1,3-diaminocyclopentane carboxamide derivatives

Abstract

Compounds of the formula I ##STR00001##
in which R.sup.1, R.sup.4, R.sup.6, R, X.sup.1, X.sup.2, X.sup.3, X.sup.4, q and W 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. A compound of formula I ##STR00208## in which R denotes Ar, Het, CCAr or CC-Het, W denotes NR.sup.2R.sup.2, Het.sup.1, CH.sub.2Het.sup.1, A, Cyc, CH.sub.2Cyc, Ar, CH.sub.2Ar, [C(R.sup.3).sub.2].sub.mNR.sup.6COA or [C(R.sup.3).sub.2].sub.mCR.sup.3(COOA)NR.sup.6COA, R.sup.1 denotes A, [C(R.sup.3).sub.2].sub.nAr.sup.1 or [C(R.sup.3).sub.2].sub.nCyc, R.sup.2, R.sup.2 each, independently of one another, denote H, A or [C(R.sup.3).sub.2].sub.nCyc, R.sup.4 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.6 denotes H or A, X.sup.1, X.sup.2, X.sup.3, X.sup.4 each, independently of one another, denotes CH or N, A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein two adjacent carbon atoms optionally form a double bond and/or one or two non-adjacent CH- and/or CH.sub.2-groups are optionally replaced by N-, O- and/or S-atoms and wherein 1-7H-atoms are optionally 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 1-5H-atoms are optionally 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.pOA, OCH.sub.2Cyc, [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, [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, 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, 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, [C(R.sup.3).sub.2].sub.nCN, COOR.sup.3, Het.sup.1, 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, and q denotes 0, 1, 2 or 3, with the proviso that only one or two of X.sup.1, X.sup.2, X.sup.3, X.sup.4 denote N, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

2. The compound according to claim 1, in which R.sup.4 denotes H, OA, Hal or A, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

3. The compound according to claim 1, in which A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein one or two non-adjacent CH- and/or CH.sub.2-groups are optionally replaced by N- and/or O-atoms and wherein 1-7H-atoms are optionally replaced by R.sup.5, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

4. The compound according to claim 1, in which Ar denotes phenyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, CN, CON(R.sup.3).sub.2, [C(R.sup.3).sub.2].sub.pOA, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, A, Cyc and/or OCH.sub.2Cyc, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

5. The compound according to claim 1, in which Ar.sup.1 denotes phenyl or naphthyl, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

6. The compound according to claim 1, in which 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- or trisubstituted by Hal, [C(R.sup.3).sub.2].sub.nOA, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, CON(R.sup.3).sub.2, Het.sup.1, A, [C(R.sup.3).sub.2].sub.nCN and/or O, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

7. The compound according to claim 1, in which Het.sup.1 denotes a monocyclic saturated, unsaturated or 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, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

8. The compound 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, oxazolo[5,4-b]pyridyl, imidazo[1,2-a]pyrimidinyl, imidazo[1,2-a]pyridyl, oxazolo[5,4-c]pyridyl, 2,3-dihydro-indolyl, 2,3-dihydro-benzo[1,4]dioxinyl, tetrahydropyranyl, 2,3-dihydro-benzimidazolyl, pyrrolo[2,3-c]pyridyl, oxazolo[4,5-b]pyridyl, furo[3,2-b]pyridyl or pyrrolo[3,2-b]pyridyl, each of which is unsubstituted or mono-, di- or trisubstituted by Hal, [C(R.sup.3).sub.2].sub.nOA, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, CON(R.sup.3).sub.2, Het.sup.1, A, [C(R.sup.3).sub.2].sub.nCN and/or O, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

9. The compound 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, tetrahydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, each of which is unsubstituted or mono- or disubstituted by Hal, A and/or O, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

10. The compound according to claim 1, in which R denotes Ar, Het, CCAr or CC-Het, W denotes NR.sup.2R.sup.2, Het.sup.1, CH.sub.2Het.sup.1, A, Cyc, CH.sub.2Cyc, Ar, CH.sub.2Ar, [C(R.sup.3).sub.2].sub.mNR.sup.6COA or [C(R.sup.3).sub.2].sub.mCR.sup.3(COOA)NR.sup.6COA, R.sup.1 denotes A, R.sup.3 denotes H or unbranched or branched alkyl with 1-6 C-atoms, R.sup.4 denotes H, OA, Hal or A, X.sup.1, X.sup.2, X.sup.3, X.sup.4 each, independently of one another, denotes CH or N, A denotes unbranched or branched alkyl with 1-10 C-atoms, wherein one or two non-adjacent CH- and/or CH.sub.2-groups are optionally replaced by N- and/or O-atoms and wherein 1-7H-atoms are optionally replaced by R.sup.5, 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, wherein 1-5H-atoms are optionally replaced by F, R.sup.5 denotes F or Cl, R.sup.6 denotes H or A, Ar denotes phenyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, CN, CON(R.sup.3).sub.2, [C(R.sup.3).sub.2].sub.pOA, [C(R.sup.3).sub.2].sub.pCOOR.sup.3, A, Cyc and/or OCH.sub.2Cyc, 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, oxazolo[5,4-b]pyridyl, imidazo[1,2-a]pyrimidinyl, imidazo[1,2-a]pyridyl, oxazolo[5,4-c]pyridyl, 2,3-dihydro-indolyl, 2,3-dihydro-benzo[1,4]dioxinyl, tetrahydropyranyl, 2,3-dihydro-benzimidazolyl, pyrrolo[2,3-c]pyridyl, oxazolo[4,5-b]pyridyl, furo[3,2-b]pyridyl or pyrrolo[3,2-b]pyridyl, each of which is unsubstituted or mono-, di- or trisubstituted by Hal, [C(R.sup.3).sub.2].sub.nOA, [C(R.sup.3).sub.2].sub.nN(R.sup.3).sub.2, CON(R.sup.3).sub.2, Het.sup.1, A, [C(R.sup.3).sub.2].sub.nCN 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, tetrahydropyranyl, 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, m denotes 1, 2 or 3, n denotes 0, 1 or 2, p denotes 0, 1, 2, 3 or 4, and q denotes 0, 1, 2 or 3, with the proviso that only one or two of X.sup.1, X.sup.2, X.sup.3, X.sup.4 denote N, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

