00120##

(276) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.25 (br s, 1H), 8.83 (br s, 1H), 8.57 (br s, 1H), 8.31 (d, 1H), 8.08 (d, 2H), 7.70 (d, 2H), 7.27 (br s, 1H), 4.34 (s, 2H), 2.74 (s, 6H).

3-(1-phenyl-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one (A6)

(277) ##STR00121##

(278) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.22 (br s, 1H), 8.85 (br s, 1H), 8.57 (brs, 1H), 8.35 (d, 1H), 7.98 (d, 1H), 7.59 (m, 2H), 7.50 (m, 2H), 7.30 (br s, 1H).

3-[1-(4-hydroxymethyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-[1,8]naphthyridin-2-one (A7)

(279) ##STR00122##

(280) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.20 (br s, 1H), 8.81 (br s, 1H), 8.55 (br s, 1H), 8.30 (d, 1H), 7.80 (d, 1H), 5.70 (s, 2H), 7.47 (d, 2H), 7.27 (d, 1H), 4.53 (s, 2H).

N-(2-hydroxy-ethyl)-4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A8)

(281) ##STR00123##

(282) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.31 (br s, 1H), 8.87 (br s, 1H), 8.57 (br s, 1H), 8.36 (d, 1H), 8.13 (dd, 4H), 7.31 (br s, 1H), 3.51 (m, 2H), 3.37 (m, 2H).

N-(2-methoxy-ethyl)-4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A9)

(283) ##STR00124##

(284) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.29 (br s, 1H), 8.83 (br s, 1H), 8.55 (br s, 1H), 8.30 (br s, 1H), 8.05 (br s, 4H), 7.83 (br s, 0.5H), 7.54 (br s, 0.5H), 7.26 (br s, 1H), 3.44 (s, 4H), 3.23 (s, 3H).

3-[1-(4-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A10)

(285) ##STR00125##
yellow-brown solid; HPLC/MS 1.43 min (B), [M+H].sup.+ 319; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.19 (s, 1H), 9.09 (s, 1H), 8.82 (s, 1H), 7.95-7.86 (m, 3H), 7.55 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.25 (ddd, J=8.2, 7.2, 1.1 Hz, 1H), 7.19-7.11 (m, 2H), 3.85 (s, 3H).

4-[4-(6-chloro-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-N,N-dimethyl-benzamide (A11)

(286) ##STR00126##
light brown solid; HPLC/MS 1.31 min (B), [M+H].sup.+ 395; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.78 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.60 (d, J=2.5 Hz, 1H), 8.55 (d, J=2.5 Hz, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.65 (d, J=8.5 Hz, 2H), 3.02 (s, 3H), 2.97 (s, 3H).

3-[1-(4-fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A12)

(287) ##STR00127##
light yellow solid; HPLC/MS 1.44 min (B), [M+H].sup.+ 307; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.19 (s, 1H), 8.83 (s, 1H), 8.12-8.02 (m, 2H), 7.90 (dd, J=7.9, 1.4 Hz, 1H), 7.56 (ddd, J=8.5, 7.2, 1.4 Hz, 1H), 7.51-7.43 (m, 2H), 7.40 (dd, J=8.2, 1.0 Hz, 1H), 7.25 (ddd, J=8.1, 7.2, 1.1 Hz, 1H).

3-[1-(2-fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A13)

(288) ##STR00128##
light yellow solid; HPLC/MS 1.43 min (B), [M+H].sup.+ 307; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.06 (d, J=2.4 Hz, 1H), 8.85 (s, 1H), 7.95 (td, J=7.9, 1.6 Hz, 1H), 7.91 (dd, J=8.0, 1.4 Hz, 1H), 7.68-7.52 (m, 3H), 7.51-7.44 (m, 1H), 7.41 (dd, J=8.2, 1.0 Hz, 1H), 7.26 (ddd, J=8.1, 7.2, 1.1 Hz, 1H).

3-{1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A14)

(289) ##STR00129##
light brown crystals; HPLC/MS 1.13 min (B), [M+H].sup.+ 402; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.17 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 7.91-7.86 (m, 3H), 7.55 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.28-7.22 (m, 1H), 7.19-7.11 (m, 2H), 4.16 (t, J=5.9 Hz, 2H), 2.82 (t, J=5.8 Hz, 2H), 2.56-2.52 (m, 3H), 1.72-1.68 (m, 4H).

N-(1-methyl-piperidin-4-ylmethyl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A15)

(290) ##STR00130##
brown solid; HPLC/MS 1.50 min (B), [M+H].sup.+ 443; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.63 (t, J=5.8 Hz, 1H), 8.13 (d, J=8.7 Hz, 2H), 8.08 (d, J=8.8 Hz, 2H), 7.91 (dd, J=8.0, 1.3 Hz, 1H), 7.56 (ddd, J=8.4, 7.0, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (t, J=7.7 Hz, 1H), 3.19 (t, J=6.3 Hz, 2H), 2.84-2.74 (m, 2H), 2.19 (s, 3H), 2.06-1.73 (m, 2H), 1.75-1.64 (m, 2H), 1.62-1.50 (m, 1H), 1.32-1.13 (m, 2H).

4-[4-(6-methoxy-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-N,N-dimethyl-benzamide (A16)

(291) ##STR00131##
yellow solid; HPLC/MS 1.23 min (B), [M+H].sup.+ 391; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.51 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.36 (d, J=3.0 Hz, 1H), 8.13-8.06 (m, 2H), 8.03 (d, J=3.0 Hz, 1H), 7.71-7.62 (m, 2H), 3.91 (s, 3H), 3.03 (s, 3H), 2.98 (s, 3H).

4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-pyridine-2-carboxylic acid methyl ester (A17)

(292) ##STR00132##
brown solid; HPLC/MS 1.30 min (B), [M+H].sup.+ 348; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.23 (s, 1H), 9.52 (s, 1H), 8.91 (d, J=5.3 Hz, 1H), 8.87 (s, 1H), 8.66 (d, J=2.1 Hz, 1H), 8.38 (dd, J=5.3, 2.2 Hz, 1H), 7.91 (d, J=7.6 Hz, 1H), 7.57 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (t, J=7.4 Hz, 1H), 3.96 (s, 3H).

4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N,N-dimethyl-benzamide (A18)

(293) ##STR00133##
light yellow solid; HPLC/MS 1.31 min (B), [M+H].sup.+ 378; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.14-8.07 (m, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.70-7.63 (m, 2H), 7.52-7.40 (m, 2H), 3.03 (s, 3H), 2.99 (s, 3H).

N-(2-hydroxy-ethyl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A19)

(294) ##STR00134##
light brown crystals; HPLC/MS 1.20 min (B), [M+H].sup.+ 376; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.60 (t, J=5.6 Hz, 1H), 8.14 (d, J=8.8 Hz, 2H), 8.09 (d, J=8.8 Hz, 2H), 7.91 (d, J=7.1 Hz, 0H), 7.56 (ddd, J=8.5, 7.2, 1.5 Hz, 1H), 7.41 (d, J=8.3 Hz, 1H), 7.30-7.21 (m, 1H), 4.73 (t, J=5.6 Hz, 1H), 3.55 (q, J=6.0 Hz, 2H), 3.37 (q, J=6.0 Hz, 2H).

3-[1-(1H-indol-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A20)

(295) ##STR00135##
brown solid; HPLC/MS 1.38 min (B), [M+H].sup.+ 328; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.19 (s, 1H), 11.43 (s, 1H), 9.09 (s, 1H), 8.83 (s, 1H), 8.11 (s, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.70-7.50 (m, 4H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (t, J=7.5 Hz, 1H), 6.60 (s, 1H).

N-(2-morpholin-4-yl-ethyl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A21)

(296) ##STR00136##
light brown powder; HPLC/MS 1.10 min (B), [M+H].sup.+ 445; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.58 (t, J=5.7 Hz, 1H), 8.20-8.11 (m, 2H), 8.11-8.02 (m, 2H), 7.91 (dd, J=8.0, 1.4 Hz, 1H), 7.56 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 0H), 7.26 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 3.60-3.56 (m, 4H), 3.43 (q, J=6.8 Hz, 2H), 2.52-2.48 (m, 2H), 2.47-2.39 (m, 4H).

4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(1-methyl-piperidin-4-ylmethyl)-benzamide (A22)

(297) ##STR00137##
red-brown solid; HPLC/MS 1.12 min (B), [M+H].sup.+ 461; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.31 (s, 1H), 8.85 (s, 1H), 8.62 (t, J=5.8 Hz, 1H), 8.13 (d, J=8.8 Hz, 2H), 8.07 (d, J=8.8 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.53-7.34 (m, 2H), 3.18 (t, J=6.3 Hz, 2H), 2.81-2.71 (m, 2H), 2.15 (s, 3H), 1.93-1.75 (m, 2H), 1.71-1.61 (m, 2H), 1.60-1.48 (m, 1H), 1.26-1.14 (m, 2H).

3-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid methyl ester (A23)

(298) ##STR00138##
light brown solid; HPLC/MS 1.45 min (B), [M+H].sup.+ 347; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.31 (s, 1H), 8.85 (s, 1H), 8.50 (t, J=2.0 Hz, 1H), 8.32 (dd, J=8.1, 1.4 Hz, 1H), 8.08 (dt, J=7.8, 1.3 Hz, 1H), 7.91 (dd, J=8.0, 1.3 Hz, 1H), 7.78 (t, J=8.0 Hz, 1H), 7.56 (ddd, J=8.4, 7.2, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (t, J=7.4 Hz, 1H), 3.94 (s, 3H).

3-[1-(3-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A24)

(299) ##STR00139##
yellow solid; HPLC/MS 1.45 min (B), [M+H].sup.+ 319; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.17 (s, 1H), 9.22 (s, 1H), 8.82 (s, 1H), 7.90 (dd, J=8.1, 1.4 Hz, 1H), 7.60-7.48 (m, 4H), 7.43-7.38 (m, 1H), 7.25 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 7.08 (ddd, J=8.1, 2.4, 1.2 Hz, 1H), 3.89 (s, 3H).

3-{1-[4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A25)

(300) ##STR00140##
white solid; HPLC/MS 1.27 min (B), [M+H].sup.+ 388; .sup.1H NMR (400 MHz, DMSO-d6) 12.20 (s, 1H), 9.23 (s, 1H), 8.85 (s, 1H), 8.11-8.03 (m, 2H), 7.95-7.88 (m, 1H), 7.74-7.65 (m, 2H), 7.57 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.42 (d, J=8.2 Hz, 1H), 7.32-7.22 (m, 1H), 4.27 (s, 2H), 4.01-4.05 (m, 2H), 3.87-3.82 (m, 2H).

3-{1-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A26)

(301) ##STR00141##
beige solid; HPLC/MS 1.08 min (B), [M+H].sup.+ 418; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.17 (s, 1H), 9.09 (s, 1H), 8.82 (s, 1H), 7.92-7.87 (m, 3H), 7.56 (ddd, J=8.4, 7.2, 1.4 Hz, 1H), 7.45-7.38 (m, 1H), 7.32-7.24 (m, 1H), 7.22-7.13 (m, 2H), 4.20 (t, J=5.7 Hz, 2H), 3.65-3.57 (m, 4H), 2.75 (t, J=5.7 Hz, 2H), 2.52-2.49 (m, 4H).

3-(1-phenyl-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A27)

(302) ##STR00142##
yellow crystals; HPLC/MS 1.43 min (B), [M+H].sup.+ 289; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.19 (s, 1H), 9.19 (s, 1H), 8.83 (s, 1H), 8.03-7.97 (m, 2H), 7.90 (dd, J=7.9, 1.3 Hz, 1H), 7.67-7.59 (m, 2H), 7.59-7.49 (m, 2H), 7.43-7.39 (m, 1H), 7.26 (ddd, J=8.1, 7.2, 1.1 Hz, 1H).

3-[1-(3H-benzimidazol-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A28)

(303) ##STR00143##
beige solid; HPLC/MS 1.09 min (B), [M+H].sup.+ 329; .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.67 (s, 1H), 9.32 (s, 1H), 8.82 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 8.21 (dd, J=8.9, 2.0 Hz, 1H), 8.03 (d, J=8.9 Hz, 1H), 7.82 (dd, J=8.0, 1.3 Hz, 1H), 7.49 (ddd, J=8.4, 7.0, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.27-7.12 (m, 1H).

3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,7]naphthyridin-2-one (A29)

(304) ##STR00144##
beige solid; HPLC/MS 1.11 min (B), [M+H].sup.+ 403; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.47 (s, 1H), 9.37 (s, 1H), 8.88 (s, 1H), 8.85 (bs, 1H), 8.48 (bs, 1H), 8.17-8.06 (m, 2H), 7.91 (b, 1H), 7.75-7.60 (m, 2H), 3.80-3.35 (m, 8H).

7-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A30)

(305) ##STR00145##
brown solid; HPLC/MS 1.24 min (B), [M+H].sup.+ 417; .sup.1H NMR (500 MHz, DMSO-d.sub.6) b 12.46 (s, 1H), 9.24 (s, 1H), 8.82 (s, 1H), 8.24 (d, J=7.9 Hz, 1H), 8.13-8.05 (m, 2H), 7.96 (s, 1H), 7.71-7.61 (m, 2H), 7.22 (d, J=7.9 Hz, 1H), 3.64 (bs, 4H), 2.51 (bs, 4H), 1.25 (s, 3H).

6-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A31)

(306) ##STR00146##
brown solid, HPLC/MS 1.24 min (B), [M+H].sup.+ 421; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.73 (s, 1H), 9.31 (s, 1H), 8.88 (s, 1H), 8.63 (d, J=2.9 Hz, 1H), 8.36 (dd, J=8.7, 3.0 Hz, 1H), 8.17-8.04 (m, 2H), 7.77-7.55 (m, 2H), 3.75-3.40 (m, 8H).

3-{1-[3-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A32)

(307) ##STR00147##
beige powder, HPLC/MS 1.42 min (A), [M+H].sup.+ 406; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.32 (s, 1H), 8.84 (s, 1H), 8.12 (dd, J=11.0, 2.4 Hz, 1H), 8.04-7.95 (m, 1H), 7.90 (dd, J=8.0, 1.4 Hz, 1H), 7.73 (t, J=8.4 Hz, 1H), 7.56 (ddd, J=8.4, 7.2, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (td, J=7.6, 1.1 Hz, 1H), 4.28 (s, 2H), 4.05-4.00 (m, 2H), 3.81-3.65 (m, 2H).

6-fluoro-3-{1-[3-fluoro-4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A33)

(308) ##STR00148##
beige powder, HPLC/MS 1.47 min (A), [M+H].sup.+ 424; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.34 (s, 1H), 8.85 (s, 1H), 8.13 (dd, J=11.0, 2.4 Hz, 1H), 8.01-7.95 (m, 1H), 7.80 (dd, J=9.3, 2.7 Hz, 1H), 7.73 (t, J=8.4 Hz, 1H), 7.52-7.38 (m, 2H), 4.28 (s, 2H), 4.08-3.99 (m, 2H), 3.90-3.66 (m, 2H).

3-{1-[6-(3-oxo-morpholin-4-yl)-pyridin-3-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A34)

(309) ##STR00149##
beige solid, HPLC/MS 1.41 min (A), [M+H].sup.+ 389; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.32 (s, 1H), 9.11 (d, J=2.7 Hz, 1H), 8.86 (s, 1H), 8.50 (dd, J=9.1, 2.8 Hz, 1H), 8.31 (d, J=9.0 Hz, 1H), 7.95-7.90 (m, 1H), 7.57 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.42 (d, J=8.2 Hz, 1H), 7.31-7.24 (m, 1H), 4.33 (s, 2H), 4.05 (s, 4H).

3-{1-[2-methyl-4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A35)

(310) ##STR00150##
beige solid, HPLC/MS 1.40 min (A), [M+H].sup.+ 416; .sup.1H NMR (300 MHz, DMSO-d.sub.6) b 12.16 (s, 1H), 8.92 (s, 1H), 8.84 (s, 1H), 7.89 (dd, J=8.0, 1.4 Hz, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.59-7.52 (m, 2H), 7.46 (dd, J=8.1, 1.9 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.26 (ddd, J=8.1, 7.2, 1.2 Hz, 1H), 3.75-3.35 (m, 8H), 2.26 (s, 3H).

3-{1-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A36)

(311) ##STR00151##
light brown solid, HPLC/MS 1.47 min (A), [M+H].sup.+ 347; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.15 (s, 1H), 8.82 (s, 1H), 7.93-7.88 (m, 3H), 7.73-7.66 (m, 2H), 7.55 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.41 (dd, J=8.2, 1.0 Hz, 1H), 7.25 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 5.17 (s, 1H), 1.49 (s, 6H).

3-{1-[3-fluoro-4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A37)

(312) ##STR00152##
yellow solid, HPLC/MS 1.45 min (A), [M+H].sup.+ 420; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.22 (s, 1H), 9.35 (s, 1H), 8.86 (s, 1H), 8.12 (dd, J=10.4, 2.0 Hz, 1H), 8.02 (dd, J=8.3, 2.0 Hz, 1H), 7.92 (dd, J=8.1, 1.4 Hz, 1H), 7.68 (dd, J=8.3, 7.4 Hz, 1H), 7.58 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.42 (d, J=8.2 Hz, 1H), 7.27 (ddd, J=8.1, 7.1, 1.1 Hz, 1H), 3.69 (s, 4H), 3.61-3.56 (m, 2H), 3.35-3-30 (m, 2H).

3-[1-(3,4,5-trimethoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A38)

(313) ##STR00153##
beige solid, HPLC/MS 1.57 min (A), [M+H].sup.+ 379; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.27 (s, 1H), 8.83 (s, 1H), 7.91 (dd, J=8.0, 1.4 Hz, 1H), 7.56 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.42 (d, J=7.7 Hz, 1H), 7.31 (s, 2H), 7.26 (ddd, J=8.2, 7.2, 1.1 Hz, 1H), 3.93 (s, 6H), 3.75 (s, 3H).

2-fluoro-N-methyl-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A39)

(314) ##STR00154##
beige solid, HPLC/MS 1.42 min (A), [M+H].sup.+ 364; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.23 (s, 1H), 9.36 (s, 1H), 8.86 (s, 1H), 8.42-8.35 (m, 1H), 8.11 (dd, J=11.3, 2.1 Hz, 1H), 8.00 (dd, J=8.4, 2.1 Hz, 1H), 7.92 (dd, J=8.0, 1.3 Hz, 1H), 7.86 (t, J=8.1 Hz, 1H), 7.57 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.42 (d, J=8.2 Hz, 1H), 7.33-7.23 (m, 1H), 2.83 (d, J=4.6 Hz, 3H).

3-{1-[3-methyl-4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A40)

(315) ##STR00155##
yellow powder, HPLC/MS 1.43 min (A), [M+H].sup.+ 416; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.25 (s, 1H), 8.85 (s, 1H), 8.00 (d, J=2.5 Hz, 1H), 7.93-7.89 (m, 2H), 7.57 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.46-7.40 (m, 2H), 7.27 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 3.70 (s, 4H), 3.55 (s, 2H), 3.21 (s, 2H), 2.37 (s, 3H).

Example 2

3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridin-2-one (A41)

(316) ##STR00156##

(317) To a solution of 4-Amino-pyridine-3-carbaldehyde (61.1 mg, 0.50 mmol), {1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid (158 mg, 0.50 mmol) and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluorophosphate (HATU; 380 mg, 1.0 mmol) in DMF (1.3 ml) is added N-ethyldiisopropylamine (257 l, 1.5 mmol) and the reaction mixture is stirred for 17 hours at room temperature. Water is added to the reaction mixture. The resultant precipitate is filtered off, dried and chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridin-2-one as beige solid; HPLC/MS 1.02 min (A), [M+H].sup.+ 403.

(318) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.46 (s, 1H), 9.28 (s, 1H), 9.10 (s, 1H), 8.93 (s, 1H), 8.52 (d, J=5.7 Hz, 1H), 8.11 (d, J=8.6 Hz, 1H), 7.67 (d, J=8.6 Hz, 2H), 7.30 (d, J=5.7 Hz, 1H), 3.35-3.75 (m, 8H).

(319) The following compounds are prepared similarly:

N,N-dimethyl-4-[4-(2-oxo-1,2-dihydro-[1,7]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A42)

(320) ##STR00157##
brown powder, MS-ESI: [M+H].sup.+ 361.

3-(1-phenyl-1H-pyrazol-4-yl)-1H-[1,8]naphthyridin-2-one (A43)

(321) ##STR00158##
brown powder, HPLC/MS 1.34 min (B), [M+H].sup.+ 289; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.40 (s, 1H), 9.12 (s, 1H), 8.51 (dd, J=4.7, 1.7 Hz, 1H), 8.44 (s, 1H), 8.42 (s, 1H), 8.11 (dd, J=7.8, 1.8 Hz, 1H), 7.96-7.82 (m, 2H), 7.63-7.50 (m, 2H), 7.40-7.33 (m, 1H), 7.29 (dd, J=7.7, 4.7 Hz, 1H).

3-(1-phenyl-1H-pyrazol-4-yl)-1H-[1,7]naphthyridin-2-one (A44)

(322) ##STR00159##
brown powder, HPLC/MS 1.21 min (B), [M+H].sup.+ 289; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.19 (s, 1H), 8.69 (s, 1H), 8.50 (s, 1H), 8.44 (s, 1H), 8.35 (d, J=5.2 Hz, 1H), 7.97-7.80 (m, 2H), 7.60 (d, J=5.0 Hz, 1H), 7.58-7.50 (m, 2H), 7.42-7.26 (m, 1H).

3-[1-(4-fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-[1,6]naphthyridin-2-one (A45)

(323) ##STR00160##
brown solid, HPLC/MS 1.09 min (B), [M+H].sup.+ 308; .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.44 (s, 1H), 9.17 (s, 1H), 9.07 (s, 1H), 8.61 (d, J=6.7 Hz, 1H), 8.02-7.92 (m, 2H), 7.70 (d, J=6.7 Hz, 1H), 7.31 (t, J=8.7 Hz, 2H).

3-(1-phenyl-1H-pyrazol-4-yl)-1H-[1,6]naphthyridin-2-one (A46)

(324) ##STR00161##
beige powder, HPLC/MS 1.06 min (B), [M+H].sup.+ 289; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.11 (s, 1H), 8.86 (d, J=0.7 Hz, 1H), 8.50 (s, 1H), 8.46 (d, J=5.5 Hz, 2H), 7.91-7.85 (m, 2H), 7.57-7.50 (m, 2H), 7.39-7.32 (m, 1H), 7.25 (d, J=5.7 Hz, 1H).

3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one A47)

(325) ##STR00162##
beige solid, HPLC/MS 1.27 min (A), [M+H].sup.+ 403; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.58 (s, 1H), 9.28 (s, 1H), 8.87 (s, 1H), 8.59 (dd, J=4.7, 1.8 Hz, 1H), 8.38 (dd, J=7.8, 1.8 Hz, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.78-7.60 (m, 2H), 7.34 (dd, J=7.8, 4.7 Hz, 1H), 3.76-3.36 (m, 8H).

5-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A48)

(326) ##STR00163##
beige solid, HPLC/MS 1.45 min (A), [M+H].sup.+ 420; 1 H NMR (400 MHz, DMSO-d.sub.6) 12.44 (s, 1H), 9.28 (s, 1H), 8.82 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H), 7.57 (td, J=8.2, 6.0 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.18-7.05 (m, 1H), 3.75-3.35 (m, 8H).

3-{1-[4-(3-oxo-morpholin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,7]naphthyridin-2-one (A49)

(327) ##STR00164##
beige solid, HPLC/MS 1.45 min (A), [M+H].sup.+ 420; 1 H NMR (400 MHz, DMSO-d.sub.6) 12.44 (s, 1H), 9.28 (s, 1H), 8.82 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H), 7.57 (td, J=8.2, 6.0 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.18-7.05 (m, 1H), 3.75-3.35 (m, 8H).

Example 3

3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one

(328) ##STR00165##

(329) A suspension of 4-{4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (43 mg, 0.09 mmol; synthesized in analogy to example 1) in a 4 M solution of hydrochloric acid in dioxane (0.5 ml) is heated to 80 C. and stirred at this temperature in a closed reaction vial for 1 hour. The reaction mixture is allowed to reach room temperature. The solids are filtered off and washed with THF. The residue is treated with aqueous sodium carbonate solution. The solid is filtered off, washed with water and ethanol and dried under vacuum to afford 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as light grey powder; HPLC/MS 1.07 min (B), [M+H].sup.+ 401.

(330) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.21 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.0 Hz, 2H), 7.90 (d, J=7.9 Hz, 1H), 7.61 (d, J=8.0 Hz, 2H), 7.56 (t, J=7.6 Hz, 1H), 7.41 (d, J=8.3 Hz, 1H), 7.26 (t, J=7.5 Hz, 1H), 3.65-3.35 (m, 4H), 2.8-2.6 (m, 4H).

(331) The following compounds are prepared similarly:

4-[4-(2-oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-N-piperidin-4-yl-benzamide (A51)

(332) ##STR00166##
trifluoroacetate: .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.62 (br s, 1H), 9.33 (br s, 1H), 8.87 (br s, 1H), 8.64-8.58 (m, 3H), 8.34 (m, 2H), 8.17 (d, 2H), 8.10 (d, 2H), 7.34 (br s, 1H), 4.09 (br s, 1H), 3.06 (m, 2H), 2.02 (d, 2H), 1.78-1.70 (m, 2H),

3-[1-(4-piperazin-1-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A52)

(333) ##STR00167##
light brown crystals; HPLC/MS 1.10 min (B), [M+H].sup.+ 373; .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.11 (s, 1H), 8.83 (s, 1H), 7.91-7.86 (m, 3H), 7.55 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.45 (d, J=8.2 Hz, 1H), 7.28-7.19 (m, 3H), 3.53-3.49 (m, 4H), 3.34-3.30 (m, 4H).

6-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A53)

(334) ##STR00168##
hydrochloride: light brown solid; HPLC/MS 1.07 min (B), [M+H].sup.+ 419; 1 H NMR (500 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.31 (s, 1H), 9.22 (bs, 2H), 8.86 (s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.72 (d, J=8.6 Hz, 2H), 7.51-7.38 (m, 2H), 3.72 (bs, 4H), 3.20 (bs, 4H).

3-[1-(2-piperazin-1-yl-pyrimidin-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A54)

(335) ##STR00169##
hydrochloride: brown solid; HPLC/MS 1.14 min (A), [M+H].sup.+ 375; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.18 (m, 3H), 8.99 (s, 2H), 8.82 (s, 1H), 7.90 (d, J=7.8 Hz, 1H), 7.56 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.30-7.21 (m, 1H), 4.06 (t, J=5.3 Hz, 4H), 3.26-3.19 (m, 4H).

3-[1-(4-[1,4]diazepan-1-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A55)

(336) ##STR00170##
brown solid; HPLC/MS 1.22 min (A), [M+H].sup.+ 387; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.13 (s, 1H), 8.95 (s, 1H), 8.79 (s, 1H), 7.88 (dd, J=8.0, 1.4 Hz, 1H), 7.68 (d, J=9.1 Hz, 2H), 7.54 (ddd, J=8.5, 7.2, 1.4 Hz, 1H), 7.40 (dd, J=8.2, 1.0 Hz, 1H), 7.24 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 6.85 (d, J=9.1 Hz, 2H), 3.60 (t, J=6.1 Hz, 2H), 3.52 (t, J=5.3 Hz, 2H), 2.95-2.85 (m, 2H), 2.70-2.61 (m, 2H), 1.80 (p, J=6.1 Hz, 2H).

Example 4

6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A56)

(337) ##STR00171##

(338) To a solution of 4-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (52 mg, 0.10 mmol; prepared in analogy to example 1) in formic acid (0.5 ml) is added formaldehyde (37% aqueous solution, 22.5 l, 0.30 mmol) and the reaction mixture is stirred for 1 hour at 80 C. The reaction mixture is evaporated and the residue is purified by preparative HPLC to afford 6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as white powder; HPLC/MS 1.07 min (B), [M+H].sup.+ 433.

