1,3-Disubstituted cyclopentane derivatives

Abstract

Compounds of the formula I ##STR00001##
in which R, Y, R.sup.1, X.sup.1, X.sup.2, X.sup.3 and q have the meanings indicated in claim 1, are inhibitors of fatty acid synthase, and can be employed, inter alia, for the treatment of diseases such as cancer, cardiovascular diseases, central nervous system injury and different forms of inflammation.

Claims

1. Compounds of the formula I ##STR00134## in which R denotes Ar or Het, Y denotes —CO—W or —N(R.sup.4)CO—W.sup.1, W denotes NR.sup.2R.sup.2′, CH.sub.2Het.sup.1, A, Cyc, Ar, CH.sub.2Ar, —CONR.sup.2R.sup.2′ or Het.sup.1, W.sup.1 denotes NR.sup.2R.sup.2′, Het.sup.1, CH.sub.2Het.sup.1, A, Cyc, Ar, CH.sub.2Ar, CH.sub.2Cyc or CH(OH)CH.sub.2OH, R.sup.1 denotes H, F, Cl, Br, OH, CN, NO.sub.2, A′, OA′, SA′, SO.sub.2Me, COA′, CONH.sub.2, CONHA′ or CONA′.sub.2, R.sup.2 and R.sup.2′ each, independently of one another, denote H, A or [C(R.sup.3).sub.2].sub.nCyc, X.sup.1, X.sup.2 and X.sup.3 each, independently of one another, denote CR.sup.8 or N, X.sup.4 denotes CR.sup.8 or N, X.sup.5 denotes CR.sup.8 or N, 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, Cyc denotes cycloalkyl with 3-7 C-atoms, which is unsubstituted or monosubstituted by OH, Hal or A, A′ denotes unbranched or branched alkyl with 1-6 C-atoms, wherein 1-5 H-atoms may be replaced by F, R.sup.5 denotes F, Cl or OH, Ar denotes phenyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, O[C(R.sup.3).sub.2].sub.nHet.sup.1, Ar.sup.1, [C(R.sup.3).sub.2].sub.pOR.sup.3, [C(R.sup.3).sub.2].sub.pN(R.sup.3).sub.2, NO.sub.2, CN, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, CON(R.sup.3).sub.2, Het.sup.1, OCH.sub.2Cyc, N(R.sup.3).sub.2COA, NR.sup.3SO.sub.2A, [C(R.sup.3).sub.2].sub.pSO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2 and/or COA, Ar.sup.1 denotes phenyl or naphthyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, [C(R.sup.3).sub.2].sub.pOR.sup.3, [C(R.sup.3).sub.2].sub.pN(R.sup.3).sub.2, NO.sub.2, CN, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, [C(R.sup.3).sub.2].sub.pN(R.sup.3).sub.2, N(R.sup.3).sub.2COA, NR.sup.3SO.sub.2A, [C(R.sup.3).sub.2].sub.pSO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2 and/or COA, R.sup.3 denotes H or unbranched or branched alkyl with 1-6 C-atoms, R.sup.8 denotes H or A′, Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, [C(R.sup.3).sub.2].sub.nOA′, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, SR.sup.3, NO.sub.2, CN, COOR.sup.3, CON(R.sup.3).sub.2, COHet.sup.1, NR.sup.3COA, NR.sup.3SO.sub.2A, SO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2, CHO, COA, ═S, ═NH, ═NA and/or ═O (carbonyl oxygen), Het.sup.1 denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, [C(R.sup.3).sub.2].sub.nOR.sup.3, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, SR.sup.3, NO.sub.2, CN, COOR.sup.3, CON(R.sup.3).sub.2, NR.sup.3COA, NR.sup.3SO.sub.2A, SO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2, CHO, COA, ═S, ═NH, ═NA and/or ═O (carbonyl oxygen), Hal denotes F, Cl, Br or I, m denotes 1, 2 or 3, n denotes 0, 1 or 2, p denotes 0, 1, 2, 3 or 4, q denotes 0, 1, 2 or 3, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

2. Compounds according to claim 1 in which R.sup.4 denotes H, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

3. Compounds according to claim 1, in which A denotes unbranched or branched alkyl with 1-6 C-atoms, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

4. Compounds according to claim 1, in which Ar denotes phenyl, which is unsubstituted or mono-, di- or trisubstituted by Hal, A, Het.sup.1, [C(R.sup.3).sub.2].sub.pOR.sup.3, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, OCH.sub.2Cyc, CON(R.sup.3).sub.2 and/or CN, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

5. Compounds according to claim 1, in which Het denotes a mono- or bicyclic aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or mono- or disubstituted by Hal, A and/or ═O, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

6. Compounds according to claim 1, in which Het denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, benzo-1,3-dioxolyl, benzodioxanyl, benzothiadiazolyl, indazolyl, benzofuranyl, quinolyl, isoquinolyl, pyrrolo[2,3-b]pyridyl, oxazolo[5,4-b]pyridyl, imidazo[1,2-a]pyrimidinyl, 2,3-dihydro-indolyl, 2,3-dihydro-benzimidazolyl, imidazo[1,2-a]pyridyl, pyrrolo[3,2-b]pyridyl or oxazolo[5,4-c]pyridyl, each of which is unsubstituted or mono- or disubstituted by Hal, A and/or ═O, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

7. Compounds according to claim 1, in which Het.sup.1 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, tetrahydrofuranyl, [1,3]dioxolanyl, pyrrolidinyl, piperidinyl or morpholinyl, each of which is unsubstituted or mono- or disubstituted by Hal, A and/or ═O, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

8. Compounds according to claim 1, in which R denotes Ar or Het, Y denotes —CO—W or —N(R.sup.4)CO—W.sup.1, W denotes NR.sup.2R.sup.2′, W.sup.1 denotes A, Cyc, Het.sup.1, CH.sub.2Cyc or CH(OH)CH.sub.2OH, R.sup.1 denotes H or F, R.sup.2 and R.sup.2′ each, independently of one another, denote H, A or [C(R.sup.3).sub.2].sub.nCyc, X.sup.1, X.sup.2, X.sup.3 each, independently of one another, denote CR.sup.8 or N, X.sup.4 denotes CR.sup.8 or N, X.sup.5 denotes CR.sup.8 or N, R.sup.4 denotes H, A denotes unbranched or branched alkyl with 1-6 C-atoms, Cyc denotes cycloalkyl with 3-7 C-atoms, which is unsubstituted or monosubstituted by A, A′ denotes unbranched or branched alkyl with 1-6 C-atoms, Ar denotes phenyl, which is unsubstituted or mono-, di- or trisubstituted by Hal, A, Het.sup.1, [C(R.sup.3).sub.2].sub.pOR.sup.3, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, OCH.sub.2Cyc, CON(R.sup.3).sub.2 and/or CN, R.sup.3 denotes H or unbranched or branched alkyl with 1-6 C-atoms, R.sup.8 denotes H or A′, Het denotes a mono- or bicyclic aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or mono- or disubstituted by Hal, A and/or ═O, Het.sup.1 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, tetrahydrofuranyl, [1,3]dioxolanyl, pyrrolidinyl, piperidinyl or morpholinyl, each of which is unsubstituted or mono- or disubstituted by Hal, A and/or ═O, Hal denotes F, Cl, Br or I, n denotes 0, 1 or 2, p denotes 0, 1, 2, 3 or 4, q denotes 1, and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

9. Compounds according to claim 1, selected from the group consisting of TABLE-US-00002 No. Name “A1” 4-(1,3-benzoxazol-2-yl)-N-[(1R,3S)-3- (ethylcarbamoyl)cyclopentyl]-N-methyl-benzamide, “A2” (1S,3R)-3-(5-biphenyl-4-yl-imidazol-1-yl)- cyclopentanecarboxylic acid ethylamide, “A3” (1S,3R)-3-[5-(4′-Chloro-biphenyl-4-yl)-imidazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A4” (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-imidazol-1-yl]- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A5” (1S,3R)-3-{5-[4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]- imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl- cyclopropyl)-amide, “A6” (1S,3R)-3-[5-(4-benzothiazol-6-yl-phenyl)-imidazol-1-yl]- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide amide, “A7” (1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-imidazol-1-yl}- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A8” (1S,3R)-3-{5-[4-(5-fluoro-1H-indol-2-yl)-phenyl]-imidazol-1- yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A9” (1S,3R)-3-{5-[4-(1H-benzotriazol-5-yl)-phenyl]-imidazol-1-yl}- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A10” (1S,3R)-3-{5-[4-(1H-indol-5-yl)-phenyl]-imidazol-1-yl}- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A11” (1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-imidazol-1-yl}- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A12” (1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-imidazol-1-yl]- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A13” (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A14” (1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A15” (1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-[1,2,3]triazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A16” (1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}- cyclopentanecarboxylic acid ethylamide, “A17” (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]- cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A18” (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]- cyclopentanecarboxylic acid propylamide, “A19” N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-imidazol-1-yl]- cyclopentyl}-propionamide, “A20” N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-imidazol-1-yl]- cyclopentyl}-propionamide, “A21” N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-imidazol-1-yl]- cyclopentyl}-propionamide, “A22” N-((1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-imidazol-1-yl}- cyclopentyl)-propionamide, “A23” N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-propionamide, “A24” N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-acetamide, “A25” N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]- cyclopentyl}-propionamide, “A26” N-((1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-[1,2,3]triazol- 1-yl}-cyclopentyl)-propionamide, “A27” N-((1S,3R)-3-{5-[4-(1H-indol-5-yl)-phenyl]-[1,2,3]triazol- 1-yl}-cyclopentyl)-propionamide, “A28” N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-propionamide, “A29” (1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]- cyclopentanecarboxylic acid ethylamide, “A30” (1S,3R)-3-{3-[4-(1H-indol-6-yl)-phenyl]-[1,2,4]triazol-4-yl}- cyclopentanecarboxylic acid ethylamide, “A31” (1S,3R)-3-[3-(4′-chloro-biphenyl-4-yl)-[1,2,4]triazol-4-yl]- cyclopentanecarboxylic acid ethylamide, “A32” (1S,3R)-3-[3-(4′-cyano-biphenyl-4-yl)-[1,2,4]triazol-4-yl]- cyclopentanecarboxylic acid ethylamide, “A33” (1S,3R)-3-[3-(4-benzothiazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]- cyclopentanecarboxylic acid ethylamide, “A34” (1S,3R)-3-[3-(4-benzothiazol-6-yl-phenyl)-[1,2,4]triazol-4- yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide, “A35” (1S,3R)-3-{3-[4-(1H-indazol-4-yl)-phenyl]-[1,2,4]triazol- 4-yl}-cyclopentanecarboxylic acid ethylamide, “A36” (1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-5-methyl- [1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide, “A37” N-{(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-[1,2,4]triazol- 4-yl]-cyclopentyl}-propionamide, “A38” N-{(1S,3R)-3-[3-(4-benzothiazol-2-yl-phenyl)-[1,2,4]triazol-4- yl]-cyclopentyl}-propionamide, “A39” N-{(1S,3R)-3-[3-(4′-chloro-biphenyl-4-yl)-[1,2,4]triazol-4-yl]- cyclopentyl}-propionamide, “A40” N-{(1S,3R)-3-[3-(4′-cyano-biphenyl-4-yl)-[1,2,4]triazol-4-yl]- cyclopentyl}-propionamide, “A41” N-{(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-5-ethyl- [1,2,4]triazol-4-yl]-cyclopentyl}-propionamide, “A42” N-((1S,3R)-3-{3-[4-(1H-indazol-4-yl)-phenyl]-[1,2,4]triazol-4- yl}-cyclopentyl)-propionamide, “A43” N-{(1S,3R)-3-[3-(4-benzothiazol-6-yl-phenyl)-[1,2,4]triazol-4- yl]-cyclopentyl}-propionamide, “A44” N-((1S,3R)-3-{3-[4-(1H-indol-6-yl)-phenyl]-[1,2,4]triazol-4-yl}- cyclopentyl)-propionamide, “A45” (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-pyrazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A46” N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-pyrazol-1-yl]- cyclopentyl}-propionamide, “A47” (1S,3R)-3-{5-[4-(1H-Indazol-4-yl)-phenyl]-pyrazol-1-yl}- cyclopentanecarboxylic acid ethylamide, “A48” (1S,3R)-3-[5-(4-benzothiazol-6-yl-phenyl)-pyrazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A49” (1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-pyrazol-1-yl}- cyclopentanecarboxylic acid ethylamide, “A50” (1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-pyrazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A51” (1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-pyrazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A52” (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-pyrazol-1-yl]- cyclopentanecarboxylic acid ethylamide, “A53” N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-pyrazol-1-yl]- cyclopentyl}-propionamide, “A54” N-{(1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-pyrazol-1-yl]- cyclopentyl}-propionamide, “A55” (N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-pyrazol-1-yl]- cyclopentyl}-propionamide, “A56” N-((1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-pyrazol-1-yl}- cyclopentyl)-propionamide, “A57” N-((1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-pyrazol-1-yl}- cyclopentyl)-propionamide, “A58” N-{(1S,3R)-3-[5-(4′-Cyano-biphenyl-4-yl)-[1,2,3]triazol-1-yl]- cyclopentyl}-propionamide, “A59” N-((1S,3R)-3-{5-[4-(1H-Indol-6-yl)-phenyl]-[1,2,3]triazol- 1-yl}-cyclopentyl)-propionamide, “A60” N-{(1S,3R)-3-[5-(4-Benzothiazol-6-yl-phenyl)-[1,2,3]triazol-1- yl]-cyclopentyl}-propionamide, “A61” N-((1S,3R)-3-{5-[4-(1-Methyl-1H-indazol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A62” N-{(1S,3R)-3-[5-(4′-Cyano-2′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A63” N-((1S,3R)-3-{5-[4-(1-Methyl-1H-indazol-6-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A64” N-((1S,3R)-3-{5-[4′-(1-Methyl-1H-pyrazol-4-yl)-biphenyl- 4-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A65” (1S,3R)-3-[3-(4-Benzothiazol-6-yl-phenyl)-[1,2,4]triazol- 4-yl]-cyclopentanecarboxylic acid ethylamide, “A66” Cyclopropanecarboxylic acid {(1S,3R)-3-[5-(4-benzooxazol-2- yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-amide, “A67” N-{(1S,3R)-3-[5-(4-Benzoxazol-2-yl-phenyl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-2-cyclopentyl-acetamide, “A68” (R)-Tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[5-(4- benzooxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}- amide, “A69” (S)-Tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[5-(4- benzooxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}- amide, “A70” N-{(1S,3R)-3-[5-(4-Quinolin-3-yl-phenyl)-[1,2,3]triazol-1-yl]- cyclopentyl}-propionamide, “A71” N-((1S,3R)-3-{5-[4-(1-Methyl-1H-indol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A72” N-((1S,3R)-3-{5-[4-(1H-Indazol-6-yl)-phenyl]-[1,2,3]triazol-1- yl}-cyclopentyl)-propionamide, “A73” N-((1S,3R)-3-{5-[4-(1H-Benzimidazol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A74” N-((1S,3R)-3-{5-[4-(1H-Indazol-5-yl)-phenyl]-[1,2,3]triazol-1- yl}-cyclopentyl)-propionamide, “A75” N-{(1S,3R)-3-[5-(4′-Chloro-3′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A76” N-{(1S,3R)-3-[5-(4′-Pyrazol-1-yl-biphenyl-4-yl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-propionamide, “A77” N-((1S,3R)-3-{5-[4-(1-Methyl-2-oxo-2,3-dihydro-1H-indol- 6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A78” N-((1S,3R)-3-{5-[4-(6-Methyl-1H-indazol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A79” N-((1S,3R)-3-{5-[4-(2-Oxo-2,3-dihydro-1H-indol-5-yl)- phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A80” N-{(1S,3R)-3-[5-(4′-Cyano-3′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A81” N-{(1S,3R)-3-[5-(4′-Chloro-2′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A82” N-{(1S,3R)-3-[5-(4′-Methoxy-2′-methyl-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A83” N-{(1S,3R)-3-[5-(3′-Fluoro-4′-methyl-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A84” N-{(1S,3R)-3-[5-(4′-Methyl-biphenyl-4-yl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-propionamide, “A85” N-{(1S,3R)-3-[5-(3′-Chloro-4′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A86” N-{(1S,3R)-3-[5-(2′,4′-Dimethoxy-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A87” N-((1S,3R)-3-{5-[4-(2-Oxo-2,3-dihydro-1H-benzimidazol- 5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A88” N-{(1S,3R)-3-[5-(3′,4′-Dimethoxy-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A89” N-{(1S,3R)-3-[5-(2′,4′-Dimethyl-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A90” (S)-2,2-Dimethyl-[1,3]dioxolane-4-carboxylic acid {(1S,3R)- 3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]- cyclopentyl}-amide, “A91” N-((1S,3R)-3-{5-[4-(2-Oxo-2,3-dihydro-1H-indol-6-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A92” N-{(1S,3R)-3-[5-(4′-Cyclopropylmethoxy-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A93” (S)-N-{(1S,3R)-3-[5-(4-Benzoxazol-2-yl-phenyl)-[1,2,3]triazol- 1-yl]-cyclopentyl}-2,3-dihydroxy-propionamide, “A94” N-{(1S,3R)-3-[3-(4′-Methoxy-2′-methyl-biphenyl-4-yl)- [1,2,4]triazol-4-yl]-cyclopentyl}-propionamide, “A95” N-{(1S,3R)-3-[3-(4′-Chloro-3′-fluoro-biphenyl-4-yl)- [1,2,4]triazol-4-yl]-cyclopentyl}-propionamide, “A96” N-{(1S,3R)-3-[3-(4′-Pyrazol-1-yl-biphenyl-4-yl)- [1,2,4]triazol-4-yl]-cyclopentyl}-propionamide, “A97” N-((1S,3R)-3-{3-[4-(1-Methyl-1H-indol-5-yl)-phenyl]- [1,2,4]triazol-4-yl}-cyclopentyl)-propionamide, “A98” N-((1S,3R)-3-{3-[4-(6-Methyl-1H-indazol-5-yl)-phenyl]- [1,2,4]triazol-4-yl}-cyclopentyl)-propionamide, “A99” 4′-[3-((1R,3S)-3-Ethylcarbamoyl-cyclopentyl)-3H- [1,2,3]triazol-4-yl]-biphenyl-4-carboxylic acid amide, “A100” 4′-[3-((1R,3S)-3-Ethylcarbamoyl-cyclopentyl)-3H- [1,2,3]triazol-4-yl]-biphenyl-4-carboxylic acid, “A101” (1S,3R)-3-[5-(4′-Isopropyl-biphenyl-4-yl)-[1,2,3]triazol- 1-yl]-cyclopentanecarboxylic acid ethylamide, “A102” (1S,3R)-3-[5-(3′,4′-Dimethoxy-biphenyl-4-yl)-[1,2,3]triazol- 1-yl]-cyclopentanecarboxylic acid ethylamide, “A103” (1S,3R)-3-[5-(4′-Cyclopropylmethoxy-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide, “A104” (1S,3R)-3-[5-(4′-Chloro-3′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide, “A105” (1S,3R)-3-[5-(4′-Cyano-3′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide, “A106” (1S,3R)-3-[5-(4′-Cyano-2′-fluoro-biphenyl-4-yl)- [1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide, “A107” N-((1S,3R)-3-{5-[6-(1H-Indol-5-yl)-pyridin-3-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A108” N-((1S,3R)-3-{5-[6-(4-Fluoro-1H-indol-5-yl)-pyridin-3-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A109” N-{(1S,3R)-3-[5-(6-Imidazo[1,2-a]pyridin-6-yl-pyridin-3-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A110” N-((1S,3R)-3-{5-[4-(4-Fluoro-1H-indol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A111” N-{(1S,3R)-3-[5-(4-Imidazo[1,2-a]pyridin-6-yl-phenyl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A112” N-((1S,3R)-3-{5-[4-(6-Fluoro-1H-indol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A113” N-((1S,3R)-3-{5-[4-(1H-Pyrrolo[3,2-b]pyridin-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A114” N-((1S,3R)-3-{5-[5-(6-Chloro-benzoxazol-2-yl)-pyridin- 2-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A115” N-{(1S,3R)-3-[5-(5-Benzoxazol-2-yl-pyridin-2-yl)- [1,2,3]triazol-1-yl]-cyclopentyl}-propionamide, “A116” N-((1S,3R)-3-{5-[5-(4-Fluoro-1H-indol-5-yl)-pyridin-2-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A117” N-((1S,3R)-3-{5-[5-(1H-Indol-5-yl)-pyridin-2-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A118” N-((1S,3R)-3-{5-[5-(1H-Pyrrolo[3,2-b]pyridin-5-yl)- pyridin-2-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A119” N-((1S,3R)-3-{5-[3-Fluoro-4-(4-fluoro-1H-indol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A120” N-((1S,3R)-3-{5-[3-Fluoro-4-(6-fluoro-1H-indol-5-yl)-phenyl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A121” N-((1S,3R)-3-{5-[6-(1H-Indol-6-yl)-pyridin-3-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, “A122” N-((1S,3R)-3-{5-[6-(1-Methyl-1H-indol-6-yl)-pyridin-3-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide, and “A123” N-((1S,3R)-3-{5-[6-(1H-Indazol-4-yl)-pyridin-3-yl]- [1,2,3]triazol-1-yl}-cyclopentyl)-propionamide and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