11. The compound according to claim 1, which is one of the following compounds TABLE-US-00002 No. Name A1 4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A2 4-benzoxazol-2-yl-N-[(1R,3S)-3-(cyclopropanecarbonyl-amino)- cyclopentyl]-N-methyl-benzamide A3 4-benzoxazol-2-yl-N-methyl-N-{(1R,3S)-3-[(1-methyl- cyclopropanecarbonyl)-amino]-cyclopentyl}-benzamide A4 N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4- pyridin-4-yl-benzamide A5 4-chloro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A6 4-benzothiazol-2-yl-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A7 4-(1H-benzimidazol-2-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A8 biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino- cyclopentyl)-amide A9 4-(5-chloro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A10 4-imidazo[1,2-a]pyrimidin-2-yl-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A11 4-(1H-imidazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A12 4-cyano-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A13 4-benzoxazol-2-yl-3-methoxy-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A14 4-(4-chloro-phenylethynyl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A15 N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4- pyridin-4-ylethynyl-benzamide A16 5-benzoxazol-2-yl-pyridine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A17 4-benzoxazol-2-yl-N-((1R,3S)-3-isobutyrylamino-cyclopentyl)- N-methyl-benzamide A18 N-((1R,3S)-3-acetylamino-cyclopentyl)-4-benzooxazol-2-yl- N-methyl-benzamide A19 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(4-methyl- pentanoylamino)-cyclopentyl]-benzamide A20 4-benzoxazol-2-yl-N-((1R,3S)-3-benzoylamino-cyclopentyl)-N- methyl-benzamide A21 4-benzoxazol-2-yl-N-[(1R,3S)-3-(cyclopentanecarbonyl-amino)- cyclopentyl]-N-methyl-benzamide A22 N-{(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]- cyclopentyl}-isonicotinamide A23 4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-phenylacetylamino- cyclopentyl)-benzamide A24 4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-pentanoylamino- cyclopentyl)-benzamide A25 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(2,2,3,3,3- pentafluoro-propionylamino)-cyclopentyl]-benzamide A26 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(3-methyl- pentanoylamino)-cyclopentyl]-benzamide A27 4-benzoxazol-2-yl-N-[(1R,3S)-3-(2,2-difluoro-butyrylamino)- cyclopentyl]-N-methyl-benzamide A28 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(2-pyridin-4-yl- acetylamino)-cyclopentyl]-benzamide A29 N-((1R,3S)-3-ethylcarbamoyl-cyclopentyl)-4-(1H-indazol-4- yl)-N-methyl-benzamide A30 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-((S)-3-methyl- pentanoylamino)-cyclopentyl]-benzamide A31 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-((R)-3-methyl- pentanoylamino)-cyclopentyl]-benzamide A32 4-benzoxazol-2-yl-N-[(1R,3S)-3-((R)-2-methoxy- propionylamino)-cyclopentyl]-N-methyl-benzamide A33 4-benzoxazol-2-yl-N-[(1R,3S)-3-((S)-2-methoxy- propionylamino)-cyclopentyl]-N-methyl-benzamide A34 4-benzoxazol-2-yl-N-[(1R,3S)-3-(2-methoxy-acetylamino)- cyclopentyl]-N-methyl-benzamide A35 4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(3-methyl- butyrylamino)-cyclopentyl]-benzamide A36 4-benzoxazol-2-yl-N-[(1R,3S)-3-(2-dimethylamino- acetylamino)-cyclopentyl]-N-methyl-benzamide A37 4-benzoxazol-2-yl-N-[(1R,3S)-3-((S)-2-hydroxy- propionylamino)-cyclopentyl]-N-methyl-benzamide A38 N-[(1R,3S)-3-(3-acetylamino-propionylamino)-cyclopentyl]-4- benzoxazol-2-yl-N-methyl-benzamide A39 (S)-2-acetylamino-N-{(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)- methyl-amino]-cyclopentyl}-succinamic acid methyl ester A40 (R)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3- [(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}- amide A41 (S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4- benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-amide A42 N-[(1R,3S)-3-((R)-2-acetylamino-3-methyl-butyrylamino)- cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide A43 N-[(1R,3S)-3-((S)-2-acetylamino-3-methyl-butyrylamino)- cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide A44 4-benzoxazol-2-yl-N-[(1R,3S)-3-(2-cyclopentyl-acetylamino)- cyclopentyl]-N-methyl-benzamide A45 4-benzoxazol-2-yl-N-methyl-N-{(1R,3S)-3-[2-((S)-5-oxo- pyrrolidin-2-yl)-acetylamino]-cyclopentyl}-benzamide A46 4-(1H-indazol-6-yl)-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A47 N-[(1R,3S)-3-((S)-2-acetylamino-propionylamino)- cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide A48 N-[(1R,3S)-3-((R)-2-acetylamino-propionylamino)- cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide A49 4-(7-fluoro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A50 N-[(1R,3S)-3-(cyclopropanecarbonyl-amino)-cyclopentyl]-4- (7-fluoro-benzoxazol-2-yl)-N-methyl-benzamide A51 4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]- biphenyl-4-carboxylic acid A52 3-methyl-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)- carbamoyl]-biphenyl-4-carboxylic acid A53 4-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A54 2-fluoro-4-(4-methyl-cyclohexyl)-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A55 tert-butyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A56 3,4-dimethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A57 biphenyl-4,4-dicarboxylic acid 4-amide 4-[methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide] A58 4-benzo[1,3]dioxol-5-yl-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A59 4-benzothiazol-6-yl-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A60 N-methyl-4-(2-oxo-2,3-dihydro-1H-indol-6-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A61 4-cyano-3,5-difluoro-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A62 4-trifluoromethoxy-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A63 3-chloro-4-fluoro-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A64 4-trifluoromethyl-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A65 4-methoxy-2-methyl-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A66 3-fluoro-4-methyl-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A67 4-(1H-indol-6-yl)-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A68 4-pyrazol-1-yl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A69 3-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)- carbamoyl]-biphenyl-4-carboxylic acid methyl ester A70 4-cyclopropylmethoxy-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A71 4-cyano-3-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)- 3-propionylamino-cyclopentyl)-amide A72 N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4- quinolin-3-yl-benzamide A73 4-methyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A74 N-methyl-4-(1-methyl-1H-indazol-6-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A75 N-methyl-4-(1-methyl-1H-indazol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A76 4-(1H-benzimidazol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A77 cyano-2-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A78 biphenyl-4,4-dicarboxylic acid 4-methylamide 4-[methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide] A79 fluoro-4-trifluoromethoxy-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A80 N-methyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A81 4-(2H-pyrazol-3-yl)-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A82 4-methoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A83 2,4-difluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A84 4-(1H-indazol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A85 4-difluoromethoxy-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A86 4-chloro-3-fluoro-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A87 4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A88 2,4-dimethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A89 4-(5-propyl-tetrahydro-pyran-2-yl)-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A90 2,4-dimethyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A91 4-(1H-benzotriazol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A92 4-chloro-2-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)- 3-propionylamino-cyclopentyl)-amide A93 N-methyl-4-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-N- ((1R,3S)-3-propionylamino-cyclopentyl)-benzamide A94 N-methyl-4-(2-oxo-2,3-dihydro-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A95 4-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A96 4-isopropyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A97 2-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)- carbamoyl]-biphenyl-4-carboxylic acid methyl ester A98 3-fluoro-4-trifluoromethoxy-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A99 2-fluoro-4-methoxy-biphenyl-4-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A99a 4-(3-cyano-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A100 N-methyl-4-(3-methyl-1H-indazol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A101 4-(1H-indol-5-yl)-3,N-dimethyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A102 N-methyl-4-(6-methyl-1H-indazol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A103 5-(6-methyl-1H-indazol-5-yl)-pyridine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A104 5-(7-methyl-1H-indazol-5-yl)-pyridine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A105 5-(3-methyl-1H-indazol-5-yl)-pyridine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A106 2-fluoro-4-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A107 N-methyl-4-(7-methyl-1H-indazol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A108 3-fluoro-N-methyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A109 5-(1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A110 5-(1-methyl-1H-indol-5-yl)-pyridine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A111 2-fluoro-N-methyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A112 3-fluoro-4-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A113 6-(1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A114 3,N-dimethyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A115 N-methyl-4-(3-methyl-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A116 4-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A117 6-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-nicotinamide A118 6-(1-methyl-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A119 2,N-dimethyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A120 4-(1H-indol-5-yl)-2,N-dimethyl-N-((1R,3S)-3-propionylamino- cyclopentyl)-benzamide A121 4-(7-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A122 4-(6-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A123 N-methyl-4-(1-methyl-1H-benzimidazol-2-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A124 3,N-dimethyl-4-(4-methyl-1H-indazol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A125 5-(1-methyl-1H-indol-5-yl)-pyrazine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A126 N-methyl-4-(4-methyl-1H-indazol-5-yl)-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A127 4-(6-fluoro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A128 4-(6-chloro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A129 N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-(1H- pyrrolo[3,2-b]pyridin-5-yl)-benzamide A130 4-(3-aminomethyl-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A131 5-(1H-indol-5-yl)-pyrimidine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A132 5-(1H-indol-5-yl)-pyrazine-2-carboxylic acid methyl-((1R,3S)-3- propionylamino-cyclopentyl)-amide A133 5-(1-methyl-1H-indol-5-yl)-pyrimidine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A134 6-(7-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A135 6-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A136 6-(7-fluoro-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A137 6-(4-fluoro-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A138 (S)-tetrahydro-furan-2-carboxylic acid ((1S,3R)-3-{[4-(6-chloro- benzooxazol-2-yl)-benzoyl]-methyl-amino}-cyclopentyl)-amide A139 2-(1H-indol-5-yl)-pyrimidine-5-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A140 5-fluoro-6-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A141 6-(7-fluoro-1H-indol-5-yl)-4,N-dimethyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A142 5-fluoro-6-(7-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A143 5-fluoro-6-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A144 6-imidazo[1,2-a]pyridin-6-yl-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A145 6-(7-fluoro-2,3-dihydro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A146 6-(4-fluoro-1H-indol-5-yl)-4,N-dimethyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A147 6-(3,3-difluoro-2-oxo-2,3-dihydro-1H-indol-5-yl)-N-methyl-N- ((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide A148 5-(6-chloro-benzoxazol-2-yl)-pyrazine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A149 5-(6-chloro-benzoxazol-2-yl)-pyrimidine-2-carboxylic acid methyl-{(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)- amino]-cyclopentyl}-amide A150 6-(4-methyl-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A151 3-fluoro-4-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-benzamide A152 4-(3-aminomethyl-1-methyl-1H-indol-5-yl)-N-methyl-N- ((1R,3S)-3-propionylamino-cyclopentyl)-benzamide A153 6-(6-chloro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A154 6-(6-chloro-benzoxazol-2-yl)-N-methyl-N-{(1R,3S)-3-[((S)- tetrahydro-furan-2-carbonyl)-amino]-cyclopentyl}-nicotinamide A155 6-(6-chloro-benzoxazol-2-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A156 5-(6-chloro-benzoxazol-2-yl)-pyrimidine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A157 6-(7-fluoro-1H-indol-6-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A158 6-(6-chloro-1,3-benzoxazol-2-yl)-N-methyl-N-[(1R,3S)-3- [[(2S)-tetrahydrofuran-2- carbonyl]amino]cyclopentyl]pyridazine-3-carboxamide A159 5-(6-chloro-benzoxazol-2-yl)-pyrazine-2-carboxylic acid methyl- {(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)-amino]- cyclopentyl}-amide A160 5-{2-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)- carbamoyl]-phenyl}-1H-indole-3-carboxylic acid amide A161 3-fluoro-5-(7-fluoro-1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A162 3-fluoro-5-(4-fluoro-1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide A163 3-fluoro-5-(1H-indol-5-yl)-pyridine-2-carboxylic acid methyl- ((1R,3S)-3-propionylamino-cyclopentyl)-amide A165 4-benzoxazol-2-yl-N-methyl-N-((1R,3R)-3-propionylamino- cyclopentyl)-benzamide A166 N-((1R,3R)-3-acetylamino-cyclopentyl)-4-benzooxazol-2-yl- N-methyl-benzamide A167 4-benzoxazol-2-yl-N-methyl-N-((1R,3R)-3-phenylacetylamino- cyclopentyl)-benzamide A168 4-benzoxazol-2-yl-N-methyl-N-[(1R,3R)-3-((R)-3-methyl- pentanoylamino)-cyclopentyl]-benzamide A169 6-(3-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3- propionylamino-cyclopentyl)-nicotinamide A171 7-fluoro-5-{4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)- carbamoyl]-phenyl}-1H-indole-3-carboxylic acid amide A172 7-fluoro-5-{2-fluoro-4-[methyl-((1R,3S)-3-propionylamino- cyclopentyl)-carbamoyl]-phenyl}-1H-indole-3-carboxylic acid amide A174 (S)-tetrahydro-furan-2-carboxylic acid ((1S,3R)-3-{[4-(5-chloro- benzoxazol-2-yl)-benzoyl]-methyl-amino}-cyclopentyl)-amide A175 (S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4- benzoxazol-2-yl-2-fluoro-benzoyl)-methyl-amino]- cyclopentyl}-amide A176 5-(6-chloro-benzoxazol-2-yl)-3-fluoro-pyridine-2-carboxylic acid methyl-{(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)- amino]-cyclopentyl}-amide A177 (S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4- benzoxazol-2-yl-3-methoxy-benzoyl)-methyl-amino]- cyclopentyl}-amide A178 (S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4- benzooxazol-2-yl-3-fluoro-benzoyl)-methyl-amino]- cyclopentyl}-amide A179 N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-(1H- pyrrolo[2,3-c]pyridin-5-yl)-benzamide A180 (S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(3-fluoro-4- oxazolo[4,5-b]pyridin-2-yl-benzoyl)-methyl-amino]- cyclopentyl}-amide A181 (S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(2-fluoro-4- oxazolo[4,5-b]pyridin-2-yl-benzoyl)-methyl-amino]- cyclopentyl}-amide A182 (S)-tetrahydro-furan-2-carboxylic acid ((1S,3R)-3-{[4-(4-fluoro- benzooxazol-2-yl)-benzoyl]-methyl-amino}-cyclopentyl)-amide A183 N-methyl-4-[3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indol-5-yl]- N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide A184 4-[6-fluoro-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indol-5-yl]-N- methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide A185 (2S)N-[(1S,3R)-3-[[4-(4-cyano-1,3-benzoxazol-2- yl)benzoyl]-methyl-amino]cyclopentyl]tetrahydrofuran-2- carboxamide A186 (2S)N-[(1S,3R)-3-[[4-(1,3-benzoxazol-2-yl)benzoyl]-ethyl- amino]cyclopentyl]tetrahydrofuran-2-carboxamide A187 4-(3-cyano-6-fluoro-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)-cyclopentyl]benzamide A188 N-ethyl-4-(1H-indol-5-yl)-N-[(1R,3S)-3-(propanoylamino)- cyclopentyl]benzamide A189 4-(3-cyano-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methyl-N- [(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide A190 6-(6-fluoro-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)cyclopentyl]-pyridine-3-carboxamide A191 N-methyl-N-[(1R,3S)-3-(propanoylamino)cyclopentyl]-4-[4- (trifluoromethyl)-1H-indol-5-yl]benzamide A192 4-(5-fluoro-1-methyl-indazol-4-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)cyclopentyl]benzamide A193 4-(5-fluoro-1-methyl-indol-4-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)-cyclopentyl]benzamide A194 4-(5-fluoro-1H-indol-4-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)-cyclopentyl]benzamide A195 (2S)N-[(1S,3R)-3-[Methyl-(4-oxazolo[4,5-b]pyridin-2- ylbenzoyl)amino]cyclopentyl]tetrahydrofuran-2-carboxamide A196 (2S)N-[(1S,3R)-3-[[4-(6-chlorooxazolo[4,5-b]pyridin-2- yl)benzoyl]-methyl-amino]cyclopentyl]tetrahydrofuran-2- carboxamide A197 (2S)N-[(1S,3R)-3-[(4-furo[3,2-b]pyridin-2-ylbenzoyl)-methyl- amino]cyclopentyl]tetrahydrofuran-2-carboxamide A198 4-(4-cyano-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)-cyclopentyl]benzamide A199 4-[3-(cyanomethyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-N-methyl-N- [(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide or A200 6-(3-cyano-6-fluoro-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3- (propanoylamino)cyclopentyl]pyridine-3-carboxamide or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

12. A compound, which is 2-(1H-indol-5-yl)-thiazole-5-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A170), or 2-(1H-indol-5-yl)-4-methyl-thiazole-5-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A173), or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

13. A compound, which is 7-(1,3-benzoxazol-2-yl)-N-methyl-N-[(1R,3S)-3-[[(2S)-tetrahydrofuran-2-carbonyl]amino]cyclopentyl]-3H-benzimidazole-4-carboxamide (A201) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

14. A pharmaceutical composition comprising at least one compound of formula I according to claim 1 or the pharmaceutically acceptable salt, tautomer or stereoisomer thereof, and a pharmaceutically acceptable carrier, excipient or vehicle.

15. The pharmaceutical composition according to claim 14, further comprising at least one additional pharmaceutically active ingredient.

16. A pharmaceutical composition comprising at least one compound according to claim 12 or the pharmaceutically acceptable salt, tautomer or stereoisomer thereof, and a pharmaceutically acceptable carrier, excipient or vehicle.

17. A kit comprising separate packs of (a) an effective amount of the compound of formula I according to claim 1 or the pharmaceutically acceptable salt, tautomer or stereoisomer thereof, and (b) an effective amount of an additional pharmaceutically active ingredient.

18. A process for preparing the compound of formula I according to claim 1 or the pharmaceutically acceptable salt, tautomer or stereoisomer thereof, comprising reacting a compound of formula II ##STR00209## in which R.sup.1, R.sup.6 and W have the meanings indicated for formula I, with a compound of formula III ##STR00210## in which R, R.sup.4, X.sup.1, X.sup.2, X.sup.3, X.sup.4 and q have the meanings indicated for formula I, and L denotes Cl, Br, I or a free or reactively functionally modified OH group, and/or converting a base or acid of the compound of formula I into one of its salts.

Description

Example 1

4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A1)

(1) ##STR00007##

(2) a) (1S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-cyclopentanecarboxylic acid (Roberto J. Brea Angew. Chem. Int. Ed. 2005, 44, 5710-5713) (200 mg; 0.82 mmol), diphenylphosphorylazide (DPPA) (233.2 mg; 0.82) and triethylamine (83.2 mg; 0.82 mmol) in 5 ml toluene were stirred at 80 C. for 1 h. Benzyl alcohol (BzIOH) (84.7 l; 0.82 mmol) was added to the mixture, which was stirred at 110 C. for 14 h. The mixture was evaporated, and the residue was dissolved in 10 ml ethyl acetate. The solution was successively washed with 10 ml water and 10 ml brine, dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue is purified by flash chromatography (n-heptane:ethyl acetate 95:5) to yield 174 mg (50.4%) [(1S,3R)-3-(tert-butoxycarbonyl-methyl-amino)-cyclopentyl]-carbamic acid benzyl ester(A) as a pale brown resin. LC/MS: 249 (M+H-BOC).

(3) b) A mixture of [(1S,3R)-3-(tert-butoxycarbonyl-methyl-amino)-cyclopentyl]-carbamic acid benzyl ester (1) (174 mg; 0.5 mmol) and 5 percent Pd/C (100 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)-methyl-carbamic acid tert-butyl ester (B) (108 mg; 100%) as a pale brown resin. LC/MS: 215 (M+H).

(4) c) To the cooled (0 C.) solution of ((1R,3S)-3-amino-cyclopentyl)-methyl-carbamic acid tert-butyl ester (2) (36 mg; 0.17 mmol) and triethylamine (70 l; 0.50 mmol) in dichloromethane (5 ml) is added dropwise propionyl chloride (15.5 mg; 0.17 mmol) dissolved in dichloromethane (5 ml). The mixture was stirred for 14 h at room temperature, washed with 5% NaHCO.sub.3 solution (10 ml) and water (10 ml), dried over Na.sub.2SO.sub.4, filtered, and evaporated to dryness. The residue is purified by flash chromatography to yield methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamic acid tert-butyl ester (C) (31 mg 68.3%) as a brown oil; LC/MS: 271 (M+H).