(339) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.66-7.60 (m, 2H), 7.50-7.40 (m, 2H), 3.78-3.50 (m, 4H), 2.47-2.26 (m, 4H), 2.22 (s, 3H).

(340) The following compounds are prepared similarly:

3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A57)

(341) ##STR00172##
white powder; HPLC/MS 1.08 min (B), [M+H].sup.+ 415; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.89 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.28-8.07 (m, 2H), 7.90 (d, J=7.3 Hz, 1H), 7.72-7.68 (m, 2H), 7.56 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 3.7-3.0 (m, 8H), 2.81 (s, 3H).

N-(1-Methyl-piperidin-4-yl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A58)

(342) ##STR00173##
formate: white solid; HPLC/MS 1.10 min (B), [M+H].sup.+ 429; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.22 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.43 (d, J=7.7 Hz, 1H), 8.20 (s, 2H), 8.14 (d, J=8.7 Hz, 2H), 8.11-8.07 (m, 2H), 7.92 (dd, J=8.0, 1.3 Hz, 1H), 7.57 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.27 (td, J=7.6, 1.1 Hz, 1H), 3.79 (tdt, J=11.7, 8.3, 4.4 Hz, 1H), 2.87-2.78 (m, 2H), 2.21 (s, 3H), 2.02 (td, J=11.8, 2.5 Hz, 2H), 1.88-1.77 (m, 2H), 1.63 (qd, J=12.1, 3.8 Hz, 2H).

N-methyl-N-(1-methyl-piperidin-4-yl)-4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A59)

(343) ##STR00174##
beige solid; HPLC/MS 1.09 min (B), [M+H].sup.+ 443; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.12-8.04 (m, 2H), 7.90 (dd, J=8.0, 1.4 Hz, 1H), 7.60 (d, J=8.2 Hz, 2H), 7.56 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.32-7.22 (m, 1H), 4.4-4.2 (m, 1H), 2.85 (s, 6H), 2.25-2.05 (m, 4H), 1.90-1.78 (m, 2H), 1.67-1.58 (m, 2H).

3-{1-[4-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A60)

(344) ##STR00175##
white solid; HPLC/MS 1.12 min (B), [M+H].sup.+ 416; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.16 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 7.91-7.84 (m, 3H), 7.55 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.40 (d, J=8.2 Hz, 1H), 7.33-7.22 (m, 1H), 7.19-7.07 (m, 2H), 3.92 (d, J=6.0 Hz, 2H), 2.82-2.76 (m, 2H), 2.17 (s, 3H), 1.92-1.84 (m, 2H), 1.81-1.70 (m, 3H), 1.45-1.26 (m, 2H).

3-{1-[4-(4-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A61)

(345) ##STR00176##
light yellow solid; HPLC/MS 1.06 min (B), [M+H].sup.+ 443; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.19 (s, 1H), 9.25 (s, 1H), 8.84 (s, 1H), 8.11-8.03 (m, 2H), 7.90 (dd, J=8.0, 1.4 Hz, 1H), 7.66-7.60 (m, 2H), 7.56 (ddd, J=8.5, 7.2, 1.4 Hz, 1H), 7.41 (d, J=8.3 Hz, 1H), 7.26 (ddd, J=8.1, 7.1, 1.1 Hz, 1H), 4.45 (bs, 1H), 3.64 (bs, 1H), 3.06 (bs, 1H), 2.89 (bs, 1H), 2.36 (tt, J=11.0, 3.6 Hz, 1H), 2.19 (s, 6H), 1.90-1.65 (m, 2H), 1.45-1.30 (m, 2H).

3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,6]naphthyridin-2-one (A62)

(346) ##STR00177##
white solid; HPLC/MS 0.87 min (A), [M+H].sup.+ 416; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.48 (s, 1H), 9.27 (s, 1H), 9.09 (bs, 1H), 8.92 (s, 1H), 8.52 (bs, 1H), 8.15-8.04 (m, 2H), 7.70-7.56 (m, 2H), 7.29 (d, J=5.6 Hz, 1H), 3.72-3.54 (m, 4H), 2.44-2.26 (m, 4H), 2.21 (s, 3H).

3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,7]naphthyridin-2-one (A63)

(347) ##STR00178##
light brown solid; HPLC/MS 0.98 min (A), [M+H].sup.+ 416; .sup.1H NMR (300 MHz, DMSO-d.sub.6) 12.47 (bs, 1H), 9.34 (s, 1H), 8.86 (s, 1H), 8.75 (s, 1H), 8.39 (d, J=5.2 Hz, 1H), 8.10 (d, J=8.6 Hz, 1H), 7.86 (d, J=5.2 Hz, 1H), 7.63 (d, J=8.6 Hz, 1H), 3.5-3.2 (m, 4H), 2.42-2.29 (m, 4H), 2.21 (s, 3H).

3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A64)

(348) ##STR00179##
beige solid; HPLC/MS 1.06 min (A), [M+H].sup.+ 416; .sup.1H NMR (400 MHz, DMSO-d.sub.6) b 12.59 (s, 1H), 9.28 (s, 1H), 8.87 (s, 1H), 8.59 (dd, J=4.7, 1.8 Hz, 1H), 8.38 (dd, J=7.9, 1.8 Hz, 1H), 8.10 (d, J=8.5 Hz, 1H), 7.64 (d, J=8.5 Hz, 1H), 7.34 (dd, J=7.7, 4.7 Hz, 1H), 3.7-3.3 (m, 4H), 2.45-2.25 (m, 4H), 2.23 (s, 3H).

7-methyl-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A65)

(349) ##STR00180##
light yellow solid; HPLC/MS 1.11 min (A), [M+H].sup.+ 430.

3-{1-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A66)

(350) ##STR00181##
beige solid; HPLC/MS 1.16 min (A), [M+H].sup.+ 389; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.17 (s, 1H), 9.12 (s, 1H), 8.88 (s, 2H), 8.81 (s, 1H), 7.89 (dd, J=8.1, 1.3 Hz, 1H), 7.55 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.40 (d, J=8.3 Hz, 1H), 7.28-7.23 (m, 1H), 3.88-3.77 (m, 4H), 2.45-2.35 (m, 4H), 2.24 (s, 3H).

6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A67)

(351) ##STR00182##
white solid; HPLC/MS 1.09 min (A), [M+H].sup.+ 434; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.73 (s, 1H), 9.30 (s, 1H), 8.87 (s, 1H), 8.61 (d, J=2.9 Hz, 1H), 8.35 (dd, J=8.7, 2.9 Hz, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.63 (d, J=8.5 Hz, 2H), 3.74-3.30 (m, 4H), 2.44-2.26 (m, 4H), 2.21 (s, 3H).

3-{1-[4-(4-methyl-2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A68)

(352) ##STR00183##
white solid; HPLC/MS 1.19 min (A), [M+H].sup.+ 401; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.21 (s, 1H), 8.83 (s, 1H), 8.02 (d, J=8.9 Hz, 2H), 7.90 (dd, J=8.1, 1.4 Hz, 1H), 7.67-7.58 (m, 2H), 7.55 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.25 (td, J=7.5, 1.1 Hz, 1H), 3.76-3.72 (m, 2H), 3.16 (s, 2H), 2.84-2.70 (m, 2H), 2.31 (s, 3H).

3-{1-[4-(4-methyl-[1,4]diazepan-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A69)

(353) ##STR00184##
beige solid; HPLC/MS 1.23 min (A), [M+H].sup.+ 401; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.15 (s, 1H), 8.97 (s, 1H), 8.77 (s, 1H), 7.86 (dd, J=8.0, 1.4 Hz, 1H), 7.68 (d, J=9.1 Hz, 2H), 7.52 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.22 (ddd, J=8.1, 7.1, 1.2 Hz, 1H), 6.85 (d, J=9.2 Hz, 2H), 3.65-3.55 (m, 2H), 3.50 (t, J=6.2 Hz, 2H), 2.70-2.58 (m, 2H), 2.49-2.45 (m, 2H), 2.27 (s, 3H), 1.92 (p, J=5.9 Hz, 2H).

6-fluoro-3-{1-[4-(4-methyl-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A70)

(354) ##STR00185##
off-white solid; HPLC/MS 1.24 min (A), [M+H].sup.+ 405; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.23 (s, 1H), 9.05 (s, 1H), 8.81 (s, 1H), 7.92-7.66 (m, 3H), 7.49-7.37 (m, 2H), 7.11 (d, J=9.2 Hz, 2H), 3.24 (t, J=5.0 Hz, 4H), 2.47 (t, J=5.0 Hz, 4H), 2.24 (s, 3H).

6-fluoro-3-{1-[4-(4-methyl-2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A71)

(355) ##STR00186##
beige solid; HPLC/MS 1.19 min (A), [M+H].sup.+ 419; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.23 (s, 1H), 8.84 (s, 1H), 8.03 (d, J=8.9 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.60 (d, J=8.9 Hz, 2H), 7.48-7.40 (m, 2H), 3.74 (t, J=5.3 Hz, 2H), 3.16 (s, 2H), 2.76 (t, J=5.4 Hz, 2H), 2.31 (s, 3H).

3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A72)

(356) ##STR00187##
white solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 431; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.16 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 7.92-7.85 (m, 3H), 7.55 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.25 (ddd, J=8.1, 7.1, 1.1 Hz, 1H), 7.20-7.12 (m, 2H), 4.16 (t, J=5.8 Hz, 2H), 2.72 (t, J=5.8 Hz, 2H), 2.54-2.50 (m, 4H), 2.33 (bs, 4H), 2.15 (s, 3H).

Example 5

3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A73) and 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A74)

a) synthesis of 4-{4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester

(357) ##STR00188##

b) Suzuki reactionsynthesis of 4-{4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-pyrazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester

(358) ##STR00189##

3-(1-phenyl-1H-pyrazol-4-yl)-1H-quinolin-2-one (A75) is prepared similarly

(359) ##STR00190##
white powder; HPLC/MS 1.45 min (B), [M+H].sup.+ 288; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.00 (s, 1H), 9.11 (s, 1H), 8.45 (s, 1H), 8.42 (s, 1H), 7.91-7.85 (m, 2H), 7.68 (dd, J=7.9, 1.3 Hz, 1H), 7.56-7.51 (m, 2H), 7.49 (ddd, J=8.4, 7.1, 1.5 Hz, 1H), 7.39-7.31 (m, 2H), 7.22 (ddd, J=8.2, 7.2, 1.2 Hz, 1H).

c) synthesis of 3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A73) and 3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A74)

(360) ##STR00191##
A73: white solid; HPLC/MS 1.06 min (B), [M+H].sup.+ 400; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.03 (s, 1H), 9.18 (s, 1H), 8.50 (s, 1H), 8.44 (s, 1H), 8.18 (s, 1H), 7.99-7.93 (m, 2H), 7.70 (dd, J=8.0, 1.3 Hz, 1H), 7.59-7.54 (m, 2H), 7.51 (ddd, J=8.5, 7.2, 1.5 Hz, 1H), 7.38 (d, J=8.2 Hz, 1H), 7.24 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 3.46 (bs, 4H), 2.78 (bs, 4H).
A74 formate: white solid; HPLC/MS 1.17 min (A), [M+H].sup.+ 400; .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.05 (s, 1H), 9.19 (s, 1H), 8.50 (s, 1H), 8.45 (s, 1H), 8.00-7.93 (m, 2H), 7.69 (dd, J=8.0, 1.3 Hz, 1H), 7.60-7.53 (m, 2H), 7.53-7.48 (m, 1H), 7.37 (d, J=8.1 Hz, 1H), 7.23 (t, J=7.4 Hz, 1H), 3.65 (bs, 2H), 3.40 (bs, 2H), 2.34 (bs, 4H), 2.21 (s, 3H).

Example 6

3-{1-[3-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A76)

a) synthesis of 3-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid

(361) ##STR00192##

(362) To a suspension of 3-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid methyl ester (346 mg, 1.0 mmol) in THF/water (1:1, 4 ml) is added lithium hydroxide (211 mg, 8.8 mmol) and the reaction mixture is stirred for 2 hours at 65 C. After cooling to room temperature, 1 N aqueous hydrochloric acid is added until a pH of 1 is reached. The resultant precipitate is filtered off, washed with water and dried under vacuum to afford 3-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid as olive green solid; HPLC/MS 1.31 min (B), [M+H].sup.+ 333; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 13.40 (s, 1H), 12.22 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.47 (d, J=1.9 Hz, 1H), 8.31-8.24 (m, 2H), 8.06 (dt, J=7.6, 1.3 Hz, 1H), 7.91 (d, J=7.5 Hz, 1H), 7.76 (t, J=7.9 Hz, 1H), 7.56 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.29-7.23 (m, 1H).

4-[4-(2-Oxo-1,2-dihydro-[1,8]naphthyridin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid (A77) is prepared similarly

(363) ##STR00193##

(364) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.31 (d, 1H), 8.86 (br s, 1H), 8.54-8.53 (m, 3H), 8.34 (dd, 2H), 8.16 (m, 4H), 7.30 (m, 1H).

b) synthesis of A76

(365) ##STR00194##

(366) To a solution of 3-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid (99.7 mg, 0.30 mmol), morpholine (26 l, 0.39 mmol) and [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (HATU; 114 mg, 0.30 mmol) in DMF (0.6 ml) is added ethyl-diisopropyl-amine (153 l, 0.90 mmol) and the reaction mixture is stirred for 16 hours at room temperature. The reaction mixture is treated with saturated aqueous Na.sub.2CO.sub.3 solution and water. The resultant precipitate is filtered off, washed with water and dried under vacuum to afford 3-{1-[3-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as off-white solid; HPLC/MS 1.28 min (B), [M+H].sup.+ 402.

(367) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.11 (ddd, J=8.1, 2.3, 1.0 Hz, 1H), 8.05 (t, J=1.9 Hz, 1H), 7.90 (dd, J=8.0, 1.3 Hz, 1H), 7.69 (t, J=7.9 Hz, 1H), 7.59-7.50 (m, 2H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (td, J=7.5, 1.1 Hz, 1H), 3.74-3.34 (m, 8H).

Example 7

3-{1-[3-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A78) and 3-{1-[3-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A79)

(368) ##STR00195##

(369) A78: light yellow solid; HPLC/MS 1.15 min (A), [M+H].sup.+ 401.

(370) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.27 (s, 1H), 8.83 (s, 1H), 8.12-8.05 (m, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.89 (dd, J=8.0, 1.4 Hz, 1H), 7.68 (t, J=7.9 Hz, 1H), 7.55 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.49 (dt, J=7.7, 1.3 Hz, 1H), 7.40 (d, J=8.2 Hz, 1H), 7.32-7.21 (m, 1H), 3.58 (bs, 2H), 3.29 (bs, 2H), 2.81-2.62 (m, 4H).

(371) A79: white solid; HPLC/MS 1.15 min (A), [M+H].sup.+ 415.

(372) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.19 (s, 1H), 9.27 (s, 1H), 8.83 (s, 1H), 8.10 (ddd, J=8.1, 2.3, 1.0 Hz, 1H), 8.02 (t, J=1.8 Hz, 1H), 7.90 (dd, J=8.0, 1.4 Hz, 1H), 7.68 (t, J=7.9 Hz, 1H), 7.56 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.50 (dt, J=7.7, 1.2 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.25 (ddd, J=8.2, 7.2, 1.1 Hz, 1H), 3.66 (bs, 2H), 3.38 (bs, 2H), 2.45-2.25 (m, 4), 2.21 (s, 3H).

Example 8

3-[1-(4-isopropenyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A80) and 3-{1-[4-(1-methanesulfonyl-1-methyl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A81)

(373) ##STR00196##

(374) To a solution of 3-{1-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (97.0 mg, 0.28 mmol) in dichloromethane (0.5 ml) is added sodium methanesulfinate (62.6 mg, 0.61 mmol), followed by a solution of trifluoroacetic acid (176 l, 2.28 mmol) in dichloromethane (0.4 ml). The reaction mixture is stirred for 19 hours at room temperature. The reaction mixture is diluted with dichloromethane and water. The organic phase is separated and the organic phase is extracted twice with water. The combined organic phases are dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford two products:

(375) A80: 3-[1-(4-isopropenyl-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one, white crystals; HPLC/MS 1.80 min (A), [M+H].sup.+ 329;

(376) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.20 (s, 1H), 8.83 (s, 1H), 8.03-7.95 (m, 2H), 7.90 (dd, J=8.0, 1.3 Hz, 1H), 7.78-7.70 (m, 2H), 7.56 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.1 Hz, 1H), 7.25 (ddd, J=8.1, 7.1, 1.1 Hz, 1H), 5.56 (s, 1H), 5.23-5.20 (m, 1H), 2.18 (d, J=1.1 Hz, 3H).

(377) A81: 3-{1-[4-(1-methanesulfonyl-1-methyl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one, white platelets; HPLC/MS 1.50 min (A), [M+H].sup.+ 409;

(378) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.24 (s, 1H), 8.83 (s, 1H), 8.12-8.02 (m, 2H), 7.90 (dd, J=8.1, 1.4 Hz, 1H), 7.87-7.81 (m, 2H), 7.56 (ddd, J=8.4, 7.1, 1.4 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.26 (ddd, J=8.1, 7.2, 1.1 Hz, 1H), 2.77 (s, 3H), 1.83 (s, 6H).

Example 9

7-chloro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A82)

(379) ##STR00197##

(380) To a suspension of {1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid (158 mg, 0.50 mmol) and 2-amino-4-chlorobenzaldehyde (77.8 mg, 0.5 mmol) in acetic acid anhydride (0.5 ml) is added triethylamine (277 l, 2.0 mmol) and the reaction mixture is stirred for 18 hours at room temperature. The reaction mixture is diluted with ethyl acetate. The solid is filtered off and dried. The residue is treated with water. The solid is filtered off, washed with water and dried under vacuum to afford 7-chloro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as beige powder; HPLC/MS 1.53 min (A), [M+H].sup.+ 436.

(381) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.26 (s, 1H), 8.85 (s, 1H), 8.15-8.04 (m, 2H), 7.95 (d, J=8.5 Hz, 1H), 7.75-7.59 (m, 2H), 7.42 (d, J=2.1 Hz, 1H), 7.30 (dd, J=8.5, 2.0 Hz, 1H), 3.85-3.33 (m, 8H).

(382) The following compounds are prepared similarly:

7-fluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A83)

(383) ##STR00198##
off-white crystals; HPLC/MS 1.44 min (A), [M+H].sup.+ 420; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.24 (s, 1H), 8.86 (s, 1H), 8.17-8.04 (m, 2H), 8.00 (dd, J=9.6, 6.1 Hz, 1H), 7.69-7.62 (m, 2H), 7.17-7.10 (m, 2H), 3.80-3.35 (m, 8H).

7-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A84)

(384) ##STR00199##
beige solid; HPLC/MS 1.47 min (A), [M+H].sup.+ 416; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.13 (s, 1H), 9.24 (s, 1H), 8.80 (s, 1H), 8.13-8.07 (m, 2H), 7.79 (d, J=8.1 Hz, 1H), 7.70-7.63 (m, 2H), 7.20 (s, 1H), 7.11 (dd, J=8.1, 1.5 Hz, 1H), 3.75-3.35 (m, 8H), 2.43 (s, 3H).

3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,5]naphthyridin-2-one (A85)

(385) ##STR00200##
light yellow crystals; HPLC/MS 1.20 min (A), [M+H].sup.+ 403; .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.40 (s, 1H), 9.34 (s, 1H), 8.76 (s, 1H), 8.58 (dd, J=4.5, 1.4 Hz, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.78 (dd, J=8.3, 1.4 Hz, 1H), 7.66 (d, J=8.5 Hz, 2H), 7.58 (dd, J=8.3, 4.4 Hz, 1H), 3.65 (bs, 4H), 3.40 (bs, 4H).

6-fluoro-3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A86)

(386) ##STR00201##
beige solid; HPLC/MS 1.23 min (A), [M+H].sup.+ 491; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.1, 2.6 Hz, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.50-7.37 (m, 2H), 3.75-3.30 (m, 4H), 3.35 (t, J=6.4 Hz, 2H), 3.22 (s, 3H), 2.47-2.32 (m, 6H), 1.67 (p, J=6.7 Hz, 2H).

5-fluoro-3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A87)

(387) ##STR00202##
off-white solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 491; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.43 (s, 1H), 9.28 (s, 1H), 8.82 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 7.57 (td, J=8.2, 6.1 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.11 (ddd, J=10.1, 8.1, 0.9 Hz, 1H), 3.70-3.30 (m, 4H), 3.35 (t, J=6.4 Hz, 2H), 3.22 (s, 3H), 2.40 (bs, 4H), 2.36 (t, J=7.3 Hz, 2H), 1.78-1.57 (m, 2H).

6-fluoro-3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one (A88)

(388) ##STR00203##
beige solid; HPLC/MS 1.14 min (A), [M+H].sup.+ 492; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.70 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.61 (d, J=2.9 Hz, 1H), 8.35 (dd, J=8.7, 3.0 Hz, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.63 (d, J=8.6 Hz, 2H), 3.75-3.30 (m, 4H), 3.35 (t, J=6.4 Hz, 2H), 3.22 (s, 3H), 2.39 (bs, 4H) 2.36 (t, J=7.3 Hz, 2H), 1.67 (p, J=6.6 Hz, 2H).

3-(1-{4-[4-(3-methoxy-propyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one (A89)

(389) ##STR00204##
white solid; HPLC/MS 1.08 min (A), [M+H].sup.+ 474; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.58 (s, 1H), 9.27 (s, 1H), 8.86 (s, 1H), 8.57 (dd, J=4.7, 1.8 Hz, 1H), 8.36 (dd, J=7.8, 1.8 Hz, 1H), 8.08 (d, J=8.5 Hz, 2H), 7.63 (d, J=8.5 Hz, 2H), 7.33 (dd, J=7.7, 4.7 Hz, 1H), 3.70-3.32 (m, 4H), 3.35 (t, J=6.4 Hz, 2H), 3.22 (s, 3H), 2.40 (bs, 4H), 2.36 (t, J=7.3 Hz, 2H), 1.67 (m, 2H).

5,7-difluoro-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A90)

(390) ##STR00205##
beige solid; HPLC/MS 1.51 min (A), [M+H].sup.+ 438; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.54 (s, 1H), 9.28 (s, 1H), 8.77 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.67 (d, J=8.6 Hz, 2H), 7.24 (td, J=9.9, 2.4 Hz, 1H), 7.03 (dd, J=9.9, 2.1 Hz, 1H), 3.75-3.35 (m, 8H).

7-bromo-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A91)

(391) ##STR00206##
beige solid; HPLC/MS 1.56 min (A), [M+H].sup.+ 482; .sup.1H NMR (400 MHz, DMSO-d.sub.6) b 12.27 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.15-8.07 (m, 2H), 7.89 (d, J=8.5 Hz, 1H), 7.72-7.63 (m, 2H), 7.59 (d, J=1.9 Hz, 1H), 7.44 (dd, J=8.4, 1.9 Hz, 1H), 3.74-3.38 (m, 8H).

6-fluoro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A92)

(392) ##STR00207##
off-white powder; UPLC/MS 0.62 min, [M+H].sup.+ 447; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.15-8.07 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.75-7.66 (m, 2H), 7.52-7.38 (m, 2H), 4.12 (bs, 2H), 3.94-3.58 (m, 2H), 3.40 (t, J=5.5 Hz, 2H), 2.89 (s, 3H).

7-methoxy-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A93)

(393) ##STR00208##
beige powder; UPLC/MS 0.66 min, [M+H].sup.+ 432; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.06 (s, 1H), 9.19 (s, 1H), 8.76 (s, 1H), 8.13-8.04 (m, 2H), 7.82 (d, J=8.3 Hz, 1H), 7.73-7.62 (m, 2H), 6.96-6.83 (m, 2H), 3.85 (s, 3H), 3.72-3.38 (m, 8H).

6-{1-[4-(Morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-8H-pyrido[2,3-d]pyrimidin-7-one (A94)

(394) ##STR00209##
yellow solid; HPLC/MS 1.15 min (A), [M+H].sup.+ 404; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.97 (s, 1H), 9.30 (s, 1H), 9.29 (s, 1H), 9.03 (s, 1H), 8.91 (s, 1H), 8.15-8.10 (m, 2H), 7.71-7.66 (m, 3H), 3.64 (s, 16H).

6-fluoro-3-{1-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A94a)

(395) ##STR00210##
light beige solid; HPLC/MS 1.24 min (A), [M+H].sup.+ 436; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.25 (s, 1H), 9.25 (s, 1H), 8.83 (s, 1H), 7.79 (dd, J=9.2, 2.6 Hz, 1H), 7.59-7.54 (m, 2H), 7.50 (t, J=8.4 Hz, 1H), 7.46-7.39 (m, 2H), 7.08 (ddd, J=8.2, 2.4, 1.2 Hz, 1H), 4.24 (t, J=5.7 Hz, 2H), 3.64-3.55 (m, 4H), 2.74 (t, J=5.7 Hz, 2H), 2.53-2.49 (m, 4H).

5,7-difluoro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A95)

(396) ##STR00211##
off-white powder; UPLC/MS 0.66 min, [M+H].sup.+ 465; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.50 (s, 1H), 9.28 (s, 1H), 8.75 (s, 1H), 8.27-8.03 (m, 2H), 7.81-7.59 (m, 2H), 7.21 (td, J=9.9, 2.4 Hz, 1H), 7.01 (dd, J=9.9, 2.3 Hz, 1H), 4.13 (bs, 2H), 3.94-3.60 (m, 2H), 3.44-3.36 (m, 2H), 2.89 (s, 3H).

6-chloro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A96)

(397) ##STR00212##
off-white powder; UPLC/MS 0.67 min, [M+H].sup.+ 463; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.29 (s, 1H), 8.84 (s, 1H), 8.16-8.08 (m, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.74-7.67 (m, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 4.13 (bs, 2H), 3.94-3.60 (m, 2H), 3.40 (t, J=5.4 Hz, 2H), 2.89 (s, 3H).

7-chloro-3-{1-[4-(4-methyl-3-oxo-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A97)

(398) ##STR00213##
off-white powder; UPLC/MS 0.67 min, [M+H].sup.+ 463; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.27 (s, 1H), 8.86 (s, 1H), 8.16-8.08 (m, 2H), 7.95 (d, J=8.5 Hz, 1H), 7.77-7.66 (m, 2H), 7.42 (d, J=2.0 Hz, 1H), 7.30 (dd, J=8.4, 2.1 Hz, 1H), 4.12 (bs, 2H), 3.94-3.60 (m, 2H), 3.40 (t, J=5.5 Hz, 2H), 2.89 (s, 3H).

6-fluoro-3-{1-[4-(2-oxo-oxazolidin-3-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A98)

(399) ##STR00214##
off-white powder; HPLC/MS 1.51 min (A), [M+H].sup.+ 392; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.19 (s, 1H), 8.83 (s, 1H), 8.23-7.95 (m, 2H), 7.90-7.77 (m, 3H), 7.51-7.34 (m, 2H), 4.49 (m, 2H), 4.15 (m, 2H).

3-{1-[4-(1,1-dioxo-116-isothiazolidin-2-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A99)

(400) ##STR00215##
pale brown powder; HPLC/MS 1.53 min (A), [M+H].sup.+ 426; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.18 (s, 1H), 8.84 (s, 1H), 8.13-7.94 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.48-7.37 (m, 4H), 3.84 (t, J=6.5 Hz, 2H), 3.58 (t, J=7.4 Hz, 2H), 2.45 (p, J=6.8 Hz, 2H).

3-{1-[4-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A100)

(401) ##STR00216##
beige solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 473; .sup.1H NMR (700 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.32 (s, 1H), 8.87 (s, 1H), 8.12 (d, J=8.3 Hz, 2H), 7.81 (d, J=8.1 Hz, 2H), 7.65 (dd, J=9.0, 2.8 Hz, 1H), 7.50 (dd, J=9.0, 4.7 Hz, 1H), 7.37 (td, J=8.7, 2.8 Hz, 1H), 4.18-3.46 (m, 7H), 3.33-3.01 (m, 2H), 2.51-1.95 (m, 6H).