10. Process for the preparation of compounds of the formula I according to claim 1 and pharmaceutically acceptable salts, tautomers and stereoisomers thereof, characterised in that a compound of the ##STR00135## wherein R denotes Br, Y denotes —CO—W or —N(R.sup.4)CO—W.sup.1, W denotes NR.sup.2R.sup.2′, CH.sub.2Het.sup.1, A, Cyc, Ar, CH.sub.2Ar, —CONR.sup.2R2′ or Het.sup.1, W.sup.1 denotes NR.sup.2R.sup.2′, Het.sup.1, CH.sub.2Het.sup.1, A, Cyc, Ar, CH.sub.2Ar, CH.sub.2Cyc or CH(OH)CH.sub.2OH, R.sup.1 denotes H, F, Cl, Br, OH, CN, NO.sub.2, A′, OA′, SA′, SO.sub.2Me, COA′, CONH.sub.2, CONHA′ or CONA′.sub.2, R.sup.2 and R.sup.2′ each, independently of one another, denote H, A or [C(R.sup.3).sub.2].sub.nCyc, X.sup.1, X.sup.2, X.sup.3 each, independently of one another, denote CR.sup.8 or N, X.sup.4 denotes CR.sup.8 or N, X.sup.5 denotes CR.sup.8 or N, 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, Cyc denotes cycloalkyl with 3-7 C-atoms, which is unsubstituted or monosubstituted by OH, Hal or A, A′ denotes unbranched or branched alkyl with 1-6 C-atoms, wherein 1-5 H-atoms may be replaced by F, R.sup.5 denotes F, Cl or OH, Ar denotes phenyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, O[C(R.sup.3).sub.2].sub.nHet.sup.1, Ar.sup.1, [C(R.sup.3).sub.2].sub.nOR.sup.3, [C(R.sup.3).sub.2].sub.pN(R.sup.3).sub.2, NO.sub.2, CN, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, CON(R.sup.3).sub.2, Het.sup.1, OCH.sub.2Cyc, N(R.sup.3).sub.2COA, NR.sup.3SO.sub.2A, [C(R.sup.3).sub.2].sub.pSO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3)].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2 and/or COA, Ar.sup.1 denotes phenyl or naphthyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, [C(R.sup.3).sub.2].sub.pOR.sup.3, [C(R.sup.3)].sub.2].sub.pN(R.sup.3).sub.2, NO.sub.2, CN, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, [C(R.sup.3).sub.2].sub.pN(R.sup.3).sub.2, N(R.sup.3).sub.2COA, NR.sup.3SO.sub.2A, [C(R.sup.3).sub.2].sub.pSO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2 and/or COA, R.sup.3 denotes H or unbranched or branched alkyl with 1-6 C-atoms, R.sup.8 denotes H or A′, Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, [C(R.sup.3).sub.2].sub.nOR′, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, SR.sup.3, NO.sub.2, CN, COOR.sup.3, CON(R.sup.3).sub.2, COHet.sup.1, NR.sup.3COA, NR.sup.3SO.sub.2A, SO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2, CHO, COA, ═S, ═NH, ═NA and/or ═O (carbonyl oxygen), Het.sup.1 denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, [C(R.sup.3).sub.2].sub.nOR.sup.3, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, SR.sup.3, NO.sub.2, CN, COOR.sup.3, CON(R.sup.3).sub.2, NR.sup.3COA, NR.sup.3SO.sub.2A, SO.sub.2N(R.sup.3).sub.2, S(O).sub.nA, O[C(R.sup.3).sub.2].sub.mN(R.sup.3).sub.2, NHCOOA, NHCON(R.sup.3).sub.2, CHO, COA, ═S, ═NH, ═NA and/or ═O (carbonyl oxygen), Hal denotes F, Cl, Br or I, m denotes 1, 2 or 3, n denotes 0, 1 or 2, p denotes 0, 1,2, 3 or 4, q denotes 0, 1, 2 or 3, is reacted with a compound of the formula II
R—Z  II in which R denotes Ar or Het, and Z denotes H, or Z denotes a boronic acid or a boronic acid ester group, in a Suzuki-type coupling, and/or a base or acid of the formula I is converted into one of its salts.

11. Medicaments comprising at least one compound of the formula I of claim 1 and/or pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, and optionally an pharmaceutically acceptable carrier, excipient or vehicle.

12. A medicament composition comprising at least one compound of the formula I of claim 1 and/or pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, and at least one further medicament active ingredient.

13. Set (kit) consisting of separate packs of (a) an effective amount of a compound of the formula I of claim 1 and/or pharmaceutically acceptable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, and (b) an effective amount of a further medicament active ingredient.

Description

EXAMPLE 1

4-(1,3-benzoxazol-2-yl)-N-[(1R,3S)-3-(ethylcarbamoyl)cyclopentyl]-N-methyl-benzamide (“A1”)

(1) ##STR00006##

(2) 1.1 (1S,3R)-3-(tert-Butoxycarbonylamino)-cyclopentanecarboxylic acid (500 mg; 2.18 mmol), ethylamine (2.0 M solution in tetrahydrofurane) (1.09 ml; 2.18 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidhydrochlorid (0.63 g; 3.27 mmol) and 1-hydroxybenzotriazol hydrat (0.33 g; 2.18 mmol) are dissolved in 5 ml N,N-dimethylformamide. 4-Methylmorpholine (0.66 g; 6.54 mmol) is added and the mixture is stirred at r. t. for 14 h. The reaction solution is evaporated, the residue is diluted with 10 ml aqueous sodium hydrogen carbanate (5%) and the precipitated product is filtered and dried; yield 0.5 g (89.4%) of ((1R,3S)-3-ethylcarbamoyl-cyclopentyl)-carbamic acid tert-butyl ester (1); LC/MS: 157 (M+-tert-butyloxycarbonyl (BOC)).

(3) 1.2 To tert-butyl N-[(1R,3S)-3-(ethylcarbamoyl)cyclopentyl]-N-methyl-carbamate (1) (500 mg; 1.95 mmol) in 15 ml of dichloromethane is added trifluoroacetic acid (3 ml; 38.9 mmol). The solution is stirred for 14 h at room temperature and then reduced to dryness under vacuo to afford 820 mg of the crude (1S,3R)-3-amino-cyclopentanecarboxylic acid ethylamide (2) as the TFA salt; LC/MS: 157 (M+H). 530 mg of the TFA salt are dissolved in 20 ml aqueous sodium hydrogen carbanate (10%) and the solution is extracted 3× with 10 ml of ethylacetate and 3× with 10 ml of n-butanol. The combined organic layers (ethylacetate and n-butanol) are dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness to give 440 mg of the free base (1S,3R)-3-amino-cyclopentanecarboxylic acid ethylamide (2) as a colorless oil.

(4) 1.3 A solution of 4-bromobenzaldehyde (625.3 mg; 3.4 mmol) and (1S,3R)-3-amino-cyclopentanecarboxylic acid ethylamide (2) (440 mg, 2.8 mmol) in 10 ml methanol was refluxed with stirring for 2 h and then evaporated to dryness. The crude imine (1S,3R)-3-{[1-(4-bromo-phenyl)-meth-(E)-ylidene]-amino}-cyclopentanecarboxylic acid ethylamide (3) (1.13 g) was used in the next step without further purification.

(5) 1.4 To a solution of (1S,3R)-3-{[1-(4-bromo-phenyl)-meth-(E)-ylidene]-amino}-cyclopentanecarboxylic acid ethylamide (3) (1.13 g; 3.5 mmol) in ethanol (5 ml) was added tosyl isocyanide (1.02 g; 5.24 mmol). After being stirred for 14 h at 65° C., the reaction mixture was filtered through a pad of Celite and the filtrate was concentrated at reduced pressure. The residue was diluted with 5% aqueous sodium hydrogen carbanate (10 ml) and extracted 3× with 10 ml ethylacetate. The combined organic layers were dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by flash chromatography (ethylacetate:methanol 80:20) to yield 150 mg (12%) (1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid ethylamide (4) as a colorless oil; LC/MS: 363 (M+H).

(6) 1.5 A mixture of (1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid ethylamide (4) (50 mg, 0.14 mmol), benzoxazole (16.4 mg, 0.14 mmol), palladium(II) acetate (0.31 mg, 0.001 mmol), copper(II) acetate (5.01 mg, 0.028 mmol), potassium carbonate (38.15 mg) and triphenylphosphine (18.1 mg, 0.07 mmol) in toluene (2 ml) was stirred at 170° C. for 4 h in a microwave oven. The mixture was then cooled to room temperature, diluted with water (10 ml) and extracted 3× with 10 ml ethylacetate. The combined organic layers were dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by RP chromatography to yield 10 mg (13%) (1S,3R)-3-[5-(4-benzooxazol-2-yl-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid ethylamide trifluoroacetate (“A1”) as a white foam; LC/MS: M+H 401; .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.54 (s, 1H), 8.38 (d, J=8.4 Hz, 2H), 7.93 (s, 2H), 7.88-7.82 (m, 2H), 7.81 (d, J=8.4 Hz, 2H), 7.51-7.42 (m, 2H), 4.88-4.73 (m, 1H), 3.11-3.05 (m, 2H), 2.82-2.67 (m, 1H), 2.42-2.31 (m, 1H), 2.18-1.96 (m, 3H), 1.95-1.82 (m, 2H), 1.01 (t, J=7.2 Hz, 3H).

EXAMPLE 2

(1S,3R)-3-(5-biphenyl-4-yl-imidazol-1-yl)-cyclopentanecarboxylic acid ethylamide (“A2”)

(7) ##STR00007##

(8) A mixture of (1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid ethylamide (4) (50 mg, 0.14 mmol), benzeneboronic acid (18.5 mg, 0.15 mmol), tetrakis(triphenylphosphine)-palladium(0) (8 mg, 0.007 mmol), potassium carbonate (108.35 mg) in tetrydrofuran (1.5 ml), water (0.5 ml), ethanol (0.5) ml and toluene (2 ml) was stirred at 100° C. for 1 h in a microwave oven. The mixture was then cooled to room temperature, diluted with water (5 ml) and extracted 3× with 5 ml ethylacetate. The combined organic layers were dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by RP chromatography to yield 28 mg (43%) (1S,3R)-3-(5-biphenyl-4-yl-imidazol-1-yl)-cyclopentanecarboxylic acid ethylamide trifluoroacetate (“A2”) as a white foam; LC/MS: M+H 360; .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.54 (s, 1H), 8.38 (d, J=8.4 Hz, 2H), 7.93 (s, 2H), 7.85 (dd, J=14.1, 7.9 Hz, 2H), 7.81 (d, J=8.4 Hz, 2H), 7.53-7.41 (m, 2H), 4.85-4.77 (m, 1H), 4.81 (d, J=28.7 Hz, OH), 3.11-3.04 (m, 2H), 2.80-2.66 (m, 1H), 2.37 (dt, J=13.3, 8.0 Hz, 1H), 2.18-1.96 (m, 3H), 1.95-1.83 (m, 2H), 1.01 (t, J=7.2 Hz, 3H).