(5) d) To methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamic acid tert-butyl ester (3) (31 mg; 0,115 mmol) in 15 ml of dichloromethane was added trifluoroacetic acid (1 ml; 13 mmol). The solution was stirred 14 h at room temperature and then reduced to dryness under vacuo to afford 33 mg (100%) N-((1S,3R)-3-methylamino-cyclopentyl)-propionamide trifluoroacetate (D) as a colorless resin; LC/MS: 171 (M+H).)

(6) e) 4-Benzoxazol-2-yl-benzoic acid (E) (Dinesh Kumar Aust. J. Chem. 2008 (61) 881-887) (27.8 mg; 0,116 mmol), N-((1S,3R)-3-methylamino-cyclopentyl)-propionamide trifluoroacetate (4) 33 mg; 0,116 mmol.), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride for synthesis (33.4 mg; 0,174 mmol), and 1-hydroxybenzotriazole (17.8 mg; 0,116 mmol) were dissolved in 3 ml of N,N-dimethylformamide and then was added 4-methyl-morpholine for synthesis (51 l; 0.46 mmol). The reaction mixture was stirred 14 h at room temperature. The reaction solution was diluted with 10 ml of water and extracted 3 with 10 ml of ethylacetate. The combined organic layer were washed 3 with water and 1 with brine, dried over Na.sub.2SO.sub.4, filtered, evaporated to dryness and the residue was purified by flash chromatography (dichloromethane:methanol 95:5) to yield 22 mg (48.4%) 4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A1) as a white foam; LC/MS: 392 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.83 (m, 2H+NH), 7.59 (s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.84 (2br.s, 1H, ratio=1:2.6 mixture of rotamers), 4.01 (br. s, 1H), 2.90 (br. s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.87-1.66 (m, 3H), 1.66-1.38 (m, 2H), 0.98 (t, J=7.6 Hz, 3H).

(7) Analogously to the method described above in example 1 c)-e) are synthesized the following compounds:

4-benzoxazol-2-yl-N-[(1R,3S)-3-(cyclopropanecarbonyl-amino)-cyclopentyl]-N-methyl-benzamide (A2)

(8) ##STR00008##

(9) LC/MS: M+H=404; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 8.11 (d, J=6.8 Hz, 1H, NH), 7.83 (dd, J=14.8, 7.2 Hz, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.87 (2br.s, 1H, ratio=1:2.1 mixture of rotamers), 4.00 (br. s, 1H), 2.91 (br. s, 3H), 2.06 (br. s, 1H), 1.95-1.39 (m, 6H), 0.74-0.51 (m, 4H);

4-benzoxazol-2-yl-N-methyl-N-{(1R,3S)-3-[(1-methyl-cyclopropanecarbonyl)-amino]-cyclopentyl}-benzamide (A3)

(10) ##STR00009##

(11) LC/MS: M+H=418; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.83 (dd, J=14.6, 7.2 Hz, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 7.36 (s, 1H, NH), 4.76, 3.91 (2br.s, 1H, ratio=1:1.4 mixture of rotamers), 3.98 (br. s, 1H), 2.92 (br. s, 3H), 1.83 (br. s, 1H), 1.97 (br. s, 1), 1.91-1.46 (m, 5H), 1.25 (s, 3H), 0.92 (s, 2H), 0.48 (s, 2H).

(12) Treatment of the amine (D) (example 1 d) with a carboxylic acid analogously to the method described above in example (1e) leads to the following compounds:

N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-pyridin-4-yl-benzamide (A4)

(13) ##STR00010##

(14) LC/MS: M+H=352; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.66 (d, J=6.1 Hz, 2H), 7.87 (d, J=8.2 Hz, 2H), 7.80 (d, J=7.0 Hz, 1H; NH), 7.75 (d, J=6.1 Hz, 2H), 7.50 (d, J=6.3 Hz, 2H), 4.80, 3.80 (2br.s, 1H, ratio=1:2,6 mixture of rotamers), 4.13, 4.02 (2br.s, 1H, ratio=1:2,6 mixture of rotamers), 2.88 (br. s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.88-1.63 (m, 3H), 1.64-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-chloro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A5)

(15) ##STR00011##

(16) LC/MS: M+H=385; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.82 (d, J=7.2 Hz, 1H; NH), 7.74 (dd, J=8.5, 3.6 Hz, 4H), 7.54 (d, J=8.6 Hz, 2H), 7.45 (d, J=7.3 Hz, 2H), 4.78, 3.88 (2br.s, 1H, ratio=1:1,3 mixture of rotamers), 4.08 (br. s, 1H), 2.88 (br. s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.91-1.63 (m, 3H), 1.66-1.36 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-benzothiazol-2-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A6)

(17) ##STR00012##

(18) LC/MS: M+H=408; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.22-8.12 (m, 3H), 8.09 (d, J=8.0 Hz, 1H), 7.81 (d, J=6.7 Hz, 1H; NH), 7.64-7.51 (m, 3H), 7.49 (t, J=8.1 Hz, 1H), 4.80, 3.86 (2br.s, 1H, ratio=1:3 mixture of rotamers) 4.02 (br. s, 1H), 2.89 (s, 3H), 2.05 (q, J=7.5 Hz, 3H), 1.92-1.63 (m, 3H), 1.65-1.37 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(1H-benzimidazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A7)

(19) ##STR00013##

(20) LC/MS: M+H=391; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 12.97 (s, 1H; NH), 8.22 (d, J=8.3 Hz, 2H), 7.81 (d, J=6.9 Hz, 1H), 7.68 (d, J=7.7 Hz, 1H), 7.60-7.45 (m, 3H), 7.29-7.16 (m, 2H), 4.80, 3.87 (2br.s, 1H, ratio=1:2.5, mixture of rotamers), 4.14, 4.02 (2br.s, 1H, ratio=1:2.5, mixture of rotamers) 2.89 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.91-1.65 (m, 3H), 1.65-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A8)

(21) ##STR00014##

(22) LC/MS: M+H=351; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.82 (d, J=7.1 Hz, 1H; NH), 7.72 (t, J=8.0 Hz, 4H), 7.56-7.34 (m, 5H), 4.83, 4.10 (2br.s, 1H, ratio=1:1,5 mixture of rotamers), 3.88 (br. s, 1H), 2.88 (br. s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.90-1.66 (m, 3H), 1.65-1.46 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(5-chloro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A9)

(23) ##STR00015##

(24) LC/MS: M+H=426; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.25 (d, J=8.3 Hz, 2H), 7.95 (d, J=2.1 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.80 (d, J=6.6 Hz, 1H; NH), 7.59 (s, 2H), 7.50 (dd, J=8.7, 2.1 Hz, 1H), 4.82, 3.83 (2br.s, 1H, ratio=1:2.7 mixture of rotamers), 3.99 (br. s, 1H) 2.90 (s, 3H), 2.04 (q, J=7.8 Hz, 3H), 1.92-1.64 (m, 3H), 1.67-1.41 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-imidazo[1,2-a]pyrimidin-2-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A10)

(25) ##STR00016##

(26) LC/MS: M+H=392; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.98 (d, J=5.4 Hz, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 8.06 (d, J=7.3 Hz, 2H), 7.83 (s, 1H), 7.45 (d, J=4.9 Hz, 2H), 7.07 (s, 1H), 4.76, 3.90 (2br.s, 1H, ratio=1:3 mixture of rotamers), 4.15 (br. s, 1H), 2.89 (s, 3H), 2.21-1.92 (m, 3H), 1.95-1.65 (m, 3H), 1.66-1.40 (m, 2H), 0.98 (t, J=7.0 Hz, 3H);

4-(1H-imidazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A11)

(27) ##STR00017##

(28) LC/MS: M+H=341; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 12.61 (s, 1H; NH), 7.97 (d, J=8.4 Hz, 2H), 7.81 (d, J=7.1 Hz, 1H; NH), 7.42 (d, J=7.5 Hz, 2H), 7.16 (s, 2H), 4.77, 3.86 (2br.s, 1H, ratio=1:1.8 mixture of rotamers), 4.04 (br. s, 1H), 2.87 (s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.93-1.62 (m, 3H), 1.66-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-cyano-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A12)

(29) ##STR00018##

(30) LC/MS: M+H=376; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.97-7.90 (m, 4H), 7.83-7.78 (m, 3H), 7.48 (d, J=6.6 Hz, 2H), 4.80, 3.87 (2br.s, 1H, ratio=1:3 mixture of rotamers), 4.14, 4.07 (2br.s, 1H, ratio=1:3 mixture of rotamers) 2.88 (s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.90-1.64 (m, 3H), 1.66-1.46 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-benzoxazol-2-yl-3-methoxy-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A13)

(31) ##STR00019##

(32) LC/MS: M+H=422; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.08 (d, J=7.9 Hz, 1H), 7.91-7.69 (m, 3H), 7.52-7.32 (m, 2H), 7.20 (s, 1H), 7.10 (s, 1H), 4.83, 3.86 (2br.s, 1H, ratio=1:2.8 mixture of rotamers) 4.03 (br. s, 1H), 3.97 (s, 3H), 2.90 (s, 3H), 2.18-1.96 (m, 3H), 1.93-1.65 (m, 3H), 1.68-1.39 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(4-chloro-phenylethynyl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A14)

(33) ##STR00020##

(34) LC/MS: M+H=409. .sup.1H NMR (500 MHz, DMSO-d6) 7.80 (d, J=7.0 Hz, 1H; NH), 7.60 (t, J=8.3 Hz, 4H), 7.51 (d, J=8.5 Hz, 2H), 7.47-7.33 (m, 2H), 4.77, 3.84 (2br. s, 1H, ratio=1:2.4, mixture of rotamers), 4.12, 3.94 (2br. s, 1H, ratio=1:2.4 mixture of rotamers), 2.86 (s, 3H), 2.04 (q, J=7.6 Hz, 2H), 1.99 (br. s, 1H), 1.85-1.62 (m, 3H), 1.60-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-pyridin-4-ylethynyl-benzamide (A15)

(35) ##STR00021##

(36) LC/MS: M+H=376; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.64 (d, J=6.0 Hz, 2H), 7.80 (d, J=6.9 Hz, 1H; NH), 7.66 (d, J=8.2 Hz, 2H), 7.54 (d, J=6.0 Hz, 2H), 7.43 (s, 2H), 4.77, 3.85 (2br.s, 1H, ratio=1:2.4, mixture of rotamers), 3.95 (br. s, 1H), 2.86 (s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.90-1.62 (m, 3H), 1.64-1.39 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

5-benzoxazol-2-yl-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A16)

(37) ##STR00022##

(38) LC/MS: M+H=393; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 9.35 (s, 1H), 8.65-8.60 (m, 1H), 7.89-7.70 (m, 4H), 7.54-7.42 (m, 2H), 4.87, 3.82 (2br.s, 1H, ratio=1:1.6, mixture of rotamers), 4.06, 4.00 (2q, J=8.4 Hz, 1H, ratio=1:1.6, mixture of rotamers), 2.94, 2.85 (2s, ratio=1:1.6, mixture of rotamers 3H), 2.17-1.99 (m, 3H), 1.95-1.77 (m, 3H), 1.63-1.42 (m, 2H), 1.03-0.94 (m, 3H).

Example 17

4-benzoxazol-2-yl-N-((1R,3S)-3-isobutyrylamino-cyclopentyl)-N-methyl-benzamide (A17)

(39) ##STR00023##

(40) a) Treatment of the compound (A) (example 1a) with trifluoroacetic acid as described above in example (1d) leads to ((1S,3R)-3-methylamino-cyclopentyl)-carbamic acid benzyl ester trifluoroacetate; LC/MS: 249 (M+H).

(41) b) Treatment of the amine ((1S,3R)-3-methylamino-cyclopentyl)-carbamic acid benzyl ester trifluoroacetate with 4-benzoxazol-2-yl-benzoic acid (E) as described above in example (1e) leads to {(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-carbamic acid benzyl ester; LC/MS: 470 (M+H).

(42) c) Hydrogenation of {(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-carbamic acid benzyl ester with 5 percent Pd/C/H.sub.2 as described above in example (1 b) leads to N-((1R,3S)-3-amino-cyclopentyl)-4-benzoxazol-2-yl-N-methyl-benzamide; LC/MS: 336 (M+H).

(43) d) Treatment of the amine N-((1R,3S)-3-amino-cyclopentyl)-4-benzoxazol-2-yl-N-methyl-benzamide with isobutyryl chloride as described above in example (1c) leads to 4-benzoxazol-2-yl-N-((1R,3S)-3-isobutyrylamino-cyclopentyl)-N-methyl-benzamide (A17); LC/MS: 406 (M+H); .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.90-7.79 (m, 2H), 7.76 (d, J=6.4 Hz, 1H; NH), 7.59 (br. s, 2H), 7.51-7.37 (m, 2H), 4.83, 3.83 (2br.s, 1H, ratio=1:2.0 mixture of rotamers), 3.99 (br. s, 1H), 2.90 (br. s, 3H), 2.32 (p, J=6.8 Hz, 1H), 2.04 (br. s, 1H), 1.88-1.43 (m, 5H), 0.98 (d, J=6.8 Hz, 6H).