3-(1-{4-[2-(4-acetyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-6-fluoro-1H-quinolin-2-one (A100a)

(402) ##STR00217##
brown solid; HPLC/MS 1.21 min (A), [M+H].sup.+ 477; .sup.1H NMR (500 MHz, DMSO-d.sub.6) b 12.24 (s, 1H), 9.11 (s, 1H), 8.82 (s, 1H), 7.93-7.85 (m, 2H), 7.79 (dd, J=9.2, 2.7 Hz, 1H), 7.49-7.38 (m, 2H), 7.21-7.12 (m, 2H), 4.19 (t, J=5.7 Hz, 2H), 3.50-3.39 (m, 4H), 2.77 (t, J=5.7 Hz, 2H), 2.52 (m, 2H), 2.45 (m, 2H), 1.99 (s, 3H).

3-(1-{4-[2-(4-acetyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-6,7-difluoro-1H-quinolin-2-one (A101)

(403) ##STR00218##
brown solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 495; .sup.1H NMR (500 MHz, DMSO-d.sub.6) b 12.29 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 8.07 (dd, J=11.0, 8.6 Hz, 1H), 7.96-7.82 (m, 2H), 7.32 (dd, J=11.4, 7.0 Hz, 1H), 7.24-7.10 (m, 2H), 4.19 (t, J=5.7 Hz, 2H), 3.50-3.38 (m, 4H), 2.77 (t, J=5.7 Hz, 2H), 2.52 (m, 2H), 2.45 (t, J=5.2 Hz, 2H), 1.99 (s, 3H).

acetic acid 1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperidin-4-yl ester (A102)

(404) ##STR00219##
beige solid; HPLC/MS 1.55 min (A), [M+H].sup.+ 476.

acetic acid 1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperidin-3-yl ester (A103)

(405) ##STR00220##
off-white solid; HPLC/MS 1.55 min (A), [M+H].sup.+ 476.

3-{1-[4-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A104)

(406) ##STR00221##
brown solid; HPLC/MS 1.24 min (A), [M+H].sup.+ 491.

3-{1-[4-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-5,7-difluoro-1H-quinolin-2-one (A105)

(407) ##STR00222##
beige solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 491.

6-fluoro-3-{1-[4-(3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A106)

(408) ##STR00223##
light brown solid; HPLC/MS 1.52 min (A), [M+H].sup.+ 448.

3-{1-[3-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A107)

(409) ##STR00224##
brown solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 473.

3-{1-[3-([1,3]bipyrrolidinyl-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A108)

(410) ##STR00225##
brown solid; HPLC/MS 1.24 min (A), [M+H].sup.+ 491.

6,7-difluoro-3-{1-[4-(3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A109)

(411) ##STR00226##
brown solid; HPLC/MS 1.56 min (A), [M+H].sup.+ 466.

6-fluoro-3-{1-[4-(4-methyl-5-oxo-[1,4]diazepane-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A110)

(412) ##STR00227##
brown solid; UPLC/MS 0.89 min, [M+H].sup.+ 461.

6-fluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A111)

(413) ##STR00228##
off-white solid; UPLC/MS 0.94 min, [M+H].sup.+ 434.

6-fluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A112)

(414) ##STR00229##
off-white solid; UPLC/MS 0.94 min, [M+H].sup.+ 434.

6,7-difluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A113)

(415) ##STR00230##
off-white solid; UPLC/MS 0.96 min, [M+H].sup.+ 452.

6,7-difluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A114)

(416) ##STR00231##
off-white solid; UPLC/MS 0.96 min, [M+H].sup.+ 452.

3-{1-[4-(2-dimethylamino-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A115)

(417) ##STR00232##
beige solid; UPLC/MS 0.48 min, [M+H].sup.+ 396. .sup.1H NMR (300 MHz, DMSO-d.sub.6) 12.31 (s, 1H), 9.15 (s, 1H), 8.83 (s, 1H), 8.08 (dd, J=11.1, 8.6 Hz, 1H), 7.93-7.84 (m, 2H), 7.50-7.43 (m, 2H), 7.33 (dd, J=11.5, 7.1 Hz, 1H), 2.81 (t, J=7.5 Hz, 2H), 2.53 (t, J=7.5 Hz, 2H), 2.21 (s, 6H).

6,7-difluoro-3-{1-[4-(2-pyrrolidin-1-yl-ethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A115a)

(418) ##STR00233##
beige solid; UPLC/MS 0.49 min, [M+H].sup.+ 396. .sup.1H NMR (300 MHz, DMSO-d.sub.6) 12.31 (s, 1H), 9.15 (s, 1H), 8.83 (s, 1H), 8.08 (dd, J=11.1, 8.6 Hz, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.47 (d, J=8.5 Hz, 2H), 7.33 (dd, J=11.5, 7.1 Hz, 1H), 2.81 (t, J=7.5 Hz, 2H), 2.56-2.49 (m, 6H), 2.21 (s, 4H).

3-{1-[4-(2-diethylamino-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A116)

(419) ##STR00234##
beige solid; HPLC/MS 1.31 min (A), [M+H].sup.+ 440; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 8.07 (dd, J=11.0, 8.5 Hz, 1H), 7.96-7.82 (m, 2H), 7.31 (dd, J=11.4, 7.0 Hz, 1H), 7.19-7.07 (m, 2H), 4.10 (t, J=6.1 Hz, 2H), 2.81 (t, J=6.1 Hz, 2H), 2.57 (q, J=7.1 Hz, 4H), 0.99 (t, J=7.1 Hz, 6H).

6,7-difluoro-3-{1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A186)

(420) ##STR00235##

(421) Beige solid; HPLC/MS 1.28 min (A), [M+H].sup.+ 438; .sup.1H NMR (500 MHz, DMSO-d.sub.6) b 12.29 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 8.06 (dd, J=11.0, 8.6 Hz, 1H), 7.87 (d, J=9.0 Hz, 2H), 7.31 (dd, J=11.4, 7.1 Hz, 1H), 7.15 (d, J=9.0 Hz, 2H), 4.16 (t, J=5.9 Hz, 2H), 2.83 (t, J=5.8 Hz, 2H), 2.58-2.53 (m, 4H), 1.74-1.66 (m, 4H).

N-{4-[4-(6,7-difluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-N-methyl-acetamide (A352)

(422) ##STR00236##

(423) HPLC/MS 1.50 min (A), [M+H].sup.+ 396;

(424) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.24 (s, 1H), 8.84 (s, 1H), 8.12-8.05 (m, 3H), 7.68-7.54 (m, 2H), 7.33 (dd, J=11.5, 7.1 Hz, 1H), 3.24 (bs, 3H), 1.90 (bs, 3H).

N-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-N-methyl-acetamide (A353)

(425) ##STR00237##

(426) HPLC/MS 1.45 min (A), [M+H].sup.+ 378;

(427) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.07 (d, J=8.2 Hz, 2H), 7.80 (dd, J=9.3, 2.6 Hz, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.53-7.38 (m, 2H), 3.24 (bs, 3H), 1.90 (bs, 3H).

6-fluoro-3-[1-(2-methyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A354)

(428) ##STR00238##

(429) UPLC/MS 0.66 min, [M+H].sup.+ 376;

(430) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.34 (s, 1H), 8.88 (s, 1H), 8.31 (d, J=1.9 Hz, 1H), 8.15 (dd, J=8.2, 2.0 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.54-7.30 (m, 2H), 3.13 (s, 3H), 2.55 (s, 2H).

6-Fluoro-3-{1-[4-((trans)-3-methoxy-cyclopentyloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A355)

(431) ##STR00239##

(432) HPLC/MS 1.73 min (A), [M+H].sup.+ 421;

(433) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.09 (s, 1H), 8.82 (s, 1H), 7.92-7.83 (m, 2H), 7.79 (dd, J=9.1, 2.6 Hz, 1H), 7.51-7.37 (m, 2H), 7.15-7.00 (m, 2H), 4.85 (tt, J=7.2, 3.4 Hz, 1H), 3.83 (p, J=4.7 Hz, 1H), 3.20 (s, 3H), 2.39 (dt, J=14.1, 7.0 Hz, 1H), 2.07-1.96 (m, 1H), 1.90-1.74 (m, 2H), 1.69 (dt, J=14.4, 3.9 Hz, 1H).

6-chloro-3-{1-[4-((1S,3R)-3-methoxy-cyclopentyloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A356)

(434) ##STR00240##

(435) HPLC/MS 1.83 min (A), [M+H].sup.+ 437;

(436) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.10 (s, 1H), 8.82 (s, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.87 (d, J=9.0 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.19-6.97 (m, 2H), 4.86 (tt, J=7.1, 3.8 Hz, 1H), 3.84 (dq, J=6.6, 4.7 Hz, 1H), 3.21 (s, 3H), 2.40 (dt, J=14.1, 7.0 Hz, 1H), 2.02 (dtd, J=15.1, 7.6, 5.8 Hz, 1H), 1.89-1.74 (m, 3H), 1.70 (dt, J=14.4, 4.0 Hz, 1H).

6-fluoro-3-[1-(4-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A357)

(437) ##STR00241##

(438) UPLC/MS 0.77 min, [M+H].sup.+ 337;

(439) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.25 (s, 1H), 9.11 (s, 1H), 8.82 (s, 1H), 8.09-7.86 (m, 2H), 7.79 (dd, J=9.1, 2.5 Hz, 1H), 7.58-7.36 (m, 2H), 7.23-7.01 (m, 2H), 3.86 (s, 3H).

6-fluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A358)

(440) ##STR00242##

(441) HPLC/MS 1.63 min (A), [M+H].sup.+ 470;

(442) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.40 (s, 1H), 8.88 (s, 1H), 8.31 (d, J=8.7 Hz, 2H), 8.13-7.97 (m, 2H), 7.82 (dd, J=9.1, 2.8 Hz, 1H), 7.47 (td, J=8.8, 2.9 Hz, 1H), 7.43 (dd, J=9.0, 4.8 Hz, 1H), 3.86 (dq, J=5.7, 3.0 Hz, 1H), 3.37-3.30 (m, 3H), 3.17 (td, J=9.6, 7.2 Hz, 1H), 3.04 (s, 3H), 1.92-1.72 (m, 2H).

6-chloro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A359)

(443) ##STR00243##

(444) HPLC/MS 1.73 min (A), [M+H].sup.+ 486;

(445) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.35 (s, 1H), 9.38 (s, 1H), 8.86 (s, 1H), 8.38-8.23 (m, 2H), 8.06 (d, J=2.3 Hz, 1H), 8.05-7.97 (m, 2H), 7.60 (dd, J=8.8, 2.3 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 3.87 (p, J=3.2 Hz, 1H), 3.38-3.30 (m, 3H), 3.18 (td, J=9.4, 7.5 Hz, 1H), 1.89-1.70 (m, 2H).

6-fluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A360)

(446) ##STR00244##

(447) HPLC/MS 1.63 min (A), [M+H].sup.+ 470;

(448) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.40 (s, 1H), 8.88 (s, 1H), 8.31 (d, J=8.7 Hz, 2H), 8.13-7.97 (m, 2H), 7.82 (dd, J=9.1, 2.8 Hz, 1H), 7.47 (td, J=8.8, 2.9 Hz, 1H), 7.43 (dd, J=9.0, 4.8 Hz, 1H), 3.86 (dq, J=5.7, 3.0 Hz, 1H), 3.37-3.30 (m, 3H), 3.17 (td, J=9.6, 7.2 Hz, 1H), 3.04 (s, 3H), 1.92-1.72 (m, 2H).

6-chloro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A361)

(449) ##STR00245##

(450) HPLC/MS 1.73 min (A), [M+H].sup.+ 486;

(451) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.35 (s, 1H), 9.38 (s, 1H), 8.86 (s, 1H), 8.38-8.23 (m, 2H), 8.06 (d, J=2.3 Hz, 1H), 8.05-7.97 (m, 2H), 7.60 (dd, J=8.8, 2.3 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 3.87 (p, J=3.2 Hz, 1H), 3.38-3.30 (m, 3H), 3.18 (td, J=9.4, 7.5 Hz, 1H), 1.89-1.70 (m, 2H).

6-fluoro-3-{1-[4-((1S,2S)-2-methoxy-cyclopentyloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A362)

(452) ##STR00246##

(453) HPLC/MS 1.83 min (A), [M+H].sup.+ 421;

(454) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.13 (s, 1H), 8.84 (s, 1H), 8.03-7.86 (m, 2H), 7.81 (dd, J=9.2, 2.8 Hz, 1H), 7.46 (td, J=8.8, 2.8 Hz, 1H), 7.42 (dd, J=9.0, 4.9 Hz, 1H), 7.20-7.13 (m, 2H), 4.74 (dt, J=6.0, 2.9 Hz, 1H), 3.85-3.81 (m, 1H), 3.30 (s, 3H), 2.19-2.07 (m, 1H), 2.03-1.90 (m, 1H), 1.75-1.61 (m, 4H).

6-chloro-3-[1-(4-cyclopentyloxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A363)

(455) ##STR00247##

(456) UPLC/MS 0.97 min, [M+H].sup.+ 407;

(457) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.11 (s, 1H), 8.82 (s, 1H), 8.06 (d, J=2.4 Hz, 1H), 7.95-7.82 (m, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.16-7.06 (m, 2H), 4.95-4.90 (m, 1H), 2.07-1.85 (m, 2H), 1.84-1.68 (m, 4H), 1.67-1.57 (m, 2H).

3-[1-(4-cyclopentyloxy-phenyl)-1H-[1,2,3]triazol-4-yl]-6-fluoro-1H-quinolin-2-one (A364)

(458) ##STR00248##

(459) UPLC/MS 0.91 min, [M+H].sup.+ 391;

(460) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.11 (s, 1H), 8.83 (s, 1H), 7.91-7.85 (m, 2H), 7.81 (dd, J=9.3, 2.8 Hz, 1H), 7.46 (td, J=8.8, 2.8 Hz, 1H), 7.42 (dd, J=9.1, 4.9 Hz, 1H), 7.15-7.09 (m, 2H), 4.95-4.90 (m, 1H), 2.02-1.92 (m, 2H), 1.80-1.68 (m, 4H), 1.68-1.56 (m, 2H).

6-fluoro-3-{1-[4-(tetrahydro-furan-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A365)

(461) ##STR00249##

(462) UPLC/MS 0.77 min, [M+H].sup.+ 393;

(463) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.13 (s, 1H), 8.83 (s, 1H), 8.04-7.87 (m, 2H), 7.81 (dd, J=9.2, 2.8 Hz, 1H), 7.46 (td, J=8.8, 2.8 Hz, 1H), 7.42 (dd, J=9.0, 4.9 Hz, 1H), 7.18-7.11 (m, 2H), 5.15 (ddt, J=6.2, 3.9, 1.7 Hz, 1H), 3.93 (dd, J=10.2, 4.5 Hz, 1H), 3.91-3.82 (m, 2H), 3.79 (td, J=8.4, 4.6 Hz, 1H), 2.28 (dtd, J=16.4, 8.2, 6.2 Hz, 1H), 2.06-1.94 (m, 1H).

6-chloro-3-{1-[4-(tetrahydro-furan-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A366)

(464) ##STR00250##

(465) UPLC/MS 0.82 min, [M+H].sup.+ 409;

(466) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.12 (s, 1H), 8.82 (s, 1H), 8.06 (d, J=2.3 Hz, 1H), 7.98-7.83 (m, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.14 (d, J=9.0 Hz, 2H), 5.14 (ddd, J=6.2, 4.2, 1.9 Hz, 1H), 3.93 (dd, J=10.2, 4.5 Hz, 1H), 3.91-3.82 (m, 2H), 3.79 (td, J=8.4, 4.6 Hz, 1H), 2.28 (dtd, J=14.4, 8.2, 6.2 Hz, 1H), 2.07-1.95 (m, 1H).

Example 10

7-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A117) and 7-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A118)

(467) ##STR00251##

(468) To a suspension of 4-[4-(4-carboxymethyl-[1,2,3]triazol-1-yl)-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester (291 mg, 0.70 mmol) and 2-Amino-4-fluoro-benzaldehyde (97.4 mg, 0.7 mmol) in acetic acid anhydride (1.17 ml) is added triethylamine (388 l, 2.80 mmol) and the reaction mixture is stirred for 16 hours at room temperature. The reaction mixture is treated with dichloromethane and water. The organic phase is separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 4-{4-[4-(7-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester as beige solid; HPLC/MS 1.70 min (A), [M+H].sup.+ 519.

Example 10a

Synthesis of A117

(469) A suspension of 4-{4-[4-(7-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (83.0 mg, 0.16 mmol) in a 4 M solution of hydrochloric acid in dioxane (362 l) is heated to 70 C. and stirred at this temperature in a closed reaction vial for 4 hours. The reaction mixture is allowed to reach room temperature and concentrated under vacuum. The residue is treated with saturated Na.sub.2CO.sub.3 solution and the mixture is evaporated. The solid residue is extracted with a mixture of dichloromethane and methanol. The extraction solution is evaporated and the residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 7-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as off-white solid; HPLC/MS 1.18 min (A), [M+H].sup.+ 419.

(470) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.26 (s, 1H), 8.87 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.90 (dd, J=8.8, 6.0 Hz, 1H), 7.74 (d, J=8.6 Hz, 2H), 7.22 (dd, J=10.2, 2.5 Hz, 1H), 7.06 (td, J=8.8, 2.5 Hz, 1H), 3.83 (bs, 4H), 3.27 (bs, 4H).

(471) The following compounds are prepared similarly:

5-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A119)

(472) ##STR00252##
beige solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 419; .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.17 (s, 1H), 8.84 (s, 1H), 8.00 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 7.40 (td, J=8.2, 5.9 Hz, 1H), 7.19 (d, J=8.3 Hz, 1H), 6.95-6.86 (m, 1H), 3.72 (bs, 4H), 3.15 (bs, 4H).

8-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A120)

(473) ##STR00253##
beige solid; HPLC/MS 1.17 min (A), [M+H].sup.+ 419; .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.27 (s, 1H), 8.90 (d, J=1.5 Hz, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.73 (d, J=8.5 Hz, 2H), 7.66 (d, J=7.8 Hz, 1H), 7.37 (ddd, J=11.0, 8.1, 1.2 Hz, 1H), 7.23 (td, J=8.0, 4.8 Hz, 1H), 3.85 (bs, 4H), 3.27 (bs, 4H).

3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A121)

(474) ##STR00254##
beige solid; HPLC/MS 1.05 min (A), [M+H].sup.+ 402; .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.21 (s, 1H), 8.83 (s, 1H), 8.52 (dd, J=4.9, 1.8 Hz, 1H), 8.31 (dd, J=7.9, 1.7 Hz, 1H), 8.04 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H), 7.27 (dd, J=7.8, 4.9 Hz, 1H), 3.72 (bs, 4H), 3.18 (bs, 4H).

6-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A122)

(475) ##STR00255##
beige solid; HPLC/MS 1.08 min (A), [M+H].sup.+ 420; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.74 (s, 1H), 9.32 (s, 1H), 9.30 (bs, 1H), 8.88 (s, 1H), 8.63 (d, J=2.7 Hz, 1H), 8.37 (dd, J=8.7, 2.9 Hz, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.73 (d, J=8.6 Hz, 2H), 3.75 (bs, 4H), 3.19 (s, 4H).

6-chloro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A123)

(476) ##STR00256##
off-white solid; HPLC/MS 1.26 min (A), [M+H].sup.+ 435; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.35 (s, 1H), 9.30 (s, 1H), 9.28 (bs, 1H), 8.85 (s, 1H), 8.13 (d, J=8.5 Hz, 2H), 8.06 (d, J=2.3 Hz, 1H), 7.73 (d, J=8.6 Hz, 1H), 7.60 (dd, J=8.7, 2.4 Hz, 1H), 7.43 (d, J=8.7 Hz, 1H), 3.75 (bs, 4H), 3.20 (s, 4H).

3-[1-(4-[1,4]diazepan-1-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-6-fluoro-1H-[1,8]naphthyridin-2-one (A124)

(477) ##STR00257##
green-brown solid; HPLC/MS 1.17 min (A), [M+H].sup.+ 406; .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.05 (s, 1H), 8.84 (s, 1H), 8.52 (d, J=2.9 Hz, 1H), 8.18 (dd, J=8.5, 2.9 Hz, 1H), 7.78 (d, J=9.1 Hz, 2H), 6.99 (d, J=9.2 Hz, 2H), 3.85 (t, J=5.2 Hz, 2H), 3.65 (t, J=6.1 Hz, 2H), 3.38 (t, J=5.1 Hz, 2H), 3.29-3.19 (m, 2H), 2.19 (p, J=5.9 Hz, 2H).

6-fluoro-3-{1-[3-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A125)

(478) ##STR00258##
beige solid; HPLC/MS 1.19 min (A), [M+H].sup.+ 419; .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.31 (s, 1H), 8.86 (s, 1H), 8.18-8.10 (m, 2H), 7.75-7.64 (m, 2H), 7.59 (d, J=7.6 Hz, 1H), 7.50 (dd, J=9.0, 4.7 Hz, 1H), 7.37 (td, J=8.8, 2.8 Hz, 1H), 3.89 (bs, 4H), 3.27 (s, 4H).

7-chloro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A126)

(479) ##STR00259##
white solid; HPLC/MS 1.27 min (A), [M+H].sup.+ 435; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (bs, 1H), 9.25 (s, 1H), 8.85 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.95 (d, J=8.5 Hz, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.42 (d, J=2.0 Hz, 1H), 7.30 (dd, J=8.4, 2.0 Hz, 1H), 3.65-3.35 (m, 4H), 2.72 (bs, 4H).

5,6-difluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A127)

(480) ##STR00260##
beige solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 437; .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.27 (s, 1H), 8.83 (s, 1H), 8.13-8.04 (m, 2H), 7.69 (d, J=8.2 Hz, 2H), 7.51 (q, J=9.3, 8.9 Hz, 1H), 7.22 (dd, J=9.4, 3.6 Hz, 1H), 3.73 (bs, 4H), 3.20 (bs, 4H).

6,7-difluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A128)

(481) ##STR00261##
hydrochloride: beige solid; UPLC/MS 0.48 min, [M+H].sup.+ 437; H NMR (500 MHz, DMSO-d6) 12.35 (s, 1H), 9.29 (s, 1H), 8.97 (bs, 2H), 8.85 (s, 1H), 8.23-8.02 (m, 3H), 7.71 (d, J=8.5 Hz, 2H), 7.35 (dd, J=11.4, 7.0 Hz, 1H), 3.71 (bs, 4H), 3.16 (bs, 4H).

6-fluoro-3-{1-[4-(piperazine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A129)

(482) ##STR00262##
hydrochloride: beige powder; UPLC/MS 0.50 min, [M+H].sup.+ 455; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.42 (s, 1H), 9.07 (s, 2H), 8.87 (s, 1H), 8.58-8.28 (m, 2H), 8.17-7.95 (m, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.56-7.37 (m, 2H), 3.26-3.19 (m, 8H).

6,7-difluoro-3-{1-[4-(2-piperazin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A130)

(483) ##STR00263##
light brown solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 453.

6-fluoro-3-{1-[4-(3-piperazin-1-yl-propoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A131)

(484) ##STR00264##
off-white powder; HPLC/MS 1.15 min (A), [M+H].sup.+ 449.

6-fluoro-3-{1-[4-(piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A132)

(485) ##STR00265##
hydrochloride: beige solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 418. .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.31 (s, 1H), 9.40 (s, 1H), 8.88 (s, 1H), 8.64 (d, J=11.5 Hz, 1H), 8.45-8.33 (m, 1H), 8.25 (m, 4H), 7.83 (dd, J=9.2, 2.7 Hz, 1H), 7.48 (td, J=8.7, 2.8 Hz, 1H), 7.44 (dd, J=9.1, 5.0 Hz, 1H), 3.86 (tt, J=11.2, 3.6 Hz, 1H), 3.37 (d, J=13.0 Hz, 2H), 3.15-3.02 (m, 2H), 2.06-1.96 (m, 2H), 1.79 (dtd, J=14.5, 11.4, 10.9, 4.0 Hz, 2H).

6-fluoro-3-{1-[4-(2-piperidin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A133)

(486) ##STR00266##
beige solid; HPLC/MS 1.31 min (A), [M+H].sup.+ 434.

6,7-difluoro-3-{1-[4-(2-piperidin-4-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A134)

(487) ##STR00267##
off-white solid; HPLC/MS 1.34 min (A), [M+H].sup.+ 452.

6,7-difluoro-3-{1-[4-(3-piperazin-1-yl-propoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A135)

(488) ##STR00268##
off-white powder; HPLC/MS 1.19 min (A), [M+H].sup.+ 467.

6,7-difluoro-3-{1-[4-(piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A136)

(489) ##STR00269##
hydrochloride; beige solid; UPLC/MS 0.76 min, [M+H].sup.+ 436. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.36 (s, 1H), 9.37 (s, 1H), 8.86 (s, 1H), 8.83 (bs, 1H), 8.55 (bs, 1H), 8.24 (s, 4H), 8.10 (dd, J=11.0, 8.6 Hz, 1H), 7.35 (dd, J=11.5, 7.1 Hz, 1H), 3.86 (ddd, J=11.2, 7.7, 3.5 Hz, 1H), 3.33 (m, 2H), 3.08 (q, J=11.8 Hz, 2H), 2.01 (d, J=14.0 Hz, 2H), 1.89-1.68 (m, 2H).

6-methyl-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A137)

(490) ##STR00270##
hydrochloride: beige solid; UPLC/MS 0.72 min, [M+H].sup.+ 415. .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.14 (s, 1H), 9.28 (s, 1H), 9.14 (bs, 2H), 8.77 (s, 1H), 8.29-8.00 (m, 2H), 7.75-7.70 (m, 2H), 7.69 (bs, 1H), 7.41 (dd, J=8.4, 1.9 Hz, 1H), 7.33 (d, J=8.3 Hz, 1H), 3.74 (bs, 4H), 3.20 (bs, 4H), 2.40 (s, 3H).

5,7-difluoro-3-{1-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indol-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A138)

(491) ##STR00271##
hydrochloride: beige solid; UPLC/MS 0.92 min, [M+H].sup.+ 490. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.29 (bs, 2H), 9.11 (s, 1H), 8.84 (s, 1H), 8.12 (d, J=2.1 Hz, 1H), 8.09 (dd, J=11.1, 8.7 Hz, 1H), 7.69 (dd, J=8.8, 2.1 Hz, 1H), 7.62 (d, J=8.9 Hz, 1H), 7.41 (d, J=3.1 Hz, 1H), 7.35 (dd, J=11.5, 7.1 Hz, 1H), 5.34 (s, 2H), 3.84 (bs, 2H), 3.71 (bs, 2H), 3.26 (bs, 2H), 3.12 (bs, 2H).

6,7-difluoro-3-{1-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indol-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A139)

(492) ##STR00272##
hydrochloride: light yellow solid; UPLC/MS 0.93 min, [M+H].sup.+ 490.

6,7-difluoro-3-{1-[4-(2-oxo-2-piperazin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A140)

(493) ##STR00273##
hydrochloride: beige solid; UPLC/MS 0.87 min, [M+H].sup.+ 467. H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.15 (bs, 2H), 9.10 (s, 1H), 8.82 (s, 1H), 8.08 (dd, J=11.0, 8.6 Hz, 1H), 7.93-7.83 (m, 2H), 7.34 (dd, J=11.5, 7.1 Hz, 1H), 7.24-7.11 (m, 2H), 5.01 (s, 2H), 3.71 (bs, 4H), 3.20 (bs, 2H), 3.11 (bs, 2H).

6-fluoro-3-{1-[4-(2-oxo-2-piperazin-1-yl-ethoxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A141)

(494) ##STR00274##
hydrochloride: beige solid; UPLC/MS 0.84 min, [M+H].sup.+ 449.

3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-trifluoromethyl-1H-quinolin-2-one (A142)

(495) ##STR00275##
hydrochloride: beige solid; UPLC/MS 0.92 min, [M+H].sup.+ 469.