(1S,3R)-3-[5-(4′-Chloro-biphenyl-4-yl)-imidazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A3”)

(9) ##STR00008##

(10) “A3” was synthesized analogously to method described in example 2 from the compound (4) (example 1.4) and 4-chlorophenylboronic acid; LC/MS: M+H 394; .sup.1H NMR (400 MHz, DMSO-d.sub.6+CF.sub.3COOD): δ 9.70 (d, J=1.5 Hz, 1H), 7.88 (d, J=8.5 Hz, 2H), 7.84 (d, J=1.5 Hz, 1H), 7.78 (d, J=8.7 Hz, 2H), 7.66 (d, J=8.4 Hz, 2H), 7.56 (d, J=8.7 Hz, 2H), 4.88-4.78 (m, 1H), 3.14 (q, J=7.2 Hz, 2H), 2.88-2.75 (m, 2H), 2.49-2.38 (m, 1H), 2.18 (dq, J=13.8, 7.0 Hz, 2H), 2.11-2.01 (m, 1H), 2.01-1.89 (m, 2H), 1.06 (t, J=7.2 Hz, 3H).

EXAMPLE 3

(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A4”)

(11) ##STR00009##

(12) “A4” is synthesized analogously to method 1.5 (example 1) from (1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (5) (synthesized analogously to methods 1.1 to 1.4 (example 1) and benzoxazole;

(13) LC/MS: M+H 427; .sup.1H NMR (400 MHz, DMSO-d.sub.6+CF.sub.3COOD): δ 9.65 (d, J=1.4 Hz, 1H), 8.38 (d, J=8.4 Hz, 2H), 7.92 (s, 1H), 7.86-7.74 (m, 4H), 7.43 (p, J=7.4 Hz, 2H), 4.80 (p, J=7.5 Hz, 1H), 2.76-2.61 (m, 1H), 2.42-2.26 (m, 1H), 2.21-1.94 (m, 2H), 1.94-1.78 (m, 2H), 1.25 (s, 3H), 0.65-0.44 (m, 4H).

(14) The following compounds are synthesized analogously to method described in example 2 from (1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (5) and an appropriate arylboronic acid derivative:

(1S,3R)-3-{5-[4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A5”)

(15) ##STR00010##

(16) LC/MS: M+H 426; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 8.58 (d, J=2.1 Hz, 1H), 8.27 (s, 2H), 8.05 (s, 2H), 7.82 (d, J=8.2 Hz, 2H), 7.56-7.47 (m, 3H), 7.01 (s, 1H), 6.53 (s, 1H), 4.59 (p, J=7.7 Hz, 1H), 2.61 (p, J=8.5 Hz, 1H), 2.31 (dt, J=12.8, 7.8 Hz, 1H), 2.18-1.74 (m, 5H), 1.28 (s, 3H), 0.66-0.43 (m, 4H);

(1S,3R)-3-[5-(4-benzothiazol-6-yl-phenyl)-imidazol-1-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide amide (“A6”)

(17) ##STR00011##

(18) LC/MS: M+H 443; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 9.42 (s, 1H), 8.54 (s, 1H), 8.18 (d, J=8.5 Hz, 1H), 8.04 (d, J=9.7 Hz, 2H), 7.90 (dd, J=8.5, 1.9 Hz, 1H), 7.87 (d, J=8.3 Hz, 2H), 7.54 (d, J=8.3 Hz, 2H), 7.01 (s, 1H), 4.58 (p, J=7.7 Hz, 1H), 2.60 (p, J=8.6 Hz, 1H), 2.29 (dt, J=12.9, 7.8 Hz, 1H), 2.14-1.72 (m, 5H), 1.27 (s, 3H), 0.63-0.44 (m, 4H);

(1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A7”)

(19) ##STR00012##

(20) LC/MS: M+H 425; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 11.21 (s, 1H), 8.04 (s, 2H), 7.78 (d, J=8.3 Hz, 2H), 7.70 (s, 1H), 7.65 (d, J=8.2 Hz, 1H), 7.49 (d, J=8.3 Hz, 2H), 7.43-7.39 (m, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.00 (s, 1H), 4.59 (p, J=7.7 Hz, 1H), 2.61 (q, J=8.5, 8.0 Hz, 1H), 2.31 (dt, J=12.9, 7.8 Hz, 1H), 2.18-1.73 (m, 5H), 1.28 (s, 3H), 0.61-0.44 (m, 4H);

(1S,3R)-3-{5-[4-(5-fluoro-1H-indol-2-yl)-phenyl]-imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A8”)

(21) ##STR00013##

(22) LC/MS: M+H 443; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 11.67 (s, 1H), 8.03 (d, J=8.1 Hz, 2H), 7.93 (d, J=8.4 Hz, 2H), 7.50 (d, J=8.3 Hz, 2H), 7.39 (dd, J=8.8, 4.5 Hz, 1H), 7.29 (dd, J=9.9, 2.5 Hz, 1H), 7.01 (s, 1H), 6.98-6.88 (m, 2H), 4.57 (p, J=7.7 Hz, 1H), 2.59 (p, J=8.6 Hz, 1H), 2.34-2.23 (m, 1H), 2.14-1.73 (m, 5H), 1.26 (s, 3H), 0.62-0.44 (m, 4H);

(1S,3R)-3-{5-[4-(1H-benzotriazol-5-yl)-phenyl]-imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A9”)

(23) ##STR00014##

(24) LC/MS: M+H 427; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 15.81 (s, 1H), 8.41 (s, 1H), 8.11 (s, 1H), 8.06 (s, 1H), 7.90 (d, J=8.2 Hz, 2H), 7.80 (s, 1H), 7.57 (d, J=8.2 Hz, 2H), 7.22 (s, 1H), 4.63 (p, J=7.7 Hz, 1H), 2.62 (p, J=8.4 Hz, 1H), 2.31 (dt, J=15.6, 7.9 Hz, 1H), 2.16-1.74 (m, 5H), 1.27 (s, 3H), 0.61-0.44 (m, 4H);

(1S,3R)-3-{5-[4-(1H-indol-5-yl)-phenyl]-imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A10”)

(25) ##STR00015##

(26) LC/MS: M+H 425; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 11.15 (s, 1H), 8.04 (d, J=8.9 Hz, 2H), 7.87 (s, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.53-7.41 (m, 4H), 7.39-7.35 (m, 1H), 6.98 (s, 1H), 6.50 (s, 1H), 4.57 (p, J=7.7 Hz, 1H), 2.66-2.55 (m, 1H), 2.29 (dt, J=12.7, 7.8 Hz, 1H), 2.13-1.72 (m, 5H), 1.27 (s, 3H), 0.62-0.47 (m, 4H);

(1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-imidazol-1-yl}-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A11”)

(27) ##STR00016##

(28) LC/MS: M+H 426; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 13.25 (s, 1H), 8.23 (s, 1H), 8.05 (d, J=11.7 Hz, 2H), 7.84 (d, J=8.1 Hz, 2H), 7.57 (d, J=7.9 Hz, 3H), 7.46 (t, J=7.7 Hz, 1H), 7.29 (d, J=7.0 Hz, 1H), 7.03 (s, 1H), 4.61 (p, J=7.7 Hz, 1H), 2.62 (p, J=8.3 Hz, 1H), 2.32 (dt, J=13.0, 7.8 Hz, 1H), 2.15-1.76 (m, 5H), 1.27 (s, 3H), 0.64-0.39 (m, 4H);

(1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-imidazol-1-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A12”)

(29) ##STR00017##

(30) LC/MS: M+H 411; .sup.1H NMR (500 MHz, DMSO-d.sub.6): δ 8.04 (d, J=15.2 Hz, 2H), 7.94 (s, 4H), 7.85 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.02 (s, 1H), 4.61-4.53 (m, 1H), 2.59 (qd, J=8.6, 6.9 Hz, 1H), 2.28 (dt, J=12.9, 7.9 Hz, 1H), 2.14-1.72 (m, 5H), 1.26 (s, 3H), 0.60-0.43 (m, 4H).

General Synthesis 2

(31) ##STR00018##

EXAMPLE 3

(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A13”)

(32) ##STR00019##

(33) 3.1 To a solution of (1S,3R)-3-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid (500 mg; 2.18 mmol) in dioxane (5 ml) was added 4 N HCl in dioxane (2.73 ml) at room temperature and the resulting mixture was stirred for 18 h. The reaction solution was evaporated to dryness and the crude (1S,3R)-3-amino-cyclopentanecarboxylic acid hydrochloride (365 mg) was used in the next step without further purification.

(34) 3.2 To (1S,3R)-3-amino-cyclopentanecarboxylic acid hydrochloride (365 mg) (365 mg; 2.2 mmol), copper(II)sulfate (7.03 mg; 0.044 mmol) and potassium carbonate (0.61 g, 4.42 mmol) in 20 ml methanol is added under nitrogen imidazole-1-sulfonyl azide hydrochloride (E. D. Goddard-Borger et. al., Organic Letters 2007 Vol 9, page 3797-3800) and the resulting mixture was stirred for 18 h at room temperature. Water (25 ml) and 2N HCl (10 ml) are added and the reaction mixture is extracted 2× with ethylacetate (75 ml). The combined organic layers are dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by flash chromatography (dichloromethane:methanol 80:20) to yield 440 mg (88.8%) (1S,3R)-3-azido-cyclopentanecarboxylic acid as a colourless thin oil; .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 4.06 (dtd, J=7.6, 5.9, 4.6 Hz, 1H), 2.84-2.70 (m, 1H), 2.17 (ddd, J=13.6, 9.3, 6.6 Hz, 1H), 1.93-1.73 (m, 4H), 1.71-1.57 (m, 1H).

(35) 3.3 A mixture of (1S,3R)-3-azido-cyclopentanecarboxylic acid (435 mg; 1.96 mmol), pentamethylcyclopentadienylbis(triphenylphosphine)ruthenium-(11)chloride (31.25 mg; 0.04 mmol) and 1-bromo-4-ethynyl-benzene (532.92 mg; 2.94 mmol) was stirred for 1.5 h at 110° C., then poured in ice water (100 ml) and saturated sodium chloride solution (50 ml) and extracted 2× with ethylacetate (100 ml). The combined organic layers are dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by flash chromatography (dichloromethane:methanol 80:20) to yield 330 mg (50%) (1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid (6) as brown crystals; .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 12.17 (s, 1H), 7.87 (s, 1H), 7.76 (d, J=8.6 Hz, 2H), 7.47 (d, J=8.6 Hz, 2H), 4.84 (p, J=7.4 Hz, 1H), 2.86 (p, J=8.3 Hz, 1H), 2.42 (dt, J=12.9, 7.8 Hz, 1H), 2.32 (ddd, J=12.9, 9.6, 8.5 Hz, 1H), 2.17-2.01 (m, 3H), 2.00-1.89 (m, 1H).

(36) 3.4 The reaction of (1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid (6) with ethylamine analogously to method 1.1 (example 1) yields (1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (7) as yellow crystals; LC/MS: 363-365 (M+H).

(37) 3.5 The title compound (“A13”) is synthesized analogously to method 1.5 (example 1) from (1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (7) and benzoxazole; LC/MS: M+H 402; .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 8.35 (d, J=8.4 Hz, 2H), 7.97 (s, 1H), 7.85 (ddd, J=9.4, 7.1, 1.5 Hz, 2H), 7.82-7.71 (m, 3H), 7.53-7.39 (m, 2H), 4.92 (p, J=8.0 Hz, 1H), 3.13-2.99 (m, 2H), 2.76-2.61 (m, 1H), 2.34 (t, J=9.3 Hz, 2H), 2.26-2.08 (m, 2H), 2.00 (dtd, J=13.3, 9.0, 7.1 Hz, 1H), 1.94-1.81 (m, 1H), 1.01 (t, J=7.2 Hz, 3H).

(38) The following compounds are synthesized analogously to method described in example 2 from ((1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (7) (example 3.4) and an appropriate arylboronic acid derivative:

(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A14”)

(39) ##STR00020##

(40) LC/MS: M+H 395; .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 7.95-7.83 (m, 3H), 7.83-7.73 (m, 3H), 7.59 (dd, J=18.2, 7.9 Hz, 4H), 5.09-4.51 (m, 1H), 3.14-2.97 (m, 2H), 2.69 (t, J=9.1 Hz, 1H), 2.34 (t, J=8.8 Hz, 2H), 2.28-2.07 (m, 2H), 2.08-1.94 (m, 1H), 1.96-1.72 (m, 1H), 1.12-0.94 (m, 3H);

(1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A15”)

(41) ##STR00021##

(42) LC/MS: M+H 386; .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 7.97 (s, 4H), 7.93 (d, J=8.4 Hz, 2H), 7.89 (s, 1H), 7.78 (t, J=5.3 Hz, 1H; NH), 7.65 (d, J=8.4 Hz, 2H), 4.88 (p, J=8.1 Hz, 1H), 3.14-2.99 (m, 2H), 2.68 (p, J=8.7 Hz, 1H), 2.33 (t, J=8.9 Hz, 2H), 2.25-2.07 (m, 2H), 2.06-1.92 (m, 1H), 1.91-1.80 (m, 1H), 1.01 (t, J=7.2 Hz, 3H);

(1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentanecarboxylic acid ethylamide (“A16”)

(43) ##STR00022##

(44) LC/MS: 400 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 11.22 (s, 1H), 7.90-7.82 (m, 3H), 7.79 (t, J=4.9 Hz, 1H), 7.72 (s, 1H), 7.65 (d, J=8.2 Hz, 1H), 7.57 (d, J=8.2 Hz, 2H), 7.46-7.32 (m, 2H), 6.47 (s, 1H), 4.90 (p, J=8.2 Hz, 1H), 3.08 (p, J=7.1 Hz, 2H), 2.70 (p, J=9.1 Hz, 1H), 2.34 (t, J=8.7 Hz, 2H), 2.26-2.08 (m, 2H), 2.08-1.94 (m, 1H), 1.94-1.80 (m, 1H), 1.01 (t, J=7.2 Hz, 3H).

(45) The following compounds are synthesized from (1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid (6) (example 3.3) analogously to methods described in 3.4-3.5 (example 3):

(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A17”)

(46) ##STR00023##

(47) LC/MS: 428 (M+H);

(48) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.35 (d, J=8.5 Hz, 2H), 8.00 (s, 1H; NH), 7.96 (s, 1H), 7.89-7.81 (m, 2H), 7.77 (d, J=8.5 Hz, 2H), 7.51-7.41 (m, 2H), 4.89 (p, J=7.8 Hz, 1H), 2.61 (dq, J=10.3, 8.2 Hz, 1H), 2.37-2.24 (m, 2H), 2.22-2.08 (m, 2H), 2.02-1.90 (m, 1H), 1.90-1.76 (m, 1H), 1.25 (s, 2H), 0.62-0.53 (m, 2H), 0.53-0.42 (m, 2H).

(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid propylamide (“A18”)

(49) ##STR00024##

(50) LC/MS: 416 (M+H);

(51) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.35 (d, J=8.4 Hz, 2H), 7.96 (s, 1H), 7.88-7.81 (m, 2H), 7.77 (d, J=8.4 Hz, 3H; 2H+NH), 7.51-7.39 (m, 2H), 4.92 (p, J=8.0 Hz, 1H), 3.01 (q, J=6.9 Hz, 2H), 2.76-2.66 (m, 1H), 2.39-2.31 (m, 2H), 2.26-2.12 (m, 2H), 2.05-1.95 (m, 1H), 1.93-1.82 (m, 1H), 1.40 (q, J=7.2 Hz, 2H), 0.83 (t, J=7.4 Hz, 3H).

General Synthesis 3

(52) ##STR00025## ##STR00026##

EXAMPLE 4

N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (“A19”)

(53) ##STR00027##

(54) 4.1 (1S,3R)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid (1.0 g; 4.36 mmol), diphenylphosphorylazide (DPPA) (1.24 g; 4.36) and triethylamine (0.6 ml; 4.36 mmol) in 30 ml toluene were stirred at 80° C. for 1 h. Benzyl alcohol (BzIOH) (0.45 ml; 4.36 mmol) was added to the mixture, which was stirred at 110° C. for 14 h. The mixture was evaporated, the residue was dissolved in 10% aqueous sodium hydrogen carbonate solution (10 ml) and extracted 3× with ethyl acetate (10 ml). The combined organic layer were dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by flash chromatography (n-heptane:ethylacetate=80:20) to yield 0.75 g (48.2%) ((1S,3R)-3-tert-butoxycarbonylamino-cyclopentyl)-carbamic acid benzyl ester (A) as beige solid; LC/MS: 235 (M+H-BOC).