(44) Analogously to the method described above in example 17 (d) are synthesized the following compounds:

N-((1R,3S)-3-acetylamino-cyclopentyl)-4-benzooxazol-2-yl-N-methyl-benzamide (A18)

(45) ##STR00024##

(46) LC/MS: M+H=378; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.90 (d, J=6.6 Hz, 1H; NH), 7.83 (ddd, J=13.0, 7.3, 1.8 Hz, 2H), 7.58 (br. s, 2H), 7.44 (qd, J=7.5, 1.4 Hz, 2H), 4.82, 3.82 (2br.s, 1H, ratio=1:2.9 mixture of rotamers), 3.99 (br. s, 1H), 2.90 (s, 2H), 2.04 (br. s, 1H), 1.87-1.64 (m, 6H). 1.64-1.42 (m, 2H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(4-methyl-pentanoylamino)-cyclopentyl]-benzamide (A19)

(47) ##STR00025##

(48) LC/MS: M+H=434; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.89-7.78 (m, 3H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.85 (2br.s, 1H, ratio=1:2.7 mixture of rotamers), 4.01 (br. s, 1H), 2.89 (br. s, 3H), 2.10-1.98 (m, 3H), 1.89-1.63 (m, 3H), 1.63-1.53 (m, 1H), 1.49 (td, J=13.3, 12.2, 5.5 Hz, 2H), 1.38 (q, J=7.1 Hz, 2H), 0.85 (d, J=6.6 Hz, 6H);

4-benzoxazol-2-yl-N-((1R,3S)-3-benzoylamino-cyclopentyl)-N-methyl-benzamide (A20)

(49) ##STR00026##

(50) LC/MS: M+H=440; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.41 (s, 1H; NH), 8.27 (d, J=8.2 Hz, 2H), 7.83 (q, J=7.2 Hz, 4H), 7.61 (s, 2H), 7.52 (t, J=7.3 Hz, 1H), 7.45 (dtd, J=9.8, 7.5, 6.7, 5.1 Hz, 4H), 4.85, 4.06 (2br.s, 1H, ratio=1:2.3 mixture of rotamers), 4.28 (br. s, 1H), 2.94 (s, 3H), 2.12 (br. s, 1H), 1.95-1.62 (m, 5H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-(cyclopentanecarbonyl-amino)-cyclopentyl]-N-methyl-benzamide (A21)

(51) ##STR00027##

(52) LC/MS: M+H=432; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.83 (dd, J=14.6, 7.3 Hz, 2H), 7.79 (s, 1H; NH), 7.59 (s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.84 (2br.s, 1H, ratio=1:2 mixture of rotamers), 3.99 (br. s, 1H), 2.90 (s, 3H), 2.54-2.46 (m, 1H) 2.05 (br. s, 1H), 1.93-1.37 (m, 13H);

N-{(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-isonicotinamide (A22)

(53) ##STR00028##

(54) LC/MS: M+H=441; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.72 (d, J=6.0 Hz, 2H), 8.68 (br. s, 1H; NH), 8.27 (d, J=8.2 Hz, 2H), 7.83 (dd, J=14.5, 7.2 Hz, 2H), 7.74 (d, J=5.4 Hz, 2H), 7.61 (s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.87, 4.10 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.24 (br. s, 1H), 2.94 (s, 3H), 2.14 (br. s, 1H), 2.03-1.58 (m, 5H);

4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-phenylacetylamino-cyclopentyl)-benzamide (A23)

(55) ##STR00029##

(56) LC/MS: M+H=454; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.25 (d, J=8.3 Hz, 2H), 8.14 (d, J=7.1 Hz, 1H; NH), 7.83 (dd, J=14.7, 7.3 Hz, 2H), 7.58 (br. s, 2H), 7.49-7.40 (m, 2H), 7.32-7.17 (m, 5H), 4.82, 3.84 (2br.s, 1H, ratio=1:2.5 mixture of rotamers), 4.01 (br. s, 1H), 3.38 (s, 2H), 2.88 (s, 3H), 2.06 (br. s, 1H), 1.92-1.42 (m, 5H);

4-benzoxazol-2-yl-N-methyl-N-((1R,3S)-3-pentanoylamino-cyclopentyl)-benzamide (A24)

(57) ##STR00030##

(58) LC/MS: M+H=420; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.87-7.78 (m, 3H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.84 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.01 (br. s, 1H), 2.89 (s, 3H), 2.03 (t, J=7.4 Hz, 3H), 1.88-1.64 (m, 3H), 1.65-1.40 (m, 4H), 1.25 (h, J=7.4 Hz, 2H), 0.86 (t, J=7.4 Hz, 3H).

(59) Treatment of the amine N-((1R,3S)-3-amino-cyclopentyl)-4-benzooxazol-2-yl-N-methyl-benzamide (example 17c) with a carboxylic acid analogously to the method described above in example (1e) leads to the following compounds:

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(2,2,3,3,3-pentafluoro-propionylamino)-cyclopentyl]-benzamide (A25)

(60) ##STR00031##

(61) LC/MS: M+H=482; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 9.53 (s, 1H; NH), 8.26 (d, J=8.3 Hz, 2H), 7.83 (ddd, J=12.7, 7.2, 1.7 Hz, 2H), 7.60 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 4.03 (2br.s, 1H, ratio=1:1.8 mixture of rotamers), 4.22, 4.06 (2br.s, 1H, ratio=1:1.8 mixture of rotamers), 2.91 (s, 3H), 2.11 (br. s, 1H), 1.99-1.58 (m, 5H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(3-methyl-pentanoylamino)-cyclopentyl]-benzamide (A26)

(62) ##STR00032##

(63) LC/MS: M+H=434; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.89-7.77 (m, 3H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.87 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.01 (br. s, 1H), 2.90 (br. s, 3H), 2.03 (dd, J=13.4, 6.0 Hz, 2H), 1.96-1.64 (m, 5H), 1.58 (q, J=9.6 Hz, 1H), 1.50 (br. s, 1H), 1.30 (dp, J=13.2, 7.3 Hz, 1H), 1.14 (dp, J=14.6, 7.4 Hz, 1H), 0.85-0.79 (m, 6H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-(2,2-difluoro-butyrylamino)-cyclopentyl]-N-methyl-benzamide (A27)

(64) ##STR00033##

(65) LC/MS: M+H=442; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.72 (br. s, 1H; NH), 8.26 (d, J=8.3 Hz, 2H), 7.88-7.79 (m, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.97 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.17, 4.04 (2br.s, 1H, ratio=1:2 mixture of rotamers), 2.91 (br. s, 3H), 2.03 (tq, J=15.4, 7.3 Hz, 3H), 1.95-1.69 (m, 4H), 1.64 (br. s, 1H), 0.91 (t, J=7.5 Hz, 3H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(2-pyridin-4-yl-acetylamino)-cyclopentyl]-benzamide (A28)

(66) ##STR00034##

(67) LC/MS: M+H=455; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.68 (d, J=5.8 Hz, 2H), 8.35 (d, J=7.1 Hz, 1H; NH), 8.26 (d, 2H), 7.89-7.76 (m, 2H), 7.65 (d, J=5.3 Hz, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.77 (2br.s, 1H, ratio=1:2 mixture of rotamers), 3.65 (s, 2H), 2.89 (br. s, 3H), 2.09 (br. s, 1H), 1.98-1.66 (m, 3H), 1.69-1.39 (m, 2H);

N-((1R,3S)-3-ethylcarbamoyl-cyclopentyl)-4-(1H-indazol-4-yl)-N-methyl-benzamide (A29)

(68) ##STR00035##

(69) LC/MS: M+H=391; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 13.24 (s, 1H), 8.21 (s, 1H), 7.87-7.74 (m, 3H), 7.57 (d, J=8.3 Hz, 1H), 7.51 (d, J=7.4 Hz, 2H), 7.48-7.41 (m, 1H), 7.28 (d, J=6.9 Hz, 1H), 4.79, 4.15 (2br.s, 1H, ratio=1:2.2, mixture of rotamers), 3.92 (br. s, 1H), 2.91 (s, 3H), 2.12-2.06 (br. s, 1H), 2.05 (q, J=7.6 Hz, 2H), 1.91-1.69 (m, 3H), 1.66-1.56 (m, 1H), 1.56-1.45 (m, 1H), 0.98 (t, J=7.6 Hz, 3H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-((S)-3-methyl-pentanoylamino)-cyclopentyl]-benzamide (A30)

(70) ##STR00036##

(71) LC/MS: M+H=434; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.27 (d, J=8.5 Hz, 2H), 7.91-7.80 (m, 3H), 7.60 (d, J=6.6 Hz, 2H), 7.52-7.38 (m, 2H), 4.82, 3.87 (2br.s, 1H, ratio=1:2 mixture of rotamers) 4.01 (br. s, 1H), 2.90 (br. s, 3H), 2.05 (dd, J=13.3, 6.0 Hz, 2H), 1.93-1.66 (m, 5H), 1.65-1.44 (m, 2H), 1.29 (td, J=15.2, 14.3, 7.7 Hz, 1H), 1.15 (dp, J=14.6, 7.3 Hz, 1H), 0.88-0.79 (m, J=6.9 Hz, 6H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-((R)-3-methyl-pentanoylamino)-cyclopentyl]-benzamide (A31)

(72) ##STR00037##

(73) LC/MS: M+H=434; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.27 (d, J=8.5 Hz, 2H), 7.91-7.80 (m, 3H), 7.60 (d, J=6.6 Hz, 2H), 7.52-7.38 (m, 2H), 4.82, 3.87 (2br.s, 1H, ratio=1:2 mixture of rotamers) 4.01 (br. s, 1H), 2.90 (br. s, 3H), 2.05 (dd, J=13.3, 6.0 Hz, 2H), 1.93-1.66 (m, 5H), 1.65-1.44 (m, 2H), 1.29 (td, J=15.2, 14.3, 7.7 Hz, 1H), 1.15 (dp, J=14.6, 7.3 Hz, 1H), 0.88-0.79 (m, J=6.9 Hz, 6H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-((R)-2-methoxy-propionylamino)-cyclopentyl]-N-methyl-benzamide (A32)

(74) ##STR00038##

(75) LC/MS: M+H=422; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.27 (d, J=8.3 Hz, 2H), 7.89 (s, 1H; NH), 7.85 (ddd, J=12.6, 6.9, 1.5 Hz, 2H), 7.60 (br. s, 2H), 7.46 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.93 (2br.s, 1H, ratio=1:2 mixture of rotamers) 4.03 (br. s, 1H), 3.75-3.55 (m, 1H), 3.26 (s, 3H), 2.93 (br. s, 3H), 2.02 (br. s, 1H), 1.94-1.53 (m, 5H), 1.21 (d, J=6.7 Hz, 3H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-((S)-2-methoxy-propionylamino)-cyclopentyl]-N-methyl-benzamide (A33)

(76) ##STR00039##

(77) LC/MS: M+H=422; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.27 (d, J=8.3 Hz, 2H), 7.89 (s, 1H; NH), 7.85 (ddd, J=12.6, 6.9, 1.5 Hz, 2H), 7.60 (br. s, 2H), 7.46 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.93 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.03 (br. s, 1H), 3.75-3.55 (m, 1H), 3.26 (s, 3H), 2.93 (br. s, 3H), 2.02 (br. s, 1H), 1.94-1.53 (m, 5H), 1.21 (d, J=6.7 Hz, 3H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-(2-methoxy-acetylamino)-cyclopentyl]-N-methyl-benzamide (A34)

(78) ##STR00040##

(79) LC/MS: M+H=408; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.88-7.77 (m, 3H), 7.58 (s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.81, 4.12 (2br.s, 1H, ratio=1:2 mixture of rotamers), 3.98 (br. s, 1H), 3.77 (s, 2H), 3.30 (s, 3H), 2.91 (br. s, 3H), 2.18-1.47 (m, 6H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3S)-3-(3-methyl-butyrylamino)-cyclopentyl]-benzamide (A35)

(80) ##STR00041##

(81) LC/MS: M+H=420; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.92-7.73 (m, 3H), 7.59 (s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.86 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.00 (br. s, 1H), 2.90 (br. s, 3H), 2.06 (br. s, 1H), 2.01-1.87 (m, 3H), 1.88-1.64 (m, 3H), 1.64-1.35 (m, 2H), 0.86 (d, J=6.3 Hz, 6H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-(2-dimethylamino-acetylamino)-cyclopentyl]-N-methyl-benzamide (A36)

(82) ##STR00042##

(83) LC/MS: M+H=421; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.87-7.79 (m, 2H), 7.77 (d, J=7.5 Hz, 1H; NH), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.94 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.00 (br. s, 1H), 2.91 (br. s, 3H), 2.82 (s, 2H), 2.19 (s, 6H), 2.13-1.91 (m, 1H), 1.91-1.65 (m, 4H), 1.66-1.46 (m, 1H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-((S)-2-hydroxy-propionylamino)-cyclopentyl]-N-methyl-benzamide (A37)

(84) ##STR00043##

(85) LC/MS: M+H=408; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.88-7.78 (m, 2H), 7.72 (d, J=6.4 Hz, 1H; NH), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 5.40 (d, J=5.0 Hz, 1H; OH), 4.82, 4.07 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.00 (br. s, 1H) 3.93 (dt, J=12.2, 6.3 Hz, 1H), 2.91 (s, 3H), 1.99 (br. s, 1H), 1.92-1.64 (m, 4H), 1.66-1.49 (m, 1H), 1.19 (d, J=6.7 Hz, 3H);

N-[(1R,3S)-3-(3-acetylamino-propionylamino)-cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide (A38)