3-{1-[4-(4-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A143)

(496) ##STR00276##
hydrochloride: light beige solid; UPLC/MS 0.85 min, [M+H].sup.+ 451.

3-{1-[4-(4-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A144)

(497) ##STR00277##
hydrochloride: beige solid; UPLC/MS 0.81 min, [M+H].sup.+ 433.

6,7-difluoro-3-{1-[4-(2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A145)

(498) ##STR00278##
hydrochloride: light brown solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 423. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.72 (s, 2H), 9.23 (s, 1H), 8.84 (s, 1H), 8.13-8.03 (m, 3H), 7.64-7.55 (m, 2H), 7.34 (dd, J=11.5, 7.1 Hz, 1H), 3.96 (bs, 2H), 3.91 (s, 2H), 3.57 (bs, 2H).

6,7-difluoro-3-{1-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indazol-5-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A146)

(499) ##STR00279##
trifluoroacetate: brown solid; UPLC/MS 0.48 min, [M+H].sup.+ 491. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.21 (s, 1H), 8.85 (s, 1H), 8.76 (s, 2H), 8.39 (d, J=2.0 Hz, 1H), 8.24 (d, J=0.9 Hz, 1H), 8.09 (dd, J=11.0, 8.6 Hz, 1H), 8.02 (dd, J=9.0, 2.1 Hz, 1H), 7.80 (d, J=9.0 Hz, 1H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 5.61 (s, 2H), 3.80 (bs, 2H), 3.65 (bs, 2H), 3.26 (bs, 2H), 3.12 (bs, 2H).

6-fluoro-7-methoxy-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A147)

(500) ##STR00280##
light beige solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 449. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.24 (s, 1H), 9.09 (s, 2H), 8.77 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 7.83 (d, J=11.6 Hz, 1H), 7.77-7.66 (m, 2H), 7.08 (d, J=7.6 Hz, 1H), 3.93 (s, 3H), 3.74 (bs, 4H), 3.20 (b, 4H).

6-chloro-7-fluoro-3-{1-[4-(piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A148)

(501) ##STR00281##
hydrochloride: beige solid; UPLC/MS 0.49 min, [M+H].sup.+ 453. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.41 (s, 1H), 9.28 (s, 1H), 9.21 (bs, 2H), 8.85 (s, 1H), 8.27 (d, J=8.0 Hz, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.72 (d, J=8.6 Hz, 2H), 7.33 (d, J=10.3 Hz, 1H), 3.36 (bs, 4H), 3.19 (bs, 4H).

Example 10b

Synthesis of A118

(502) To a solution of 4-{4-[4-(7-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (83.0 mg, 0.16 mmol) in formic acid (0.9 ml) is added formaldehyde (37% aqueous solution, 36.5 l, 0.49 mmol) and the reaction mixture is stirred for 2 hours at 80 C. The reaction mixture is concentrated under reduced pressure and treated with saturated NaHCO.sub.3 solution. The resultant precipitate is filtered off, washed with water and dried under vacuum. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 7-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A118) as off-white solid; HPLC/MS 1.19 min (A), [M+H].sup.+ 433.

(503) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.23 (s, 1H), 8.85 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.99 (dd, J=9.5, 6.1 Hz, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.18-7.09 (m, 2H), 3.86-3.32 (m, 4H), 2.35 (bs, 4H), 2.21 (s, 3H).

(504) The following compounds are prepared similarly:

5-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A149)

(505) ##STR00282##
beige solid; HPLC/MS 1.22 min (A), [M+H].sup.+ 433; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.46 (s, 1H), 9.30 (s, 1H), 8.83 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H), 7.58 (td, J=8.2, 6.0 Hz, 1H), 7.26 (d, J=8.3 Hz, 1H), 7.17-7.08 (m, 1H), 3.75-3.30 (m, 4H), 2.35 (bs, 4H), 2.23 (s, 3H).

8-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A150)

(506) ##STR00283##
off-white solid; HPLC/MS 1.17 min (A), [M+H].sup.+ 433; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.28 (s, 1H), 8.88 (d, J=1.5 Hz, 1H), 8.13-8.05 (m, 2H), 7.75 (dd, J=8.0, 1.1 Hz, 1H), 7.66-7.59 (m, 2H), 7.46 (ddd, J=11.1, 8.1, 1.2 Hz, 1H), 7.24 (td, J=8.0, 4.9 Hz, 1H), 3.78-3.30 (m, 4H), 2.44-2.27 (m, 4H), 2.21 (s, 3H).

6-chloro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A151)

(507) ##STR00284##
off-white solid; HPLC/MS 1.31 min (A), [M+H].sup.+ 449; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 8.07 (d, J=2.4 Hz, 1H), 7.63 (d, J=8.5 Hz, 2H), 7.60 (dd, J=9.1, 2.7 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 3.75-3.30 (m, 4H), 2.36 (bs, 4H), 2.23 (s, 3H).

5,7-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A152)

(508) ##STR00285##
beige solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 451; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.54 (s, 1H), 9.28 (s, 1H), 8.77 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.63 (d, J=8.6 Hz, 2H), 7.24 (td, J=10.0, 2.4 Hz, 1H), 7.03 (dt, J=9.8, 1.7 Hz, 1H), 3.72-3.32 (m, 4H), 2.35 (bs, 4H), 2.22 (s, 3H).

6-Fluoro-3-{1-[3-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A153)

(509) ##STR00286##
off-white solid; HPLC/MS 1.20 min (A), [M+H].sup.+ 433; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.30 (s, 1H), 8.84 (s, 1H), 8.10 (ddd, J=8.1, 2.3, 1.0 Hz, 1H), 8.02 (t, J=1.8 Hz, 1H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.68 (t, J=7.9 Hz, 1H), 7.50 (dt, J=7.6, 1.3 Hz, 1H), 7.49-7.39 (m, 2H), 3.75-3.30 (m, 4H), 2.45-2.25 (m, 4H), 2.21 (s, 3H).

7-chloro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A154)

(510) ##STR00287##
white solid; HPLC/MS 1.27 min (A), [M+H].sup.+ 449; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.26 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.96 (d, J=8.5 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 7.42 (d, J=2.0 Hz, 1H), 7.30 (dd, J=8.4, 2.0 Hz, 1H), 3.70-3.30 (m, 4H), 2.35 (bs, 4H), 2.22 (s, 3H).

6-fluoro-3-{1-[4-(4-methyl-[1,4]diazepan-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-[1,8]naphthyridin-2-one (A155)

(511) ##STR00288##
brown solid; HPLC/MS 1.18 min (A), [M+H].sup.+ 420; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.64 (s, 1H), 9.02 (s, 1H), 8.74 (s, 1H), 8.55 (d, J=2.9 Hz, 1H), 8.22 (dd, J=8.8, 3.0 Hz, 1H), 7.68 (d, J=9.0 Hz, 2H), 6.86 (d, J=9.2 Hz, 2H), 3.63-3.54 (m, 2H), 3.50 (t, J=6.2 Hz, 2H), 2.71-2.58 (m, 2H), 2.49-2.45 (m, 2H), 2.27 (s, 3H), 1.92 (p, J=5.9 Hz, 3H).

5,6-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A156)

(512) ##STR00289##
white solid; HPLC/MS 1.21 min (A), [M+H].sup.+ 451; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.48 (s, 1H), 9.31 (s, 1H), 8.81 (s, 1H), 8.13-8.06 (m, 2H), 7.72-7.60 (m, 3H), 7.23 (ddd, J=9.3, 3.9, 1.6 Hz, 1H), 3.64 (bs, 4H), 2.36 (bs, 4H), 2.23 (s, 3H).

6,7-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A157)

(513) ##STR00290##
white solid; UPLC/MS 0.49 min, [M+H].sup.+ 451; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.92 (bs, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.17-8.12 (m, 2H), 8.09 (dd, J=10.9, 8.6 Hz, 1H), 7.75-7.67 (m, 2H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 4.44 (bs, 2H), 3.7 (bs, 2H), 3.18 (bs, 4H), 2.81 (s, 3H).

6-fluoro-3-{1-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A158)

(514) ##STR00291##
beige powder; UPLC/MS 0.50 min, [M+H].sup.+ 469; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.31 (s, 1H), 9.39 (s, 1H), 8.87 (s, 1H), 8.51-8.15 (m, 2H), 8.14-7.90 (m, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.62-7.33 (m, 2H), 2.98 (t, J=4.9 Hz, 4H), 2.38 (t, J=4.9 Hz, 4H), 2.15 (s, 3H).

6,7-difluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A159)

(515) ##STR00292##
brown solid; HPLC/MS 1.25 min (A), [M+H].sup.+ 467; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.09 (s, 1H), 8.78 (s, 1H), 8.03 (dd, J=11.0, 8.6 Hz, 1H), 7.92-7.81 (m, 2H), 7.30 (dd, J=11.5, 7.1 Hz, 1H), 7.21-7.08 (m, 2H), 4.16 (t, J=5.8 Hz, 2H), 2.72 (t, J=5.8 Hz, 2H), 2.50 (m, 4H), 2.32 (m, 4H), 2.15 (s, 3H).

6-fluoro-3-(1-{4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A160)

(516) ##STR00293##
off-white powder; HPLC/MS 1.20 min (A), [M+H].sup.+ 463; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.10 (s, 1H), 8.81 (s, 1H), 7.91-7.84 (m, 2H), 7.78 (dd, J=9.3, 2.6 Hz, 1H), 7.48-7.38 (m, 2H), 7.18-7.06 (m, 2H), 4.09 (t, J=6.4 Hz, 2H), 2.43 (t, J=7.1 Hz, 2H), 2.42-2.26 (m, 8H), 2.15 (s, 3H), 1.89 (p, J=6.7 Hz, 2H).

6-fluoro-3-{1-[4-(1-methyl-piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A161)

(517) ##STR00294##
light beige solid; HPLC/MS 1.24 min (A), [M+H].sup.+ 432.

6,7-difluoro-3-(1-{4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A162)

(518) ##STR00295##
light brown powder; HPLC/MS 1.23 min (A), [M+H].sup.+ 481. .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.09 (s, 1H), 8.79 (s, 1H), 8.04 (dd, J=11.0, 8.6 Hz, 1H), 7.87 (d, J=9.0 Hz, 2H), 7.30 (dd, J=11.5, 7.1 Hz, 1H), 7.13 (d, J=9.0 Hz, 2H), 4.09 (t, J=6.4 Hz, 2H), 2.43 (t, J=7.1 Hz, 2H), 2.45-2.24 (m, 8H), 2.15 (s, 3H), 1.89 (p, J=6.7 Hz, 2H).

6-fluoro-3-(1-{4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A163)

(519) ##STR00296##
off-white solid; HPLC/MS 1.72 min (A), [M+H].sup.+ 448.

6,7-difluoro-3-{1-[4-(1-methyl-piperidine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A164)

(520) ##STR00297##
formate; brown solid; UPLC/MS 0.77 min, [M+H].sup.+ 450.

6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A165)

(521) ##STR00298##
beige solid; UPLC/MS 0.84 min, [M+H].sup.+ 463.

6,7-difluoro-3-(1-{4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A166)

(522) ##STR00299##
formate: beige solid; HPLC/MS 1.35 min (A), [M+H].sup.+ 466. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.08 (s, 1H), 8.81 (s, 1H), 8.30 (s, 1H, formate), 8.07 (dd, J=11.0, 8.6 Hz, 1H), 7.95-7.73 (m, 2H), 7.32 (dd, J=11.5, 7.1 Hz, 1H), 7.20-7.03 (m, 2H), 4.09 (t, J=6.6 Hz, 2H), 2.82-2.76 (m, 2H), 2.18 (s, 3H), 1.92 (td, J=11.7, 2.6 Hz, 2H), 1.65-1.72 (m, 4H), 1.50-1.40 (m, 1H), 1.25 (qd, J=12.1, 3.8 Hz, 2H).

6,7-difluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A167)

(523) ##STR00300##
formate: beige solid; UPLC/MS 0.86 min, [M+H].sup.+ 481.

6-methyl-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A168)

(524) ##STR00301##
off-white solid; HPLC/MS 1.22 min (A), [M+H].sup.+ 429. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.14 (s, 1H), 9.25 (s, 1H), 8.77 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.69 (s, 1H), 7.63 (d, J=8.6 Hz, 2H), 7.40 (dd, J=8.4, 1.9 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 3.64 (bs, 2H), 3.40 (bs, 2H), 2.39 (s, 3H), 2.36 (bs, 4H), 2.22 (s, 3H).

6,7-difluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A169)

(525) ##STR00302##
beige solid; UPLC/MS 0.97 min, [M+H].sup.+ 465. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.17 (s, 1H), 8.84 (s, 1H), 8.08 (dd, J=11.0, 8.5 Hz, 1H), 8.00-7.87 (m, 2H), 7.57-7.41 (m, 2H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 3.83 (s, 2H), 3.51 (dt, J=15.5, 5.0 Hz, 4H), 2.27 (t, J=5.1 Hz, 4H), 2.18 (s, 3H).

3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-trifluoromethyl-1H-quinolin-2-one (A170)

(526) ##STR00303##
beige solid; UPLC/MS 0.92 min, [M+H].sup.+ 483. .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.48 (s, 1H), 9.32 (s, 1H), 8.95 (s, 1H), 8.17 (d, J=8.2 Hz, 1H), 8.13-8.07 (m, 2H), 7.72 (s, 1H), 7.66-7.61 (m, 2H), 7.57 (dd, J=8.3, 1.7 Hz, 1H), 3.73-3.34 (m, 4H), 2.34 (bs, 4H), 2.23 (s, 3H).

3-{1-[4-(4-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A171)

(527) ##STR00304##
beige solid; UPLC/MS 0.86 min, [M+H].sup.+ 479.

3-{1-[4-(4-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A172)

(528) ##STR00305##
beige solid; UPLC/MS 0.83 min, [M+H].sup.+ 461.

6,7-difluoro-3-(1-{1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-indazol-5-yl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A173)

(529) ##STR00306##
trifluoroacetate: brown solid; UPLC/MS 0.48 min, [M+H].sup.+ 505. H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.87 (s, 1H), 9.21 (s, 1H), 8.85 (s, 1H), 8.39 (d, J=1.9 Hz, 1H), 8.24 (d, J=0.8 Hz, 1H), 8.09 (dd, J=11.0, 8.6 Hz, 1H), 8.02 (dd, J=9.0, 2.1 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 5.63 (bs, 2H), 4.5-4.1 (m, 2H), 3.6-2.9 (m, 6H), 2.86 (s, 3H).

6,7-difluoro-3-{1-[4-(4-methyl-2-oxo-piperazin-1-yl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A174)

(530) ##STR00307##
beige solid; HPLC/MS 1.22 min (A), [M+H].sup.+ 437. H NMR (400 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.21 (s, 1H), 8.83 (s, 1H), 8.08 (dd, J=11.0, 8.6 Hz, 1H), 8.05-8.00 (m, 2H), 7.62-7.55 (m, 2H), 7.33 (dd, J=11.5, 7.0 Hz, 1H), 3.78-3.71 (m, 2H), 3.16 (s, 2H), 2.77 (t, J=5.4 Hz, 2H), 2.31 (s, 3H).

6-fluoro-3-{1-[4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A367)

(531) ##STR00308##

(532) HPLC/MS 1.23 min (A), [M+H].sup.+ 406;

(533) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.10 (s, 1H), 8.82 (s, 1H), 7.98-7.85 (m, 2H), 7.80 (dd, J=9.3, 2.6 Hz, 1H), 7.53-7.36 (m, 2H), 7.17-7.02 (m, 2H), 5.05-4.93 (m, 1H), 2.81 (dd, J=10.4, 6.0 Hz, 1H), 2.74-2.63 (m, 2H), 2.42-2.30 (m, 2H), 2.28 (s, 3H), 1.87-1.76 (m, 1H).

6-chloro-3-{1-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A368)

(534) ##STR00309##

(535) HPLC/MS 1.31 min (A), [M+H].sup.+ 422;

(536) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.10 (s, 1H), 8.81 (s, 1H), 8.05 (d, J=2.3 Hz, 1H), 7.87 (d, J=8.9 Hz, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.09 (d, J=8.9 Hz, 2H), 5.01-4.93 (m, 1H), 2.81 (dd, J=10.5, 6.0 Hz, 1H), 2.76-2.63 (m, 2H), 2.43-2.29 (m, 2H), 2.29 (s, 3H), 1.90-1.74 (m, 1H).

6-chloro-3-{1-[4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A369)

(537) ##STR00310##

(538) HPLC/MS 1.30 min (A), [M+H].sup.+ 422;

(539) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.30 (s, 1H), 9.10 (s, 1H), 8.82 (s, 1H), 8.16 (s, 1H, formate-H), 8.05 (d, J=2.4 Hz, 1H), 7.87 (d, J=9.0 Hz, 2H), 7.59 (dd, J=8.8, 2.3 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.15-7.04 (m, 2H), 5.06-4.91 (m, 1H), 2.90-2.65 (m, 3H), 2.47-2.26 (m, 5H), 1.88-1.77 (m, 1H).

6-fluoro-3-{1-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A370)

(540) ##STR00311##

(541) HPLC/MS 1.22 min (A), [M+H].sup.+ 406;

(542) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.11 (s, 1H), 8.82 (s, 1H), 8.16 (s, 1H, formate-H), 7.92-7.85 (m, 2H), 7.80 (dd, J=9.3, 2.6 Hz, 1H), 7.50-7.38 (m, 2H), 7.14-7.06 (m, 2H), 5.03-4.92 (m, 1H), 2.93-2.63 (m, 3H), 2.45-2.23 (m, 5H), 1.88-1.77 (m, 1H).

6-fluoro-3-{1-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A371)

(543) ##STR00312##

(544) UPLC/MS 0.52 min, [M+H].sup.+ 418;

(545) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.11 (s, 1H), 8.76 (s, 1H), 7.89-7.78 (m, 2H), 7.60 (dd, J=9.1, 2.8 Hz, 1H), 7.41 (dd, J=9.0, 4.7 Hz, 1H), 7.35 (d, J=8.6 Hz, 2H), 7.29 (td, J=8.8, 2.9 Hz, 1H), 3.38 (d, J=12.2 Hz, 2H), 2.90-3.74 (m, 2H), 2.70 (s, 3H), 2.61 (d, J=6.6 Hz, 2H), 1.85-1.73 (m, 3H), 1.41 (q, J=12.3, 11.9 Hz, 2H).

6,7-difluoro-3-{1-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A372)

(546) ##STR00313##

(547) UPLC/MS 0.50 min, [M+H].sup.+ 424;

(548) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 10.25 (s, 1H, NH.sup.+), 9.13 (s, 1H), 8.82 (s, 1H), 8.08 (dd, J=10.8, 8.5 Hz, 1H), 7.98-7.90 (m, 2H), 7.33 (dd, J=11.3, 7.0 Hz, 1H), 7.25-7.12 (m, 2H), 5.28 (bs, 1H), 4.2-3.1 (m, 4H), 2.93 (s, 3H), 2.8-2.0 (m, 2H).

6,7-difluoro-3-{1-[4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A373)

(549) ##STR00314##

(550) UPLC/MS 0.50 min, [M+H].sup.+ 424;

(551) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 10.25 (s, 1H, NH.sup.+), 9.13 (s, 1H), 8.82 (s, 1H), 8.08 (dd, J=10.8, 8.5 Hz, 1H), 7.98-7.90 (m, 2H), 7.33 (dd, J=11.3, 7.0 Hz, 1H), 7.25-7.12 (m, 2H), 5.28 (bs, 1H), 4.2-3.1 (m, 4H), 2.93 (s, 3H), 2.8-2.0 (m, 2H).

6-chloro-3-{1-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A374)

(552) ##STR00315##

(553) UPLC/MS 0.55 min, [M+H].sup.+ 434;

(554) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.18 (s, 1H), 8.83 (s, 1H), 8.06 (d, J=2.4 Hz, 1H), 8.03-7.89 (m, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.47-7.39 (m, 3H), 3.44-3.26 (m, 2H), 2.96-2.81 (m, 2H), 2.74 (s, 3H), 2.71-2.61 (m, 2H), 1.87-1.73 (m, 3H), 1.49-1.30 (m, 2H).

6-fluoro-3-{1-[4-(1-methyl-piperidin-4-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A375)

(555) ##STR00316##

(556) HPLC/MS 1.28 min (A), [M+H].sup.+ 420;

(557) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.10 (s, 1H), 8.82 (s, 1H), 7.93-7.83 (m, 2H), 7.79 (dd, J=9.2, 2.6 Hz, 1H), 7.51-7.38 (m, 2H), 7.16 (d, J=9.0 Hz, 1H), 4.48 (tt, J=8.2, 4.0 Hz, 1H), 2.67-2.58 (m, 2H), 2.31-2.14 (m, 5H), 2.04-1.92 (m, 2H), 1.74-1.62 (m, 2H).

6-chloro-3-{1-[4-(1-methyl-piperidin-4-yloxy)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A376)

(558) ##STR00317##

(559) HPLC/MS 1.36 min (A), [M+H].sup.+ 436;

(560) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.10 (s, 1H), 8.81 (s, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.91-7.74 (m, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.7 Hz, 1H), 7.22-7.00 (m, 2H), 4.48 (tt, J=8.3, 3.9 Hz, 1H), 2.71-2.58 (m, 2H), 2.22-2.17 (m, 5H), 2.00-1.94 (m, 2H), 1.71-1.64 (m, 2H).

Example 11

6-Fluoro-3-(1-{4-[4-(2-methoxy-ethyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-[1,8]naphthyridin-2-one (A175)

(561) ##STR00318##
beige solid; HPLC/MS 1.12 min (A), [M+H].sup.+ 478; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.72 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.61 (d, J=2.9 Hz, 1H), 8.35 (dd, J=8.7, 3.0 Hz, 1H), 8.09 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 3.62 (bs, 2H), 3.45 (t, J=5.7 Hz, 2H), 3.36 (bs, 2H), 3.24 (s, 3H), 2.55-2.40 (m, 6H).

Example 12

6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A176)

(562) ##STR00319##

(563) A suspension of 6-fluoro-3-[1-(4-methoxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (211 mg, 0.63 mmol, prepared in analogy to example 1) in dichloromethane (6 ml) is cooled to 78 C. and boron tribromide (9.38 ml of a 1 M solution in dichloromethane, 9.38 mmol) is added. The mixture is allowed to reach room temperature and is stirred for 18 hours. To the reaction mixture is added saturated aqueous NaHCO.sub.3 solution. The insoluble solid that has formed is filtered off, washed with dichloromethane and water and dried under vacuum to afford 6-fluoro-3-[1-(4-hydroxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one as grey solid; UPLC/MS 0.68 min, [M+H].sup.+ 323.

(564) To a suspension of 6-fluoro-3-[1-(4-hydroxy-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (203 mg, 0.63 mmol) in THF (2 ml) are added sequentially triphenylphosphine (198 mg, 0.76 mmol), 2-(4-methyl-piperazin-1-yl)-ethanol (109 mg, 0.76 mmol) and diisopropylazodicarboxylate (148 l, 0.76 mmol). The reaction mixture is stirred for 18 hours at room temperature. Triphenylphosphine (198 mg, 0.76 mmol) and diisopropylazodicarboxylate (148 l, 0.76 mmol) are added and the reaction mixture is stirred for 55 hours at room temperature. The reaction mixture is evaporated and treated with methanol. The insoluble solid is collected and purified by preparative HPLC to afford 6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one as white solid. UPLC/MS 0.49 min, [M+H].sup.+ 449.

(565) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.25 (s, 1H), 9.11 (s, 1H), 8.82 (s, 1H), 7.93-7.85 (m, 2H), 7.79 (dd, J=9.2, 2.6 Hz, 1H), 7.51-7.38 (m, 2H), 7.20-7.10 (m, 2H), 4.16 (t, J=5.8 Hz, 2H), 2.72 (t, J=5.8 Hz, 2H), 2.50 (bs, 4H), 2.33 (bs, 4H), 2.15 (s, 3H).

Example 13

3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-2-oxo-1,2-dihydro-quinoline-7-carbonitrile (A177)

(566) ##STR00320##

(567) A reaction vial is charged with 7-bromo-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (250 mg, 0.52 mmol), N-methyl-pyrrolidone (2.5 ml) and copper(I) cyanide (56.1 mg, 0.63 mmol). The reaction vial is flushed with nitrogen, closed and heated to 170. The reaction mixture is stirred in the closed reaction vial at this temperature for 8 hours. The reaction mixture is allowed to reach room temperature and treated with water. The insoluble solids are filtered off, washed with water and dried under vacuum. The residue is purified by preparative HPLC to afford 3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-2-oxo-1,2-dihydro-quinoline-7-carbonitrile as beige solid. HPLC/MS 1.42 min (A), [M+H].sup.+ 427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.48 (s, 1H), 9.34 (s, 1H), 8.94 (s, 1H), 8.18-8.08 (m, 3H), 7.76-7.73 (m, 1H), 7.71-7.63 (m, 3H), 3.74-3.34 (m, 6H).

Example 14

6-fluoro-3-(1-{1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-indol-5-yl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A178)

(568) ##STR00321##
beige solid; HPLC/MS 1.23 min (A), [M+H].sup.+ 486; .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.25 (s, 1H), 9.13 (s, 1H), 8.85 (s, 1H), 8.12 (d, J=2.1 Hz, 1H), 7.81 (dd, J=9.2, 2.4 Hz, 1H), 7.69 (dd, J=8.7, 2.1 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.52-7.38 (m, 3H), 6.62 (d, J=3.2 Hz, 1H), 5.29 (bs, 2H), 3.64 (bs, 2H), 3.52 (bs, 2H), 2.57 (bs, 2H), 2.45 (bs, 2H), 2.33 (s, 3H).

Example 15

acetic acid (R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidin-3-yl ester (A179)

(569) ##STR00322##

(570) To a suspension of {1-[4-((R)-3-hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid (94.9 mg, 0.30 mmol) and 2-amino-5-fluoro-benzaldehyde (41.7 mg, 0.3 mmol) in acetic acid anhydride (1 ml) is added triethylamine (166 l, 1.2 mmol) and the reaction mixture is stirred for 30 minutes at 80 C. The reaction mixture is allowed to reach room temperature and concentrated under vacuum. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford acetic acid (R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidin-3-yl ester as off-white solid; HPLC/MS 1.49 min (A), [M+H].sup.+ 462.

(571) .sup.1H NMR (400 MHz, DMSO-d.sub.6): 1:1 mixture of rotamers, selection of peaks: 12.27 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.86-7.73 (m, 3H), 7.51-7.39 (m, 2H), 2.06 (s, rotamer1), 1.99 (s, rotamer2).

acetic acid (S)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidin-3-yl ester (A180)

(572) ##STR00323##
is prepared similarly: off-white solid; HPLC/MS 1.49 min (A), [M+H].sup.+ 462. H NMR (400 MHz, DMSO-d6): 1:1 mixture of rotamers, selection of peaks: 12.27 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.86-7.73 (m, 3H), 7.51-7.39 (m, 2H), 2.06 (s, rotamer1), 1.99 (s, rotamer2).

Example 16

6-fluoro-3-{1-[4-((R)-3-hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A181)

(573) ##STR00324##

(574) To a solution of acetic acid (R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidin-3-yl ester (94.9 mg, 0.30 mmol) and 2-amino-5-fluorobenzaldehyde (21.9 mg, 0.05 mmol) in methanol (1 ml) is added 1 M sodium hydroxide solution (1 ml) and the reaction mixture is stirred for 3 hours at room temperature. The reaction mixture is concentrated under vacuum and the residue is treated with water. The resultant precipitate is filtered off, washed with water and dried under vacuum to afford 6-fluoro-3-{1-[4-((R)-3-hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as off-white solid; HPLC/MS 1.34 min (A), [M+H].sup.+ 420.

(575) .sup.1H NMR (400 MHz, DMSO-d.sub.6): 1:1 mixture of rotamers, selection of peaks: 12.26 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.15-8.03 (m, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.75 (m, 2H), 7.52-7.37 (m, 2H), 5.02 (d, J=3 Hz, rotamer1), 4.96 (d, J=3.1 Hz, rotamer2), 4.35 (bs, rotamer1), 4.27 (bs, rotamer2).