(55) 4.2 A mixture of [(1S,3R)-3-(tert-butoxycarbonyl-methyl-amino)-cyclopentyl]-carbamic acid benzyl ester (A) (0.75 g; 2.24 mmol) and 5% Pd/C (200 mg) in tetrahydrofuran (9 mL) was hydrogenated for 15.5 hrs. The reaction mixture was filtered through celite and concentrated to give ((1R,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester (B) (0.43 g; 95.7%) as a pale brown oil; LC/MS: 145 (M+H-t-Bu).

(56) 4.3 To the cooled (0° C.) solution of ((1R,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester (B) (0.43 g; 2.15 mmol) and triethylamine (0.56 ml; 4.3 mmol) in dichloromethane (40 ml) is added dropwise propionyl chloride (0.22 g; 2.36 mmol) dissolved in dichloromethane (10 ml). The mixture was stirred for 1 h at room temperature, washed with 5% NaHCO.sub.3 solution (10 ml) and brine (10 ml), dried over Na.sub.2SO.sub.4, filtered, and evaporated to dryness. The residue is purified by flash chromatography to yield ((1R,3S)-3-propionyl-amino-cyclopentyl)-carbamic acid tert-butyl ester (C) (0.45 g 81.8%) as a white solid; LC/MS: 157 (M+H-BOC).

(57) 4.4 To ((1R,3S)-3-propionylamino-cyclopentyl)-carbamic acid tert-butyl ester (C) (0.45 g; 1.75 mmol) in 15 ml of dichloromethane was added trifluoroacetic acid (3 ml; 39 mmol). The solution was stirred 3 h at room temperature and then reduced to dryness under vacuo to afford 0.68 g (100%) N-((1S,3R)-3-amino-cyclopentyl)-propionamide trifluoroacetate (D) as a a pale yellow powder; LC/MS: 157 (M+H).

(58) 4.5 Starting from N-((1S,3R)-3-amino-cyclopentyl)-propionamide trifluoroacetate (D)) and following the reaction sequence 1.3-1.4 (example 1) as described above in example (1) leads to N-{(1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (E); LC/MS: 362-364 (M+H).

(59) 4.6 Treatment of N-{(1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (E); with benzoxazole analogously to method 1.5 (example 1) leads to N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (“A19”) as colorless oil; LC/MS: 401 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.29 (d, J=8.4 Hz, 2H), 8.05 (s, 1H), 7.90 (d, J=7.2 Hz, 1H; NH), 7.86-7.80 (m, 2H), 7.67 (d, J=8.4 Hz, 2H), 7.44 (pd, J=7.4, 1.5 Hz, 2H), 7.14 (s, 1H), 4.63 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.3 Hz, 1H), 2.59-2.49 (m, 1H), 2.16-2.02 (m, 3H), 2.01-1.84 (m, 2H), 1.78-1.61 (m, 2H), 0.99 (t, J=7.6 Hz, 3H).

EXAMPLE 5

N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (“A20”)

(60) ##STR00028##

(61) Treatment of N-{(1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (E) with benzothiazole analogously to method 1.5 (example 1) leads to N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (“A20”); LC/MS: 417 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.21-8.14 (m, 3H), 8.09 (d, J=7.9 Hz, 1H), 8.04 (s, 1H), 7.90 (d, J=7.2 Hz, 1H; NH), 7.57 (td, J=8.3, 7.8, 1.2 Hz, 1H), 7.48 (td, J=7.8, 1.1 Hz, 1H), 7.12 (s, 1H), 4.62 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.4 Hz, 1H), 2.56-2.50 (m, 1H), 2.15-2.03 (m, 3H), 2.03-1.81 (m, 2H), 1.79-1.60 (m, 2H), 0.99 (t, J=7.6 Hz, 3H).

(62) The following compounds are synthesized analogously to method described in example 2 from N-{(1S,3R)-3-[5-(4-bromo-phenyl)-imidazol-1-yl]-cyclopentyl}-propionamide (E) and an appropriate arylboronic acid derivative:

N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-imidazol-1-yl]-cyclopentyl}-propionamide (“A21”)

(63) ##STR00029##

(64) LC/MS: 394 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.96 (s, 1H), 7.90 (d, J=7.2 Hz, 1H; NH), 7.81-7.71 (m, 4H), 7.54 (d, J=8.5 Hz, 2H), 7.50 (d, J=8.3 Hz, 2H), 7.00 (s, 1H), 4.56 (p, J=7.9 Hz, 1H), 4.07 (h, J=7.4 Hz, 1H), 2.49-2.40 (m, 1H), 2.07 (q, J=7.6 Hz, 3H), 2.01-1.80 (m, 2H), 1.80-1.60 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-imidazol-1-yl}-cyclopentyl)-propionamide (“A22”)

(65) ##STR00030##

(66) LC/MS: 400 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.24 (s, 1H; NH), 8.23 (s, 1H), 7.98 (s, 1H), 7.92 (d, J=7.2 Hz, 1H; NH), 7.84 (d, J=8.3 Hz, 2H), 7.56 (dd, J=8.2, 4.7 Hz, 3H), 7.49-7.42 (m, 1H), 7.29 (d, J=6.8 Hz, 1H), 7.04 (s, 1H), 4.62 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.4 Hz, OH), 2.56-2.50 (m, 1H), 2.19-2.10 (m, 1H), 2.08 (q, J=7.6 Hz, 2H), 2.03-1.86 (m, 2H), 1.80-1.63 (m, 2H), 1.00 (t, J=7.6 Hz, 3H).

EXAMPLE 6

N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A23”)

(67) ##STR00031##

(68) 6.1 Treatment of ((1S,3R)-3-tert-butoxycarbonylamino-cyclopentyl)-carbamic acid benzyl ester (A) (example 4.1) with 4N HCl in dioxane analogously to method 3.1 (example 3) leads to ((1S,3R)-3-amino-cyclopentyl)-carbamic acid benzyl ester hydrochloride; LC/MS: 235 (M+H).

(69) 6.2 Treatment of ((1S,3R)-3-amino-cyclopentyl)-carbamic acid benzyl ester hydrochloride (example 6.1) with imidazole-1-sulfonyl azide hydrochloride and copper(II)sulfate analogously to method 3.2 (example 3) leads to ((1S,3R)-3-azido-cyclopentyl)-carbamic acid benzyl ester; LC/MS: 233 (M+H-N.sub.2).

(70) 6.3 Treatment of ((1S,3R)-3-azido-cyclopentyl)-carbamic acid benzyl ester (example 6.2) with 1-bromo-4-ethynyl-benzene and [Cp*RuCl(PPh.sub.3).sub.2] analogously to method 3.3 (example 3) leads to {(1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-carbamic acid benzyl ester (F); LC/MS: 441-443 (M+H).

(71) 6.4 Treatment of {(1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-carbamic acid benzyl ester (F) with benzoxazole analogously to method 1.5 (example 1) leads to {(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-carbamic acid benzyl ester as pale brown crystals; LC/MS: 480 (M+H).

(72) 6.5 Hydrogenation of {(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-carbamic acid benzyl ester analogously to method 4.2 (example 4) leads to (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentylamine (G); LC/MS: 345 (M+H).

(73) 6.6 Treatment of (G) (example 6.5) with propionyl chloride analogously to method 4.3 (example 4) leads to N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A23”) as white foam; LC/MS: 402 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.36 (d, J=8.5 Hz, OH), 7.98 (s, 1H), 7.96 (d, J=7.4 Hz, 1H; NH), 7.88-7.81 (m, 2H), 7.76 (d, J=8.5 Hz, 2H), 7.51-7.42 (m, 2H), 4.94 (q, J=7.8 Hz, 1H), 4.16 (h, J=7.6 Hz, 1H), 2.57-2.51 (m, 1H), 2.17 (qd, J=7.8, 7.2, 2.2 Hz, 2H), 2.10-2.01 (m, 3H), 1.96 (dq, J=13.4, 6.9 Hz, 1H), 1.78 (dq, J=12.5, 8.3 Hz, 1H).

N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-acetamide (“A24”)

(74) ##STR00032##

(75) Treatment of (G) (example 6.5) with acetyl chloride analogously to method 4.3 (example 4) leads to N-{(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-acetamide (“A24”) as white foam; LC/MS: 388 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.36 (d, J=8.5 Hz, 2H), 8.05 (d, J=7.4 Hz, 1H; NH), 7.98 (s, 1H), 7.88-7.81 (m, 2H), 7.76 (d, J=8.5 Hz, 2H), 7.50-7.43 (m, 2H), 4.94 (p, J=7.9 Hz, 1H), 4.14 (h, J=7.6 Hz, 1H), 2.59-2.51 (m, 1H), 2.21-2.11 (m, 2H), 2.06 (dt, J=12.9, 8.8 Hz, 1H), 1.96 (dq, J=13.6, 6.8 Hz, 1H), 1.80 (s, 3H), 1.79-1.73 (m, 1H).

EXAMPLE 7

N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A25”)

(76) ##STR00033##

(77) 7.1 Starting from N-((1S,3R)-3-amino-cyclopentyl)-propionamide trifluoroacetate (D) (example 4.4) and following the reaction sequence 6.2-6.3 (example 6) leads to N-{(1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (H); LC/MS: 364 (M+H).

(78) 7.2 N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A25”) was synthesized analogously to method described in example 2 from N-{(1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (H) (example 7.1) and 4-chlorophenylboronic acid; LC/MS: 395 (M+H);

(79) “A25”: .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.97 (d, J=7.4 Hz, 1H; NH), 7.89 (s, 1H), 7.85 (d, J=8.5 Hz, 2H), 7.78 (d, J=8.7 Hz, 2H), 7.60 (d, J=8.5 Hz, 2H), 7.56 (d, J=8.6 Hz, 2H), 4.90 (p, J=7.9 Hz, 1H), 4.14 (h, J=7.7 Hz, 1H), 2.21-2.11 (m, 2H), 2.12-2.02 (m, 3H), 1.96 (dq, J=13.7, 7.0 Hz, 1H), 1.78 (dq, J=12.5, 8.1 Hz, 1H), 0.99 (t, J=7.6 Hz, 3H).

(80) The following compounds are synthesized analogously to method described in example 7.2 from N-{(1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (H) (example 7.1) and an appropriate arylboronic acid derivative:

N-((1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A26”)

(81) ##STR00034##

(82) LC/MS: 401 (M+H);

(83) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 13.30 (br. s, 1H; NH), 8.24 (d, J=1.0 Hz, 1H), 7.97 (d, J=7.4 Hz, 1H; NH), 7.92 (t, J=4.1 Hz, 3H), 7.66 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.4 Hz, 1H), 7.48 (dd, J=8.3, 7.1 Hz, 1H), 7.32 (d, J=6.4 Hz, 1H), 4.96 (p, J=7.7 Hz, 1H), 4.17 (h, J=7.0 Hz, 1H), 2.60-2.51 (m, 1H), 2.19 (q, J=7.2 Hz, 2H), 2.14-2.03 (m, 3H), 1.98 (dq, J=13.7, 6.9 Hz, 1H), 1.87-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A27”)

(84) ##STR00035##

(85) LC/MS: 400 (M+H);

(86) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 11.20 (s, 1H; NH), 7.99 (d, J=7.4 Hz, 1H; NH), 7.90 (s, 1H), 7.87 (s, 1H), 7.84 (d, J=8.3 Hz, 2H), 7.55 (d, J=8.3 Hz, 2H), 7.51 (d, J=8.5 Hz, 1H), 7.46 (dd, J=8.5, 1.7 Hz, 1H), 7.42-7.36 (m, 1H), 6.51 (ddd, J=2.9, 1.8, 0.8 Hz, 1H), 4.93 (p, J=7.8 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.58-2.50 (m, 1H), 2.22-2.11 (m, 2H), 2.11-2.02 (m, 3H), 1.96 (dq, J=13.6, 6.9 Hz, 1H), 1.79 (dq, J=12.5, 8.3 Hz, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A28”)

(87) ##STR00036##

(88) Treatment of N-{(1S,3R)-3-[5-(4-bromo-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (H) (example 7.1) with benzothiazole analogously to method 1.5 (example 1) leads to N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A28”); LC/MS: 418 (M+H);

(89) .sup.1H NMR (500 MHz, DMSO-d.sub.6)δ 8.26 (d, J=8.3 Hz, 2H), 8.20 (d, J=7.9 Hz, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.99 (d, J=7.5 Hz, 1H; NH), 7.97 (s, 1H), 7.72 (d, J=8.3 Hz, 2H), 7.59 (t, J=7.7 Hz, 1H), 7.51 (t, J=8.0 Hz, 1H), 4.94 (p, J=7.8 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.57-2.51 (m, 1H), 2.24-2.12 (m, 2H), 2.12-2.00 (m, 3H), 1.96 (dq, J=13.6, 6.9 Hz, 1H), 1.85-1.69 (m, 1H), 0.99 (t, J=7.6 Hz, 3H).

General Synthesis 4: Synthesis of 1,2,4-triazol Derivatives

(90) ##STR00037##

EXAMPLE 8

(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A29”)

(91) ##STR00038##

(92) 8.1 (1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (K) was synthesized from 4-bromo-benzoic acid hydrazid, dimethoxymethyl-dimethyl-amine and (1S,3R)-3-amino-cyclopentanecarboxylic acid ethylamide (2) (example 1.2) according to literature (M. J. Stocks et. Al., Org. Letters, 2004 Vol 6 (17) 2969-2971); LC/MS: 364 (M+H).

(93) 8.2 Treatment of (1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (K) with benzoxazole analogously to method 1.5 (example 1) leads to (1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A29”); LC/MS: 402 (M+H);

(94) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.00 (s, 1H), 8.37 (d, J=8.4 Hz, 2H), 7.89 (d, J=8.5 Hz, 2H), 7.88-7.79 (m, 3H), 7.53-7.38 (m, 2H), 4.68 (p, J=7.6 Hz, 1H), 3.14-3.04 (m, 2H), 2.77-2.65 (m, 1H), 2.38 (dt, J=13.0, 7.9 Hz, 1H), 2.20-2.07 (m, 1H), 2.09-1.78 (m, 4H), 1.02 (t, J=7.2 Hz, 3H).