(86) ##STR00044##

(87) LC/MS: M+H=449; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.93 (d, J=6.9 Hz, 1H; NH), 7.88-7.76 (m, 3H), 7.59 (s, 2H), 7.50-7.37 (m, 2H), 4.82, 3.86 (2br. s, 1H, ratio=1:2.5 mixture of rotamers) 4.06 (br. s, 1H), 3.25-3.12 (m, 2H), 2.89 (br. s, 3H), 2.20 (t, J=7.0 Hz, 2H), 2.15-1.98 (m, 1H), 1.87-1.79 (m, 1H), 1.77 (s, 3H), 1.76-1.65 (m, 1H), 1.63-1.45 (m, 3H);

(S)-2-acetylamino-N-{(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-succinamic acid methyl ester (A39)

(88) ##STR00045##

(89) LC/MS: M+H=507; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 8.19 (d, J=7.8 Hz, 1H; NH), 7.99 (d, J=7.0 Hz, 1H; NH), 7.89-7.76 (m, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.85 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.55 (q, J=6.8 Hz, 1H), 3.59 (s, 3H), 4.32, 3.99 (2br. s, 1H, ratio=1:2 mixture of rotamers), 2.89 (br. s, 3H), 2.54 (dd, J=15.1, 6.2 Hz, 1H), 2.45 (dd, J=15.1, 6.9 Hz, 1H), 2.08 (br. s, 1H), 1.83 (s, 3H), 1.81-1.63 (m, 3H), 1.64-1.44 (m, 2H);

(R)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-amide (A40)

(90) ##STR00046##

(91) LC/MS: M+H=434; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.83 (dd, J=13.8, 7.2 Hz, 2H), 7.80 (s, 1H; NH), 7.58 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.81, 4.00 (2br.s, 1H, ratio=1:2.3 mixture of rotamers), 4.17 (s, 1H), 4.13, 3.91 (2br. s, 1H, ratio=1:2.3 mixture of rotamers), 3.91-3.85 (m, 1H), 3.79-3.72 (m, 1H), 2.92 (br. s, 3H), 2.18-2.02 (m, 1H), 1.96 (br. s, 1H), 1.90-1.64 (m, 7H), 1.65-1.50 (m, 1H);

(S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4-benzoxazol-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-amide (A41)

(92) ##STR00047##

(93) LC/MS: M+H=434; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.4 Hz, 2H), 7.91-7.73 (m, 3H), 7.58 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.81, 4.00 (2br.s, 1H, ratio=1:2.3 mixture of rotamers), 4.17 (br. s, 1H), 4.13, 3.91 (2br. s, 1H, ratio=1:2.3 mixture of rotamers), 3.91-3.83 (m, 1H), 3.81-3.69 (m, 1H), 2.93 (br. s, 3H), 2.18-2.02 (m, 1H), 1.95 (q, J=7.8 Hz, 1H), 1.91-1.64 (m, 7H), 1.65-1.46 (m, 1H);

N-[(1R,3S)-3-((R)-2-acetylamino-3-methyl-butyrylamino)-cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide (A42)

(94) ##STR00048##

(95) LC/MS: M+H=477; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 8.10 (br. s, 1H; NH), 7.91-7.77 (m, 3H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.86 (2br. s, 1H, ratio=1:2.5 mixture of rotamers), 4.07 (t, J=8.2 Hz, 1H), 4.00 (br. s, 1H), 2.91 (s, 3H), 2.22-1.93 (m, 1H), 1.89-1.76 (m, 3H), 1.85 (s, 3H), 1.76-1.41 (m, 3H), 0.83 (d, J=6.7 Hz, 6H);

N-[(1R,3S)-3-((S)-2-acetylamino-3-methyl-butyrylamino)-cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide (A43)

(96) ##STR00049##

(97) LC/MS: M+H=477; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 8.10 (br. s, 1H; NH), 7.91-7.77 (m, 3H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.83, 3.86 (2br. s, 1H, ratio=1:2.5 mixture of rotamers), 4.07 (t, J=8.2 Hz, 1H), 4.00 (br. s, 1H), 2.91 (s, 3H), 2.22-1.93 (m, 1H), 1.89-1.76 (m, 3H), 1.85 (s, 3H), 1.76-1.41 (m, 3H), 0.83 (d, J=6.7 Hz, 6H);

4-benzoxazol-2-yl-N-[(1R,3S)-3-(2-cyclopentyl)-acetylamino)-cyclopentyl]-N-methyl-benzamide (A44)

(98) ##STR00050##

(99) LC/MS: M+H=446; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.91-7.77 (m, 3H), 7.58 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.83 (2br. s, 1H, ratio=1:2.2 mixture of rotamers), 4.00 (br. s, 1H), 2.91 (br. s, 3H), 2.20-1.96 (m, 4H), 1.91-1.62 (m, 5H), 1.63-1.39 (m, 6H), 1.18-1.03 (m, 2H);

4-benzoxazol-2-yl-N-methyl-N-{(1R,3S)-3-[2-((S)-5-oxo-pyrrolidin-2-yl)-acetylamino]-cyclopentyl}-benzamide (A45)

(100) ##STR00051##

(101) LC/MS: M+H=461; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.27 (d, J=8.3 Hz, 2H), 8.04 (d, J=5.7 Hz, 1H; NH), 7.84 (dd, J=13.3, 7.3 Hz, 2H), 7.59 (br. s, 2H), 7.53 (s, 1H; NH), 7.46 (pd, J=7.4, 1.5 Hz, 2H), 4.83, 3.81 (2br. s, 1H, ratio=1:2.2 mixture of rotamers), 4.00 (br. s, 1H), 2.92 (br. s, 3H), 2.31 (dd, J=14.0, 5.9 Hz, 1H), 2.25-1.97 (m, 5H), 1.94-1.42 (m, 6H);

4-(1H-indazol-6-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A46)

(102) ##STR00052##

(103) LC/MS: M+H=391; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 13.15 (s, 1H), 8.10 (s, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.84-7.74 (m, 4H), 7.51-7.40 (m, 3H), 4.77, 4.15 (2br. s, 1H, ratio=1:2.5 mixture of rotamers), 3.91 (br. s, 1H), 2.89 (br. s, 3H), 2.13-2.00 (m, 3H), 1.93-1.67 (m, 3H), 1.66-1.45 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-[(1R,3S)-3-((S)-2-acetylamino-propionylamino)-cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide (A47)

(104) ##STR00053##

(105) LC/MS: M+H=449; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.98 (d, J=7.1 Hz, 2H; 2NH), 7.84 (dd, J=13.3, 7.2 Hz, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.84 (2br. s, 1H, ratio=1:2 mixture of rotamers), 4.22 (p, J=7.1 Hz, 1H), 4.01 (br. s, 1H), 2.89 (br. s, 3H), 2.21-1.44 (m, 9H), 1.16 (d, J=7.1 Hz, 3H);

N-[(1R,3S)-3-((R)-2-acetylamino-propionylamino)-cyclopentyl]-4-benzoxazol-2-yl-N-methyl-benzamide (A48)

(106) ##STR00054##

(107) LC/MS: M+H=449; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.94 (d, J=7.1 Hz, 2H; 2NH), 7.84 (dd, J=13.3, 7.2 Hz, 2H), 7.59 (br. s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 4.82, 3.84 (2br. s, 1H, ratio=1:2 mixture of rotamers), 4.22 (p, J=7.1 Hz, 1H), 4.01 (br. s, 1H), 2.89 (br. s, 3H), 2.21-1.44 (m, 9H), 1.16 (d, J=7.1 Hz, 3H);

4-(7-fluoro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A49)

(108) ##STR00055##

(109) LC/MS: M+H=410; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.29 (d, J=8.3 Hz, 2H), 7.86 (d, J=7.3 Hz, 1H; NH), 7.71 (d, J=8.7 Hz, 1H), 7.61 (br. s, 2H), 4.85, 3.84 (2br.s, 1H, ratio=1:1,5 mixture of rotamers), 4.16, 3.99 (2br. s, 1H, ratio=1:1,5 mixture of rotamers), 7.50-7.37 (m, 2H), 2.92 (br. s, 3H), 2.22-1.93 (m, 3H), 1.92-1.65 (m, 3H), 1.65-1.41 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-[(1R,3S)-3-(cyclopropanecarbonyl-amino)-cyclopentyl]-4-(7-fluoro-benzoxazol-2-yl)-N-methyl-benzamide (A50)

(110) ##STR00056##

(111) LC/MS: M+H=422; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.33-8.24 (m, 2H), 7.16 (d, J=7.3 Hz, 1H; NH), 7.71 (dd, J=7.8, 1.1 Hz, 1H), 7.61 (br. s, 2H), 7.51-7.34 (m, 2H), 4.85, 3.87 (2br.s, 1H, ratio=1:2 mixture of rotamers), 4.17, 4.00 (2br. s, 1H, ratio=1:2 mixture of rotamers), 2.94 (br. s, 3H), 2.23-1.96 (m, 1H), 1.97-1.67 (m, 3H), 1.67-1.43 (m, 3H), 0.78-0.51 (m, 4H);

4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-biphenyl-4-carboxylic acid (A51)

(112) ##STR00057##

(113) LC/MS: M+H=395; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.04 (d, J=8.3 Hz, 2H), 7.91 (d, J=7.2 Hz, 1H), 7.85 (d, J=8.3 Hz, 2H), 7.81 (d, J=8.1 Hz, 2H), 7.48 (br., 2H), 2.88 (br. s, 3H), 2.22-1.92 (m, 3H), 1.90-1.64 (m, 3H), 1.64-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

3-methyl-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-biphenyl-4-carboxylic acid (A52)

(114) ##STR00058##

(115) LC/MS: M+H=409; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 12.94 (s, 1H), 7.90 (s, 1H), 7.88-7.79 (m, 2H), 7.45 (br. s, 4H), 7.37 (d, J=7.9 Hz, 1H), 4.81, 3.88 (2br. s, 1H, ratio=1:2 mixture of rotamers), 4.10 (br. s, 1H), 2.89 (br. s, 3H), 2.31 (s, 3H), 2.15-1.91 (m, 3H), 1.91-1.65 (m, 3H), 1.65-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A53)

(116) ##STR00059##

(117) LC/MS: M+H=369; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.86 (d, J=7.3 Hz, 1H; NH), 7.79-7.74 (m, 2H), 7.72 (d, J=8.3 Hz, 2H), 7.45 (d, J=6.1 Hz, 2H), 7.32 (t, J=8.9 Hz, 2H), 4.83, 3.88 (2br. s, 1H, ratio=1:2,2 mixture of rotamers) 4.12 (br. s, 1H), 2.89 (s, 3H), 2.15-1.91 (m, 3H), 1.91-1.65 (m, 3H), 1.65-1.43 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

2-fluoro-4-(4-methyl-cyclohexyl)-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A54)

(118) ##STR00060##

(119) LC/MS: M+H=465; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.85 (d, J=7.1 Hz, 1H; NH), 7.60 (d, J=6.9 Hz, 2H), 7.52-7.39 (m, 3H), 7.21 (dd, J=5.6, 1.6 Hz, 1H), 7.19 (s, 1H), 4.79, 3.90 (2br. s, 1H, ratio=1:3,6 mixture of rotamers), 4.11 (br. s, 1H), 2.89 (s, 3H), 2.59-2.53 (m, 1H), 2.16-1.92 (m, 2H), 1.89-1.67 (m, 7H), 1.65-1.37 (m, 5H), 1.16-1.02 (m, 2H), 0.99 (t, J=7.6 Hz, 3H), 0.93 (d, J=6.5 Hz, 3H);

tert-butyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A55)

(120) ##STR00061##

(121) LC/MS: M+H=407; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.85 (d, J=7.3 Hz, 1H; NH), 7.71 (d, J=8.3 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H), 7.51 (d, J=8.5 Hz, 2H), 7.44 (br. s, 2H), 4.80, 4.14 (2br. s, 1H, ratio=1:2,5 mixture of rotamers), 3.89 (br. s, 1H), 2.89 (s, 3H), 2.14-1.92 (m, 3H), 1.90-1.66 (m, 3H), 1.65-1.46 (m, 2H), 1.33 (s, 9H), 0.99 (t, J=7.6 Hz, 3H);

3,4-dimethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A56)

(122) ##STR00062##

(123) LC/MS: M+H=411; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.83 (d, J=7.1 Hz, 1H; NH), 7.71 (d, J=8.3 Hz, 2H), 7.41 (d, J=7.0 Hz, 2H), 7.29-7.21 (m, 2H), 7.05 (d, J=8.3 Hz, 1H), 4.78, 4.11 (2br. s, 1H, ratio=1:2,5 mixture of rotamers), 3.85 (s, 3H), 3.80 (s, 3H), 2.88 (s, 3H), 2.14-1.91 (m, 3H), 1.92-1.65 (m, 3H), 1.65-1.42 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

biphenyl-4,4-dicarboxylic acid 4-amide 4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide] (A57)

(124) ##STR00063##

(125) LC/MS: M+H=394; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.03 (s, 1H), 7.98 (d, J=8.4 Hz, 2H), 7.83 (d, J=7.1 Hz, 1H), 7.79 (dd, J=8.4, 1.8 Hz, 4H), 7.46 (s, 2H), 7.39 (s, 1H), 4.80, 4.09 (2br. s, 1H, ratio=1:2,2 mixture of rotamers), 3.89 (br. s, 1H), 2.88 (s, 3H), 2.18-1.92 (m, 3H), 1.90-1.63 (m, 3H), 1.64-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-benzo[1,3]dioxol-5-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A58)