(576) The following compounds are prepared similarly:

6-fluoro-3-{1-[4-((S)-3-hydroxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A182)

(577) ##STR00325##
off-white solid; HPLC/MS 1.34 min (A), [M+H].sup.+ 420; .sup.1H NMR (400 MHz, DMSO-d.sub.6): 1:1 mixture of rotamers, selection of peaks: 12.26 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.15-8.03 (m, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.75 (m, 2H), 7.52-7.37 (m, 2H), 5.02 (d, J=3 Hz, rotamer1), 4.96 (d, J=3.1 Hz, rotamer2), 4.35 (bs, rotamer1), 4.27 (bs, rotamer2).

6-fluoro-3-{1-[4-(4-hydroxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A183)

(578) ##STR00326##
off-white solid; HPLC/MS 1.36 min (A), [M+H].sup.+ 434; .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.34 (s, 1H), 8.91 (s, 1H), 8.21-8.00 (m, 2H), 7.86 (dd, J=9.3, 2.8 Hz, 1H), 7.74-7.60 (m, 2H), 7.59-7.39 (m, 2H), 4.85 (d, J=3.9 Hz, 1H), 4.08 (bs, 1H), 3.83 (tq, J=8.0, 3.8 Hz, 1H), 3.59 (bs, 1H), 3.29 (bs, 2H), 1.84 (m, 2H), 1.46 (m, 2H).

6-fluoro-3-{1-[4-(3-hydroxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A184)

(579) ##STR00327##
beige solid; HPLC/MS 1.40 min (A), [M+H].sup.+ 434.

Example 17

4-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A185)

(580) ##STR00328##

(581) To a suspension of {1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-acetic acid (94.9 mg, 0.30 mmol) and 1-(2-amino-phenyl)-ethanone (40.6 mg, 0.3 mmol) in acetic acid anhydride (1 ml) is added triethylamine (166 l, 1.2 mmol) and the reaction mixture is stirred for 5 hours at 100 C. The reaction mixture is allowed to reach room temperature and water is added. The solids are filtered off and partially dissolved in a small amount of DMSO. Methanol is added. The solid is filtered off, washed with methanol and dried under vacuum to afford 4-methyl-3-{1-[4-(morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as brown powder; UPLC/MS 0.87 min, [M+H].sup.+ 416.

(582) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 11.98 (s, 1H), 9.10 (s, 1H), 8.20-8.03 (m, 2H), 7.91 (dd, J=8.3, 1.3 Hz, 1H), 7.76-7.63 (m, 2H), 7.57 (ddd, J=8.3, 7.1, 1.3 Hz, 1H), 7.38 (dd, J=8.2, 1.2 Hz, 1H), 7.27 (ddd, J=8.3, 7.1, 1.2 Hz, 1H), 3.70-3.35 (m, 8H), 2.65 (s, 3H).

Example 18

6-fluoro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A186)

(583) ##STR00329##

(584) To a suspension of copper(II) sulfate pentahydrate (449 mg, 1.80 mmol) and sodium (2R)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxy-ethanolate hydrate (389 mg, 1.80 mmol) in a mixture of tert-butanol (20 ml) and water (20 ml) are added 3-butynoic acid (1.51 g, 18.0 mmol) and 4-azido-benzoic acid methyl ester (3.19 g, 18.0 mmol). The reaction mixture is stirred at 80 C. for 3 hours. The reaction mixture is allowed to reach room temperature and poured into water. The resultant precipitate is filtered off, washed with water and dried under vacuum to afford 4-(4-carboxymethyl-[1,2,3]triazol-1-yl)-benzoic acid methyl ester as beige solid; UPLC/MS 0.55 min, [M+H].sup.+ 262.

(585) To a suspension of 4-(4-carboxymethyl-[1,2,3]triazol-1-yl)-benzoic acid methyl ester (1.23 g, 4.70 mmol) and 2-amino-5-fluoro-benzaldehyde (654 mg, 4.70 mmol) in acetic acid anhydride (4 ml) is added triethylamine (2.61 ml, 18.8 mmol) and the reaction mixture is stirred for 30 minutes at 80 C. The reaction mixture is diluted cautiously with methanol. The solid is filtered off, washed with tert-butyl methyl ether and dried under vacuum to afford 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid methyl ester as beige solid; UPLC/MS 0.80 min, [M+H].sup.+ 365.

(586) To a suspension of 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid methyl ester (1.24 g, 3.30 mmol) in methanol (30 ml) is added aqueous 2 M sodium hydroxide solution (8.25 ml, 16.5 mmol) and the reaction mixture is stirred for 2 hours at 80 C. The reaction mixture is allowed to reach room temperature and is filtered. The solid residue is triturated with excess 0.5 N hydrochloric acid. The solid is filtered off, washed with water and acetonitrile and dried under vacuum to afford 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid as beige solid; UPLC/MS 0.70 min, [M+H].sup.+ 351.

(587) To a suspension of 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoic acid (35.0 mg, 0.10 mmol) in a mixture of 1,4-dioxane (0.5 ml) and DMF (0.5 ml) are added (R)-2-methylpyrrolidine p-toluenesulfonate (30.9 mg, 0.12 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (28.8 mg, 0.15 mmol), 1-hydroxybenotriazole hydrate (13.5 mg, 0.10 mmol) and 4-methylmorpholine (16.5 l, 0.15 mmol). The resultant suspension is stirred at room temperature for 5 hours. The reaction mixture is poured into water. The resultant precipitate is filtered off, washed with water and dried. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 6-fluoro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one as white crystals; HPLC/MS 1.59 min (A), [M+H].sup.+ 418.

(588) .sup.1H NMR (500 MHz, DMSO-d.sub.6), mixture of rotamers; main rotamer: 12.31 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.26-7.95 (m, 2H), 7.82 (dd, J=9.2, 2.8 Hz, 1H), 7.73 (d, J=8.1 Hz, 2H), 7.47 (td, J=8.8, 2.8 Hz, 1H), 7.43 (dd, J=9.0, 4.9 Hz, 1H), 4.25-4.14 (m, 1H), 3.57-3.51 (m, 1H), 3.37-3.32 (m, 1H), 2.10 (dq, J=13.4, 6.8 Hz, 1H), 1.99-1.84 (m, 1H), 1.79-1.68 (m, 1H), 1.64-1.53 (m, 1H), 1.29 (d, J=6.2 Hz, 3H).

(589) The following compounds are prepared similarly:

N-(2-diethylamino-ethyl)-4-[4-(6,7-difluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A187)

(590) ##STR00330##

(591) HPLC/MS 1.27 min (A), [M+H].sup.+ 467;

(592) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.33 (s, 1H), 8.86 (s, 1H), 8.20 (d, J=8.9 Hz, 2H), 8.15 (d, J=8.8 Hz, 2H), 7.95 (dd, J=10.8, 8.5 Hz, 1H), 7.37 (dd, J=11.4, 7.0 Hz, 1H), 3.73 (t, J=6.3 Hz, 2H), 3.36 (t, J=6.3 Hz, 2H), 3.30 (qd, J=7.0, 3.8 Hz, 4H), 1.29 (t, J=7.3 Hz, 6H).

4-[4-(7-chloro-6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(2-diethylamino-ethyl)-benzamide (A188)

(593) ##STR00331##

(594) HPLC/MS 1.36 min (A), [M+H].sup.+ 483;

(595) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.28 (s, 1H), 8.81 (s, 1H), 8.14 (d, J=8.8 Hz, 2H), 8.08 (d, J=8.8 Hz, 2H), 7.87 (d, J=9.6 Hz, 1H), 7.52 (d, J=6.5 Hz, 1H), 3.65 (t, J=6.3 Hz, 2H), 3.29 (t, J=6.5 Hz, 2H), 3.22 (qd, J=6.9, 3.5 Hz, 3H), 1.22 (t, J=7.2 Hz, 6H).

3-(1-{4-[4-(2-diethylamino-ethyl)-piperazine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-6,7-difluoro-1H-quinolin-2-one (A189)

(596) ##STR00332##

(597) UPLC/MS 0.48 min, [M+H].sup.+ 534;

(598) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.24 (s, 1H), 8.80 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.90 (dd, J=10.8, 8.4 Hz, 1H), 7.69 (d, J=8.6 Hz, 2H), 7.31 (dd, J=11.3, 7.1 Hz, 1H), 4.0-3.6 (m, 4H), 3.63-3.55 (m, 2H), 3.52 (dt, J=10.0, 3.3 Hz, 2H), 3.5-3.35 (m, 4H), 3.20 (q, J=7.2 Hz, 4H), 1.22 (t, J=7.3 Hz, 6H).

6-fluoro-3-{1-[4-(4-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A190)

(599) ##STR00333##

(600) UPLC/MS 0.70 min, [M+H].sup.+ 448;

(601) 1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.13-8.01 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.69-7.58 (m, 2H), 7.47 (dd, J=9.0, 2.7 Hz, 1H), 7.45-7.39 (m, 1H), 4.1-3.8 (m, 1H), 3.65-3.41 (m, 2H), 3.27 (s, 3H), 3.4-3.1 (m, 2H), 1.87 (bs, 2H), 1.48 (bs, 2H).

6,7-difluoro-3-{1-[4-(4-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A191)

(602) ##STR00334##

(603) UPLC/MS 0.73 min, [M+H].sup.+ 466;

(604) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.25 (s, 1H), 8.84 (s, 1H), 8.29-7.99 (m, 3H), 7.76-7.58 (m, 2H), 7.32 (dd, J=11.4, 7.1 Hz, 1H), 4.1-3.8 (m, 1H), 3.65-3.41 (m, 2H), 3.27 (s, 3H), 3.4-3.1 (m, 2H), 1.87 (bs, 2H), 1.48 (bs, 2H).

6,7-difluoro-3-{1-[4-((R)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A192)

(605) ##STR00335##

(606) HPLC/MS 1.56 min (A), [M+H].sup.+ 466;

(607) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.13-8.04 (m, 3H), 7.61 (d, J=8.0 Hz, 2H), 7.32 (dd, J=11.4, 7.1 Hz, 1H), 4.0-3-6 (m, 1H), 3.5-3.0 (m, 7H), 2.0-1.35 (m, 4H).

6,7-difluoro-3-{1-[4-((S)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A193)

(608) ##STR00336##

(609) HPLC/MS 1.56 min (A), [M+H].sup.+ 466;

(610) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.13-8.04 (m, 3H), 7.61 (d, J=8.0 Hz, 2H), 7.32 (dd, J=11.4, 7.1 Hz, 1H), 4.0-3.6 (m, 1H), 3.5-3.0 (m, 7H), 2.0-1.35 (m, 4H).

6-fluoro-3-{1-[4-((R)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A194)

(611) ##STR00337##

(612) HPLC/MS 1.52 min (A), [M+H].sup.+ 448.

(613) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.18-8.04 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.65-7.55 (m, 2H), 7.52-7.37 (m, 2H), 4.0-3.6 (m, 1H), 3.5-3.0 (m, 7H), 2.01-1.34 (m, 4H).

6-fluoro-3-{1-[4-((S)-3-methoxy-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A195)

(614) ##STR00338##

(615) HPLC/MS 1.52 min (A), [M+H].sup.+ 448;

(616) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.18-8.04 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.65-7.55 (m, 2H), 7.52-7.37 (m, 2H), 4.0-3.6 (m, 1H), 3.5-3.0 (m, 7H), 2.01-1.34 (m, 4H).

N-(2-diethylamino-ethyl)-4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A196)

(617) ##STR00339##

(618) HPLC/MS 1.23 min (A), [M+H].sup.+ 449;

(619) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.55 (t, J=5.7 Hz, 1H), 8.14 (d, J=8.8 Hz, 2H), 8.06 (d, J=8.8 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.56-7.36 (m, 2H), 3.38-3.32 (m, 2H), 2.61-2.50 (m, 6H), 0.98 (t, J=7.1 Hz, 6H).

6-fluoro-3-{1-[4-((S)-2-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A197)

(620) ##STR00340##

(621) MS [M+H].sup.+ 434;

(622) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.75 (d, J=8.1 Hz, 2H), 7.51-7.39 (m, 2H), 4.88-4.68 (m, 1H), 4.18 (br. s, 0,7H), 3.91 (br. s, 0,3H), 3.71-3.54 (m, 2H), 3.54-3.43 (m, 1H), 3.37 (br. s, 0,7H), 3.11 (br. s, 0,3H), 2.04-1.84 (m, 3H), 1.80-1.65 (m, 1H).

6-fluoro-3-{1-[4-((R)-2-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A198)

(623) ##STR00341##

(624) MS [M+H].sup.+ 448:

(625) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.2 Hz, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.72 (d, J=8.2 Hz, 2H), 7.53-7.35 (m, 2H), 4.37-4.23 (m, 1H), 3.68-3.56 (m, 1H), 3.48 (t, J=8.5 Hz, 2H), 3.33 (s, 3H), 3.11-2.97 (m, 1H), 2.09-1.96 (m, 1H), 1.96-1.82 (m, 2H), 1.81-1.68 (m, 1H).

6-fluoro-3-{1-[4-((R)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A199)

(626) ##STR00342##

(627) HPLC/MS 1.51 min (A), [M+H].sup.+ 448;

(628) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.11-8.05 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.70 (m, 2H), 7.51-7.37 (m, 2H), 3.69-3.57 (m, 1H), 3.58-3.44 (m, 2H), 3.41-3.17 (m, 6H), 2.55-2.40 (m, 1H), 2.05-1.90 (m, 1H), 1.72-1.60 (m, 1H).

6,7-difluoro-3-{1-[4-((R)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A200)

(629) ##STR00343##

(630) HPLC/MS 1.55 min (A), [M+H].sup.+ 466;

(631) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.25 (s, 1H), 8.83 (s, 1H), 8.10-8-04 (m, 3H), 7.77-7.72 (m, 2H), 7.32 (dd, J=11.4, 7.0 Hz, 1H), 3.69-3.57 (m, 1H), 3.58-3.44 (m, 2H), 3.42-3.46 (m, 1H), 3.36-3.19 (m, 5H), 2.55-2.40 (m, 1H), 2.05-1.90 (m, 1H), 1.72-1.60 (m, 1H).

6,7-difluoro-3-{1-[4-((S)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A201)

(632) ##STR00344##

(633) HPLC/MS 1.55 min (A), [M+H].sup.+ 466;

(634) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.25 (s, 1H), 8.83 (s, 1H), 8.10-8-04 (m, 3H), 7.77-7.72 (m, 2H), 7.32 (dd, J=11.4, 7.0 Hz, 1H), 3.69-3.57 (m, 1H), 3.58-3.44 (m, 2H), 3.42-3.46 (m, 1H), 3.36-3.19 (m, 5H), 2.55-2.40 (m, 1H), 2.05-1.90 (m, 1H), 1.72-1.60 (m, 1H).

6-fluoro-3-{1-[4-((S)-3-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A202)

(635) ##STR00345##

(636) HPLC/MS 1.51 min (A), [M+H].sup.+ 448.

(637) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.11-8.05 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.70 (m, 2H), 7.51-7.37 (m, 2H), 3.69-3.57 (m, 1H), 3.58-3.44 (m, 2H), 3.41-3.17 (m, 6H), 2.55-2.40 (m, 1H), 2.05-1.90 (m, 1H), 1.72-1.60 (m, 1H).

3-(1-{4-[3-(2-diethylamino-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-6-fluoro-1H-quinolin-2-one (A203)

(638) ##STR00346##

(639) MS [M+H].sup.+ 519;

(640) .sup.1H NMR (400 MHz, DMSO-d.sub.6)) mixture of 2 rotamers 12.27 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.3 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.75 (d, J=8.6 Hz, 2H), 7.51-7.39 (m, 2H), 4.16 (s, 0,4H), 4.07 (s, 0,6H), 3.64 (td, J=13.1, 12.2, 4.6 Hz, 1H), 3.53 (dt, J=23.1, 6.6 Hz, 2H), 3.44-3.37 (m, 3H), 2.57 (t, J=6.2 Hz, 1H), 2.42 (q, J=7.1 Hz, 2H), 2.05-1.91 (m, 2H), 0.96 (t, J=7.1 Hz, 3H), 0.88 (t, J=7.1 Hz, 3H).

6-fluoro-3-{1-[4-(2-oxa-7-aza-spiro[4.4]nonane-7-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A204)

(641) ##STR00347##

(642) MS [M+H].sup.+ 460;

(643) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.29 (d, J=3.0 Hz, 1H), 8.85 (s, 1H), 8.08 (d, J=8.5 Hz, 2H), 7.84-7.72 (m, 3H), 7.51-7.38 (m, 2H), 3.81 (t, J=7.1 Hz, 1H), 3.78-3.47 (m, 6H), 3.43 (s, 1H), 2.03-1.85 (m, 3H), 1.82 (t, J=7.1 Hz, 1H).

6-fluoro-3-{1-[4-(2-oxa-6-aza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A205)

(644) ##STR00348##

(645) MS [M+H].sup.+ 446;

(646) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (d, J=4.0 Hz, 1H), 8.86 (s, 1H), 8.10 (t, J=8.7 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.76 (dd, J=8.2, 6.1 Hz, 2H), 7.50-7.41 (m, 2H), 4.65 (d, J=5.9 Hz, 1H), 4.55-4.44 (m, 3H), 3.74 (d, J=17.9 Hz, 2H), 3.51 (dt, J=20.1, 7.0 Hz, 2H), 2.26-2.12 (m, 2H).

6-fluoro-3-{1-[4-(3-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A206)

(647) ##STR00349##

(648) MS [M+H].sup.+ 434;

(649) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.09 (dd, J=8.6, 3.4 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.50-7.41 (m, 2H), 4.72 (t, J=5.3 Hz, 0,4H), 4.65 (t, J=5.2 Hz, 0,6H), 3.69-3.57 (m, 1H), 3.57-3.37 (m, 3H), 3.30-3.23 (m, 2H), 2.45-2.24 (m, 1H), 2.03-1.87 (m, 1H), 1.75-1.60 (m, 1H).

3-{1-[4-(3-dimethylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A207)

(650) ##STR00350##

(651) MS [M+H].sup.+ 447;

(652) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.29 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.77 (t, J=8.9 Hz, 2H), 7.50-7.40 (m, 2H), 3.81-3.72 (m, 0,5H), 3.71-3.63 (m, 0,5H), 3.62-3.44 (m, 2H), 3.41-3.17 (m, 1H), 2.81-2.75 (m, 0,5H), 2.74-2.64 (m, 0,5H), 2.22 (s, 3H), 2.11 (s, 3H), 2.09-2.00 (m, 1H), 1.84-1.69 (m, 1H).

6-fluoro-3-(1-{4-[3-(4-hydroxy-piperidin-1-yl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A208)

(653) ##STR00351##

(654) MS [M+H].sup.+ 503;

(655) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.29 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.08 (d, J=7.7 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.79-7.72 (m, 2H), 7.51-7.40 (m, 2H), 3.84-3.39 (m, 5H), 3.32 (s, 1H), 2.94-2.68 (m, 2H), 2.22-1.94 (m, 3H), 1.84-1.58 (m, 3H), 1.51-1.29 (m, 2H).

6-fluoro-3-(1-{4-[3-(2-morpholin-4-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A209)

(656) ##STR00352##

(657) UPLC/MS 0.48 min, [M+H].sup.+ 533;

(658) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.13-8.08 (m, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.73 (m, 2H), 7.51-7.39 (m, 2H), 4.20-4.50 (m, 1H), 3.74-3.37 (m, 12H), 2.46-2.32 (m, 4H), 2.05-1.95 (m, 2H).

6-fluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A210)

(659) ##STR00353##

(660) UPLC/MS 0.69 min, [M+H].sup.+ 492;

(661) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.11-8.07 (m, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.73 (m, 2H), 7.49-7.40 (m, 2H), 3.73-3.14 (m, 13H), 2.54-2.42 (m, 1H), 2.08-1.90 (m, 1H), 1.73-1.62 (m, 1H).

4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(2-methoxy-ethyl)-N-methyl-benzamide (A211)

(662) ##STR00354##

(663) HPLC/MS 1.47 min (A), [M+H].sup.+ 422;

(664) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.07 (d, J=8.1 Hz, 2H), 7.80 (dd, J=9.3, 2.6 Hz, 1H), 7.69-7.60 (m, 2H), 7.50-7.39 (m, 2H), 3.72-3.55 (m, 2H), 3.45 (bs, 2H), 3.36-3.16 (m, 3H), 3.00 (s, 3H).

4-[4-(6,7-difluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-(2-methoxy-ethyl)-N-methyl-benzamide (A212)

(665) ##STR00355##

(666) HPLC/MS 1.51 min (A), [M+H].sup.+ 440;

(667) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.25 (s, 1H), 8.84 (s, 1H), 8.14-8.01 (m, 3H), 7.67-7.59 (m, 2H), 7.32 (dd, J=11.4, 7.0 Hz, 1H), 3.72-3.55 (m, 2H), 3.45 (bs, 2H), 3.36-3.16 (m, 3H), 3.00 (s, 3H).

6-fluoro-3-{1-[4-((R)-3-hydroxymethyl-morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A213)

(668) ##STR00356##

(669) MS [M+H].sup.+ 450;

(670) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.5 Hz, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.67 (d, J=8.5 Hz, 2H), 7.51-7.39 (m, 2H), 4.94 (t, J=5.5 Hz, 1H), 4.52-3.35 (m, 8H), 3.30-2.94 (m, 1H).

6-fluoro-3-{1-[4-(2-hydroxymethyl-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A214)

(671) ##STR00357##

(672) MS [M+H].sup.+ 448;

(673) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.05 (d, J=8.5 Hz, 2H), 7.79 (dd, J=9.2, 2.5 Hz, 1H), 7.60 (d, J=8.5 Hz, 2H), 7.51-7.38 (m, 2H), 4.79 (t, J=5.5 Hz, 1H), 4.34 (s, 1H), 3.81-3.60 (m, 2H), 3.61-3.34 (m, 1H), 3.14-2.71 (m, 1H), 1.90-1.49 (m, 6H), 1.50-1.30 (m, 1H).

6-fluoro-3-{1-[4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A215)

(674) ##STR00358##

(675) MS [M+H].sup.+ 448;

(676) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.08 (d, J=8.7 Hz, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.71 (d, J=8.2 Hz, 2H), 7.50-7.39 (m, 2H), 4.29 (br. s, 1H), 3.61 (br. s, 1H), 3.53-3.42 (m, 2H), 3.04 (br. s, 1H), 2.11-1.96 (m, 1H), 1.96-1.83 (m, 2H), 1.81-1.64 (m, 1H).

6-fluoro-3-{1-[4-((S)-3-hydroxymethyl-morpholine-4-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A216)

(677) ##STR00359##

(678) MS [M+H].sup.+ 450;

(679) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.5 Hz, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.67 (d, J=8.5 Hz, 2H), 7.51-7.39 (m, 2H), 4.94 (t, J=5.5 Hz, 1H), 4.52-3.35 (m, 8H), 3.30-2.94 (m, 1H).

3-{1-[4-((2S,5S)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A217)

(680) ##STR00360##

(681) UPLC/MS 0.75 min, [M+H].sup.+ 492;

(682) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.27-8.03 (m, 2H), 7.82 (dd, J=9.2, 2.7 Hz, 1H), 7.71 (d, J=8.6 Hz, 2H), 7.59-7.36 (m, 2H), 4.38-4.27 (m, 1H), 4.20-4.12 (m, 1H), 3.58-3.51 (m, 1H), 3.40 (t, J=8.4 Hz, 1H), 3.32 (s, 3H), 3.05-2.88 (m, 5H), 2.26-2.13 (m, 1H), 2.10-1.96 m, 1H), 1.90-1.75 (m, 2H).

3-{1-[4-((2R,5R)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A218)

(683) ##STR00361##

(684) UPLC/MS 0.74 min, [M+H].sup.+ 492;

(685) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.27-8.03 (m, 2H), 7.82 (dd, J=9.2, 2.7 Hz, 1H), 7.71 (d, J=8.6 Hz, 2H), 7.59-7.36 (m, 2H), 4.38-4.27 (m, 1H), 4.20-4.12 (m, 1H), 3.58-3.51 (m, 1H), 3.40 (t, J=8.4 Hz, 1H), 3.32 (s, 3H), 3.05-2.88 (m, 5H), 2.26-2.13 (m, 1H), 2.10-1.96 m, 1H), 1.90-1.75 (m, 2H).

3-{1-[4-((2S,5S)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A219)

(686) ##STR00362##

(687) UPLC/MS 0.75 min, [M+H].sup.+ 510;

(688) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.28 (s, 1H), 8.86 (s, 1H), 8.22-7.99 (m, 3H), 7.78-7.66 (m, 2H), 7.33 (dd, J=11.5, 7.1 Hz, 1H), 4.38-4.27 (m, 1H), 4.20-4.12 (m, 1H), 3.58-3.51 (m, 1H), 3.40 (t, J=8.4 Hz, 1H), 3.32 (s, 3H), 3.05-2.88 (m, 5H), 2.26-2.13 (m, 1H), 2.10-1.96 m, 1H), 1.90-1.75 (m, 2H).

3-{1-[4-((2R,5R)-2,5-bis-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A220)

(689) ##STR00363##

(690) UPLC/MS 0.76 min, [M+H].sup.+ 510;

(691) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.28 (s, 1H), 8.86 (s, 1H), 8.22-7.99 (m, 3H), 7.78-7.66 (m, 2H), 7.33 (dd, J=11.5, 7.1 Hz, 1H), 4.38-4.27 (m, 1H), 4.20-4.12 (m, 1H), 3.58-3.51 (m, 1H), 3.40 (t, J=8.4 Hz, 1H), 3.32 (s, 3H), 3.05-2.88 (m, 5H), 2.26-2.13 (m, 1H), 2.10-1.96 m, 1H), 1.90-1.75 (m, 2H).

6,7-difluoro-3-(1-{4-[3-(2-morpholin-4-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A221)

(692) ##STR00364##

(693) UPLC/MS 0.49 min, [M+H].sup.+ 551;

(694) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.28 (s, 1H), 8.13-8.06 (m, 3H), 7.78-7.73 (m, 2H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 4.23-3.93 (m, 1H), 3.73-3.36 (m, 1 OH), 2.47-2.30 (m, 6H), 2.06-1.94 (m, 2H).

6-fluoro-7-methyl-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A222)

(695) ##STR00365##

6,7-difluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A223)

(696) ##STR00366##

(697) HPLC/MS 1.54 min (A), [M+H].sup.+ 510;

(698) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.27 (s, 1H), 8.85 (s, 1H), 8.17-8.04 (m, 3H), 7.78-7.72 (m, 2H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 3.73-3.37 (m, 9H), 3.36-3.18 (m, 5H), 2.56-2.41 (m, 1H), 2.06-1.90 (m, 1H), 1.76-1.58 (m, 1H).

6-fluoro-3-(1-{4-[3-(2-pyrrolidin-1-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A224)

(699) ##STR00367##

(700) UPLC/MS 0.49 min, [M+H].sup.+ 517;

(701) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.32 (s, 1H), 8.88 (s, 1H), 8.17-8.11 (m, 2H), 7.84-7.72 (m, 3H), 7.48 (dd, J=9.0, 4.9 Hz, 1H), 7.43 (td, J=8.7, 2.8 Hz, 1H), 4.32-4.12 (m, 1H), 3.83-3.31 (m, 10H), 3.21-2.98 (m, 3H), 2.21-1.76 (m, 5H).

6,7-difluoro-3-(1-{4-[3-(2-pyrrolidin-1-yl-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A225)

(702) ##STR00368##

(703) UPLC/MS 0.50 min, [M+H].sup.+ 535;

(704) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.30 (s, 1H), 8.87 (s, 1H), 8.17-8.06 (m, 2H), 8.02 (dd, J=10.9, 8.5 Hz, 1H), 7.82-7.76 m, 2H), 7.37 (dd, J=11.4, 7.1 Hz, 1H), 4.32-4.12 (m, 1H), 3.83-3.31 (m, 10H), 3.21-2.98 (m, 3H), 2.21-1.76 (m, 5H).