(95) The following compounds are synthesized analogously to method described in example 7.2 from (1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (K) (example 8.1) and an appropriate arylboronic acid derivative:

(1S,3R)-3-{3-[4-(1H-indol-6-yl)-phenyl]-[1,2,4]triazol-4-yl}-cyclopentanecarboxylic acid ethylamide (“A30”)

(96) ##STR00039##

(97) LC/MS: 400 (M+H);

(98) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.22 (s, 1H; NH), 8.97 (s, 1H), 7.95-7.76 (m, 3H), 7.73 (s, 1H), 7.70 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.2 Hz, 1H), 7.43-7.36 (m, 2H), 6.47 (ddd, J=2.9, 1.9, 0.9 Hz, 1H), 4.72-4.61 (m, 1H), 3.09 (qd, J=7.2, 5.4 Hz, 2H), 2.78-2.64 (m, 1H), 2.44-2.30 (m, 1H), 2.21-2.08 (m, 1H), 2.08-1.80 (m, 4H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[3-(4′-chloro-biphenyl-4-yl)[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A31”)

(99) ##STR00040##

(100) LC/MS: 395 (M+H);

(101) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.95 (s, 1H), 7.86 (d, J=8.5 Hz, 2H), 7.84 (d, J=5.7 Hz, 1H; NH), 7.79 (d, J=8.6 Hz, 2H), 7.72 (d, J=8.5 Hz, 2H), 7.56 (d, J=8.6 Hz, 2H), 4.63 (p, J=7.7 Hz, 1H), 3.09 (qd, J=7.2, 5.4 Hz, 2H), 2.77-2.62 (m, 1H), 2.43-2.28 (m, 1H), 2.19-2.06 (m, 1H), 2.06-1.75 (m, 4H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[3-(4′-cyano-biphenyl-4-yl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A32”)

(102) ##STR00041##

(103) LC/MS: 386 (M+H);

(104) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.97 (s, 1H), 7.97 (s, 4H), 7.94 (d, J=8.5 Hz, 2H), 7.84 (t, J=5.4 Hz, 1H), 7.77 (d, J=8.5 Hz, 2H), 4.64 (p, J=7.6 Hz, 1H), 3.09 (qd, J=7.2, 5.5 Hz, 2H), 2.81-2.59 (m, 1H), 2.43-2.26 (m, 1H), 2.17-2.05 (m, 1H), 2.05-1.78 (m, 4H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[3-(4-benzothiazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A33”)

(105) ##STR00042##

(106) LC/MS: 418 (M+H);

(107) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.01 (s, 1H), 8.27 (d, J=8.4 Hz, 2H), 8.21 (d, J=7.9 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H), 7.88 (t, J=5.5 Hz, 1H; NH), 7.85 (d, J=8.4 Hz, 2H), 7.59 (ddd, J=8.3, 7.2, 1.3 Hz, 1H), 7.51 (ddd, J=8.2, 7.2, 1.2 Hz, 1H), 4.67 (p, J=7.6 Hz, 1H), 3.09 (qd, J=7.2, 5.4 Hz, 2H), 2.77-2.65 (m, 1H), 2.44-2.31 (m, 1H), 2.24-2.07 (m, 1H), 2.08-1.80 (m, 4H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[3-(4-benzothiazol-6-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid (1-methyl-cyclopropyl)-amide (“A34”)

(108) ##STR00043##

(109) LC/MS: 444 (M+H);

(1S,3R)-3-{3-[4-(1H-indazol-4-yl)-phenyl]-[1,2,4]triazol-4-yl}-cyclopentanecarboxylic acid ethylamide (“A35”)

(110) ##STR00044##

(111) LC/MS: 401 (M+H);

(112) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.29 (s, 1H; NH), 8.99 (s, 1H), 8.25 (s, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.89 (t, J=5.4 Hz, 1H; NH), 7.78 (d, J=8.3 Hz, 2H), 7.60 (d, J=8.3 Hz, 1H), 7.51-7.44 (m, 1H), 7.33 (d, J=6.9 Hz, 1H), 4.69 (p, J=7.6 Hz, 1H), 3.09 (qd, J=7.2, 5.4 Hz, 2H), 2.73 (qd, J=8.5, 7.0 Hz, 1H), 2.46-2.34 (m, 1H), 2.19-2.11 (m, 1H), 2.11-1.79 (m, 4H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-5-methyl-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A36”)

(113) ##STR00045##

(114) LC/MS: 416 (M+H).

EXAMPLE 9

N-{(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A37”)

(115) ##STR00046##

(116) 9.1 N-{(1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (L) was synthesized from 4-bromo-benzoic acid hydrazid, dimethoxymethyl-dimethyl-amine and (1S,3R)-3-amino-cyclopentanecarboxylic acid ethylamide (2) (example 1.2) according to literature (M. J. Stocks et. al., Org. Letters, 2004 Vol 6 (17) 2969-2971); LC/MS: 364 (M+H).

(117) 9.2 Treatment of N-{(1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (L) with benzoxazole analogously to method 1.5 (example 1) leads to N-{(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A37”); LC/MS: 402 (M+H);

(118) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.88 (s, 1H), 8.37 (d, J=8.5 Hz, 2H), 7.92 (d, J=7.2 Hz, 1H; NH), 7.90-7.85 (m, 3H), 7.85-7.82 (m, 1H), 4.67 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.4 Hz, 1H), 2.55 (dt, J=13.3, 7.7 Hz, 1H), 2.20-2.10 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.02-1.85 (m, 2H), 1.75-1.63 (m, 2H), 0.99 (t, J=7.6 Hz, 3H).

EXAMPLE 10

N-{(1S,3R)-3-[3-(4-benzothiazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A38”)

(119) ##STR00047##

(120) Treatment of N-{(1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (L) (example 9.1) with benzothiazole analogously to method 1.5 (example 1) leads to N-{(1S,3R)-3-[3-(4-benzothiazol-2-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A38”); LC/MS: 418 (M+H).

(121) The following compounds are synthesized analogously to method described in example 7.2 from N-{(1S,3R)-3-[3-(4-bromo-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (L) (example 9.1) and appropriate arylboronic acid derivative:

N-{(1S,3R)-3-[3-(4′-chloro-biphenyl-4-yl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A39”)

(122) ##STR00048##

(123) LC/MS: 395 (M+H);

(124) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.93 (s, 1H), 7.93-7.84 (m, 3H), 7.79 (d, J=8.6 Hz, 2H), 7.72 (d, J=8.5 Hz, 2H), 7.57 (d, J=8.6 Hz, 2H), 4.64 (p, J=7.9 Hz, 1H), 4.07 (h, J=7.4 Hz, 1H), 2.57-2.51 (m, 1H), 2.19-2.10 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.03-1.84 (m, 2H), 1.77-1.63 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[3-(4′-cyano-biphenyl-4-yl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A40”)

(125) ##STR00049##

(126) LC/MS: 386 (M+H);

(127) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.84 (s, 1H), 7.97 (s, 4H), 7.94 (d, J=8.5 Hz, 2H), 7.89 (d, J=7.2 Hz, 1H; NH), 7.76 (d, J=8.5 Hz, 2H), 4.63 (p, J=7.8 Hz, 1H), 4.07 (h, J=7.4 Hz, 1H), 2.58-2.51 (m, 1H), 2.19-2.10 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.03-1.82 (m, 2H), 1.70 (dt, J=13.3, 8.3 Hz, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[3-(4-benzoxazol-2-yl-phenyl)-5-ethyl-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A41”)

(128) ##STR00050##

(129) LC/MS: 430 (M+H);

N-((1S,3R)-3-{3-[4-(1H-indazol-4-yl)-phenyl]-[1,2,4]triazol-4-yl}-cyclopentyl)-propionamide (“A42”)

(130) ##STR00051##

(131) LC/MS: 401 (M+H);

(132) .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.29 (s, 1H; NH), 8.86 (s, 1H), 8.26 (s, 1H), 7.97-7.88 (m, 3H), 7.77 (d, J=8.3 Hz, 2H), 7.60 (d, J=8.3 Hz, 1H), 7.52-7.43 (m, 1H), 7.33 (d, J=6.8 Hz, 1H), 4.68 (p, J=8.0 Hz, 1H), 4.10 (h, J=7.4 Hz, 1H), 2.57 (dt, J=13.3, 7.7 Hz, 1H), 2.17 (dq, J=13.6, 7.2 Hz, 1H), 2.08 (q, J=7.6 Hz, 2H), 2.04-1.87 (m, 2H), 1.77-1.67 (m, 2H), 1.00 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[3-(4-benzothiazol-6-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A43”)

(133) ##STR00052##

(134) LC/MS: 418 (M+H);

(135) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.44 (s, 1H), 8.83 (s, 1H), 8.59 (d, J=1.6 Hz, 1H), 8.20 (d, J=8.5 Hz, 1H), 7.99-7.92 (m, 3H), 7.89 (d, J=7.1 Hz, 1H; NH), 7.74 (d, J=8.3 Hz, 2H), 4.65 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.3 Hz, 1H), 2.61-2.51 (m, 1H), 2.20-2.11 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.03-1.84 (m, 2H), 1.77-1.64 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{3-[4-(1H-indol-6-yl)-phenyl]-[1,2,4]triazol-4-yl}-cyclopentyl)-propionamide (“A44”)

(136) ##STR00053##

(137) LC/MS: 400 (M+H);

(138) .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.22 (s, 1H; NH), 8.94 (s, 1H), 7.91 (d, J=7.2 Hz, 1H; NH), 7.87 (d, J=8.4 Hz, 2H), 7.73 (s, 1H), 7.70 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.3 Hz, 1H), 7.43-7.38 (m, 2H), 4.67 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.6 Hz, 1H), 2.64-2.51 (m, 1H), 2.21-2.11 (m, 1H), 2.08 (q, J=7.6 Hz, 2H), 2.03-1.86 (m, 2H), 1.78-1.65 (m, 2H), 0.99 (t, J=7.6 Hz, 3H).

General Synthesis 5: Synthesis of Pyrazole Derivatives

(139) ##STR00054##

EXAMPLE 11

(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A45”)

(140) ##STR00055##

(141) 11.1 (1S,3R)-3-Hydrazino-cyclopentanecarboxylic acid ethylamide (M) was synthesized from oxaziridine-3,3-dicarboxylic acid diethyl ester and (1S,3R)-3-amino-cyclopentanecarboxylic acid ethylamide (2) (example 1.2) according to literature (Alan Armstrong et. al. Organic Letters, 7(4), 713-716, (2005));

(142) LC/MS: 172 (M+H).

(143) 11.2 Treatment of (1S,3R)-3-hydrazino-cyclopentanecarboxylic acid ethylamide (M) with (E)-1-(4-bromo-phenyl)-3-dimethylamino-propenone according to literature (C. P. Frizzo et al./Catalysis Communications 10 (2009) 1967-1970) leads (1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (O); LC/MS: 363 (M+H).

(144) 11.3 Treatment of (1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (O) with benzoxazole analogously to method 1.5 (example 1) leads (1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A45”); LC/MS: 401 (M+H).

EXAMPLE 12

N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (“A46”)

(145) ##STR00056##

(146) Treatment of (1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (O) (example 11.2) with benzothiazole analogously to method 1.5 (example 1) leads N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (“A46”);

(147) LC/MS: 417 (M+H).

(148) The following compounds are synthesized analogously to method described in example 7.2 from (1S,3R)-3-[5-(4-Bromo-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (O) (example 11.2) and an appropriate Arylboronic acid derivative:

(1S,3R)-3-{5-[4-(1H-Indazol-4-yl)-phenyl]-pyrazol-1-yl}-cyclopentanecarboxylic acid ethylamide (“A47”)

(149) ##STR00057##

(150) LC/MS: 400 (M+H);

(1S,3R)-3-[5-(4-benzothiazol-6-yl-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A48”)

(151) ##STR00058##

(152) LC/MS: 417 (M+H);

(1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-pyrazol-1-yl}-cyclopentanecarboxylic acid ethylamide (“A49”)

(153) ##STR00059##

(154) LC/MS: 399 (M+H);

(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A50”)

(155) ##STR00060##

(156) LC/MS: 394 (M+H);

(1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A51”)

(157) ##STR00061##

(158) LC/MS: 385 (M+H).

EXAMPLE 13

(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A52”)

(159) ##STR00062##

(160) 13.1 N-((1S,3R)-3-Hydrazino-cyclopentyl)-propionamide (N) was synthesized from oxaziridine-3,3-dicarboxylic acid diethyl ester and N-((1S,3R)-3-amino-cyclopentyl)-propionamide (D) (example 4.4) according to literature (Alan Armstrong et. al. Organic Letters, 7(4), 713-716, (2005)); LC/MS: 172 (M+H).

(161) 13.2 Treatment of N-((1S,3R)-3-hydrazino-cyclopentyl)-propionamide (N) with (E)-1-(4-bromo-phenyl)-3-dimethylamino-propenone according to literature (C. P. Frizzo et al./Catalysis Communications 10 (2009) 1967-1970) leads to N-{(1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (P); LC/MS: 363 (M+H).

(162) 13.3 Treatment of N-{(1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (P) with benzoxazole analogously to method 1.5 (example 1) leads to (1S,3R)-3-[5-(4-benzooxazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A52”); LC/MS: 401 (M+H).

EXAMPLE 14

N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (“A53”)

(163) ##STR00063##

(164) Treatment of N-{(1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (P) (example 13.2) with benzothiazole analogously to method 1.5 (example 1) leads N-{(1S,3R)-3-[5-(4-benzothiazol-2-yl-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (“A53”); LC/MS: 417 (M+H).

(165) The following compounds are synthesized analogously to method described in example 7.2 from N-{(1S,3R)-3-[5-(4-bromo-phenyl)-pyrazol-1-yl]-cyclopentyl}-propionamide (P) (example 13.2) and an appropriate arylboronic acid derivative:

N-{(1S,3R)-3-[5-(4′-cyano-biphenyl-4-yl)-pyrazol-1-yl]-cyclopentyl}-propionamide (“A54”)

(166) ##STR00064##

(167) LC/MS: 385 (M+H);

(N-{(1S,3R)-3-[5-(4′-chloro-biphenyl-4-yl)-pyrazol-1-yl]-cyclopentyl}-propionamide (“A55”)

(168) ##STR00065##

(169) LC/MS: 394 (M+H);

N-((1S,3R)-3-{5-[4-(1H-indazol-4-yl)-phenyl]-pyrazol-1-yl}-cyclopentyl)-propionamide (“A56”)

(170) ##STR00066##

(171) LC/MS: 400 (M+H);

N-((1S,3R)-3-{5-[4-(1H-indol-6-yl)-phenyl]-pyrazol-1-yl}-cyclopentyl)-propionamide (“A57”)

(172) ##STR00067##

(173) LC/MS: 399 (M+H);

N-{(1S,3R)-3-[5-(4′-Cyano-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A58”)

(174) ##STR00068##

(175) LC/MS: 386 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.99-7.92 (m, 7H), 7.91 (s, 1H), 7.64 (d, J=8.5 Hz, 2H), 4.91 (p, J=8.0 Hz, 1H), 4.14 (h, J=7.6 Hz, 1H), 2.23-2.11 (m, 2H), 2.11-2.01 (m, 3H), 2.01-1.86 (m, 1H), 1.86-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-Indol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A59”)

(176) ##STR00069##

(177) LC/MS: 400 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 11.24 (s, 1H; NH), 8.00 (d, J=7.4 Hz, 1H; NH), 7.89 (s, 1H), 7.85 (d, J=8.3 Hz, 2H), 7.72 (s, 1H), 7.65 (d, J=8.2 Hz, 1H), 7.57 (d, J=8.3 Hz, 2H), 7.43-7.40 (m, 1H), 7.38 (dd, J=8.3, 1.6 Hz, 1H), 6.47 (s, 1H), 4.93 (p, J=7.8 Hz, 1H), 4.16 (h, J=7.6 Hz, 1H), 2.58-2.51 (m, 1H), 2.17 (q, J=8.0 Hz, 2H), 2.11-2.03 (m, 3H), 1.97 (dq, J=13.7, 6.9 Hz, 1H), 1.79 (dq, J=12.5, 8.3 Hz, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4-Benzothiazol-6-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A60”)

(178) ##STR00070##

(179) LC/MS: 418 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.44 (s, 1H), 8.58 (dd, J=1.9, 0.6 Hz, 1H), 8.20 (d, J=8.5 Hz, 1H), 8.02-7.86 (m, 5H), 7.63 (d, J=8.4 Hz, 2H), 4.93 (p, J=7.8 Hz, 1H), 4.15 (h, J=7.7 Hz, 1H), 2.58-2.51 (m, 1H), 2.22-2.12 (m, 2H), 2.12-2.01 (m, 3H), 1.97 (dq, J=13.8, 6.9 Hz, 1H), 1.85-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1-Methyl-1H-indazol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A61”)

(180) ##STR00071##

(181) LC/MS: 415 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.15-8.10 (m, 2H), 7.96 (d, J=7.5 Hz, 1H; NH), 7.93-7.85 (m, 3H), 7.83-7.72 (m, 2H), 7.60 (s, 1H), 7.59 (d, J=8.4 Hz, 2H), 4.92 (p, J=8.0 Hz, 1H), 4.15 (h, J=7.5 Hz, 1H), 4.09 (s, 3H), 2.22-2.12 (m, 2H), 2.11-2.01 (m, 3H), 1.96 (dq, J=13.6, 6.9 Hz, 1H), 1.78 (dq, J=12.5, 8.2 Hz, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Cyano-2′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A62”)