(126) ##STR00064##

(127) LC/MS: M+H=395; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.83 (d, J=7.2 Hz, 1H; NH), 7.66 (d, J=8.2 Hz, 2H), 7.39 (d, J=6.8 Hz, 2H), 7.29 (s, 1H), 7.19 (dd, J=8.1, 1.8 Hz, 1H), 7.01 (d, J=8.1 Hz, 1H), 6.07 (s, 2H), 4.78, 4.11 (2br. s, 1H, ratio=1:2,5 mixture of rotamers), 3.89 (br. s, 1H), 2.87 (s, 3H), 2.14-1.90 (m, 3H), 1.90-1.63 (m, 3H), 1.64-1.42 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-benzothiazol-6-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A59)

(128) ##STR00065##

(129) LC/MS: M+H=408; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 9.42 (s, 1H), 8.54 (d, J=1.8 Hz, 1H), 8.17 (d, J=8.5 Hz, 1H), 7.89 (dd, J=8.5, 1.9 Hz, 1H), 7.86-7.78 (m, 3H), 7.48 (d, J=7.9 Hz, 2H), 2.89 (s, 3H), 2.15-1.92 (m, 3H), 1.90-1.65 (m, 3H), 1.67-1.41 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-4-(2-oxo-2,3-dihydro-1H-indol-6-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A60)

(130) ##STR00066##

(131) LC/MS: M+H=406; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 10.46 (s, 1H; NH), 7.80 (d, J=7.2 Hz, 1H; NH), 7.66 (d, J=8.3 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 7.30 (d, J=7.7 Hz, 1H), 7.25 (dd, J=7.7, 1.6 Hz, 1H), 7.06 (d, J=1.3 Hz, 1H), 4.13 (br. s, 1H), 3.90 (br. s, 1H), 3.52 (s, 2H), 2.88 (s, 3H), 2.14-1.91 (m, 3H), 1.88-1.65 (m, 3H), 1.64-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-cyano-3,5-difluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A61)

(132) ##STR00067##

(133) LC/MS: M+H=412; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.95-7.89 (m, 3H), 7.88 (s, 1H), 7.80 (d, J=7.3 Hz, 1H; NH), 7.50 (d, J=7.8 Hz, 2H), 2.88 (s, 3H), 2.12-1.90 (m, 3H), 1.88-1.63 (m, 3H), 1.64-1.39 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-trifluoromethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A62)

(134) ##STR00068##

(135) LC/MS: M+H=435; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.89-7.79 (m, 3H), 7.76 (d, J=8.4 Hz, 2H), 7.54-7.42 (m, 4H), 4.14 (br. s, 1H), 3.91 (br. s, 1H), 2.89 (s, 3H), 2.19-1.92 (m, 3H), 1.92-1.66 (m, 3H), 1.67-1.42 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

3-chloro-4-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A63)

(136) ##STR00069##

(137) LC/MS: M+H=403; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.94 (dd, J=7.1, 2.3 Hz, 1H), 7.80 (d, J=7.2 Hz, 1H; NH), 7.78-7.70 (m, 3H), 7.55-7.48 (m, 1H), 7.44 (d, J=7.8 Hz, 2H), 4.76, 4.13 (2br. s, 1H, ratio=1:4.6 mixture of rotamers), 4.13 (s, OH), 3.98-3.75 (m, 1H), 2.88 (s, 3H), 2.12-1.90 (m, 3H), 1.90-1.65 (m, 3H), 1.64-1.41 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-trifluoromethyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A64)

(138) ##STR00070##

(139) LC/MS: M+H=419; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.94 (d, J=8.1 Hz, 2H), 7.90-7.76 (m, 5H), 7.49 (d, J=7.6 Hz, 2H), 2.88 (s, 3H), 2.24-1.91 (m, 3H), 1.92-1.66 (m, 3H), 1.66-1.42 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-methoxy-2-methyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A65)

(140) ##STR00071##

(141) LC/MS: M+H=395; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.85 (d, J=7.2 Hz, 1H; NH), 7.47-7.32 (m, 4H), 7.18 (d, J=8.4 Hz, 1H), 6.90 (d, J=2.6 Hz, 1H), 6.85 (dd, J=8.4, 2.6 Hz, 1H), 4.80, 4.15 (2br. s, 1H, ratio=1:4.6 mixture of rotamers), 3.92 (br. s, 1H), 3.79 (s, 3H), 2.89 (s, 3H), 2.25 (s, 3H), 2.14-1.92 (m, 3H), 1.89-1.66 (m, 3H), 1.65-1.45 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

3-fluoro-4-methyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A66)

(142) ##STR00072##

(143) LC/MS: M+H=383; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.85 (d, J=7.2 Hz, 1H; NH), 7.76 (d, J=8.3 Hz, 2H), 7.57-7.35 (m, 5H), 4.91-3.73 (br. m, 2H), 2.89 (br. s, 3H), 2.29 (s, 3H), 2.13-1.90 (m, 3H), 1.89-1.64 (m, 3H), 1.64-1.45 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

4-(1H-indol-6-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A67)

(144) ##STR00073##

(145) LC/MS: M+H=390; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.21 (s, 1H; NH), 7.84 (d, J=7.2 Hz, 1H; NH), 7.73 (d, J=8.3 Hz, 2H), 7.68 (s, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.43 (d, J=7.3 Hz, 2H), 7.41-7.38 (m, 1H), 7.34 (dd, J=8.3, 1.6 Hz, 1H), 6.46 (s, 1H), 4.76, 4.15 (2br. s, 1H, ratio=1:2,9 mixture of rotamers), 3.94 (br. s, 1H), 2.89 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.99 (s, 1H), 1.91-1.66 (m, 3H), 1.68-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-pyrazol-1-yl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A68)

(146) ##STR00074##

(147) LC/MS: M+H=417; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.58 (d, J=2.5 Hz, 2H), 7.96 (d, J=8.7 Hz, 1H), 7.90-7.82 (m, 3H), 7.82-7.75 (m, 3H), 7.46 (d, J=6.3 Hz, 2H), 6.58 (t, J=2.1 Hz, 1H), 4.81, 4.09 (2br. s, 1H, ratio=1:2,3 mixture of rotamers), 3.89 (br. s, 1H), 2.89 (s, 3H), 2.18-1.90 (m, 3H), 1.91-1.65 (m, 3H), 1.63-1.41 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

3-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-biphenyl-4-carboxylic acid methyl ester (A69)

(148) ##STR00075##

(149) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.98 (t, J=8.0 Hz, 1H), 7.85 (d, J=8.4 Hz, 2H), 7.80 (d, J=7.2 Hz, 1H; NH), 7.77-7.68 (m, 2H), 7.48 (d, J=7.7 Hz, 2H), 3.88 (s, 3H), 2.88 (s, 3H), 2.15-1.88 (m, 3H), 1.92-1.64 (m, 3H), 1.64-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-cyclopropylmethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A70)

(150) ##STR00076##

(151) LC/MS: M+H=421; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.83 (d, J=7.2 Hz, 1H; NH), 7.67 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.8 Hz, 2H), 7.40 (d, J=6.9 Hz, 2H), 7.02 (d, J=8.8 Hz, 2H), 4.13 (br. s, 1H), 3.89 (br. s, 1H), 3.86 (d, J=7.0 Hz, 2H), 2.87 (s, 3H), 2.16-1.87 (m, 3H), 1.88-1.64 (m, 3H), 1.64-1.42 (m, 2H), 1.29-1.19 (m, 1H), 0.98 (t, J=7.6 Hz, 3H), 0.61-0.55 (m, 2H), 0.36-0.31 (m, 2H);

4-cyano-3-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A71)

(152) ##STR00077##

(153) LC/MS: M+H=394; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.03 (dd, J=8.2, 7.0 Hz, 1H), 7.95 (dd, J=11.1, 1.5 Hz, 1H), 7.87 (d, J=8.4 Hz, 2H), 7.83 (d, J=7.2 Hz, 1H; NH), 7.81 (dd, J=8.2, 1.6 Hz, 1H), 7.49 (br. d, J=7.4 Hz, 2H), 2.88 (br. s, 3H), 2.13-1.86 (m, 3H), 1.90-1.63 (m, 3H), 1.64-1.39 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-quinolin-3-yl-benzamide (A72)

(154) ##STR00078##

(155) LC/MS: M+H=402; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 9.29 (d, J=2.4 Hz, 1H), 8.72 (d, J=2.1 Hz, 1H), 8.10-8.05 (m, 2H), 7.96 (d, J=8.3 Hz, 2H), 7.84 (d, J=7.1 Hz, 1H), 7.80 (ddd, J=8.4, 6.8, 1.4 Hz, 1H), 7.67 (ddd, J=8.1, 6.8, 1.2 Hz, 1H), 7.54 (s, 2H), 4.83, 4.11 (2br. s, 1H, ratio=1:3,6 mixture of rotamers), 3.89 (br. s, 1H), 2.90 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.92-1.66 (m, 3H), 1.65-1.45 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-methyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A73)

(156) ##STR00079##

(157) LC/MS: M+H=365; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.82 (d, J=7.2 Hz, 1H; NH), 7.71 (d, J=8.4 Hz, 2H), 7.61 (d, J=8.2 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 7.30 (d, J=7.9 Hz, 2H), 4.15 (br. s, 1H), 3.91 (br. s, 1H), 2.89 (s, 3H), 2.37 (s, 3H), 2.06 (q, J=7.6 Hz, 3H), 1.80 (d, J=8.7 Hz, 3H), 1.67-1.43 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-methyl-4-(1-methyl-1H-indazol-6-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A74)

(158) ##STR00080##

(159) LC/MS: M+H=405; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.08 (s, 1H), 7.99 (s, 1H), 7.91-7.82 (m, 4H), 7.55-7.45 (m, 3H), 4.81, 4.16 (2br. s, 1H, ratio=1:2,3 mixture of rotamers), 4.12 (s, 3H), 3.93 (br. s, 1H), 2.91 (s, 3H), 2.06 (q, J=7.6 Hz, 3H), 1.91-1.66 (m, 3H), 1.66-1.39 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-methyl-4-(1-methyl-1H-indazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A75)

(160) ##STR00081##

(161) LC/MS: M+H=405; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.12 (s, 1H), 8.09 (s, 1H), 7.87 (d, J=7.1 Hz, 1H; NH), 7.82-7.72 (m, 4H), 7.46 (d, J=6.7 Hz, 2H), 4.77, 4.15 (2br. s, 1H, ratio=1:1,3 mixture of rotamers), 4.09 (s, 3H), 3.95 (s, 1H), 2.90 (s, 3H), 2.06 (q, J=7.6 Hz, 3H), 1.91-1.67 (m, 3H), 1.67-1.45 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

4-(1H-benzimidazol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A76)

(162) ##STR00082##

(163) LC/MS: M+H=391; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.42 (s, 1H), 7.91 (s, 1H), 7.84 (d, J=7.2 Hz, 1H; NH), 7.77 (d, J=8.3 Hz, 2H), 7.71 (d, J=8.4 Hz, 1H), 7.59 (d, J=10.1 Hz, 1H), 7.45 (d, J=6.9 Hz, 2H), 4.78, 4.15 (2br. s, 1H, ratio=1:2,4 mixture of rotamers), 3.90 (br. s, 1H), 2.89 (s, 3H), 2.15-1.93 (m, 3H), 1.90-1.65 (m, 3H), 1.66-1.41 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

cyano-2-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A77)

(164) ##STR00083##

(165) LC/MS: M+H=394; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.00 (d, J=11.2 Hz, 1H), 7.89-7.74 (m, 3H), 7.67 (d, J=6.8 Hz, 2H), 7.50 (br. s, 2H), 4.82, 3.83 (2br. s, 1H, ratio=1:2,5 mixture of rotamers), 4.03 (br. s, 1H), 2.88 (br. s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.91-1.65 (m, 3H), 1.63-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

biphenyl-4,4-dicarboxylic acid 4-methylamide 4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide] (A78)

(166) ##STR00084##

(167) LC/MS: M+H=408; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.50 (q, J=4.3 Hz, 1H; NH), 7.94 (d, J=8.5 Hz, 2H), 7.86-7.76 (m, 5H), 7.46 (br. s, 2H), 4.81, 3.86 (2br. s, 1H, ratio=1:3 mixture of rotamers), 4.06 (br. s, 1H), 2.88 (br. s, 3H), 2.81 (d, J=4.5 Hz, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.91-1.64 (m, 3H), 1.64-1.38 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

fluoro-4-trifluoromethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A79)

(168) ##STR00085##

(169) LC/MS: M+H=453; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.93-7.85 (m, 1H), 7.84-7.75 (m, 3H), 7.70-7.61 (m, 2H), 7.52-7.40 (m, 2H), 4.79, 4.08 (2br. s, 1H, ratio=1:3 mixture of rotamers), 3.89 (br. s, 1H), 2.88 (br. s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.91-1.65 (m, 3H), 1.63-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A80)