(R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-3-carboxylic acid amide (A226)

(705) ##STR00369##

(706) UPLC/MS 0.59 min, [M+H].sup.+ 447.

(707) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.11-8.06 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.72 (m, 2H), 7.53-7.34 (m, 3H), 6.99-6.91 (m, 1H), 3.77-3.45 (m, 4H), 3.05-2.91 (m, 1H), 2.20-1.93 (m, 2H).

6-fluoro-3-{1-[4-((2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A227)

(708) ##STR00370##

(709) MS [M+H].sup.+ 450;

(710) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.87 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.82 (dd, J=9.2, 2.7 Hz, 1H), 7.76 (d, J=8.5 Hz, 2H), 7.53-7.37 (m, 2H), 4.83 (d, J=3.1 Hz, 1H), 4.78 (t, J=5.9 Hz, 1H), 4.31 (q, J=6.2, 5.2 Hz, 1H), 4.23 (br. s, 1H), 3.79-3.69 (m, 1H), 3.67-3.52 (m, 2H), 3.26 (d, J=11.1 Hz, 1H), 2.14-2.01 (m, 1H), 1.98-1.85 (m, 1H).

6-fluoro-3-{1-[4-(2-oxa-6-aza-spiro[3.5]nonane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A228)

(711) ##STR00371##

(712) MS [M+H].sup.+ 460;

(713) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.10 (d, J=8.4 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.61 (d, J=7.4 Hz, 2H), 7.50-7.37 (m, 2H), 4.49-3.98 (m, 4H), 3.88 (br. s, 1H), 3.60 (br. s, 2H), 3.33 (br. s, 1H), 1.94-1.79 (m, 2H), 1.58-1.37 (m, 2H).

6-fluoro-3-{1-[4-(2-oxa-7-aza-spiro[3.5]nonane-7-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A229)

(714) ##STR00372##

(715) MS [M+H].sup.+ 460;

(716) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.3, 2.6 Hz, 1H), 7.60 (d, J=8.6 Hz, 2H), 7.50-7.37 (m, 2H), 4.35 (s, 4H), 3.55 (br. s, 2H), 3.32 (br. s, 2H), 1.83 (br. s, 4H).

6-fluoro-3-{1-[4-(4-oxetan-3-yl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A230)

(717) ##STR00373##

(718) MS [M+H].sup.+ 475;

(719) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.32-9.23 (m, 1H), 8.85 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.79 (dd, J=9.2, 2.6 Hz, 1H), 7.63 (d, J=8.6 Hz, 2H), 7.55-7.30 (m, 2H), 4.55 (t, J=6.5 Hz, 2H), 4.46 (t, J=6.1 Hz, 2H), 3.66 (br. s, 2H), 3.47 (p, J=6.3 Hz, 1H), 3.42 (br. s, 2H), 2.32 (br. s, 4H).

3-{1-[4-(2,5-dioxa-8-aza-spiro[3.5]nonane-8-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A231)

(720) ##STR00374##

(721) MS [M+H].sup.+ 462;

(722) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.12 (d, J=8.1 Hz, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.53-7.33 (m, 2H), 4.60-4.12 (m, 4H), 4.03-3.32 (m, 6H).

4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N-oxetan-3-yl-benzamide (A232)

(723) ##STR00375##

(724) MS [M+H].sup.+ 406;

(725) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.33 (s, 1H), 9.26 (d, J=6.4 Hz, 1H), 8.86 (s, 1H), 8.17 (d, J=8.8 Hz, 2H), 8.12 (d, J=8.8 Hz, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.52-7.37 (m, 2H), 5.04 (ddt, J=14.0, 7.5, 6.5 Hz, 1H), 4.80 (dd, J=7.5, 6.4 Hz, 2H), 4.63 (t, J=6.4 Hz, 2H).

6,7-difluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A233)

(726) ##STR00376##

(727) HPLC/MS 1.54 min (A), [M+H].sup.+ 510;

(728) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.27 (s, 1H), 8.85 (s, 1H), 8.17-8.04 (m, 3H), 7.78-7.72 (m, 2H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 3.73-3.37 (m, 8H), 3.36-3.18 (m, 5H), 2.56-2.41 (m, 1H), 2.06-1.90 (m, 1H), 1.76-1.58 (m, 1H).

6-fluoro-3-{1-[4-(2-oxa-5-aza-spiro[3.4]octane-5-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A234)

(729) ##STR00377##

(730) MS [M+H].sup.+ 446;

(731) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.75 (d, J=8.6 Hz, 2H), 7.55-7.30 (m, 2H), 5.47 (d, J=5.1 Hz, 2H), 4.33 (d, J=5.2 Hz, 2H), 3.39 (t, J=6.5 Hz, 2H), 2.34 (t, J=6.7 Hz, 2H), 1.71 (p, J=6.6 Hz, 2H).

6-fluoro-3-{1-[4-(2-oxa-6-aza-spiro[3.3]heptane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A235)

(732) ##STR00378##

(733) MS [M+H].sup.+ 432;

(734) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.11 (d, J=8.7 Hz, 2H), 7.84 (d, J=8.7 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.50-7.38 (m, 2H), 4.70 (s, 4H), 4.55 (s, 2H), 4.25 (s, 2H).

6-fluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxymethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A236)

(735) ##STR00379##

(736) HPLC/MS 1.49 min (A), [M+H].sup.+ 492;

(737) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.16-8.03 (m, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.78-7.72 (m, 2H), 7.50-7.40 (m, 2H). 3.73-3.37 (m, 8H), 3.36-3.18 (m, 5H), 2.56-2.41 (m, 1H), 2.06-1.90 (m, 1H), 1.76-1.58 (m, 1H).

3-{1-[4-((3R,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A237)

(738) ##STR00380##

(739) UPLC/MS 0.65 min, [M+H].sup.+ 464;

(740) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.13-8.05 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.72 (m, 2H), 7.51-7.39 (m, 2H), 4.03 (q, J=5.1 Hz, 1H), 3.98-3.90 (m, 1H), 3.70-3.61 (m, 2H), 3.53-3.41 (m, 2H), 3.38 (s, 3H), 3.28 (s, 3H).

4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-N,N-bis-(2-methoxy-ethyl)-benzamide (A238)

(741) ##STR00381##

(742) UPLC/MS 0.70 min, [M+H].sup.+ 466;

(743) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.12-8.02 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.68-7.56 (m, 2H), 7.51-7.39 (m, 2H), 3.75-3.11 (m, 14H).

3-{1-[4-(3-diethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A239)

(744) ##STR00382##

(745) UPLC/MS 0.50 min, [M+H].sup.+ 507;

(746) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.26 (s, 1H), 8.83 (s, 1H), 8.10 (s, 1H, formate-H), 8.12-8.07 (m, 2H), 8.01 (dd, J=10.9, 8.5 Hz, 1H), 7.78-7.72 (m, 2H), 7.33 (dd, J=11.4, 7.1 Hz, 1H), 3.90-3.47 (m, 4H), 3.38-3.04 (m, 6H), 2.72-2.57 (m, 1H), 2.23-2.07 (m, 1H), 1.78-1.66 (m, 1H), 1.28-1.11 (m, 6H).

N-(3-acetyl-3-aza-bicyclo[3.1.0]hex-6-yl)-4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzamide (A240)

(747) ##STR00383##

(748) MS [M+H].sup.+ 473;

(749) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.32 (s, 1H), 8.87 (s, 1H), 8.72 (d, J=3.9 Hz, 1H), 8.15 (d, J=8.7 Hz, 2H), 8.06 (d, J=8.7 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.52-7.38 (m, 2H), 3.66 (qd, J=10.2, 4.1 Hz, 2H), 3.44-3.32 (m, 2H), 2.60 (q, J=2.8 Hz, 1H), 1.94 (s, 3H), 1.90-1.80 (m, 1H), 1.10 (t, J=7.0 Hz, 1H).

6-fluoro-3-{1-[4-((2S,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A241)

(750) ##STR00384##

(751) MS [M+H].sup.+ 464;

(752) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (s, 1H), 8.87 (s, 1H), 8.11 (d, J=8.4 Hz, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.51-7.40 (m, 2H), 4.81 (t, J=5.8 Hz, 1H), 4.24 (s, 1H), 3.92 (s, 1H), 3.82-3.71 (m, 1H), 3.67-3.50 (m, 2H), 3.40 (d, J=11.8 Hz, 1H), 3.12 (s, 3H), 2.18-2.03 (m, 2H).

(S)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-2-carboxylic acid amide (A242)

(753) ##STR00385##

(754) UPLC/MS 0.60 min, [M+H].sup.+ 447;

(755) mixture of rotamers, some signals of main rotamer: .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.88-7.73 (m, 3H), 7.53-7.38 (m, 3H), 6.97 (bs, 1H), 4.40 (dd, J=8.3, 5.2 Hz, 1H), 3.75-3.56 (m, 2H), 2.26-2.16 (m, 1H), 1.95-1.75 (m, 3H).

(S)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-3-carboxylic acid amide (A243)

(756) ##STR00386##

(757) UPLC/MS 0.60 min, [M+H].sup.+ 447;

(758) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.11-8.06 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.72 (m, 2H), 7.53-7.34 (m, 3H), 6.99-6.91 (m, 1H), 3.77-3.45 (m, 4H), 3.05-2.91 (m, 1H), 2.20-1.93 (m, 2H).

6-fluoro-3-{1-[4-((2R,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A244)

(759) ##STR00387##

(760) MS [M+H].sup.+ 464;

(761) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.28 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.80 (dd, J=9.3, 2.7 Hz, 1H), 7.73 (d, J=7.6 Hz, 2H), 7.51-7.37 (m, 2H), 4.83 (s, 0,7H), 4.70 (s, 0,3H), 4.22 (br. s, 0,7H), 4.04 (br. s, 0,3H), 3.91 (br. s, 1H), 3.64 (br. s, 2H), 3.48-3.36 (m, 1H), 3.22 (s, 3H), 2.26-2.11 (m, 1H), 2.10-1.95 (m, 1H).

6-fluoro-3-{1-[4-(2-oxa-5-aza-spiro[3.5]nonane-5-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A245)

(762) ##STR00388##

(763) MS [M+H].sup.+ 460;

(764) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.74 (d, J=8.6 Hz, 2H), 7.52-7.35 (m, 2H), 4.71 (d, J=6.8 Hz, 2H), 4.38 (d, J=6.9 Hz, 2H), 3.23 (t, J=5.5 Hz, 2H), 2.06 (t, J=6.0 Hz, 2H), 1.70 (p, J=6.0 Hz, 2H), 1.26 (p, J=5.7 Hz, 2H).

6-chloro-3-{1-[4-((S)-2-hydroxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A246)

(765) ##STR00389##

(766) MS [M+H].sup.+ 450;

(767) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.4 Hz, 2H), 8.05 (d, J=2.2 Hz, 1H), 7.73 (d, J=8.0 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.79 (t, J=5.4 Hz, 1H), 4.17 (s, 1H), 3.60 (s, 2H), 3.48 (dt, J=10.2, 6.7 Hz, 1H), 3.36 (s, 1H), 2.03-1.83 (m, 3H), 1.82-1.60 (m, 1H).

6-chloro-3-{1-[4-((2R,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A247)

(768) ##STR00390##

(769) MS [M+H].sup.+ 480;

(770) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.33 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.4 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.73 (d, J=8.1 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.81 (br. s, 0,7H), 4.68 (br. s, 0,3H), 4.22 (br. s, 0,7H), 4.05 (br. s, 0,3H), 3.90 (br. s, 1H), 3.64 (br. s, 2H), 3.49-3.35 (m, 1H), 3.22 (s, 3H), 2.24-2.12 (m, 1H), 2.11-1.94 (m, 1H).

6-chloro-3-{1-[4-((2S,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A248)

(771) ##STR00391##

(772) MS [M+H].sup.+ 480;

(773) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.29 (s, 1H), 8.84 (s, 1H), 8.10 (d, J=8.4 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.75 (d, J=8.3 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.80 (s, 1H), 4.24 (s, 1H), 3.91 (q, J=4.2 Hz, 1H), 3.74 (d, J=11.2 Hz, 1H), 3.61 (dd, J=11.7, 3.7 Hz, 1H), 3.55 (d, J=11.2 Hz, 1H), 3.40 (d, J=11.7 Hz, 1H), 3.11 (s, 3H), 2.08 (dd, J=8.2, 4.9 Hz, 2H).

6-chloro-3-(1-{4-[3-(4-hydroxy-piperidin-1-yl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A249)

(774) ##STR00392##

(775) MS [M+H].sup.+ 519;

(776) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.33 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.07 (d, J=8.4 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.75 (t, J=9.1 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.53 (d, J=4.0 Hz, 0.5H), 4.50 (d, J=4.0 Hz, 0.5H), 3.83-3.37 (m, 4H), 3.37-3.18 (m, 1H), 2.94-2.51 (m, 3H), 2.21-1.94 (m, 3H), 1.82-1.60 (m, 3H), 1.47-1.27 (m, 2H).

6-chloro-3-{1-[4-(4-oxetan-3-yl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A250)

(777) ##STR00393##

(778) MS [M+H].sup.+ 491;

(779) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.27 (s, 1H), 8.84 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.63 (d, J=8.6 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.55 (t, J=6.5 Hz, 2H), 4.46 (t, J=6.1 Hz, 2H), 3.66 (br. s, 2H), 3.54-3.33 (m, 3H), 2.32 (br. s, 4H).

6-fluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A251)

(780) ##STR00394##

(781) HPLC/MS 1.46 min (A), [M+H].sup.+ 478;

(782) .sup.1H NMR (500 MHz, DMSO-d6) mixture of 2 rotamers: 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.15-8.05 (m, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.72 (m, 0.5H), 7.54-7.38 (m, 2H), 4.21-4.17 (m, 0.5H), 4.13-4.08 (m, 0.5H), 3.71-3.37 (m, 8H), 3.28 (s, 1.5H), 3.21 (s, 11.5H), 2.06-1.95 (m, 2H).

6-fluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A252)

(783) ##STR00395##

(784) HPLC/MS 1.46 min (A), [M+H].sup.+ 478;

(785) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers: 12.29 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.15-8.05 (m, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.78-7.72 (m, 0.5H), 7.54-7.38 (m, 2H), 4.21-4.17 (m, 0.5H), 4.13-4.08 (m, 0.5H), 3.71-3.37 (m, 8H), 3.28 (s, 1.5H), 3.21 (s, 11.5H), 2.06-1.95 (m, 2H).

6-chloro-3-{1-[4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A253)

(786) ##STR00396##
MS [M+H].sup.+ 464;

(787) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.33 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.71 (d, J=8.4 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.29 (br.s, 0.7H), 4.07 (br. s, 0.3H), 3.73-3.55 (m, 1H), 3.54-3.42 (m, 2H), 3.32 (s, 3H), 3.16-2.92 (m, 1H), 2.09-1.96 (m, 1H), 1.96-1.81 (m, 2H), 1.81-1.63 (m, 1H).

6-chloro-3-{1-[4-(3-dimethylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A254)

(788) ##STR00397##

(789) MS [M+H].sup.+ 463;

(790) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.33 (s, 1H), 9.28 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.75 (t, J=8.0 Hz, 2H), 7.58 (dd, J=8.7, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 3.79-3.71 (m, 0.5H), 3.70-3.61 (m, 0.5H), 3.60-3.43 (m, 2H), 3.38-3.20 (m, 1H), 2.82-2.61 (m, 1H), 2.20 (s, 3H), 2.11 (s, 3H), 2.10-1.97 (m, 1H), 1.84-1.67 (m, 1H).

6-chloro-3-{1-[4-(2-hydroxymethyl-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A255)

(791) ##STR00398##

(792) MS [M+H].sup.+ 464;

(793) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.32 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.12-7.99 (m, 3H), 7.65-7.52 (m, 3H), 7.40 (d, J=8.8 Hz, 1H), 4.79 (t, J=5.5 Hz, 1H), 4.73-4.52 (m, 0.3H), 4.52-4.15 (m, 0.7H), 3.95-3.36 (m, 3H), 3.19-2.77 (m, 1H), 1.96-1.29 (m, 6H).

6-chloro-3-{1-[4-(2-oxa-7-aza-spiro[3.5]nonane-7-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A256)

(794) ##STR00399##

(795) MS [M+H].sup.+ 476;

(796) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.27 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.60 (d, J=8.5 Hz, 2H), 7.58 (d, J=2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.35 (br. s, 4H), 3.55 (br. s, 2H), 3.27 (br. s, 2H), 1.83 (br. s, 4H).

6-chloro-3-{1-[4-(2-oxa-6-aza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A257)

(797) ##STR00400##

(798) MS [M+H].sup.+ 462;

(799) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.28 (d, J=2.4 Hz, 1H), 8.84 (s, 1H), 8.09 (t, J=7.7 Hz, 2H), 8.05 (d, J=2.0 Hz, 1H), 7.75 (dd, J=8.4, 4.2 Hz, 2H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 4.64 (d, J=6.0 Hz, 1H), 4.55-4.42 (m, 3H), 3.73 (d, J=14.1 Hz, 2H), 3.50 (dt, J=14.7, 6.9 Hz, 2H), 2.18 (dt, J=12.8, 7.0 Hz, 2H).

6-chloro-3-{1-[4-(2-oxa-6-aza-spiro[3.3]heptane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A258)

(800) ##STR00401##

(801) MS [M+H].sup.+ 448;

(802) .sup.1H NMR (500 MHz, DMSO-d.sub.6) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.29 (s, 1H), 8.84 (s, 1H), 8.10 (d, J=8.7 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.84 (d, J=8.7 Hz, 2H), 7.58 (dd, J=8.7, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.70 (s, 4H), 4.55 (s, 2H), 4.25 (s, 2H).

6-chloro-3-(1-{4-[(S)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A259)

(803) ##STR00402##

(804) HPLC/MS 1.56 min (A), [M+H].sup.+ 494;

(805) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers: 12.33 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.3 Hz, 2H), 8.06 (d, J=2.4 Hz, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.59 (dd, J=8.8, 2.3 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 4.22-4.15 (m, 0.5H), 4.13-4.07 (m, 0.5H), 3.74-3.35 (m, 8H), 3.28 (s, 1.5H), 3.21 (s, 1.5H), 2.12-1.88 (m, 2H).

6-chloro-3-(1-{4-[(R)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A260)

(806) ##STR00403##

(807) HPLC/MS 1.56 min (A), [M+H].sup.+ 494;

(808) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers: 12.33 (s, 1H), 9.29 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.3 Hz, 2H), 8.06 (d, J=2.4 Hz, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.59 (dd, J=8.8, 2.3 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 4.22-4.15 (m, 0.5H), 4.13-4.07 (m, 0.5H), 3.74-3.35 (m, 8H), 3.28 (s, 1.5H), 3.21 (s, 1.5H), 2.12-1.88 (m, 2H).

6-fluoro-3-(1-{4-[(R)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-pyrazol-4-yl)-1H-quinolin-2-one (A261)

(809) ##STR00404##

(810) HPLC/MS 1.46 min (A), [M+H].sup.+ 477;

(811) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.12 (s, 1H), 9.20 (s, 1H), 8.47 (s, 1H), 8.42 (s, 1H), 8.01-7.91 (m, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.49 (dt, J=9.3, 1.7 Hz, 1H), 7.44-7.35 (m, 2H), 4.21-4.14 (m, 0.5H), 4.13-4.06 (m, 0.5H), 3.75-3.35 (m, 7H), 3.28 (s, 1.5H), 3.21 (s, 1.5H), 2.05-1.93 (m, 2H).

(R)-1-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-benzoyl}-pyrrolidine-2-carboxylic acid amide (A262)

(812) ##STR00405##

(813) UPLC/MS 0.62 min, [M+H].sup.+ 447; mixture of rotamers, some signals of main rotamer: .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.88-7.73 (m, 3H), 7.53-7.38 (m, 3H), 6.97 (bs, 1H), 4.40 (dd, J=8.3, 5.2 Hz, 1H), 3.75-3.56 (m, 2H), 2.26-2.16 (m, 1H), 1.95-1.75 (m, 3H).

3-{1-[4-((3R,4R)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A263)

(814) ##STR00406##

(815) HPLC/MS 1.49 min (A), [M+H].sup.+ 464;

(816) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.13-8.06 (m, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.79-7.73 (m, 2H), 7.52-7.39 (m, 2H), 3.97-3.92 (m, 1H), 3.91-3.87 (m, 1H), 3.76-3.62 (m, 2H), 3.56 (d, J=13.4 Hz, 1H), 3.43 (d, J=11.7 Hz, 1H), 3.36 (s, 3H), 3.26 (s, 3H).

3-{1-[4-((3S,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A264)

(817) ##STR00407##

(818) HPLC/MS 1.49 min (A), [M+H].sup.+ 464;

(819) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.13-8.06 (m, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.79-7.73 (m, 2H), 7.52-7.39 (m, 2H), 3.97-3.92 (m, 1H), 3.91-3.87 (m, 1H), 3.76-3.62 (m, 2H), 3.56 (d, J=13.4 Hz, 1H), 3.43 (d, J=11.7 Hz, 1H), 3.36 (s, 3H), 3.26 (s, 3H).

6-fluoro-3-{1-[4-((S)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A265)

(820) ##STR00408##

(821) MS [M+H].sup.+ 422;

(822) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 7.81 (dd, J=9.2, 2.4 Hz, 2H), 7.77 (d, J=8.4 Hz, 1H), 7.50-7.40 (m, 2H), 5.38 (dd, J=52.9, 40.3 Hz, 1H), 3.94-3.52 (m, 4H), 2.30-2.02 (m, 2H).

6-chloro-3-{1-[4-((S)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A266)

(823) ##STR00409##

(824) MS [M+H].sup.+ 438;

(825) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 8.06 (d, J=2.3 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 5.53-5.23 (m, 1H), 3.94-3.52 (m, 4H), 2.30-2.00 (m, 2H).

3-{1-[4-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A267)

(826) ##STR00410##

(827) MS [M+H].sup.+ 440;

(828) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 7.84-7.76 (m, 3H), 7.50-7.40 (m, 2H), 3.96 (t, J=13.2 Hz, 2H), 3.76 (br. s, 2H), 2.48 (br. s, 2H).

6-chloro-3-{1-[4-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A268)

(829) ##STR00411##

(830) MS [M+H].sup.+ 440;

(831) .sup.1H NMR (500 MHz, DMSO-d.sub.6) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 8.07 (d, J=2.4 Hz, 1H), 7.81 (d, J=8.2 Hz, 2H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 3.96 (t, J=13.2 Hz, 2H), 3.76 (br. s, 2H), 2.48 (br.s, 2H).

6-fluoro-3-{1-[4-((R)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A269)

(832) ##STR00412##

(833) MS [M+H].sup.+ 421;

(834) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.83-7.74 (m, 3H), 7.50-7.41 (m, 2H), 5.52-5.20 (m, 1H), 3.91-3.58 (m, 4H), 2.29-2.02 (m, 2H).

6-chloro-3-{1-[4-((R)-3-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A270)

(835) ##STR00413##

(836) MS [M+H].sup.+ 438;

(837) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.11 (d, J=8.6 Hz, 2H), 8.06 (d, J=2.3 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 5.53-5.23 (m, 1H), 3.94-3.52 (m, 4H), 2.30-2.00 (m, 2H).

6-chloro-3-{1-[4-((3R,4R)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A271)

(838) ##STR00414##

(839) HPLC/MS 1.60 min (A), [M+H].sup.+ 480;

(840) 1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.13-8.07 (m, 2H), 8.06 (d, J=2.4 Hz, 1H), 7.81-7.73 (m, 2H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 3.94 (bs, 1H), 3.89 (bs, 1H), 3.69 (td, J=14.3, 13.2, 4.5 Hz, 2H), 3.56 (d, J=13.4 Hz, 1H), 3.43 (d, J=11.7 Hz, 1H), 3.37 (s, 3H), 3.26 (s, 3H).

6-chloro-3-{1-[4-((3S,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A272)

(841) ##STR00415##

(842) HPLC/MS 1.59 min (A), [M+H].sup.+ 480;

(843) 1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.13-8.07 (m, 2H), 8.06 (d, J=2.4 Hz, 1H), 7.81-7.73 (m, 2H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 3.94 (bs, 1H), 3.89 (bs, 1H), 3.69 (td, J=14.3, 13.2, 4.5 Hz, 2H), 3.56 (d, J=13.4 Hz, 1H), 3.43 (d, J=11.7 Hz, 1H), 3.37 (s, 3H), 3.26 (s, 3H).

6-fluoro-3-{1-[4-(pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A273)

(844) ##STR00416##

(845) UPLC/MS 0.72 min, [M+H].sup.+ 404;

(846) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.18-8.03 (m, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.79-7.68 (m, 2H), 7.54-7.37 (m, 2H), 3.51 (t, J=6.7 Hz, 2H), 3.46 (t, J=6.3 Hz, 2H), 1.95-1.81 (m, 4H).

6-fluoro-3-{1-[4-((R)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A274)

(847) ##STR00417##

(848) MS [M+H].sup.+ 422;

(849) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.12 (d, J=8.7 Hz, 2H), 7.92 (d, J=8.7 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.50-7.39 (m, 2H), 5.49 (d, J=4.0 Hz, 1H), 4.71 (dt, J=6.1, 4.1 Hz, 1H), 4.03-3.91 (m, 2H), 3.87 (d, J=1.7 Hz, 1H), 3.66 (dd, J=11.5, 1.6 Hz, 1H).

6-chloro-3-{1-[4-((R)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A275)

(850) ##STR00418##

(851) MS [M+H].sup.+ 438;

(852) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.12 (d, J=8.8 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.92 (d, J=8.7 Hz, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 5.49 (d, J=4.0 Hz, 1H), 4.77-4.62 (m, 1H), 4.03-3.91 (m, 2H), 3.86 (dd, J=8.6, 1.8 Hz, 1H), 3.66 (dd, J=11.4, 1.6 Hz, 1H).

6-fluoro-3-{1-[4-((S)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A276)

(853) ##STR00419##

(854) MS [M+H].sup.+ 422;

(855) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.12 (d, J=8.7 Hz, 2H), 7.92 (d, J=8.7 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.50-7.39 (m, 2H), 5.49 (d, J=4.0 Hz, 1H), 4.71 (dt, J=6.1, 4.1 Hz, 1H), 4.03-3.91 (m, 2H), 3.87 (d, J=1.7 Hz, 1H), 3.66 (dd, J=11.5, 1.6 Hz, 1H).

6-chloro-3-{1-[4-((S)-4-hydroxy-isoxazolidine-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A277)

(856) ##STR00420##

(857) MS [M+H].sup.+ 438;

(858) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.30 (s, 1H), 8.85 (s, 1H), 8.12 (d, J=8.8 Hz, 2H), 8.05 (d, J=2.3 Hz, 1H), 7.92 (d, J=8.7 Hz, 2H), 7.59 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 5.49 (d, J=4.0 Hz, 1H), 4.77-4.62 (m, 1H), 4.03-3.91 (m, 2H), 3.86 (dd, J=8.6, 1.8 Hz, 1H), 3.66 (dd, J=11.4, 1.6 Hz, 1H).

6-fluoro-3-{1-[4-((R)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A278)

(859) ##STR00421##

(860) HPLC/MS 1.28 min (A), [M+H].sup.+ 487;

(861) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.22 (s, 1H), 9.22 (s, 1H), 8.79 (s, 1H), 8.07-7.97 (m, 2H), 7.74 (dd, J=9.2, 2.7 Hz, 1H), 7.70-7.60 (m, 2H), 7.49-7.30 (m, 2H), 4.34-3.88 (m, 1H), 3.61-3.28 (m, 3H), 2.78-2.02 (m, 6H), 2.00-1.90 (m, 1H), 1.90-1.76 (m, 2H), 1.76-1.32 (m, 4H).