(182) ##STR00072##

(183) LC/MS: 404 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.04-7.99 (m, 1H), 7.95 (d, J=7.3 Hz, 1H; NH), 7.91 (s, 1H), 7.85-7.82 (m, 2H), 7.81-7.76 (m, 2H), 7.66 (d, J=8.5 Hz, 2H), 4.92 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.5 Hz, 1H), 2.57-2.50 (m, 1H), 2.21-2.11 (m, 2H), 2.11-2.01 (m, 3H), 1.96 (dq, J=13.7, 6.9 Hz, 1H), 1.78 (dq, J=12.5, 8.2 Hz, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1-Methyl-1H-indazol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A63”)

(184) ##STR00073##

(185) LC/MS: 415 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.08 (d, J=0.9 Hz, 1H), 8.01 (s, 1H), 7.99-7.93 (m, 3H), 7.90 (s, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.52 (dd, J=8.4, 1.4 Hz, 1H), 4.93 (p, J=8.0 Hz, 1H), 4.21-4.13 (m, 1H), 4.12 (s, 3H), 2.56-2.51 (m, 1H), 2.24-2.12 (m, 2H), 2.12-2.02 (m, 3H), 1.96 (dq, J=13.6, 7.1 Hz, 1H), 1.79 (dq, J=12.5, 8.2 Hz, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4′-(1-Methyl-1H-pyrazol-4-yl)-biphenyl-4-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A64”)

(186) ##STR00074##

(187) LC/MS: 441 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6)δ 8.19 (s, 1H), 7.95 (d, J=7.3 Hz, 1H; NH), 7.91 (s, 1H), 7.86 (d, J=8.3 Hz, 3H), 7.74 (d, J=8.5 Hz, 2H), 7.68 (d, J=8.5 Hz, 2H), 7.57 (d, J=8.4 Hz, 2H), 4.91 (p, J=7.8 Hz, 1H), 4.15 (h, J=7.8 Hz, 1H), 3.88 (s, 3H), 2.57-2.50 (m, 2H), 2.23-2.12 (m, 2H), 2.12-2.01 (m, 3H), 1.96 (dq, J=13.8, 7.0 Hz, 1H), 1.87-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

(1S,3R)-3-[3-(4-Benzothiazol-6-yl-phenyl)-[1,2,4]triazol-4-yl]-cyclopentanecarboxylic acid ethylamide (“A65”)

(188) ##STR00075##

(189) LC/MS: 418 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.44 (s, 1H), 8.99 (s, 1H), 8.60 (d, J=1.8 Hz, 1H), 8.20 (d, J=8.5 Hz, 1H), 8.01-7.90 (m, 3H), 7.86 (t, J=5.4 Hz, 1H), 7.76 (d, J=8.3 Hz, 2H), 4.67 (p, J=7.4 Hz, 1H), 3.09 (qd, J=7.2, 5.5 Hz, 2H), 2.78-2.64 (m, 1H), 2.43-2.30 (m, 1H), 2.20-2.08 (m, 1H), 2.08-1.83 (m, 4H), 1.02 (t, J=7.2 Hz, 3H);

Cyclopropanecarboxylic acid {(1S,3R)-3-[5-(4-benzooxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-amide (“A66”)

(190) ##STR00076##

(191) LC/MS: 414 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.35 (d, J=8.5 Hz, 2H), 8.26 (d, J=7.4 Hz, 1H; NH), 7.98 (s, 1H), 7.88-7.81 (m, 2H), 7.76 (d, J=8.5 Hz, 2H), 7.52-7.41 (m, 2H), 4.94 (p, J=8.0 Hz, 1H), 4.18 (h, J=7.6 Hz, 1H), 2.60-2.52 (m, 1H), 2.23-2.13 (m, 2H), 2.13-2.03 (m, 1H), 1.97 (dq, J=13.6, 6.9 Hz, 1H), 1.81 (dq, J=12.5, 8.4 Hz, 1H), 1.59-1.49 (m, 1H), 0.70-0.58 (m, 4H);

N-{(1S,3R)-3-[5-(4-Benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-2-cyclopentyl-acetamide (“A67”)

(192) ##STR00077##

(193) LC/MS: 456 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.36 (d, J=8.5 Hz, 2H), 7.99 (d, J=8.6 Hz, 1H; NH),), 7.98 (s, 1H), 7.88-7.82 (m, 2H), 7.77 (d, J=8.5 Hz, 2H), 7.51-7.42 (m, 2H), 4.94 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.59-2.51 (m, 1H), 2.24-2.00 (m, 6H), 1.95 (tq, J=12.2, 6.1, 5.3 Hz, 1H), 1.86-1.73 (m, 1H), 1.73-1.62 (m, 2H), 1.62-1.52 (m, 2H), 1.52-1.41 (m, 2H), 1.21-1.05 (m, 2H);

(R)-Tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[5-(4-benzooxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-amide (“A68”)

(194) ##STR00078##

(195) LC/MS: 444 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.36 (d, J=8.4 Hz, 2H), 8.04 (d, J=8.3 Hz, 1H; NH), 8.00 (s, 1H), 7.90-7.81 (m, 2H), 7.78 (d, J=8.4 Hz, 2H), 7.51-7.42 (m, 2H), 5.00 (p, J=7.7, 7.3 Hz, 1H), 4.28 (h, J=7.2 Hz, 1H), 4.20 (dd, J=8.3, 5.0 Hz, 1H), 4.01-3.93 (m, 1H), 3.81-3.73 (m, 1H), 2.49-2.44 (m, 1H), 2.27-2.16 (m, 2H), 2.16-2.05 (m, 2H), 1.96 (dq, J=14.6, 7.3 Hz, 1H), 1.90-1.72 (m, 4H);

(S)-Tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[5-(4-benzooxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-amide (“A69”)

(196) ##STR00079##

(197) LC/MS: 444 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.36 (d, J=8.5 Hz, 2H), 8.10 (d, J=7.9 Hz, 1H; NH), 8.00 (s, 1H), 7.89-7.82 (m, 2H), 7.78 (d, J=8.5 Hz, 2H), 7.52-7.42 (m, 2H), 5.00 (p, J=6.8 Hz, 1H), 4.25 (dt, J=14.5, 7.1 Hz, 1H), 4.20 (dd, J=8.2, 5.0 Hz, 1H), 4.01-3.93 (m, 1H), 3.81-3.73 (m, 1H), 2.28-2.04 (m, 4H), 1.93 (dq, J=13.1, 7.3 Hz, 1H), 1.89-1.71 (m, 4H);

N-{(1S,3R)-3-[5-(4-Quinolin-3-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A70”)

(198) ##STR00080##

(199) LC/MS: 412 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.34 (s, 1H), 8.77 (s, 1H), 8.18-8.05 (m, 4H), 8.00 (d, J=6.5 Hz, 1H), 7.95 (s, 1H), 7.82 (t, J=7.1 Hz, 1H), 7.77-7.63 (m, 3H), 4.95 (p, J=7.8 Hz, 1H), 4.16 (h, J=7.8 Hz, 1H), 2.30-2.03 (m, 5H), 1.98 (dq, J=13.4, 6.7 Hz, 1H), 1.86-1.69 (m, 1H), 1.00 (t, J=7.5 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1-Methyl-1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A71”)

(200) ##STR00081##

(201) LC/MS: 414 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6)δ 7.95 (d, J=7.4 Hz, 1H; NH), 7.91 (s, 1H), 7.89-7.82 (m, 3H), 7.60-7.49 (m, 4H), 7.37 (d, J=3.0 Hz, 1H), 6.51 (d, J=3.0 Hz, 1H), 4.92 (p, J=8.0, 7.4 Hz, 1H), 4.15 (h, J=7.5 Hz, 1H), 3.83 (s, 3H), 2.59-2.51 (m, 1H), 2.22-2.12 (m, 2H), 2.12-2.02 (m, 3H), 1.96 (dq, J=13.8, 7.4 Hz, 1H), 1.85-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-Indazol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A72”)

(202) ##STR00082##

(203) LC/MS: 401 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.20 (s, 1H; NH), 8.12 (s, 1H), 8.00 (d, J=7.4 Hz, 1H; NH), 7.92 (d, J=8.3 Hz, 3H), 7.89 (d, J=8.1 Hz, 1H), 7.82 (s, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.49 (dd, J=8.4, 1.4 Hz, 1H), 4.93 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.59-2.52 (m, 1H), 2.22-2.12 (m, 2H), 2.12-2.02 (m, 3H), 1.97 (dq, J=13.7, 6.9 Hz, 1H), 1.87-1.70 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-Benzimidazol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A73”)

(204) ##STR00083##

(205) LC/MS: 401 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.56 (s, 1H; NH), 8.27 (s, 1H), 7.99 (d, J=7.4 Hz, 1H), 7.92 (br. s, 1H), 7.90-7.85 (m, 3H), 7.69 (br. s, 1H), 7.58 (d, J=8.3 Hz, 3H), 4.93 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.6 Hz, .sub.1H), 2.57-2.51 (m, 1H), 2.22-2.12 (m, 2H), 2.12-2.02 (m, 3H), 1.96 (dq, J=13.7, 6.9 Hz, 1H), 1.85-1.73 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-Indazol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A74”)

(206) ##STR00084##

(207) LC/MS: 401 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.16 (s, 1H; NH), 8.16 (s, 1H), 8.12 (s, 1H), 7.99 (d, J=7.4 Hz, 1H), 7.91-7.85 (m, 3H), 7.74 (d, J=8.7 Hz, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.59 (d, J=8.4 Hz, 2H), 4.93 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.56-2.51 (m, 1H), 2.23-2.11 (m, 2H), 2.10-2.02 (m, 3H), 1.96 (dq, J=13.7, 6.9 Hz, 1H), 1.85-1.73 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Chloro-3′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A75”)

(208) ##STR00085##

(209) LC/MS: 413 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J=7.4 Hz, 1H; NH), 7.93-7.89 (m, 3H), 7.86 (dd, J=10.9, 2.0 Hz, 1H), 7.72 (t, J=8.1 Hz, 1H), 7.65 (dd, J=8.4, 2.0 Hz, 1H), 7.61 (d, J=8.4 Hz, 2H), 4.90 (p, J=8.0 Hz, 1H), 4.14 (h, J=7.6 Hz, 1H), 2.22-2.10 (m, 2H), 2.10-2.00 (m, 3H), 1.95 (dq, J=13.6, 7.0 Hz, 1H), 1.84-1.69 (m, 1H), 0.98 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Pyrazol-1-yl-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A76”)

(210) ##STR00086##

(211) LC/MS: 427 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.59 (d, J=2.5 Hz, 1H), 7.98 (d, J=8.8 Hz, 3H), 7.95-7.86 (m, 5H), 7.79 (d, J=1.6 Hz, 1H), 7.61 (d, J=8.3 Hz, 2H), 6.79-6.42 (m, 1H), 4.92 (p, J=8.0 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.58-2.48 (m, 1H), 2.22-2.11 (m, 2H), 2.12-2.02 (m, 3H), 1.96 (dq, J=13.6, 7.0 Hz, 1H), 1.85-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1-Methyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A77”)

(212) ##STR00087##

(213) LC/MS: 430 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.99 (d, J=7.4 Hz, 1H; NH), 7.92-7.87 (m, 3H), 7.59 (d, J=8.3 Hz, 2H), 7.40-7.32 (m, 3H), 4.91 (p, J=8.1 Hz, 1H), 4.13 (dt, J=15.3, 7.7 Hz, 1H), 3.61 (s, 2H), 3.21 (s, 3H), 2.23-2.11 (m, 2H), 2.11-2.01 (m, 3H), 1.96 (dq, J=13.5, 7.1 Hz, 1H), 1.83-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(6-Methyl-1H-indazol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A78”)

(214) ##STR00088##

(215) LC/MS: 415 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.99 (s, 1H; NH), 8.04 (s, 1H), 8.00 (d, J=7.4 Hz, 1H; NH), 7.91 (s, 1H), 7.62 (s, 1H), 7.59-7.51 (m, 4H), 7.47 (s, 1H), 4.94 (p, J=7.8 Hz, 1H), 4.17 (h, J=7.6 Hz, 1H), 2.58-2.51 (m, 1H), 2.18 (q, J=7.2 Hz, 2H), 2.07 (p, J=7.6 Hz, 3H), 1.97 (dq, J=13.6, 6.9 Hz, 1H), 1.85-1.74 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(2-Oxo-2,3-dihydro-1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A79”)

(216) ##STR00089##

(217) LC/MS: 416 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 10.47 (s, 1H; NH), 7.95 (d, J=7.4 Hz, 1H; NH), 7.86 (s, 1H), 7.77 (d, J=8.4 Hz, 2H), 7.60 (s, 1H), 7.55 (t, J=8.3 Hz, 3H), 6.93 (d, J=8.1 Hz, 1H), 4.90 (p, J=7.8 Hz, 1H), 4.22-4.06 (m, 10H), 3.55 (s, 2H), 2.15 (qd, J=7.6, 7.0, 3.1 Hz, 2H), 2.11-2.00 (m, 3H), 1.95 (dq, J=13.6, 7.0 Hz, 1H), 1.84-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Cyano-3′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A80”)

(218) ##STR00090##

(219) LC/MS: 404 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.06 (dd, J=8.1, 7.0 Hz, 1H), 8.02-7.96 (m, 4H), 7.93 (s, 1H), 7.85 (dd, J=8.2, 1.7 Hz, 1H), 7.66 (d, J=8.4 Hz, 2H), 4.91 (qd, J=8.1, 6.5 Hz, 1H), 4.14 (h, J=7.6 Hz, 1H), 2.22-2.10 (m, 2H), 2.10-2.01 (m, 3H), 1.95 (dq, J=13.5, 7.1 Hz, 1H), 1.84-1.72 (m, 1H), 0.98 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Chloro-2′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A81”)

(220) ##STR00091##

(221) LC/MS: 413 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.95 (d, J=7.4 Hz, 1H; NH), 7.90 (s, 1H), 7.73 (dd, J=8.3, 1.5 Hz, 2H), 7.68-7.57 (m, 4H), 7.44 (dd, J=8.4, 1.8 Hz, 1H), 4.91 (p, J=7.8 Hz, 1H), 4.15 (h, J=7.5 Hz, 1H), 2.27-2.11 (m, 2H), 2.11-2.01 (m, 3H), 1.96 (dq, J=13.6, 6.9 Hz, 1H), 1.86-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Methoxy-2′-methyl-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A82”)

(222) ##STR00092##

(223) LC/MS: 405 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.99 (d, J=7.4 Hz, 1H; NH), 7.88 (s, 1H), 7.53 (d, J=8.3 Hz, 2H), 7.48 (d, J=8.3 Hz, 2H), 7.19 (d, J=8.4 Hz, 1H), 6.91 (d, J=2.6 Hz, 1H), 6.86 (dd, J=8.4, 2.7 Hz, 1H), 4.92 (p, J=7.8 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 3.79 (s, 3H), 2.56-2.50 (m, 1H), 2.27 (s, 3H), 2.22-2.13 (m, 2H), 2.13-2.01 (m, 3H), 1.96 (dq, J=13.6, 6.8 Hz, 1H), 1.85-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(3′-Fluoro-4′-methyl-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A83”)

(224) ##STR00093##

(225) LC/MS: 393 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.95 (d, J=7.5 Hz, 1H; NH), 7.88 (s, 1H), 7.86 (d, J=8.4 Hz, 2H), 7.57 (d, J=8.5 Hz, 2H), 7.55-7.48 (m, 2H), 7.41 (t, J=8.0 Hz, 1H), 4.90 (p, J=8.0 Hz, 1H), 4.21-4.07 (m, 1H), 2.29 (s, 3H), 2.19-2.11 (m, 2H), 2.11-2.01 (m, 3H), 1.95 (dq, J=13.1, 6.6 Hz, 1H), 1.83-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Methyl-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A84”)

(226) ##STR00094##

(227) LC/MS: 375 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.97 (d, J=7.4 Hz, 1H; NH), 7.88 (s, 1H), 7.83 (d, J=8.4 Hz, 2H), 7.65 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.4 Hz, 2H), 7.33 (d, J=7.9 Hz, 2H), 4.92 (p, J=8.0 Hz, 1H), 4.15 (h, J=7.8 Hz, 1H), 2.38 (s, 3H), 2.22-2.12 (m, 2H), 2.12-2.02 (m, 3H), 2.02-1.91 (m, 1H), 1.85-1.74 (m, 1H), 1.00 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(3′-Chloro-4′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A85”)