(170) ##STR00086##

(171) LC/MS: M+H=404; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.87 (s, 1H), 7.84 (d, J=7.2 Hz, 1H; NH), 7.74 (d, J=8.3 Hz, 2H), 7.56-7.47 (m, 2H), 7.46-7.38 (m, 2H), 7.37 (d, J=3.0 Hz, 1H), 6.49 (d, J=2.6 Hz, 1H), 4.78, 4.15 (2br. s, 1H; mixture of rotamers, 1:2.1), 3.89 (br. s, 1H), 3.82 (s, 3H), 2.89 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.97 (br. s, 1H), 1.90-1.65 (m, 3H), 1.66-1.39 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(2H-pyrazol-3-yl)-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A81)

(172) ##STR00087##

(173) LC/MS: M+H=417; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.91 (d, J=8.4 Hz, 3H), 7.87-7.68 (m, 6H), 7.52-7.38 (m, 2H), 6.77 (d, J=2.2 Hz, 1H), 4.75, 4.14 (2br. s, 1H; mixture of rotamers, 1:2.4), 3.90 (br. s, 1H), 2.89 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.98 (br. s, 1H), 1.90-1.65 (m, 3H), 1.66-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-methoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A82)

(174) ##STR00088##

(175) LC/MS: M+H=417; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.80 (d, J=7.4 Hz, 1H; NH), 7.66 (t, J=8.6 Hz, 4H), 7.40 (d, J=8.0 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 3.94 (Br. s, 1H), 3.81 (s, 3H), 2.88 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.97 (br. s, 1H), 1.90-1.62 (m, 3H), 1.64-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

2,4-difluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A83)

(176) ##STR00089##

(177) LC/MS: M+H=387; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.83 (d, J=7.1 Hz, 1H; NH), 7.67-7.61 (m, 1H), 7.59 (d, J=6.9 Hz, 2H), 7.46 (br. s, 2H), 7.39 (ddd, J=11.6, 9.4, 2.5 Hz, 1H), 7.22 (td, J=8.4, 2.2 Hz, 1H), 4.81, 4.07 (2br. s, 1H; mixture of rotamers, 1:2.3), 3.90 (br. s, 1H), 2.88 (s, 3H), 2.04 (q, J=7.6 Hz, 2H), 1.96 (s, 1H), 1.91-1.64 (m, 3H), 1.65-1.42 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(1H-indazol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A84)

(178) ##STR00090##

(179) LC/MS: M+H=391; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 13.12 (s, 1H; NH), 8.11 (d, J=21.8 Hz, 2H), 7.81 (d, J=7.3 Hz, 1H; NH), 7.76 (d, J=8.3 Hz, 2H), 7.70 (dd, J=8.7, 1.7 Hz, 1H), 7.63 (d, J=8.7 Hz, 1H), 7.44 (d, J=7.9 Hz, 2H), 3.90 (br. s, 1H), 2.89 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.98 (br. s, 1H), 1.91-1.67 (m, 3H), 1.67-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-difluoromethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A85)

(180) ##STR00091##

(181) LC/MS: M+H=417; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.80 (d, J=7.3 Hz, 1H; NH), 7.77 (d, J=8.8 Hz, 2H), 7.72 (d, J=8.3 Hz, 2H), 7.44 (d, J=7.9 Hz, 2H), 7.28 (d, J=8.8 Hz, 2H), 4.65, 4.14 (2br. s, 1H; mixture of rotamers, 1:1,7), 3.90 (br. s, 1H), 2.88 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.98 (br. s, 1H), 1.91-1.64 (m, 3H), 1.65-1.41 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-chloro-3-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A86)

(182) ##STR00092##

(183) LC/MS: M+H=403; .sup.1H NMR (400 MHz, DMSO-d.sub.6+TFA-d.sub.1) [ppm] 7.79 (d, J=8.1 Hz, 3H), 7.67 (t, J=8.0 Hz, 1H), 7.60 (dd, J=8.4, 1.8 Hz, 1H), 7.47 (d, J=7.9 Hz, 2H), 4.79, 4.16 (2br. s, 1H; mixture of rotamers, 1:2), 3.92 (br. s, 1H), 2.90 (s, 3H), 2.07 (q, J=7.6 Hz, 2H), 2.01 (br. s, 1H), 1.92-1.67 (m, 3H), 1.69-1.43 (m, 2H), 1.00 (t, J=7.6 Hz, 3H);

4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A87)

(184) ##STR00093##

(185) LC/MS: M+H=409; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.80 (d, J=7.2 Hz, 1H; NH), 7.64 (d, J=8.4 Hz, 2H), 7.39 (d, J=7.9 Hz, 2H), 7.21-7.13 (m, 2H), 6.94 (d, J=8.2 Hz, 1H), 4.72, 4.13 (2br. s, 1H; mixture of rotamers, 1:2,2), 4.28 (s, 4H), 3.90 (br. s, 1H), 2.87 (s, 3H), 2.04 (q, J=7.6 Hz, 2H), 1.98 (br. s, 1H), 1.89-1.63 (m, 3H), 1.63-1.40 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

2,4-dimethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A88)

(186) ##STR00094##

(187) LC/MS: M+H=411; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.81 (d, J=7.2 Hz, 1H; NH), 7.50 (d, J=8.3 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 7.26 (d, J=8.4 Hz, 1H), 6.67 (d, J=2.4 Hz, 1H), 6.63 (dd, J=8.4, 2.4 Hz, 1H), 3.90 (br. s, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 2.88 (s, 3H), 2.05 (q, J=7.6 Hz, 2H), 1.98 (br. s, 1H), 1.90-1.67 (m, 3H), 1.67-1.40 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(5-propyl-tetrahydro-pyran-2-yl)-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A89)

(188) ##STR00095##

(189) LC/MS: M+H=477; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.83 (d, J=7.2 Hz, 1H; NH), 7.71 (d, J=8.3 Hz, 2H), 7.65 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.2 Hz, 4H), 4.31 (dd, J=11.2, 1.8 Hz, 1H), 4.78, 4.12 (2br. s, 1H; mixture of rotamers, 1:2,4), 4.00 (ddd, J=11.2, 4.4, 2.0 Hz, 2H), 3.86 (br. s, 1H), 3.16 (t, J=11.1 Hz, 1H), 2.88 (s, 3H), 2.04 (q, J=7.6 Hz, 2H), 1.98-1.85 (m, 3H), 1.84-1.66 (m, 3H), 1.64-1.42 (m, 4H), 1.40-1.22 (m, 3H), 1.20-1.04 (m, 2H), 0.98 (t, J=7.6 Hz, 3H), 0.89 (t, J=7.3 Hz, 3H);

2,4-dimethyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A90)

(190) ##STR00096##

(191) LC/MS: M+H=379; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.84 (d, J=7.1 Hz, 1H), 7.47-7.31 (m, 4H), 7.15-7.10 (m, 2H), 7.08 (d, J=8.0 Hz, 1H), 4.80, 4.11 (2br. s, 1H, ratio=1:3 mixture of rotamers), 3.90 (br. s, 1H), 2.88 (s, 3H), 2.31 (s, 3H), 2.22 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.89-1.65 (m, 3H), 1.64-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(1H-benzotriazol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A91)

(192) ##STR00097##

(193) LC/MS: M+H=392; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 15.77 (br. s, 1H; NH), 8.18 (s, 1H), 8.00 (d, J=8.4 Hz, 1H), 7.91-7.71 (m, 4H), 7.48 (d, J=7.8 Hz, 2H), 4.75, 4.14 (2br. s, 1H, ratio=1:1,6 mixture of rotamers), 3.89 (br. s, 1H), 2.90 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.93-1.66 (m, 3H), 1.67-1.42 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-chloro-2-fluoro-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A92)

(194) ##STR00098##

(195) LC/MS: M+H=403; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.80 (d, J=7.0 Hz, 1H; NH), 7.65-7.59 (m, 3H), 7.57 (dd, J=10.7, 2.1 Hz, 1H), 7.46 (d, J=7.6 Hz, 2H), 7.41 (dd, J=8.3, 1.8 Hz, 1H), 4.80, 4.11 (2br. s, 1H, ratio=1:2,8 mixture of rotamers), 3.90 (br. s, 1H), 2.88 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.89-1.65 (m, 3H), 1.65-1.40 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-4-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A93)

(196) ##STR00099##

(197) LC/MS: M+H=407; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 10.71 (d, J=12.9 Hz, 2H; NH), 7.83 (d, J=7.3 Hz, 1H; NH), 7.65 (d, J=8.3 Hz, 2H), 7.40 (d, J=7.1 Hz, 2H), 7.27 (dd, J=8.1, 1.7 Hz, 1H), 7.19 (d, J=1.6 Hz, 1H), 7.01 (d, J=8.1 Hz, 1H), 4.78, 4.12 (2br. s, 1H, ratio=1:2,8 mixture of rotamers), 3.89 (s, 1H), 2.88 (s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.88-1.64 (m, 3H), 1.66-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-4-(2-oxo-2,3-dihydro-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A94)

(198) ##STR00100##

(199) LC/MS: M+H=406; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 10.48 (s, 1H; NH), 7.83 (d, J=7.2 Hz, 1H; NH), 7.65 (d, J=8.3 Hz, 2H), 7.56 (s, 1H), 7.52 (d, J=8.1 Hz, 1H), 7.40 (d, J=6.9 Hz, 2H), 6.91 (d, J=8.1 Hz, 1H), 4.76, 4.12 (2br. s, 1H, ratio=1:3 mixture of rotamers), 3.90 (br. s, 1H), 3.54 (s, 2H), 2.87 (s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.87-1.65 (m, 3H), 1.63-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A95)

(200) ##STR00101##

(201) LC/MS: M+H=390; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 11.17 (s, 1H; NH), 7.87 (s, 1H), 7.84 (d, J=7.2 Hz, 1H; NH), 7.72 (d, J=8.3 Hz, 2H), 7.48 (d, J=8.5 Hz, 1H), 7.46-7.40 (m, 3H), 7.39 (t, J=2.7 Hz, 1H), 6.50 (s, 1H), 4.77, 4.14 (2br. s, 1H, ratio=1:3 mixture of rotamers), 3.90 (br. s, 1H), 2.89 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.89-1.64 (m, 3H), 1.65-1.42 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-isopropyl-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A96)

(202) ##STR00102##

(203) LC/MS: M+H=393; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.80 (d, J=7.1 Hz, 1H; NH), 7.69 (d, J=8.4 Hz, 2H), 7.62 (d, J=8.3 Hz, 2H), 7.42 (d, J=7.9 Hz, 2H), 7.35 (d, J=8.2 Hz, 2H), 4.76, 4.14 (2br. s, 1H, ratio=1:3 mixture of rotamers), 3.89 (br. s, 1H), 2.95 (dq, J=13.8, 6.9 Hz, 1H), 2.88 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.89-1.65 (m, 3H), 1.65-1.44 (m, 2H), 1.24 (d, J=6.9 Hz, 6H), 0.98 (t, J=7.6 Hz, 3H);

2-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-biphenyl-4-carboxylic acid methyl ester (A97)

(204) ##STR00103##

(205) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.89 (dd, J=8.0, 1.7 Hz, 1H), 7.85-7.78 (m, 2H), 7.76 (t, J=8.0 Hz, 1H), 7.68 (dd, J=8.2, 1.4 Hz, 2H), 7.49 (d, J=7.9 Hz, 2H), 3.90 (s, 3H), 2.88 (s, 3H), 2.05 (q, J=7.6 Hz, 3H), 1.89-1.65 (m, 3H), 1.66-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

3-fluoro-4-trifluoromethoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A98)

(206) ##STR00104##

(207) LC/MS: M+H=453; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.92-7.85 (m, 1H), 7.84-7.75 (m, 3H), 7.70-7.62 (m, 2H), 7.52-7.40 (m, 2H), 4.78, 4.12 (2br. s, 1H, ratio=1:3 mixture of rotamers), 3.89 (br. s, 1H), 2.88 (s, 3H), 2.04 (q, J=7.6 Hz, 3H), 1.91-1.65 (m, 3H), 1.65-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

2-fluoro-4-methoxy-biphenyl-4-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A99)

(208) ##STR00105##

(209) LC/MS: M+H=399; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.80 (d, J=7.2 Hz, 1H; NH), 7.57 (d, J=8.3 Hz, 2H), 7.50 (t, J=9.0 Hz, 1H), 7.47-7.39 (m, 2H), 7.34 (br., s, 1H), 6.99-6.87 (m, 1H), 3.90 (br. s, 1H), 3.82 (s, 3H), 2.88 (s, 3H), 2.12-1.95 (m, 3H), 1.87-1.65 (m, 3H), 1.63-1.43 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

4-(3-cyano-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A99a)

(210) ##STR00106##

(211) LC/MS: M+H=415; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 12.29 (s, 1H), 8.30 (d, J=2.5 Hz, 1H), 7.90 (s, 1H), 7.84 (d, J=7.2 Hz, 1H), 7.79 (d, J=8.3 Hz, 2H), 7.69-7.60 (m, 2H), 7.45 (d, J=6.8 Hz, 2H), 5.01-4.66, 4.33-4.03, 4.03-3.69 (3m, 2H, ratio=1:2, mixture of rotamers 1:2), 2.89 (s, 3H), 2.15-1.39 (m, 8H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-4-(3-methyl-1H-indazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A100)