6-fluoro-3-{1-[4-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A279)

(862) ##STR00422##

(863) HPLC/MS 1.29 min (A), [M+H].sup.+ 487;

(864) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.22 (s, 1H), 9.22 (s, 1H), 8.79 (s, 1H), 8.07-7.97 (m, 2H), 7.74 (dd, J=9.2, 2.7 Hz, 1H), 7.70-7.60 (m, 2H), 7.49-7.30 (m, 2H), 4.34-3.88 (m, 1H), 3.61-3.28 (m, 3H), 2.78-2.02 (m, 6H), 2.00-1.90 (m, 1H), 1.90-1.76 (m, 2H), 1.76-1.32 (m, 4H).

3-{1-[4-(azetidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A280)

(865) ##STR00423##

(866) UPLC/MS 0.70 min, [M+H].sup.+ 390;

(867) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.22-8.00 (m, 2H), 7.94-7.84 (m, 2H), 7.81 (dd, J=9.3, 2.6 Hz, 1H), 7.54-7.38 (m, 2H), 4.38 (t, J=7.4 Hz, 2H), 4.10 (t, J=7.8 Hz, 2H), 2.38-2.18 (m, 2H).

6-fluoro-3-(1-{4-[2-(4-methyl-piperazine-1-carbonyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A281)

(868) ##STR00424##

(869) UPLC/MS 0.49 min, [M+H].sup.+ 530;

(870) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.20 (s, 1H), 8.76 (s, 1H), 8.00 (d, J=8.6 Hz, 2H), 7.69 (d, J=8.3 Hz, 2H), 7.56 (dd, J=9.1, 2.8 Hz, 1H), 7.39 (dd, J=9.1, 4.7 Hz, 1H), 7.26 (td, J=8.8, 2.8 Hz, 1H), 5.06-4.70 (m, 2H), 4.60-4.19 (m, 3H), 3.78-2.85 (m, 6H), 2.82 (s, 3H), 2.31-2.15 (m, 2H), 2.03-1.70 (m, 2H).

6-fluoro-3-{1-[4-((R)-3-methanesulfonyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A282)

(871) ##STR00425##

(872) HPLC/MS 1.41 min (A), [M+H].sup.+ 482;

(873) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.12 (d, J=8.4 Hz, 2H), 7.88-7.70 (m, 3H), 7.53-7.40 (m, 2H), 4.15-3.55 (m, 5H), 3.13-2.99 (m, 3H), 2.43-2.20 (m, 2H).

6-fluoro-3-{1-[4-((S)-3-methanesulfonyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A283)

(874) ##STR00426##

(875) HPLC/MS 1.40 min (A), [M+H].sup.+ 482;

(876) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.12 (d, J=8.4 Hz, 2H), 7.88-7.70 (m, 3H), 7.53-7.40 (m, 2H), 4.15-3.55 (m, 5H), 3.13-2.99 (m, 3H), 2.43-2.20 (m, 2H).

6-fluoro-3-{1-[4-(3-methanesulfonylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A284)

(877) ##STR00427##

(878) UPLC/MS 0.65 min, [M+H].sup.+ 496;

(879) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers, selected peaks b 12.30 (s, 1H), 9.31 (s, 0.5H), 9.30 (s, 0.5H), 8.86 (s, 1H), 8.13-8.08 (m, 2H), 7.81 (dd, J=9.1, 2.9 Hz, 1H), 7.79-7.71 (m, 2H), 7.47 (td, J=8.8, 2.8 Hz, 1H), 7.43 (dd, J=9.0, 4.8 Hz, 1H), 3.05 (s, 1.5H), 2.98 (s, 1.5H).

6-fluoro-3-(1-{4-[2-(1-methyl-1H-pyrazol-4-yl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A285)

(880) ##STR00428##

(881) MS [M+H].sup.+ 484;

(882) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.32 (s, 1H), 9.31 (s, 0,70H), 9.26 (s, 0,30H), 8.86 (s, 1H), 8.09 (d, J=8.1 Hz, 1,4H), 7.97 (d, J=8.1 Hz, 0,60H), 7.81 (d, J=9.1 Hz, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.68 (s, 1H), 5.26-5.14 (m, 0,70H), 4.99-4.87 (m, 0,30H), 3.80 (s, 2H), 3.72 (s, 1H), 3.71-3.61 (m, 1,40H), 3.46-3.38 (m, 0,6H), 2.29-2.13 (m, 1H), 2.02-1.75 (m, 3H).

6-fluoro-3-{1-[4-(2-pyridin-3-yl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A286)

(883) ##STR00429##

(884) MS [M+H].sup.+ 481;

(885) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of rotamers, signals of major b 12.32 (s, 1H), 9.32 (s, 1H), 8.87 (s, 1H), 8.57 (d, J=91.1 Hz, 2H), 8.12 (d, J=8.5 Hz, 2H), 7.90-7.85 (m, 2H), 7.84-7.78 (m, 2H), 7.54-7.31 (m, 3H), 5.18 (t, J=6.9 Hz, 1H), 3.98-3.89 (m, 1H), 3.62-3.54 (m, 1H), 2.49-2.39 (m, 1H), 2.03-1.74 (m, 3H).

6-fluoro-3-(1-{4-[2-(4-methyl-piperazin-1-ylmethyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A287)

(886) ##STR00430##

(887) MS [M+H].sup.+ 516;

(888) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.33 (s, 1H), 8.87 (s, 1H), 8.15 (d, J=8.6 Hz, 2H), 7.86 (d, J=8.4 Hz, 2H), 7.78 (dd, J=9.3, 2.7 Hz, 1H), 7.50-7.39 (m, 2H), 4.70-4.60 (m, 1H), 4.35-3.30 (m, 12H), 2.93 (s, 3H), 2.30-2.16 (m, 1H), 2.03-1.73 (m, 3H).

6-fluoro-3-{1-[4-(2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A288)

(889) ##STR00431##

(890) UPLC/MS 0.76 min, [M+H].sup.+ 418;

(891) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of rotamers, signals of major rotamer: 12.31 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.26-7.95 (m, 2H), 7.82 (dd, J=9.2, 2.8 Hz, 1H), 7.73 (d, J=8.1 Hz, 2H), 7.47 (td, J=8.8, 2.8 Hz, 1H), 7.43 (dd, J=9.0, 4.9 Hz, 1H), 4.25-4.14 (m, 1H), 3.57-3.51 (m, 1H), 3.37-3.32 (m, 1H), 2.10 (dq, J=13.4, 6.8 Hz, 1H), 1.99-1.84 (m, 1H), 1.79-1.68 (m, 1H), 1.64-1.53 (m, 1H), 1.29 (d, J=6.2 Hz, 3H).

6-fluoro-3-{1-[4-(2-methyl-2,6-diaza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A289)

(892) ##STR00432##

(893) UPLC/MS 0.47 min, [M+H].sup.+ 459;

(894) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers 12.33 (s, 1H), 9.89 (bs, 1H, NH.sup.+), 9.32 (s, 0.5H), 9.31 (s, 0.5H), 8.86 (s, 1H), 8.20-8.04 (m, 2H), 7.82 (dd, J=9.2, 2.8 Hz, 1H), 7.79-7.74 (m, 2H), 7.48 (ddd, J=9.2, 6.1, 2.3 Hz, 1H), 7.43 (dd, J=8.8, 4.6 Hz, 1H), 4.26-3.94 (m, 4H), 3.79-3.69 (m, 2H), 3.59-3.48 (m, 2H), 2.87 (s, 1.5H), 2.78 (s, 1.5H), 2.24-2.13 (m, 2H).

6-chloro-3-{1-[4-(2-methyl-2,6-diaza-spiro[3.4]octane-6-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A290)

(895) ##STR00433##

(896) UPLC/MS 0.50 min, [M+H].sup.+ 475;

(897) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers 12.38 (s, 1H), 9.83 (bs, 1H, NH.sup.+), 9.32 (s, 0.5H), 9.31 (s, 0.5H), 8.86 (s, 1H), 8.17-8.09 (m, 2H), 8.08 (d, J=2.3 Hz, 1H), 7.78-7.74 (m, 2H), 7.61 (dt, J=8.8, 1.8 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 4.26-3.94 (m, 4H), 3.79-3.69 (m, 2H), 3.59-3.48 (m, 2H), 2.84 (s, 1.5H), 2.75 (s, 1.5H), 2.24-2.13 (m, 2H).

6-fluoro-3-{1-[4-((3aR,6aR)-5-methyl-hexahydro-pyrrolo[3,4-b]pyrrole-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A291)

(898) ##STR00434##

(899) HPLC/MS 1.23 min (A), [M+H].sup.+ 459;

(900) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of rotamers, signals of major rotamer: 12.33 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.18-8.02 (m, 2H), 7.82 (dd, J=9.2, 2.8 Hz, 1H), 7.75-7.70 (m, 1H), 7.47 (td, J=8.8, 2.8 Hz, 1H), 7.42 (dd, J=9.0, 4.9 Hz, 1H), 4.56 (ddd, J=8.1, 5.8, 2.2 Hz, 1H), 3.62 (td, J=10.3, 6.6 Hz, 1H), 3.46 (ddd, J=10.5, 8.0, 2.7 Hz, 1H), 2.95-2.80 (m, 1H), 2.74 (dd, J=9.9, 2.2 Hz, 1H), 2.57-2.51 (m, 2H), 2.47-2.36 (m, 1H), 2.24 (s, 3H), 2.02-1.88 (m, 1H), 1.74 (ddd, J=12.1, 6.0, 2.8 Hz, 1H).

6-chloro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A292)

(901) ##STR00435##

(902) HPLC/MS 1.69 min (A), [M+H].sup.+ 434;

(903) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of rotamers, signals of major rotamer: 12.37 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.10-8.07 (m, 2H), 8.07 (d, J=2.4 Hz, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.60 (dd, J=8.8, 2.4 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.18 (h, J=5.9 Hz, 1H), 3.58-3.50 (m, 1H), 3.39-3.32 (m, 1H), 2.10 (dq, J=13.3, 6.8 Hz, 1H), 1.85-1.85 (m, 1H), 1.78-1.67 (m, 1H), 1.57 (dq, J=13.4, 6.8 Hz, 1H), 1.28 (d, J=6.2 Hz, 2H).

3-{1-[4-(2,2-dimethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A293)

(904) ##STR00436##

(905) HPLC/MS 1.68 min (A), [M+H].sup.+ 432;

(906) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.27 (s, 1H), 8.85 (s, 1H), 8.05 (d, J=8.5 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.64 (d, J=8.3 Hz, 2H), 7.53-7.37 (m, 2H), 3.40 (t, J=6.5 Hz, 2H), 1.90-1.71 (m, 4H), 1.53 (s, 6H).

6-fluoro-3-(1-{4-[3-(4-methyl-piperazine-1-carbonyl)-pyrrolidine-1-carbonyl]-phenyl}-1H-[1,2,3]triazol-4-yl)-1H-quinolin-2-one (A294)

(907) ##STR00437##

(908) UPLC/MS 0.47 min, [M+H].sup.+ 530;

(909) .sup.1H NMR (500 MHz, DMSO-d6) 1:1 mixture of rotamers, selection of signals 12.31 (s, 1H), 9.32 (s, 1H), 8.84 (s, 1H), 8.15-8.04 (m, 2H), 7.85-7.67 (m, 3H), 7.50-7.34 (m, 2H), 2.20 (s, 1.5H), 2.15 (s, 1.5H).

Example 19

6-fluoro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A295)

(910) ##STR00438##

(911) To a solution of methyl 4-(1H-pyrazol)-1-yl)-benzenecarboxylate (9.58 g, 47.4 mmol) in acetic acid (100 ml) is added N-bromosuccinimide (9.00 g, 50.6 mmol). The reaction mixture is heated to 100 C. and stirred at this temperature for 2 hours. The reaction mixture is allowed to reach room temperature. The solid is filtered off, washed with water and dried under vacuum to afford methyl 4-(4-bromo-1H-pyrazol-1-yl)benzoate as white crystalline solid; UPLC/MS 0.82 min, [M+H].sup.+ 281/283.

(912) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 8.94 (s, 1H), 8.17-8.06 (m, 2H), 8.03-7.98 (m, 2H), 7.97 (s, 1H), 3.88 (s, 3H).

(913) A suspension of methyl 4-(4-bromo-1H-pyrazol-1-yl)benzoate (5.12 g, 18.2 mmol), bis(pinacolato)diboron (6.10 g, 24.0 mmol) and dry potassium acetate (5.36 g, 54.6 mmol) in THF (110 ml) is flushed with nitrogen and bis(triphenyl-phosphine)palladium(II)chloride (260 mg, 0.37 mmol) is added. The reaction mixture is heated to 65 C. under nitrogen and stirred at this temperature for 3 days. The reaction mixture is filtered over kieselguhr and washed with dichloromethane. The filtrate is evaporated and chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-benzoic acid methyl ester as white solid; UPLC/MS 0.86 min, [M+H].sup.+ 329.

(914) .sup.1H NMR (300 MHz, DMSO-d.sub.6) 8.87 (s, 1H), 8.11-8.03 (m, 4H), 7.93 (s, 1H), 3.88 (s, 3H), 1.30 (s, 12H).

(915) A suspension of 3-bromo-6-fluoro-1H-quinolin-2-one (980 mg, 4.05 mmol), 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-benzoic acid methyl ester (1.46 g, 4.45 mmol) and 645 mg (6.44 mmol) potassium hydrogen carbonate in DMF (13 ml) and water (6.5 ml) is flushed with nitrogen and bis(triphenylphosphine)palladium(II)chloride (60 mg, 0.085 mmol) is added. The mixture is irradiated in a microwave reactor for 1 hour at 120 C. The reaction mixture is allowed to reach room temperature. The solids are filtered off, washed with water and methanol and dried under vacuum to afford 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-pyrazol-1-yl]-benzoic acid methyl ester as grey solid; UPLC/MS 0.80 min, [M+H].sup.+ 364.

(916) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.14 (s, 1H), 9.25 (s, 1H), 8.51 (s, 1H), 8.44 (s, 1H), 8.14-8.10 (m, 2H), 8.09-8.04 (m, 2H), 7.54-7.47 (m, 1H), 7.45-7.35 (m, 2H), 3.89 (s, 3H).

(917) To a solution of 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-pyrazol-1-yl]-benzoic acid methyl ester (832 mg, 2.29 mmol) in methanol (18 ml) is added aqueous 2 M sodium hydroxide solution (9.5 ml, 19 mmol) and the reaction mixture is stirred for 1 hour at 80 C. The reaction mixture is allowed to reach room temperature and is acidified with 2 N HCl. The resultant precipitate is filtered off, washed with water and dried under vacuum to afford 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-pyrazol-1-yl]-benzoic acid as grey solid; UPLC/MS 0.70 min, [M+H].sup.+ 350.

(918) To a suspension of 4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-pyrazol-1-yl]-benzoic acid (28.0.0 mg, 0.08 mmol) in a mixture of 1,4-dioxane (0.4 ml) and DMF (0.4 ml) are added (R)-2-methylpyrrolidine p-toluenesulfonate (25.5 mg, 0.10 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (23.0 mg, 0.12 mmol), 1-hydroxybenzotriazole hydrate (10.8 mg, 0.08 mmol) and 4-methylmorpholine (13.2 l, 0.12 mmol). The resultant suspension is stirred at room temperature for 2 hours. The reaction mixture is poured into water. The resultant precipitate is filtered off, washed with water and dried. The residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent to afford 6-fluoro-3-{1-[4-((R)-2-methyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one as white crystals; HPLC/MS 1.60 min (A), [M+H].sup.+ 417.

(919) .sup.1H NMR (500 MHz, DMSO-d.sub.6), mixture of rotamers; main rotamer: 12.15 (s, 1H), 9.20 (s, 1H), 8.47 (s, 1H), 8.42 (s, 1H), 8.00-7.92 (m, 2H), 7.67 (d, J=8.2 Hz, 2H), 7.49 (dd, J=9.0, 2.5 Hz, 1H), 7.43-7.35 (m, 2H), 4.20-4.11 (m, 1H), 3.59-3.50 (m, 1H), 3.42-3.34 (m, 1H), 2.09 (dq, J=12.6, 6.2, 5.7 Hz, 1H), 2.00-1.82 (m, 1H), 1.77-1.66 (m, 1H), 1.63-1.51 (m, 1H), 1.27 (d, J=6.2 Hz, 3H).

(920) The following compounds are prepared similarly:

6-fluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A296)

(921) ##STR00439##

(922) UPLC/MS 0.47 min, [M+H].sup.+ 432;

(923) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.11 (s, 1H), 9.18 (s, 1H), 8.46 (s, 1H), 8.41 (s, 1H), 8.01-7.90 (m, 2H), 7.61-7.52 (m, 2H), 7.52-7.46 (m, 1H), 7.41-7.37 (m, 2H), 3.5 (bs, 4H), 2.36 (bs, 4H), 2.22 (s, 3H).

6-fluoro-3-{1-[4-((S)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A297)

(924) ##STR00440##

(925) UPLC/MS 0.69 min, [M+H].sup.+ 433;

(926) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.12 (s, 1H), 9.19 (s, 1H), 8.47 (s, 1H), 8.41 (s, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.78-7.62 (m, 2H), 7.49 (dt, J=9.1, 1.7 Hz, 1H), 7.42-7.36 (m, 2H), 4.07-4.00 (m, 0.5H), 3.99-3.93 (m, 0.5H), 3.71-3.40 (m, 4H), 3.29 (s, 1.5H), 3.19 (s, 1.5H), 2.13-1.87 (m, 2H).

6-fluoro-3-{1-[4-((R)-3-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A298)

(927) ##STR00441##

(928) UPLC/MS 0.69 min, [M+H].sup.+ 433;

(929) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.12 (s, 1H), 9.19 (s, 1H), 8.47 (s, 1H), 8.41 (s, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.78-7.62 (m, 2H), 7.49 (dt, J=9.1, 1.7 Hz, 1H), 7.42-7.36 (m, 2H), 4.07-4.00 (m, 0.5H), 3.99-3.93 (m, 0.5H), 3.71-3.40 (m, 4H), 3.29 (s, 1.5H), 3.19 (s, 1.5H), 2.13-1.87 (m, 2H).

6-fluoro-3-(1-{4-[(S)-3-(2-methoxy-ethoxy)-pyrrolidine-1-carbonyl]-phenyl}-1H-pyrazol-4-yl)-1H-quinolin-2-one (A299)

(930) ##STR00442##

(931) UPLC/MS 0.69 min, [M+H].sup.+ 477;

(932) .sup.1H NMR (400 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.12 (s, 1H), 9.19 (s, 1H), 8.47 (s, 1H), 8.42 (s, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.49 (dt, J=9.1, 1.7 Hz, 1H), 7.44-7.34 (m, 2H), 4.22-4.14 (m, 0.5H), 4.13-4.06 (m, 0.5H), 3.73-3.36 (m, 8H), 3.28 (s, 1.5H), 3.21 (s, 1.5H), 2.06-1.90 (m, 2H).

3-{1-[4-((3R,4R)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one (A300)

(933) ##STR00443##

(934) HPLC/MS 1.50 min (A), [M+H].sup.+ 463;

(935) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.14 (s, 1H), 9.21 (s, 1H), 8.48 (s, 1H), 8.43 (s, 1H), 8.00-7.93 (m, 2H), 7.74-7.67 (m, 2H), 7.50 (dd, J=9.0, 2.5 Hz, 1H), 7.44-7.34 (m, 2H), 3.94 (d, J=4.7 Hz, 1H), 3.91-3.86 (m, 1H), 3.72 (dd, J=11.8, 4.3 Hz, 1H), 3.65 (dd, J=13.3, 4.9 Hz, 1H), 3.55 (d, J=13.4 Hz, 1H), 3.44 (d, J=11.7 Hz, 1H), 3.36 (s, 3H), 3.25 (s, 3H).

6-fluoro-3-{1-[4-((2S,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A301)

(936) ##STR00444##

(937) MS [M+H].sup.+ 463;

(938) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.11 (s, 1H), 9.19 (s, 1H), 8.46 (s, 1H), 8.41 (s, 1H), 7.96 (d, J=8.4 Hz, 2H), 7.68 (d, J=8.2 Hz, 2H), 7.49 (dt, J=9.2, 1.5 Hz, 1H), 7.39 (dd, J=7.5, 2.0 Hz, 2H), 4.79 (t, J=5.8 Hz, 1H), 4.23 (br. s, 1H), 3.90 (br. s, 1H), 3.78-3.67 (m, 1H), 3.61 (dd, J=11.8, 3.6 Hz, 1H), 3.59-3.50 (m, 1H), 3.42 (d, J=11.7 Hz, 1H), 3.17 (d, J=5.2 Hz, 2H), 3.10 (s, 3H) 2.17-1.99 (m, 2H).

6-fluoro-3-{1-[4-((2R,4R)-2-hydroxymethyl-4-methoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A302)

(939) ##STR00445##

(940) MS [M+H].sup.+ 463;

(941) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.11 (s, 1H), 9.19 (s, 1H), 8.46 (s, 1H), 8.41 (s, 1H), 7.94 (d, J=8.6 Hz, 2H), 7.67 (d, J=8.2 Hz, 2H), 7.49 (dt, J=9.2, 1.5 Hz, 1H), 7.41-7.37 (m, 2H), 4.81 (br. s, 1H), 4.22 (br. s, 1H), 3.90 (br. s, 1H), 3.76-3.48 (m, 2H), 3.41 (dd, J=11.3, 5.0 Hz, 1H), 3.22 (s, 3H), 3.17 (d, J=5.2 Hz, 1H), 2.16 (d, J=8.3 Hz, 1H), 2.02 (s, 1H).

3-{1-[4-((3S,4S)-3,4-dimethoxy-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one (A303)

(942) ##STR00446##

(943) HPLC/MS 1.50 min (A), [M+H].sup.+ 463;

(944) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 12.14 (s, 1H), 9.21 (s, 1H), 8.48 (s, 1H), 8.43 (s, 1H), 8.00-7.93 (m, 2H), 7.74-7.67 (m, 2H), 7.50 (dd, J=9.0, 2.5 Hz, 1H), 7.44-7.34 (m, 2H), 3.94 (d, J=4.7 Hz, 1H), 3.91-3.86 (m, 1H), 3.72 (dd, J=11.8, 4.3 Hz, 1H), 3.65 (dd, J=13.3, 4.9 Hz, 1H), 3.55 (d, J=13.4 Hz, 1H), 3.44 (d, J=11.7 Hz, 1H), 3.36 (s, 3H), 3.25 (s, 3H).

6,7-difluoro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A304)

(945) ##STR00447##

(946) HPLC/MS 1.24 min (A), [M+H].sup.+ 450;

(947) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.20 (s, 1H), 9.16 (s, 1H), 8.43 (s, 1H), 8.39 (s, 1H), 8.06-7.91 (m, 2H), 7.74 (dd, J=10.8, 8.4 Hz, 1H), 7.60-7.49 (m, 2H), 7.29 (dd, J=11.4, 7.1 Hz, 1H), 3.70-3.31 (m, 4H), 2.45-2.25 (m, 4H), 2.21 (s, 3H).

6-chloro-3-{1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-1H-quinolin-2-one (A305)

(948) ##STR00448##

(949) UPLC/MS 0.50 min, [M+H].sup.+ 448;

(950) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.13 (bs, 1H), 9.18 (s, 1H), 8.45 (s, 1H), 8.40 (s, 1H), 7.99-7.93 (m, 2H), 7.74 (d, J=2.4 Hz, 1H), 7.59-7.55 (m, 2H), 7.53 (dd, J=8.7, 2.4 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 3.8-3.3 (m, 4H), 2.45-2.25 (m, 4H), 2.21 (s, 3H).

Example 20

3-{1-[4-((S)-3-amino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A306)

(951) ##STR00449##

(952) MS [M+H].sup.+ 419; HCl salt;

(953) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.30 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.30 (br. s, 2H), 8.18 (br. s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.88-7.70 (m, 3H), 7.54-7.39 (m, 2H), 3.97-3.65 (m, 3H), 3.66-3.45 (m, 2H), 2.25 (br. s, 1H), 2.06 (br. s, 1H).

(954) The following compounds are prepared similarly:

6,7-difluoro-3-{1-[4-((cis)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A307)

(955) ##STR00450##

(956) UPLC/MS 0.47 min, [M+H].sup.+ 463;

(957) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.29 (s, 1H), 8.86 (s, 1H), 8.23-8.09 (m, 2H), 7.98 (dd, J=10.8, 8.5 Hz, 1H), 7.84-7.75 (m, 2H), 7.37 (dd, J=11.3, 7.0 Hz, 1H), 3.85-3.05 (m, 10H).

6-fluoro-3-{1-[4-((cis)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A308)

(958) ##STR00451##

(959) HPLC/MS 1.25 min (A), [M+H].sup.+ 445;

(960) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.32 (s, 1H), 8.87 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 7.79 (d, J=8.6 Hz, 2H), 7.72 (dd, J=9.1, 2.8 Hz, 1H), 7.49 (dd, J=9.0, 4.7 Hz, 1H), 7.40 (td, J=8.8, 2.8 Hz, 1H), 3.90-3.04 (m, 1 OH).

3-{1-[4-((R)-3-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one hydrochloride (A309)

(961) ##STR00452##

(962) UPLC/MS 0.47 min, [M+H].sup.+ 451;

(963) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.36 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.34-8.01 (m, 6H), 7.69 (d, J=8.5 Hz, 2H), 7.36 (dd, J=11.4, 7.0 Hz, 1H), 4.47-3.01 (m, 4H), 2.14-2.01 (m, 1H), 1.86-1.49 (m, 4H).

3-{1-[4-((S)-3-amino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one hydrochloride (A310)

(964) ##STR00453##

(965) UPLC/MS 0.47 min, [M+H].sup.+ 451.

(966) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.36 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.34-8.01 (m, 6H), 7.69 (d, J=8.5 Hz, 2H), 7.36 (dd, J=11.4, 7.0 Hz, 1H), 4.47-3.01 (m, 4H), 2.14-2.01 (m, 1H), 1.86-1.49 (m, 4H).

6-Fluoro-3-{1-[4-((R)-3-methylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one hydrochloride (A311)

(967) ##STR00454##

(968) MS [M+H].sup.+ 433; HCl salt;

(969) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.30 (s, 1H), 9.31 (s, 1H), 9.27-8.91 (m, 2H, NH.sub.2+), 8.86 (s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.85-7.74 (m, 3H), 7.51-7.41 (m, 2H), 3.92-3.68 (m, 3H), 3.68-3.51 (m, 2H), 2.65 (s, 1.8H), 2.56 (s, 1.2H), 2.27 (br. s, 1H), 2.17 (br. s, 1H).

6-fluoro-3-{1-[4-((S)-3-methylamino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one hydrochloride (A312)

(970) ##STR00455##

(971) MS [M+H].sup.+ 433; HCl salt;

(972) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers b 12.30 (s, 1H), 9.31 (s, 1H), 9.27-8.91 (m, 2H, NH.sub.2+), 8.86 (s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.85-7.74 (m, 3H), 7.51-7.41 (m, 2H), 3.92-3.68 (m, 3H), 3.68-3.51 (m, 2H), 2.65 (s, 1.8H), 2.56 (s, 1.2H), 2.27 (br. s, 1H), 2.17 (br. s, 1H).

3-{1-[4-((R)-3-amino-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one hydrochloride (A313)

(973) ##STR00456##

(974) MS [M+H].sup.+ 419; HCl salt;

(975) .sup.1H NMR (500 MHz, DMSO-d.sup.6) mixture of 2 rotamers 12.30 (s, 1H), 9.31 (s, 1H), 8.86 (s, 1H), 8.30 (br. s, 2H), 8.18 (br. s, 1H), 8.13 (d, J=8.6 Hz, 2H), 7.88-7.70 (m, 3H), 7.54-7.39 (m, 2H), 3.97-3.65 (m, 3H), 3.66-3.45 (m, 2H), 2.25 (br. s, 1H), 2.06 (br. s, 1H).