(228) ##STR00095##

(229) LC/MS: 413 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.00 (d, J=2.3 Hz, 1H), 7.96 (d, J=7.6 Hz, 1H; NH), 7.91 (s, 1H), 7.89 (d, J=8.4 Hz, 2H), 7.79 (ddd, J=8.7, 4.7, 2.4 Hz, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.58-7.53 (m, 1H), 4.91 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.7 Hz, 1H), 2.24-2.11 (m, 2H), 2.12-2.01 (m, 3H), 2.02-1.91 (m, 1H), 1.79 (dq, J=12.4, 8.3 Hz, 1H), 1.00 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(2′,4′-Dimethoxy-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A86”)

(230) ##STR00096##

(231) LC/MS: 421 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.99 (d, J=7.4 Hz, 1H; NH), 7.86 (s, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 7.29 (d, J=8.4 Hz, 1H), 6.70 (d, J=2.4 Hz, 1H), 6.65 (dd, J=8.4, 2.4 Hz, 1H), 4.91 (p, J=7.7 Hz, 1H), 4.15 (dp, J=8.9, 7.5 Hz, 1H), 3.82 (s, 3H), 3.80 (s, 3H), 2.55-2.48 (m, 1H), 2.16 (q, J=7.1 Hz, 2H), 2.11-2.01 (m, 3H), 2.01-1.90 (m, 1H), 1.85-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(2-Oxo-2,3-dihydro-1H-benzimidazol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A87”)

(232) ##STR00097##

(233) LC/MS: 417 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 10.75 (s, 1H), 10.72 (s, 1H), 7.99 (d, J=7.4 Hz, 1H), 7.87 (s, 1H), 7.77 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.31 (dd, J=8.1, 1.7 Hz, 1H), 7.23 (d, J=1.5 Hz, 1H), 7.03 (d, J=8.1 Hz, 1H), 4.91 (p, J=7.9 Hz, 1H), 4.15 (h, J=7.6 Hz, 1H), 2.21-2.11 (m, 2H), 2.11-2.01 (m, 3H), 2.01-1.90 (m, 1H), 1.85-1.70 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(3′,4′-Dimethoxy-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A88”)

(234) ##STR00098##

(235) LC/MS: 421 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J=7.4 Hz, 1H), 7.87 (s, 1H; NH), 7.83 (d, J=8.3 Hz, 2H), 7.54 (d, J=8.3 Hz, 2H), 7.31-7.25 (m, 2H), 7.07 (d, J=8.1 Hz, 1H), 4.90 (p, J=8.0 Hz, 1H), 4.21-4.08 (m, 1H), 3.86 (s, 3H), 3.81 (s, 3H), 2.22-2.11 (m, 2H), 2.11-2.00 (m, 3H), 1.95 (dq, J=13.5, 7.0 Hz, 1H), 1.84-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(2′,4′-Dimethyl-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A89”)

(236) ##STR00099##

(237) LC/MS: 389 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.96 (d, J=7.4 Hz, 1H; NH), 7.89 (s, 1H), 7.55 (d, J=8.3 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 7.18-7.12 (m, 2H), 7.09 (d, J=8.5 Hz, 1H), 4.92 (p, J=7.8 Hz, 1H), 4.16 (h, J=7.8 Hz, 1H), 2.32 (s, 3H), 2.25 (s, 3H), 2.16 (q, J=7.9 Hz, 2H), 2.11-2.01 (m, 3H), 1.96 (dq, J=13.7, 6.9 Hz, 1H), 1.85-1.73 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

(S)-2,2-Dimethyl-[1,3]dioxolane-4-carboxylic acid {(1S,3R)-3-[5-(4-benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-amide (“A90”)

(238) ##STR00100##

(239) LC/MS: 474 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.36 (d, J=8.5 Hz, 2H), 8.18 (d, J=8.3 Hz, 1H), 8.01 (s, 1H; NH), 7.85 (dd, J=12.9, 7.3 Hz, 2H), 7.78 (d, J=8.5 Hz, 2H), 7.51-7.42 (m, 2H), 5.02 (ddd, J=8.2, 5.9, 2.2 Hz, 1H), 4.44 (dd, J=7.4, 5.3 Hz, 1H), 4.33 (h, J=6.8 Hz, 1H), 4.18 (dd, J=8.4, 7.5 Hz, 1H), 3.92 (dd, J=8.4, 5.3 Hz, 1H), 2.56-2.51 (m, 1H), 2.29-2.07 (m, 3H), 1.97 (dq, J=13.2, 7.3 Hz, 1H), 1.89-1.75 (m, 1H), 1.45 (s, 3H), 1.35 (s, 3H);

N-((1S,3R)-3-{5-[4-(2-Oxo-2,3-dihydro-1H-indol-6-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A91”)

(240) ##STR00101##

(241) LC/MS: 416 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 10.51 (s, 1H; NH), 7.98 (d, J=7.4 Hz, 1H), 7.88 (s, 1H; NH), 7.78 (d, J=8.4 Hz, 2H), 7.58 (d, J=8.4 Hz, 2H), 7.36-7.26 (m, 2H), 7.09 (d, J=1.2 Hz, 2H), 4.97-4.83 (m, 1H), 4.15 (dp, J=8.9, 7.5 Hz, 1H), 3.53 (s, 2H), 2.55-2.51 (m, 1H), 2.21-2.11 (m, 2H), 2.10-2.01 (m, 3H), 2.00-1.90 (m, 1H), 1.84-1.73 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4′-Cyclopropylmethoxy-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A92”)

(242) ##STR00102##

(243) LC/MS: 431 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 7.95 (d, J=7.4 Hz, 1H), 7.86 (s, 1H), 7.79 (d, J=8.4 Hz, 2H), 7.67 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 4.90 (p, J=7.9 Hz, 1H), 4.14 (h, J=7.7 Hz, 1H), 3.88 (d, J=7.0 Hz, 2H), 2.20-2.11 (m, 2H), 2.12-2.00 (m, 3H), 1.95 (dq, J=13.7, 6.9 Hz, 1H), 1.84-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H), 0.63-0.55 (m, 2H), 0.38-0.31 (m, 2H);

(S)—N-{(1S,3R)-3-[5-(4-Benzoxazol-2-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-2,3-dihydroxy-propionamide (“A93”)

(244) ##STR00103##

(245) LC/MS: 434 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6+CF.sub.3COOD) δ 8.39 (d, J=8.4 Hz, 2H), 8.01 (s, 1H), 7.87 (d, J=8.9 Hz, 1H), 7.82 (d, J=6.9 Hz, 1H), 7.78 (d, J=8.3 Hz, 2H), 7.47 (pd, J=7.4, 1.3 Hz, 2H), 5.02 (p, J=7.2 Hz, 1H), 4.32 (p, J=7.3 Hz, 1H), 3.91 (dd, J=6.0, 3.5 Hz, 1H), 3.62 (dd, J=11.2, 3.6 Hz, 1H), 3.51 (dd, J=11.2, 6.0 Hz, 1H), 2.62-2.55 (m, 1H), 2.29-2.12 (m, 3H), 2.06-1.93 (m, 1H), 1.96-1.79 (m, 1H);

N-{(1S,3R)-3-[3-(4′-Methoxy-2′-methyl-biphenyl-4-yl)-[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A94”)

(246) ##STR00104##

(247) LC/MS: 405 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.83 (s, 1H), 7.92 (d, J=7.2 Hz, 1H; NH), 7.65 (d, J=8.3 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 7.20 (d, J=8.4 Hz, 1H), 6.91 (d, J=2.6 Hz, 1H), 6.87 (dd, J=8.4, 2.7 Hz, 1H), 4.63 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.4 Hz, 1H), 3.79 (s, 3H), 2.59-2.51 (m, 1H), 2.20-2.11 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.02-1.85 (m, 2H), 1.77-1.63 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[3-(4′-Chloro-3′-fluoro-biphenyl-4-yl)[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A95”)

(248) ##STR00105##

(249) LC/MS: 413 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.84 (s, 1H), 7.95-7.89 (m, 3H), 7.87 (dd, J=10.9, 2.1 Hz, 1H), 7.75-7.68 (m, 3H), 7.66 (dd, J=8.4, 2.0 Hz, 1H), 4.62 (p, J=7.9 Hz, 1H), 4.07 (h, J=7.4 Hz, 1H), 2.57-2.50 (m, 1H), 2.16-2.09 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.01-1.82 (m, 2H), 1.76-1.59 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[3-(4′-Pyrazol-1-yl-biphenyl-4-yl)[1,2,4]triazol-4-yl]-cyclopentyl}-propionamide (“A96”)

(250) ##STR00106##

(251) LC/MS: 427 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.84 (s, 1H), 8.59 (d, J=2.4 Hz, 1H), 7.99 (d, J=8.8 Hz, 2H), 7.95-7.87 (m, 5H), 7.79 (d, J=1.6 Hz, 1H), 7.72 (d, J=8.4 Hz, 2H), 6.58 (s, 1H), 4.63 (p, J=8.0 Hz, 1H), 4.08 (h, J=7.4 Hz1H), 2.59-2.51 (m, 1H), 2.20-2.10 (m, 1H), 2.07 (q, J=7.6 Hz, 2H), 2.02-1.84 (m, 2H), 1.76-1.62 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{3-[4-(1-Methyl-1H-indol-5-yl)-phenyl]-[1,2,4]triazol-4-yl}-cyclopentyl)-propionamide (“A97”)

(252) ##STR00107##

(253) LC/MS: 414 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.83 (s, 1H), 7.97-7.89 (m, 2H), 7.86 (d, J=8.4 Hz, 2H), 7.67 (d, J=8.4 Hz, 2H), 7.56 (s, 2H), 7.38 (d, J=3.0 Hz, 1H), 6.51 (d, J=3.1 Hz, 3H), 4.64 (p, J=7.9 Hz, 1H), 4.09 (h, J=7.4 Hz, 1H), 3.83 (s, 3H), 2.59-2.50 (m, 1H), 2.20-2.10 (m, 1H), 2.08 (q, J=7.6 Hz, 2H), 2.02-1.86 (m, 2H), 1.76-1.62 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{3-[4-(6-Methyl-1H-indazol-5-yl)-phenyl]-[1,2,4]triazol-4-yl}-cyclopentyl)-propionamide (“A98”)

(254) ##STR00108##

(255) LC/MS: 415 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.99 (s, 1H; NH), 8.84 (s, 1H), 8.04 (s, 1H), 7.93 (d, J=7.2 Hz, 1H; NH), 7.68 (d, J=8.2 Hz, 2H), 7.63 (s, 1H), 7.55 (d, J=8.3 Hz, 2H), 7.47 (s, 1H), 4.66 (p, J=7.9 Hz, 1H), 4.10 (h, J=7.4 Hz, 1H), 2.61-2.48 (m, 1H), 2.37 (s, 3H), 2.17 (dt, J=12.1, 7.2 Hz, 1H), 2.08 (q, J=7.6 Hz, 2H), 2.04-1.86 (m, 2H), 1.78-1.65 (m, 2H), 1.00 (t, J=7.6 Hz, 3H);

4′-[3-((1R,3S)-3-Ethylcarbamoyl-cyclopentyl)-3H-[1,2,3]triazol-4-yl]-biphenyl-4-carboxylic acid amide (“A99”)

(256) ##STR00109##

(257) LC/MS: 404 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.05 (s, 1H; NH), 8.00 (d, J=8.4 Hz, 2H), 7.92 (s, 1H), 7.90 (d, J=5.4 Hz, 2H), 7.84 (d, J=8.5 Hz, 2H), 7.81 (t, J=5.6 Hz, 1H; NH), 7.62 (d, J=8.4 Hz, 2H), 7.42 (s, 1H; NH), 4.89 (p, J=8.1 Hz, 1H), 3.07 (qd, J=7.2, 5.4 Hz, 2H), 2.68 (p, J=8.8 Hz, 1H), 2.33 (t, J=8.8 Hz, 2H), 2.25-2.07 (m, 2H), 2.05-1.93 (m, 1H), 1.93-1.79 (m, 1H), 1.01 (t, J=7.2 Hz, 3H);

4′-[3-((1R,3S)-3-Ethylcarbamoyl-cyclopentyl)-3H-[1,2,3]triazol-4-yl]-biphenyl-4-carboxylic acid (“A100”)

(258) ##STR00110##

(259) LC/MS: 405 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.04 (s, 1H; —COOH), 7.93 (d, J=8.3 Hz, 2H), 7.91 (s, 1H), 7.90 (d, J=8.4 Hz, 2H), 4.90 (p, J=8.1 Hz, 1H), 3.08 (qd, J=7.2, 5.4 Hz, 2H), 2.70 (p, J=8.8 Hz, 1H), 2.34 (t, J=8.7 Hz, 2H), 2.24-2.08 (m, 2H), 2.07-1.92 (m, 1H), 1.93-1.78 (m, 1H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[5-(4′-Isopropyl-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A101”)

(260) ##STR00111##

(261) LC/MS: 403 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.88 (s, 1H), 7.85-7.78 (m, 3H), 7.67 (d, J=8.3 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.2 Hz, 2H), 4.90 (p, J=8.2 Hz, 1H), 3.09 (qd, J=7.2, 5.4 Hz, 2H), 2.97 (p, J=6.9 Hz, 1H), 2.70 (p, J=8.8 Hz, 1H), 2.35 (t, J=8.8 Hz, 2H), 2.26-2.11 (m, 2H), 2.06-1.96 (m, 1H), 1.93-1.83 (m, 1H), 1.26 (d, J=6.9 Hz, 6H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[5-(3′,4′-Dimethoxy-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A102”)

(262) ##STR00112##

(263) LC/MS: 421 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.87 (s, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.80 (t, J=5.3 Hz, 1H; NH), 7.57 (d, J=8.3 Hz, 2H), 7.33-7.28 (m, 2H), 7.09 (d, J=8.1 Hz, 1H), 4.93-4.84 (m, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 3.09 (qd, J=7.2, 5.4 Hz, 2H), 2.69 (dt, J=9.6, 8.4 Hz, 1H), 2.38-2.29 (m, 2H), 2.26-2.09 (m, 2H), 2.06-1.95 (m, 1H), 1.93-1.82 (m, 1H), 1.02 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[5-(4′-Cyclopropylmethoxy-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A103”)

(264) ##STR00113##

(265) LC/MS: 431 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.85 (s, 1H), 7.81-7.76 (m, 3H), 7.67 (d, J=8.8 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 4.87 (p, J=8.1 Hz, 1H), 3.88 (d, J=7.0 Hz, 2H), 3.07 (qd, J=7.2, 5.4 Hz, 2H), 2.68 (p, J=8.7 Hz, 1H), 2.36-2.26 (m, 2H), 2.24-2.08 (m, 2H), 2.05-1.94 (m, 1H), 1.92-1.81 (m, 1H), 1.30-1.22 (m, 1H), 1.01 (t, J=7.2 Hz, 3H), 0.63-0.54 (m, 2H), 0.39-0.28 (m, 2H);

(1S,3R)-3-[5-(4′-Chloro-3′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A104”)

(266) ##STR00114##

(267) LC/MS: 413 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.90 (d, J=8.4 Hz, 2H), 7.88 (s, 1H), 7.85 (dd, J=10.9, 2.0 Hz, 1H), 7.78 (t, J=5.3 Hz, 1H; NH), 7.71 (t, J=8.1 Hz, 1H), 7.65 (dd, J=8.4, 2.0 Hz, 1H), 7.62 (d, J=8.4 Hz, 2H), 4.87 (p, J=8.1 Hz, 1H), 3.07 (qd, J=7.2, 5.5 Hz, 2H), 2.68 (p, J=8.7 Hz, 1H), 2.36-2.27 (m, 2H), 2.25-2.06 (m, 2H), 2.04-1.92 (m, 1H), 1.93-1.79 (m, 1H), 1.01 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[5-(4′-Cyano-3′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A105”)

(268) ##STR00115##

(269) LC/MS: 404 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.08-8.03 (m, 1H), 8.01-7.95 (m, 3H), 7.91 (s, 1H), 7.84 (dd, J=8.2, 1.6 Hz, 1H), 7.78 (t, J=5.3 Hz, 1H; NH), 7.66 (d, J=8.4 Hz, 2H), 4.88 (p, J=8.1 Hz, 1H), 3.07 (qd, J=7.2, 5.4 Hz, 2H), 2.67 (h, J=8.8 Hz, 1H), 2.37-2.27 (m, 2H), 2.25-2.06 (m, 2H), 2.06-1.93 (m, 1H), 1.93-1.79 (m, 1H), 1.01 (t, J=7.2 Hz, 3H);

(1S,3R)-3-[5-(4′-Cyano-2′-fluoro-biphenyl-4-yl)-[1,2,3]triazol-1-yl]-cyclopentanecarboxylic acid ethylamide (“A106”)

(270) ##STR00116##

(271) LC/MS: 404 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.02 (d, J=11.2 Hz, 1H), 7.90 (s, 1H), 7.86-7.81 (m, 2H), 7.80-7.75 (m, 3H), 7.67 (d, J=8.4 Hz, 2H), 4.89 (p, J=8.1 Hz, 1H), 3.07 (qd, J=7.2, 5.5 Hz, 2H), 2.69 (p, J=8.7 Hz, 1H), 2.34 (t, J=8.7 Hz, 2H), 2.27-2.08 (m, 2H), 2.06-1.95 (m, 1H), 1.93-1.81 (m, 1H), 1.01 (t, J=7.2 Hz, 3H);

N-((1S,3R)-3-{5-[6-(1H-Indol-5-yl)-pyridin-3-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A107”)

(272) ##STR00117##

(273) LC/MS: 401 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.02 (s, 1H), 8.73 (dd, J=2.4, 0.9 Hz, 1H), 8.46-8.28 (m, 1H), 8.08 (dd, J=8.3, 0.9 Hz, 1H), 8.01-7.87 (m, 3H), 7.65 (d, J=6.5 Hz, 1H), 7.58-7.45 (m, 1H), 7.38 (t, J=2.8 Hz, 1H), 6.67-6.50 (m, 1H), 5.04-4.83 (m, 1H), 4.32-4.08 (m, 1H), 2.65-2.52 (m, 1H), 2.33-1.92 (m, 6H), 1.92-1.72 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[6-(4-Fluoro-1H-indol-5-yl)-pyridin-3-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A108”)

(274) ##STR00118##

(275) LC/MS: 419 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.34 (s, 1H), 8.80 (t, J=1.7 Hz, 1H), 8.07-7.97 (m, 2H), 7.95 (s, 1H), 7.81 (dd, J=8.5, 7.4 Hz, 1H), 7.65 (d, J=6.2 Hz, 1H), 7.41 (t, J=2.8 Hz, 1H), 7.38 (d, J=8.5 Hz, 1H), 6.67-6.57 (m, 1H), 5.10-4.82 (m, 1H), 4.32-4.04 (m, 1H), 2.66-2.52 (m, 1H), 2.32-1.95 (m, 6H), 1.91-1.73 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(6-Imidazo[1,2-a]pyridin-6-yl-pyridin-3-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A109”)

(276) ##STR00119##

(277) LC/MS: 402 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.43-9.32 (m, 1H), 8.86-8.70 (m, 1H), 8.13 (dd, J=8.3, 0.9 Hz, 1H), 8.09-8.03 (m, 2H), 8.00 (dd, J=9.5, 1.9 Hz, 1H), 7.96 (s, 1H), 7.73-7.58 (m, 3H), 5.02-4.85 (m, 1H), 4.33-4.07 (m, 1H), 2.60-2.52 (m, 1H), 2.30-2.05 (m, 5H), 2.05-1.91 (m, 1H), 1.91-1.68 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(4-Fluoro-1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A110”)

(278) ##STR00120##

(279) LC/MS: 418 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.27 (s, 1H), 7.84 (s, 1H), 7.80-7.71 (m, 2H), 7.66 (d, J=7.4 Hz, 1H), 7.61-7.51 (m, 2H), 7.40 (t, J=2.8 Hz, 1H), 7.37 (dd, J=8.4, 0.9 Hz, 1H), 7.27 (dd, J=8.4, 7.4 Hz, 1H), 6.63-6.53 (m, 1H), 5.12-4.81 (m, 1H), 4.37-4.07 (m, 1H), 2.62-2.52 (m, 1H), 2.28-1.93 (m, 6H), 1.90-1.75 (m, 1H), 1.04 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(4-Imidazo[1,2-a]pyridin-6-yl-phenyl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A111”)

(280) ##STR00121##

(281) LC/MS: 401 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363K) δ 9.03-8.89 (m, 1H), 7.97 (s, 1H), 7.93-7.86 (m, 2H), 7.85 (s, 1H), 7.73-7.53 (m, 6H), 5.04-4.84 (m, 1H), 4.34-4.02 (m, 1H), 2.59-2.52 (m, 1H), 2.29-2.05 (m, 5H), 2.05-1.94 (m, 1H), 1.89-1.75 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(6-Fluoro-1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A112”)

(282) ##STR00122##

(283) LC/MS: 418 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363K) δ 9.03-8.89 (m, 1H), 7.97 (s, 1H), 7.93-7.86 (m, 2H), 7.85 (s, 1H), 7.73-7.53 (m, 6H), 5.04-4.84 (m, 1H), 4.34-4.02 (m, 1H), 2.59-2.52 (m, 1H), 2.29-2.05 (m, 5H), 2.05-1.94 (m, 1H), 1.89-1.75 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[4-(1H-Pyrrolo[3,2-b]pyridin-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A113”)

(284) ##STR00123##

(285) LC/MS: 401 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363K) δ 11.15 (s, 1H), 8.38-8.13 (m, 2H), 7.89 (dd, J=8.5, 0.9, 1H), 7.84 (s, 1H), 7.75 (d, J=8.5, 1 H), 7.70-7.61 (m, 2H), 7.61-7.53 (m, 2H), 6.74-6.52 (m, 1H), 5.08-4.81 (m, 1H), 4.30-4.08 (m, 1H), 2.63-2.51 (m, 1H), 2.33-2.06 (m, 5H), 2.06-1.91 (m, 1H), 1.91-1.73 (m, 1H), 1.03 (t, J=7.6, 3H);

N-((1S,3R)-3-{5-[5-(6-Chloro-benzoxazol-2-yl)-pyridin-2-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A114”)

(286) ##STR00124##

(287) LC/MS: 437/439 (Cl isotopy, relative peak intensity ratio 100:38); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.46 (d, J=1.8 Hz, 1H), 8.65 (dd, J=8.3, 2.2 Hz, 1H), 8.42 (s, 1H), 8.12 (d, J=8.4 Hz, 1H), 8.07 (d, J=1.9 Hz, 1H), 7.96 (d, J=7.4 Hz, 1H), 7.90 (d, J=8.5 Hz, 1H), 7.52 (dd, J=8.5, 2.0 Hz, 1H), 5.90-5.70 (m, 1H), 4.27-4.11 (m, 1H), 2.64-2.54 (m, 1H), 2.31-2.14 (m, 2H), 2.14-1.94 (m, 4H), 1.87-1.69 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-{(1S,3R)-3-[5-(5-Benzoxazol-2-yl-pyridin-2-yl)-[1,2,3]triazol-1-yl]-cyclopentyl}-propionamide (“A115”)

(288) ##STR00125##

(289) LC/MS: 403 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363K) δ 9.50 (d, J=2.3 Hz, 1H), 8.67 (dd, J=8.4, 2.2 Hz, 1H), 8.33 (s, 1H), 8.08 (d, J=8.1 Hz, 1H), 7.93-7.76 (m, 2H), 7.64 (d, J=5.3 Hz, 1H), 7.56-7.38 (m, 2H), 5.87-5.71 (m, 1H), 4.35-4.15 (m, 1H), 2.67-2.56 (m, 1H), 2.26 (q, 2H), 2.21-1.96 (m, 4H), 1.91-1.74 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[5-(4-Fluoro-1H-indol-5-yl)-pyridin-2-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A116”)

(290) ##STR00126##

(291) LC/MS: 419 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.56 (s, 1H), 8.95 (s, 1H), 8.29 (s, 1H), 8.20-8.12 (m, 1H), 8.01-7.91 (m, 2H), 7.47 (t, J=2.7 Hz, 1 H), 7.40 (d, J=8.4 Hz, 1H), 7.37-7.28 (m, 1H), 6.65-6.56 (m, 1H), 5.89-5.73 (m, 1H), 4.30-4.09 (m, 1H), 2.64-2.54 (m, 1H), 2.31-2.14 (m, 2H), 2.14-1.94 (m, 4H), 1.87-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[5-(1H-Indol-5-yl)-pyridin-2-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A117”)

(292) ##STR00127##

(293) LC/MS: 401 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.25 (s, 1H), 9.08 (d, J=2.1 Hz, 1H), 8.27 (s, 1H), 8.25 (dd, J=8.3, 2.4 Hz, 1H), 8.00 (s, 1H), 7.97 (d, J=7.3 Hz, 1H), 7.90 (d, J=8.3 Hz, 1H), 7.57-7.50 (m, 2H), 7.42 (t, J=2.7 Hz, 1H), 6.59-6.47 (m, 1H), 5.90-5.73 (m, 1H), 4.29-4.08 (m, 1H), 2.64-2.53 (m, 1H), 2.29-2.14 (m, 2H), 2.14-1.93 (m, 4H), 1.88-1.72 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[5-(1H-Pyrrolo[3,2-b]pyridin-5-yl)-pyridin-2-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A118”)

(294) ##STR00128##

(295) LC/MS: 402 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.46 (s, 1H), 9.52-9.38 (m, 1H), 8.63 (dd, J=8.3, 2.0 Hz, 1H), 8.30 (s, 1H), 8.02-7.83 (m, 4H), 7.73 (t, J=2.6 Hz, 1H), 6.73-6.60 (m, 1H), 5.91-5.74 (m, 1H), 4.29-4.10 (m, 1H), 2.65-2.54 (m, 1H), 2.30-2.16 (m, 2H), 2.16-1.95 (m, 4H), 1.88-1.71 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[3-Fluoro-4-(4-fluoro-1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A119”)

(296) ##STR00129##

(297) LC/MS: 436 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363K) δ 11.29 (s, 1H), 7.87 (s, 1H), 7.69-7.50 (m, 2H), 7.49-7.26 (m, 4H), 7.12 (t, J=7.6 Hz, 1H), 6.60-6.47 (m, 1H), 5.17-4.73 (m, 1H), 4.40-3.96 (m, 1H), 2.58-2.48 (m, 1H), 2.25-1.92 (m, 6H), 1.89-1.71 (m, 1H), 1.01 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[3-Fluoro-4-(6-fluoro-1H-indol-5-yl)-phenyl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A120”)

(298) ##STR00130##

(299) LC/MS: 436 (M+H); .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 11.29 (s, 1H), 8.12-7.85 (m, 2H), 7.72-7.56 (m, 2H), 7.50 (dd, J=10.6, 1.7 Hz, 1H), 7.46-7.38 (m, 2H), 7.32 (d, J=11.0 Hz, 1H), 6.55-6.47 (m, 1H), 4.97 (p, J=7.7 Hz, 1H), 4.30-4.06 (m, 1H), 2.61-2.51 (m, 1H), 2.25-2.13 (m, 2H), 2.12-1.91 (m, 4H), 1.87-1.69 (m, 1H), 0.99 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[6-(1H-Indol-6-yl)-pyridin-3-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A121”)

(300) ##STR00131##

(301) LC/MS: 401 (M+H); .sup.1H NMR (400 MHz, T=363K, DMSO-d.sub.6) δ 11.07 (s, 1H), 8.75 (d, J=2.3 Hz, 1H), 8.26 (s, 1H), 8.08 (d, J=8.3 Hz, 1H), 7.96 (dd, J=8.3, 2.4 Hz, 1H), 7.93 (s, 1H), 7.83 (dd, J=8.4, 1.6 Hz, 1H), 7.74-7.58 (m, 2H), 7.43 (t, J=2.8 Hz, 1H), 6.64-6.37 (m, 1H), 5.10-4.82 (m, 1H), 4.37-4.08 (m, 1H), 2.64-2.51 (m, 1H), 2.37-1.91 (m, 6H), 1.91-1.72 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[6-(1-Methyl-1H-indol-6-yl)-pyridin-3-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A122”)

(302) ##STR00132##

(303) LC/MS: 415 (M+H); .sup.1H NMR (400 MHz, 363K, DMSO-d.sub.6) δ 8.76 (d, J=2.4 Hz, 1H), 8.26 (s, 1H), 8.17 (d, J=8.3 Hz, 1H), 7.98 (dd, J=8.3, 2.4 Hz, 1H), 7.94 (s, 1H), 7.88 (dd, J=8.4, 1.6 Hz, 1H), 7.76-7.57 (m, 2H), 7.41 (d, J=3.1 Hz, 1H), 6.53-6.44 (m, 1H), 5.07-4.85 (m, 1H), 4.33-4.11 (m, 1H), 3.91 (s, 3H), 2.63-2.52 (m, 1H), 2.36-1.92 (m, 6H), 1.92-1.72 (m, 1H), 1.03 (t, J=7.6 Hz, 3H);

N-((1S,3R)-3-{5-[6-(1H-Indazol-4-yl)-pyridin-3-yl]-[1,2,3]triazol-1-yl}-cyclopentyl)-propionamide (“A123”)

(304) ##STR00133##

(305) LC/MS: 402 (M+H); .sup.1H NMR (400 MHz, T=363K, DMSO-d.sub.6) δ 13.03 (s, 1H), 8.89 (dd, J=2.4, 0.9 Hz, 1H), 8.67 (s, 1H), 8.21 (dd, J=8.3, 0.9 Hz, 1H), 8.07 (dd, J=8.3, 2.4 Hz, 1H), 7.98 (s, 1H), 7.80 (d, J=7.1 Hz, 1H), 7.75-7.58 (m, 2H), 7.51 (dd, J=8.4, 7.2 Hz, 1H), 5.09-4.89 (m, 1H), 4.37-4.10 (m, 1H), 2.65-2.54 (m, 1H), 2.37-1.92 (m, 6H), 1.92-1.74 (m, 1H), 1.03 (t, J=7.6 Hz, 3H).

(306) Pharmacological Data

(307) TABLE-US-00001 TABLE 1 Inhibition of FASN of some representative compounds of the formula I Compound IC.sub.50 FASN Compound IC.sub.50 FASN No. (enzyme assay) No. (enzyme assay) “A1” A “A21” A “A2” A “A22” A “A3” A “A4” A “A24” A “A5” Inhibition: −44% “A25” A at 3 μM “A6” A “A26” A “A7” A “A27” A “A8” B “A28” A “A9” A “A29” A “A10” A “A30” A “A11” A “A31” A “A12” B “A32” A “A13” A “A33” A “A14” A “A15” A “A35” A “A16” A “A36” “A37” A “A38” “A19” A “A39” A “A20” A “A40” A “A41” “A42” A “A43” A “A44” A “A58” A “A59” A “A60” A “A61” A “A71” A “A62” A “A72” A “A63” A “A73” A “A64” A “A74” A “A65” A “A75” A “A66” A “A76” A “A67” B “A77” A “A68” B “A78” A “A69” A “A79” A “A70” A “A80” A “A81” A “A91” A “A82” A “A92” A “A83” A “A93” B “A84” A “A94” A “A85” A “A95” A “A86” A “A96” A “A87” A “A97” A “A88” A “A98” A “A89” A “A99” B “A90” A “A100” B “A111” A “A102” A “A112” A “A103” A “A113” A “A104” A “A114” B “A105” A “A115” A “A106” A “A116” A “A107” A “A117” A “A108” A “A118” A “A109” B “A119” A “A110” A “A120” A “A121” A “A122” B “A123” B IC.sub.50: <0.3 μM = A 0.3-3 μM = B 3-50 μM = C

(308) The compounds shown in Table 1 are particularly preferred compounds according to the invention.

(309) The following examples relate to medicaments:

Example A: Injection Vials

(310) 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

(311) 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

(312) 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.4-12H.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

(313) 500 mg of an active ingredient of the formula I are mixed with 99.5 g of Vaseline under aseptic conditions.

Example E: Tablets

(314) 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

(315) 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

(316) 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

(317) 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.