6-fluoro-3-{1-[4-((R)-3-hydroxymethyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one hydrochloride (A314)

(976) ##STR00457##

(977) MS [M+H].sup.+ 449; dihydrochloride;

(978) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.42 (br. s, 1H), 9.30 (s, 1H), 9.10 (br. s, 1H), 8.85 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.50-7.40 (m, 2H), 5.47 (s, 1H), 4.49 (br. s, 1H), 3.64 (br. s, 2H), 3.57 (s, 2H), 3.47-3.33 (m, 2H), 3.22-2.95 (m, 2H).

6-fluoro-3-{1-[4-((S)-2-hydroxymethyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A315)

(979) ##STR00458##

(980) MS [M+H].sup.+ 449;

(981) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.30 (s, 1H), 9.28 (s, 1H), 8.86 (s, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.63 (d, J=8.4 Hz, 2H), 7.50-7.40 (m, 2H), 4.91 (br. s, 1H), 4.49-4.04 (m, 1H), 3.93-3.45 (m, 3H), 3.13-2.54 (m, 4H), 2.20-1.95 (m, 1H).

6-fluoro-3-{1-[4-((R)-2-hydroxymethyl-piperazine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A316)

(982) ##STR00459##

(983) MS [M+H].sup.+ 449;

(984) .sup.1H NMR (500 MHz, DMSO-d.sub.6) mixture of 2 rotamers 12.30 (s, 1H), 9.28 (s, 1H), 8.86 (s, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.63 (d, J=8.4 Hz, 2H), 7.50-7.40 (m, 2H), 4.91 (br. s, 1H), 4.49-4.04 (m, 1H), 3.93-3.45 (m, 3H), 3.13-2.54 (m, 4H), 2.20-1.95 (m, 1H).

3-{1-[4-(6-amino-3-aza-bicyclo[3.1.0]hexane-3-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A317)

(985) ##STR00460##

(986) MS [M+H].sup.+ 431;

(987) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.07 (d, J=8.7 Hz, 2H), 7.81 (dd, J=9.2, 2.6 Hz, 1H), 7.67 (d, J=8.7 Hz, 2H), 7.51-7.39 (m, 2H), 3.89 (d, J=12.1 Hz, 1H), 3.66 (dd, J=10.6, 4.4 Hz, 1H), 3.45 (dd, J=12.0, 4.4 Hz, 1H), 3.38 (d, J=10.7 Hz, 1H), 2.00 (t, J=2.2 Hz, 1H), 1.56-1.41 (m, 2H).

6-chloro-3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A318)

(988) ##STR00461##

(989) HPLC/MS 1.35 min (A), [M+H].sup.+ 477;

(990) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.21 (s, 1H), 8.75 (s, 1H), 8.11-8.01 (m, 2H), 7.84 (d, J=2.3 Hz, 1H), 7.78-7.72 (m, 2H), 7.43 (dd, J=8.8, 2.3 Hz, 1H), 7.38 (d, J=8.7 Hz, 1H), 4.55 (qd, J=7.7, 3.4 Hz, 1H), 3.56 (dt, J=10.3, 7.3 Hz, 1H), 3.50-3.38 (m, 2H), 3.18 (dd, J=13.5, 3.5 Hz, 1H), 2.98 (s, 3H), 2.84 (s, 3H), 2.16 (dq, J=13.2, 6.6 Hz, 1H), 1.86 (dq, J=11.3, 5.8 Hz, 1H), 1.80-1.61 (m, 2H).

3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A319)

(991) ##STR00462##

(992) UPLC/MS 0.50 min, [M+H].sup.+ 461;

(993) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.19 (s, 1H), 8.75 (s, 1H), 8.00 (d, J=8.2 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.55-7.48 (m, 1H), 7.39 (dd, J=9.1, 4.7 Hz, 1H), 7.23 (td, J=8.8, 2.8 Hz, 1H), 4.57-4.47 (m, 1H), 3.63-3.49 (m, 1H), 3.49-3.36 (m, 2H), 3.15 (dd, J=13.5, 3.3 Hz, 1H), 2.97 (s, 3H), 2.82 (s, 3H), 2.20-2.10 (m, 1H), 1.97-1.79 (m, 1H), 1.79-1.58 (m, 2H).

3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A320)

(994) ##STR00463##

(995) UPLC/MS 0.52 min, [M+H].sup.+ 479;

(996) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.17 (s, 1H), 8.74 (s, 1H), 8.01 (d, J=8.6 Hz, 2H), 7.83-7.71 (m, 3H), 7.27 (dd, J=11.4, 7.0 Hz, 1H), 4.58-4.48 (m, 1H), 3.63-3.50 (m, 1H), 3.49-3.36 (m, 2H), 3.16 (dd, J=13.4, 3.4 Hz, 1H), 2.20-2.10 (m, 1H), 1.92-1.80 (m, 1H), 1.80-1.57 (m, 2H).

3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A321)

(997) ##STR00464##

(998) UPLC/MS 0.50 min, [M+H].sup.+ 461;

(999) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.26 (s, 1H), 8.80 (s, 1H), 8.15-8.07 (m, 2H), 7.84-7.76 (m, 2H), 7.64 (dd, J=9.1, 2.8 Hz, 1H), 7.42 (dd, J=9.0, 4.7 Hz, 1H), 7.32 (td, J=8.8, 2.8 Hz, 1H), 4.57 (qd, J=7.5, 3.7 Hz, 1H), 3.58 (dt, J=10.5, 7.3 Hz, 1H), 3.49-3.41 (m, 2H), 3.20 (dd, J=13.4, 3.8 Hz, 1H), 3.00 (s, 3H), 2.86 (s, 3H), 2.21-2.12 (m, 1H), 1.95-1.84 (m, 1H), 1.82-1.64 (m, 2H).

6-chloro-3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A322)

(1000) ##STR00465##

(1001) UPLC/MS 0.53 min, [M+H].sup.+ 477;

(1002) .sup.1H NMR (500 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.21 (s, 1H), 8.75 (s, 1H), 8.11-8.01 (m, 2H), 7.84 (d, J=2.3 Hz, 1H), 7.78-7.72 (m, 2H), 7.43 (dd, J=8.8, 2.3 Hz, 1H), 7.38 (d, J=8.7 Hz, 1H), 4.55 (qd, J=7.7, 3.4 Hz, 1H), 3.56 (dt, J=10.3, 7.3 Hz, 1H), 3.50-3.38 (m, 2H), 3.18 (dd, J=13.5, 3.5 Hz, 1H), 2.98 (s, 3H), 2.84 (s, 3H), 2.16 (dq, J=13.2, 6.6 Hz, 1H), 1.86 (dq, J=11.3, 5.8 Hz, 1H), 1.80-1.61 (m, 2H).

3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A323)

(1003) ##STR00466##

(1004) UPLC/MS 0.51 min, [M+H].sup.+ 479;

(1005) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.35 (s, 1H), 9.30 (s, 1H), 9.11 (bs, 1H, NH.sup.+), 8.86 (s, 1H), 8.19-8.13 (m, 2H), 8.10 (dd, J=11.0, 8.6 Hz, 1H), 7.86-7.76 (m, 2H), 7.34 (dd, J=11.4, 7.1 Hz, 1H), 4.64-4.54 (m, 1H), 3.64-3.54 (m, 1H), 3.51-3.39 (m, 2H), 3.28-2.16 (m, 1H), 3.08-2.80 (m, 6H), 2.22-2.10 (m, 1H), 2.01-1.88 (m, 1H), 1.86-1.68 (m, 2H).

3-{1-[4-((S)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one (A324)

(1006) ##STR00467##

(1007) UPLC/MS 0.51 min, [M+H].sup.+ 460;

(1008) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.12 (s, 1H), 9.21 (s, 1H), 9.12 (bs, 1H, NH.sup.+), 8.48 (s, 1H), 8.42 (s, 1H), 8.10-7.96 (m, 2H), 7.84-7.66 (m, 2H), 7.50 (dd, J=8.5, 1.9 Hz, 1H), 7.44-7.30 (m, 2H), 4.63-4.54 (m, 1H), 3.66-3.56 (m, 1H), 3.55-3.14 (m, 3H), 3.01 (d, J=4.2 Hz, 3H), 2.88 (d, J=4.2 Hz, 3H), 2.22-2.11 (m, 1H), 2.04-1.87 (m, 1H), 1.85-1.66 (m, 2H).

3-{1-[4-((R)-2-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one (A325)

(1009) ##STR00468##

(1010) UPLC/MS 0.51 min, [M+H].sup.+ 460;

(1011) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.12 (s, 1H), 9.21 (s, 1H), 9.12 (bs, 1H, NH.sup.+), 8.48 (s, 1H), 8.42 (s, 1H), 8.10-7.96 (m, 2H), 7.84-7.66 (m, 2H), 7.50 (dd, J=8.5, 1.9 Hz, 1H), 7.44-7.30 (m, 2H), 4.63-4.54 (m, 1H), 3.66-3.56 (m, 1H), 3.55-3.14 (m, 3H), 3.01 (d, J=4.2 Hz, 3H), 2.88 (d, J=4.2 Hz, 3H), 2.22-2.11 (m, 1H), 2.04-1.87 (m, 1H), 1.85-1.66 (m, 2H).

Example 21

3-{1-[4-((S)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A326)

(1012) ##STR00469##

(1013) UPLC/MS 0.46 min, [M+H].sup.+ 461;

(1014) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.22 (s, 1H), 8.77 (s, 1H), 8.11-7.97 (m, 2H), 7.70 (d, J=8.1 Hz, 2H), 7.59 (dd, J=9.2, 2.8 Hz, 1H), 7.40 (dd, J=9.0, 4.7 Hz, 1H), 7.28 (td, J=8.8, 2.8 Hz, 1H), 3.87-3.07 (m, 6H), 2.87-2.57 (m, 7H), 2.16-2.01 (m, 1H), 1.74-1.59 (m, 1H).

(1015) The following compounds are prepared similarly:

6-fluoro-3-{1-[4-((cis)-5-methyl-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A327)

(1016) ##STR00470##

(1017) HPLC/MS 1.26 min (A), [M+H].sup.+ 459;

(1018) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.17 (s, 1H), 8.12-8.04 (m, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.75-7.64 (m, 2H), 7.48-7.40 (m, 2H), 3.79 (bs, 1H), 3.67 (bs, 1H), 3.48 (bs, 1H), 3.31 (bs, 1H), 2.82 (bs, 2H), 2.52-2.34 (m, 4H), 2.25 (s, 3H).

3-{1-[4-((R)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A328)

(1019) ##STR00471##

(1020) HPLC/MS 1.23 min (A), [M+H].sup.+ 479;

(1021) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.12-8.05 (m, 3H), 7.60 (d, J=8.1 Hz, 2H), 7.32 (dd, J=11.4, 7.1 Hz, 1H), 4.5-4-2 (m, 1H), 3.77-2.74 (m, 4H), 2.32-2.02 (m, 7H), 1.85-1.62 (m, 1H), 1.73 (d, J=36.7 Hz, 1H), 1.54-1.34 (m, 2H).

3-{1-[4-((S)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A329)

(1022) ##STR00472##

(1023) HPLC/MS 1.25 min (A), [M+H].sup.+ 479;

(1024) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.32 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.12-8.05 (m, 3H), 7.60 (d, J=8.1 Hz, 2H), 7.32 (dd, J=11.4, 7.1 Hz, 1H), 4.5-4-2 (m, 1H), 3.77-2.74 (m, 4H), 2.32-2.02 (m, 7H), 1.85-1.62 (m, 1H), 1.73 (d, J=36.7 Hz, 1H), 1.54-1.34 (m, 2H).

3-{1-[4-(6-dimethylamino-3-aza-bicyclo[3.1.0]hexane-3-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A330)

(1025) ##STR00473##

(1026) MS [M+H].sup.+ 459;

(1027) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.07 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.2, 2.7 Hz, 1H), 7.68 (d, J=8.7 Hz, 2H), 7.51-7.37 (m, 2H), 3.90 (d, J=12.1 Hz, 1H), 3.70 (dd, J=10.7, 4.4 Hz, 1H), 3.44 (dd, J=12.2, 4.5 Hz, 1H), 3.37 (d, J=10.6 Hz, 1H), 2.21 (s, 6H), 1.70-1.57 (m, 2H), 1.35 (t, J=2.1 Hz, 1H).

3-{1-[4-((R)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A331)

(1028) ##STR00474##

(1029) HPLC/MS 1.21 min (A), [M+H].sup.+ 461;

(1030) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.61 (d, J=8.1 Hz, 2H), 7.53-7.39 (m, 2H), 4.71-0.89 (m, 15H).

3-{1-[4-((S)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A332)

(1031) ##STR00475##

(1032) HPLC/MS 1.19 min (A), [M+H].sup.+ 461;

(1033) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.28 (s, 1H), 9.29 (s, 1H), 8.86 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.81 (dd, J=9.3, 2.7 Hz, 1H), 7.61 (d, J=8.1 Hz, 2H), 7.53-7.39 (m, 2H), 4.71-0.89 (m, 15H).

3-{1-[4-((R)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-fluoro-1H-quinolin-2-one (A333)

(1034) ##STR00476##

(1035) UPLC/MS 0.46 min, [M+H].sup.+ 461;

(1036) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.24 (s, 1H), 8.86 (s, 1H), 8.08 (d, J=8.2 Hz, 2H), 8.00 (dd, J=9.6, 6.1 Hz, 1H), 7.60 (d, J=8.1 Hz, 2H), 7.27-6.99 (m, 2H), 4.71-0.89 (m, 15H).

3-{1-[4-((R)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A334)

(1037) ##STR00477##

(1038) UPLC/MS 0.46 min, [M+H].sup.+ 461;

(1039) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.22 (s, 1H), 8.77 (s, 1H), 8.11-7.97 (m, 2H), 7.70 (d, J=8.1 Hz, 2H), 7.59 (dd, J=9.2, 2.8 Hz, 1H), 7.40 (dd, J=9.0, 4.7 Hz, 1H), 7.28 (td, J=8.8, 2.8 Hz, 1H), 3.87-3.07 (m, 6H), 2.87-2.57 (m, 7H), 2.16-2.01 (m, 1H), 1.74-1.59 (m, 1H).

3-{1-[4-((R)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6,7-difluoro-1H-quinolin-2-one (A335)

(1040) ##STR00478##

(1041) UPLC/MS 0.48 min, [M+H].sup.+ 479;

(1042) .sup.1H NMR (400 MHz, DMSO-d.sub.6, TFA-d.sub.1) 9.18 (s, 1H), 8.75 (s, 1H), 8.07-7.96 (m, 2H), 7.80 (dd, J=10.8, 8.4 Hz, 1H), 7.69 (d, J=8.1 Hz, 2H), 7.28 (dd, J=11.4, 7.0 Hz, 1H), 3.87-3.07 (m, 6H), 2.87-2.57 (m, 7H), 2.16-2.01 (m, 1H), 1.74-1.59 (m, 1H).

3-{1-[4-((S)-3-dimethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-7-fluoro-1H-quinolin-2-one (A336)

(1043) ##STR00479##

(1044) UPLC/MS 0.48 min, [M+H].sup.+ 461;

(1045) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.24 (s, 1H), 8.86 (s, 1H), 8.08 (d, J=8.2 Hz, 2H), 8.00 (dd, J=9.6, 6.1 Hz, 1H), 7.60 (d, J=8.1 Hz, 2H), 7.27-6.99 (m, 2H), 4.71-0.89 (m, 15H).

3-{1-[4-((S)-3-diethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A337)

(1046) ##STR00480##

(1047) HPLC/MS 1.25 min (A), [M+H].sup.+ 489;

(1048) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (d, J=2.5 Hz, 1H), 8.86 (s, 1H), 8.10 (d, J=8.0 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.71-7.58 (m, 2H), 7.55-7.33 (m, 2H), 4.60-4.35 (m, 1H), 3.62-3.46 (m, 1H), 3.08-2.90 (m, 1H), 2.78-2.34 (m, 6H), 2.03-1.38 (m, 4H), 0.94 (d, J=69.7 Hz, 6H).

3-{1-[4-((R)-3-diethylamino-piperidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A338)

(1049) ##STR00481##

(1050) HPLC/MS 1.24 min (A), [M+H].sup.+ 489;

(1051) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.29 (s, 1H), 9.30 (d, J=2.5 Hz, 1H), 8.86 (s, 1H), 8.10 (d, J=8.0 Hz, 2H), 7.81 (dd, J=9.2, 2.7 Hz, 1H), 7.71-7.58 (m, 2H), 7.55-7.33 (m, 2H), 4.60-4.35 (m, 1H), 3.62-3.46 (m, 1H), 3.08-2.90 (m, 1H), 2.78-2.34 (m, 6H), 2.03-1.38 (m, 4H), 0.94 (d, J=69.7 Hz, 6H).

3-{1-[4-(4-dimethylamino-3,3-difluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A339)

(1052) ##STR00482##

(1053) HPLC/MS 1.27 min (A), [M+H].sup.+ 483;

(1054) .sup.1H NMR (700 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers, 12.31 (s, 1H), 9.32 (s, 1H), 8.87 (s, 1H), 8.12 (d, J=8.3 Hz, 2H), 7.85-7.78 (m, 3H), 7.47 (td, J=8.7, 2.8 Hz, 1H), 7.43 (dd, J=9.1, 4.8 Hz, 1H), 4.21-3.78 (m, 3H), 3.68 (t, J=10.1 Hz, 0.5H), 3.47 (t, J=10.9 Hz, 0.5H), 3.23 (dq, J=17.7, 9.0 Hz, 1H), 2.33 (s, 3H), 2.24 (s, 3H).

3-{1-[4-((S)-3-dimethylaminomethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazol-4-yl}-6-fluoro-1H-quinolin-2-one (A340)

(1055) ##STR00483##

(1056) UPLC/MS 0.48 min, [M+H].sup.+ 460;

(1057) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers, selection of signals 12.16 (s, 1H), 9.20 (s, 1H), 8.47 (s, 1H), 8.43 (s, 1H), 7.99-7.90 (m, 2H), 7.78-7.65 (m, 2H), 7.50 (dd, J=9.0, 2.5 Hz, 1H), 7.45-7.32 (m, 2H), 2.18 (s, 3H), 2.08 (s, 3H).

3-{1-[4-((trans)-3-dimethylamino-4-fluoro-pyrrolidine-1-carbonyl)-phenyl]-1H-[1,2,3]triazol-4-yl}-6-fluoro-1H-quinolin-2-one (A341)

(1058) ##STR00484##

(1059) HPLC/MS 1.23 min (A), [M+H].sup.+ 465;

(1060) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers 12.32 (s, 1H), 9.32 (s, 1H), 8.87 (s, 1H), 8.24-7.95 (m, 2H), 7.86-7.76 (m, 3H), 7.47 (td, J=8.8, 2.8 Hz, 1H), 7.43 (dd, J=9.0, 4.9 Hz, 1H), 5.30 (m, 1H), 4.04-3.49 (m, 4H), 3.05-2.92 (m, 1H), 2.26 (s, 3H), 2.16 (s, 3H).

Example 22

6-fluoro-3-[1-(4-methylamino-phenyl)-1H-[1,2,3]triazol-4-yl]-1H-quinolin-2-one (A342) and (R)-tetrahydro-furan-2-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide (A343)

(1061) ##STR00485##

(1062) A342: MS [M+H].sup.+ 336;

(1063) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.22 (s, 1H), 8.98 (s, 1H), 8.80 (s, 1H), 7.80-7.74 (m, 1H), 7.69 (d, J=8.8 Hz, 2H), 7.46-7.38 (m, 2H), 6.79 (d, J=8.6 Hz, 2H), 4.07 (br. s, 1H), 2.50 (p, J=1.9 Hz, 3H).

(1064) A343: MS [M+H].sup.+ 434;

(1065) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.79 (dd, J=9.3, 2.6 Hz, 1H), 7.58 (d, J=8.6 Hz, 2H), 7.49-7.39 (m, 2H), 4.29 (br. s, 1H), 3.81 (q, J=7.1 Hz, 1H), 3.69 (br. s, 1H), 3.25 (s, 3H), 2.01 (br. s, 1H), 1.96-1.80 (m, 2H), 1.73 (br. s, 1H).

(1066) The following compounds are prepared similarly:

(S)-tetrahydro-furan-2-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide (A344)

(1067) ##STR00486##

(1068) MS [M+H].sup.+ 434;

(1069) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.26 (s, 1H), 9.26 (s, 1H), 8.84 (s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.79 (dd, J=9.3, 2.6 Hz, 1H), 7.58 (d, J=8.6 Hz, 2H), 7.49-7.39 (m, 2H), 4.29 (br. s, 1H), 3.81 (q, J=7.1 Hz, 1H), 3.69 (br. s, 1H), 3.25 (s, 3H), 2.01 (br. s, 1H), 1.96-1.80 (m, 2H), 1.73 (br. s, 1H).

tetrahydro-pyran-4-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide (A345)

(1070) ##STR00487##

(1071) MS [M+H].sup.+ 448;

(1072) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.27 (s, 1H), 9.27 (s, 1H), 8.85 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.50-7.39 (m, 2H), 3.78 (d, J=11.3 Hz, 2H), 3.23 (s, 3H), 3.11 (br. s, 2H), 1.65 (qd, J=12.3, 4.4 Hz, 2H), 1.58-1.43 (m, 2H).

(R)N-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-2-methoxy-N-methyl-propionamide (A346)

(1073) ##STR00488##

(1074) MS [M+H].sup.+ 422;

(1075) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.27 (s, 1H), 8.85 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.50-7.39 (m, 2H), 3.88 (br. s, 1H), 3.26 (s, 3H), 3.08 (s, 3H), 1.16 (br. s, 3H).

(2S,4S)-4-methoxy-pyrrolidine-2-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide (A347)

(1076) ##STR00489##

(1077) MS [M+H].sup.+ 463; hydrochloride

(1078) .sup.1H NMR (700 MHz, DMSO-d.sub.6+CF.sub.3COOD) 9.34 (s, 1H), 8.88 (s, 1H), 8.22 (d, J=8.4 Hz, 2H), 7.78 (dd, J=9.1, 2.8 Hz, 1H), 7.73 (d, J=8.3 Hz, 2H), 7.50-7.40 (m, 2H), 4.26 (dd, J=10.3, 6.9 Hz, 1H), 3.94 (br. s, 1H), 3.48-3.38 (m, 1H), 3.34 (s, 3H), 3.22 (s, 3H), 3.13 (dd, J=12.4, 4.7 Hz, 1H), 2.07 (ddd, J=16.0, 10.5, 6.1 Hz, 1H), 1.95-1.84 (m, 1H).

(S)N-{4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-2-methoxy-N-methyl-propionamide (A348)

(1079) ##STR00490##

(1080) MS [M+H].sup.+ 422;

(1081) .sup.1H NMR (400 MHz, DMSO-d.sub.6) .sup.1H NMR (400 MHz, DMSO-d.sub.6) 12.24 (s, 1H), 9.27 (s, 1H), 8.85 (s, 1H), 8.10 (d, J=8.6 Hz, 2H), 7.80 (dd, J=9.2, 2.6 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.50-7.39 (m, 2H), 3.88 (br. s, 1H), 3.26 (s, 3H), 3.08 (s, 3H), 1.16 (br. s, 3H).

1-methyl-piperidine-4-carboxylic acid {4-[4-(6-fluoro-2-oxo-1,2-dihydro-quinolin-3-yl)-[1,2,3]triazol-1-yl]-phenyl}-methyl-amide (A349)

(1082) ##STR00491##

(1083) MS [M+H].sup.+ 461; hydrochloride

(1084) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.34 (s, 1H), 9.76 (s, 1H), 9.30 (s, 1H), 8.86 (s, 1H), 8.15 (d, J=7.5 Hz, 2H), 7.82 (dd, J=9.2, 2.8 Hz, 1H), 7.65 (d, J=6.6 Hz, 2H), 7.52-7.41 (m, 2H), 3.35-3.26 (m, 2H), 3.22 (s, 3H), 2.82-2.67 (m, 2H), 2.61 (s, 3H), 2.44 (br. s, 1H), 1.99-1.74 (m, 4H).

Example 23

6-fluoro-3-{1-[5-((S)-3-methoxy-pyrrolidine-1-carbonyl)-thiophen-3-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A350)

(1085) ##STR00492##

(1086) UPLC/MS 0.70 min, [M+H].sup.+ 440;

(1087) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers b 12.30 (s, 1H), 9.35 (s, 0.5H), 9.34 (s, 0.5H), 8.85 (s, 1H), 8.42 (d, J=1.4 Hz, 1H), 8.22 (d, J=1.5 Hz, 0.5H), 8.19 (d, J=1.5 Hz, 0.5H), 7.82 (dd, J=9.3, 2.8 Hz, 1H), 7.46 (td, J=8.8, 2.8 Hz, 1H), 7.42 (dd, J=9.1, 4.9 Hz, 1H), 4.20-3.87 (m, 3H), 3.75-3.47 (m, 2H), 3.29 (s, 1.5H), 3.27 (s, 1.5H), 2.25-1.90 (m, 2H).

(1088) The following compounds are prepared similarly:

6-fluoro-3-{1-[5-((R)-3-methoxy-pyrrolidine-1-carbonyl)-thiophen-3-yl]-1H-[1,2,3]triazol-4-yl}-1H-quinolin-2-one (A351)

(1089) ##STR00493##

(1090) UPLC/MS 0.71 min, [M+H].sup.+ 440;

(1091) .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1:1 mixture of rotamers 12.30 (s, 1H), 9.35 (s, 0.5H), 9.34 (s, 0.5H), 8.85 (s, 1H), 8.42 (d, J=1.4 Hz, 1H), 8.22 (d, J=1.5 Hz, 0.5H), 8.19 (d, J=1.5 Hz, 0.5H), 7.82 (dd, J=9.3, 2.8 Hz, 1H), 7.46 (td, J=8.8, 2.8 Hz, 1H), 7.42 (dd, J=9.1, 4.9 Hz, 1H), 4.20-3.87 (m, 3H), 3.75-3.47 (m, 2H), 3.29 (s, 1.5H), 3.27 (s, 1.5H), 2.25-1.90 (m, 2H).

(1092) The following examples relate to medicaments:

Example A: Injection Vials

(1093) A solution of 100 g of an active ingredient of the formula I and 5 g of disodium hydrogenphosphate in 3 l of bidistilled water is adjusted to pH 6.5 using 2 N hydrochloric acid, sterile filtered, transferred into injection vials, lyophilised under sterile conditions and sealed under sterile conditions. Each injection vial contains 5 mg of active ingredient.

Example B: Suppositories

(1094) A mixture of 20 g of an active ingredient of the formula I with 100 g of soya lecithin and 1400 g of cocoa butter is melted, poured into moulds and allowed to cool. Each suppository contains 20 mg of active ingredient.

Example C: Solution

(1095) A solution is prepared from 1 g of an active ingredient of the formula I, 9.38 g of NaH.sub.2PO.sub.4.2H.sub.2O, 28.48 g of Na.sub.2HPO.sub.4.12 H.sub.2O and 0.1 g of benzalkonium chloride in 940 ml of bidistilled water. The pH is adjusted to 6.8, and the solution is made up to 1 l and sterilised by irradiation. This solution can be used in the form of eye drops.

Example D: Ointment

(1096) 500 mg of an active ingredient of the formula I are mixed with 99.5 g of Vaseline under aseptic conditions.

Example E: Tablets

(1097) A mixture of 1 kg of active ingredient of the formula I, 4 kg of lactose, 1.2 kg of potato starch, 0.2 kg of talc and 0.1 kg of magnesium stearate is pressed in a conventional manner to give tablets in such a way that each tablet contains 10 mg of active ingredient.

Example F: Dragees

(1098) Tablets are pressed analogously to Example E and subsequently coated in a conventional manner with a coating of sucrose, potato starch, talc, tragacanth and dye.

Example G: Capsules

(1099) 2 kg of active ingredient of the formula I are introduced into hard gelatine capsules in a conventional manner in such a way that each capsule contains 20 mg of the active ingredient.

Example H: Ampoules

(1100) A solution of 1 kg of active ingredient of the formula I in 60 l of bidistilled water is sterile filtered, transferred into ampoules, lyophilised under sterile conditions and sealed under sterile conditions. Each ampoule contains 10 mg of active ingredient.