(212) ##STR00107##

(213) LC/MS: M+H=405; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 12.71 (s, 1H), 8.06-8.03 (m, 1H), 7.85 (d, J=7.3 Hz, 1H), 7.82-7.77 (m, 2H), 7.70 (dd, J=8.7, 1.7 Hz, 1H), 7.55 (d, J=8.6 Hz, 1H), 7.49-7.43 (m, 2H), 5.06-4.54, 4.47-4.03, 4.03-3.71 (3m, 2H, ratio=1:2, mixture of rotamers), 2.90 (s, 3H), 2.55 (s, 3H), 2.10-2.02 (m, 3H), 1.89-1.67 (m, 3H), 1.66-1.43 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

4-(1H-indol-5-yl)-3,N-dimethyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A101)

(214) ##STR00108##

(215) LC/MS: M+H=404; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 11.14 (s, 1H), 7.82 (d, J=7.2 Hz, 1H), 7.51-7.48 (m, 1H), 7.47-7.43 (m, 1H), 7.38 (t, J=2.7 Hz, 1H), 7.30-7.23 (m, 2H), 7.20 (d, J=7.7 Hz, 1H), 7.07 (dd, J=8.3, 1.7 Hz, 1H), 6.49-6.43 (m, 1H), 5.07-4.54, 4.48-4.07, 4.07-3.72 (3m, 2H, ratio=1:2, mixture of rotamers), 2.89 (s, 3H), 2.28 (s, 3H), 2.14-1.98 (m, 3H), 1.88-1.68 (m, 3H), 1.65-1.44 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

N-methyl-4-(6-methyl-1H-indazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A102)

(216) ##STR00109##

(217) LC/MS: M+H=405; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 12.95 (s, 1H), 8.02 (s, 1H), 7.82 (d, J=7.2 Hz, 1H), 7.59 (s, 1H), 7.45 (s, 1H), 7.42 (s, 4H), 4.75, 4.14, 3.92 (3br. s, 2H, ratio=1:2, mixture of rotamers), 2.90 (s, 3H), 2.33 (s, 3H), 2.12-1.99 (m, 3H), 1.89-1.70 (m, 3H), 1.65-1.47 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

5-(6-methyl-1H-indazol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A103)

(218) ##STR00110##

(219) LC/MS: M+H=406; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 13.04 (s, 1H), 8.58 (d, J=1.5 Hz, 1H), 8.05 (s, 1H), 7.96-7.91 (m, 1H), 7.87, 7.83 (2d, J=6.9 Hz, J=7.2 Hz, 1H, ratio=2:3, mixture of rotamers), 7.68, 7.66 (2s, 1H, ratio=2:3, mixture of rotamers), 7.61, 7.56 (2d, J=7.9 Hz, 1H, ratio=2:3, mixture of rotamers), 7.49 (s, 1H), 4.88, 4.16 (2p, J=8.5 Hz, J=8.2 Hz, 1H, ratio=2:3, mixture of rotamers), 4.06, 3.86 (2h, J=7.1 Hz, 1H, ratio=2:3, mixture of rotamers), 2.94, 2.90 (2s, 3H, ratio=2:3, mixture of rotamers), 2.36, 2.34 (2s, 3H, ratio 2:3, mixture of rotamers), 2.18-2.00 (m, 3H), 1.99-1.69 (m, 3H), 1.66-1.44 (m, 2H), 1.03-0.94 (m, 3H);

5-(7-methyl-1H-indazol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A104)

(220) ##STR00111##

(221) LC/MS: M+H=406; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 13.10 (s, 1H), 8.91 (d, J=1.7 Hz, 1H), 8.18 (dd, J=8.1, 2.3 Hz, 1H), 8.13 (s, 1H), 7.97 (s, 1H), 7.59 (d, J=8.0 Hz, 2H), 7.54 (s, 1H), 4.36 (br. s, 1H), 3.96 (br. s, 1H), 2.95 (s, 3H), 2.63 (s, 3H), 2.19-2.01 (m, 3H), 1.90-1.74 (m, 3H), 1.71-1.46 (m, 2H), 1.02 (t, J=7.6 Hz, 3H);

5-(3-methyl-1H-indazol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A105)

(222) ##STR00112##

(223) LC/MS: M+H=406; .sup.1H NMR (400 MHz, 353 K, DMSO-d.sub.6) [ppm] 12.55 (s, 1H), 8.93 (d, J=1.8 Hz, 1H), 8.20 (dd, J=8.1, 2.3 Hz, 1H), 8.10 (s, 1H), 7.71 (dd, J=8.7, 1.5 Hz, 1H), 7.65-7.46 (m, 3H), 4.37 (br. s, 1H), 3.96 (br. s, 1H), 2.95 (s, 3H), 2.57 (s, 3H), 2.21-1.46 (m, 8H), 1.02 (t, J=7.6 Hz, 3H);

2-fluoro-4-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A106)

(224) ##STR00113##

(225) LC/MS: M+H=408; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.22, 11.18 (2s, 1H, ratio=1:2, mixture of rotamers), 8.01-7.78 (m, 2H), 7.66-7.53 (m, 2H), 7.52-7.43 (m, 2H), 7.43-7.31 (m, 2H), 6.54-6.48 (m, 1H), 4.92-4.78, 4.26-4.05, 4.09-3.91, 3.90-3.78 (4m, 2H, ratio=1:2, mixture of rotamers), 2.93, 2.80 (2s, 3H, ratio=2:1, mixture of rotamers), 2.17-1.42 (m, 8H), 1.05-0.91 (m, 3H);

N-methyl-4-(7-methyl-1H-indazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A107)

(226) ##STR00114##

(227) LC/MS: M+H=405; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 13.21 (s, 1H), 8.13 (s, 1H), 7.90 (s, 1H), 7.83 (d, J=7.2 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 7.51 (s, 1H), 7.44 (d, J=7.8 Hz, 2H), 4.67, 4.17, 3.92 (3br. s, 2H, mixture of rotamers), 2.90 (s, 3H), 2.60 (s, 3H), 2.15-2.01 (m, 3H), 1.92-1.69 (m, 3H), 1.69-1.44 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

3-fluoro-N-methyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A108)

(228) ##STR00115##

(229) LC/MS: M+H=422; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.81 (d, J=7.2 Hz, 1H), 7.76 (d, J=1.7 Hz, 1H), 7.60 (t, J=7.9 Hz, 1H), 7.54 (d, J=8.5 Hz, 1H), 7.41-7.33 (m, 2H), 7.34-7.20 (m, 2H), 6.50 (d, J=2.8 Hz, 1H), 4.78, 4.14, 3.94 (3br. s, 2H, mixture of rotamers), 3.83 (s, 3H), 2.89 (s, 3H), 2.13-1.92 (m, 3H), 1.90-1.68 (m, 3H), 1.64-1.45 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

5-(1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A109)

(230) ##STR00116##

(231) LC/MS: M+H=391; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.22 (s, 1H), 8.89 (d, J=1.8 Hz, 1H), 8.17 (dd, J=8.1, 2.3 Hz, 1H), 7.95 (s, 1H), 7.89-7.74 (m, 1H), 7.67-7.45 (m, 3H), 7.41 (t, J=2.7 Hz, 1H), 6.54-6.50 (m, 1H), 4.95-4.78, 4.27-4.12, 4.12-3.99, 3.92-3.76 (4m, 2H, ratio=2:3, mixture of rotamers), 2.93, 2.90 (2s, 3H, ratio=3:2, mixture of rotamers), 2.19-1.99 (m, 3H), 1.99-1.65 (m, 3H), 1.65-1.40 (m, 2H), 1.07-0.92 (m, 3H);

5-(1-methyl-1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A110)

(232) ##STR00117##

(233) LC/MS: M+H=405; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.91 (d, J=1.8 Hz, 1H), 8.18 (dd, J=8.1, 2.2 Hz, 1H), 7.96 (s, 1H), 7.84, 7.80 (2d, J=5.3 Hz, J=6.8 Hz, 1H, ratio=2:3, mixture of rotamers), 7.63-7.53 (m, 3H), 7.40 (d, J=3.0 Hz, 1H), 6.52 (d, J=3.0 Hz, 1H), 4.97-4.77, 4.26-4.14, 4.12-4.00, 3.89-3.83 (4m, 2H, ratio=2:3, mixture of rotamers) 3.84 (s, 3H), 2.93, 2.89 (2s, 3H), 2.16-2.00 (m, 3H), 1.99-1.65 (m, 3H), 1.65-1.43 (m, 2H), 1.03-0.95 (m, 3H);

2-fluoro-N-methyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A111)

(234) ##STR00118##

(235) LC/MS: M+H=422; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.93 (s, 1H), 7.88-7.75 (m, 1H), 7.65-7.56 (m, 2H), 7.54 (br. s, 2H), 7.45-7.33 (m, 2H), 6.50 (d, J=3.1, 1 H), 4.92-4.80, 4.24-4.08, 4.08-3.94, 3.90-3.78 (4m, 2H, ratio=2:3, mixture of rotamers), 3.82 (s, 3H), 2.93, 2.81 (2s, 3H, ratio 3:2, mixture of rotamers), 2.17-1.43 (m, 8H), 1.05-0.87 (m, 3H);

3-fluoro-4-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A112)

(236) ##STR00119##

(237) LC/MS: M+H=408; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 11.21 (s, 1H), 7.81 (d, J=7.3 Hz, 1H), 7.75 (s, 1H), 7.59 (t, J=7.9 Hz, 1H), 7.53-7.47 (m, 1H), 7.40 (t, J=2.8 Hz, 1H), 7.34-7.19 (m, 3H), 6.53-6.47 (m, 1H), 4.78, 4.14, 4.03 (3br. s, 2H, ratio=2:3, mixture of rotamers), 2.89 (s, 3H), 2.14-1.91 (m, 3H), 1.89-1.68 (m, 3H), 1.65-1.44 (m, 2H), 0.98 (t, J=7.6 Hz, 3H);

6-(1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A113)

(238) ##STR00120##

(239) LC/MS: M+H=392; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.34 (s, 1H), 8.42 (s, 1H), 8.36-8.30 (m, 1H), 8.04-7.97 (m, 1H), 7.91-7.78 (m, 2H), 7.56 (d, J=8.6 Hz, 1H), 7.47-7.42 (m, 1H), 6.61-6.55 (m, 1H), 4.99-4.13 (2m, 1H, ratio=1:1.7 mixture of rotamers), 4.12-3.79 (2m, 1H, ratio=1:1.7 mixture of rotamers), 2.99, 2.94 (2s, 3H, ratio=1:1.7 mixture of rotamers), 2.18-2.00 (m, 3H), 1.97-1.42 (m, 5H), 1.05-0.93 (m, 3H);

3,N-dimethyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A114)

(240) ##STR00121##

(241) LC/MS: M+H=418; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.34 (s, 1H), 8.42 (s, 1H), 8.36-8.30 (m, 1H), 8.04-7.97 (m, 1H), 7.91-7.78 (m, 2H), 7.56 (d, J=8.6 Hz, 1H), 7.47-7.42 (m, 1H), 6.61-6.55 (m, 1H), 4.99-4.13 (2m, 1H, ratio=1:1.7 mixture of rotamers), 4.12-3.79 (2m, 1H, ratio=1:1.7 mixture of rotamers), 2.99, 2.94 (2s, 3H, ratio=1:1.7 mixture of rotamers), 2.18-2.00 (m, 3H), 1.97-1.42 (m, 5H), 1.05-0.93 (m, 3H);

N-methyl-4-(3-methyl-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A115)

(242) ##STR00122##

(243) LC/MS: M+H=404; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 10.79 (s, 1H), 7.86-7.63 (m, 4H), 7.53-7.36 (m, 4H), 7.18-7.09 (m, 1H), 4.76-3.74 (m, 2H), 2.89 (s, 3H), 2.31 (d, J=0.9 Hz, 3H), 2.17-1.38 (m, 8H), 0.98 (t, J=7.6 Hz, 3H);

4-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A116)

(244) ##STR00123##

(245) LC/MS: M+H=408; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.46 (s, 1H), 7.81 (d, J=7.2 Hz, 1H), 7.62 (dd, 2H, J=8.3, 1.6 Hz), 7.49-7.38 (m, 3H), 7.34 (dd, J=8.4, 0.9 Hz, 1H), 7.22 (dd, J=8.4, 7.4 Hz, 1H), 6.55 (ddd, J=3.0, 2.0, 0.9 Hz, 1H), 5.19-3.58 (2m, 2H, ratio 1:1, mixture of rotamers), 2.89 (s, 3H), 2.16-1.05 (m, 8H), 0.98 (t, J=7.6 Hz, 3H);

6-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A117)

(246) ##STR00124##

(247) LC/MS: M+H=391; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 11.24 (s, 1H), 8.63 (s, 1H), 8.41-8.32 (m, 1H), 8.01 (d, J=8.1 Hz, 1H), 7.93 (dd, J=8.6, 1.7 Hz, 1H), 7.88-7.76 (m, 2H), 7.50 (d, J=8.6 Hz, 1H), 7.46-7.34 (m, 1H), 6.63-6.48 (m, 1H), 5.19-3.79 (2m, 2H, ratio 1:1, mixture of rotamers), 2.93 (s, 3H), 2.25-1.45 (m, 8H), 1.00 (t, J=7.6 Hz, 3H);

6-(1-methyl-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A118)

(248) ##STR00125##

(249) LC/MS: M+H=406; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.44 (s, 1H), 8.35 (d, J=8.8 Hz, 1H), 8.08 (d, J=8.7 Hz, 1H), 7.91-7.71 (m, 2H), 7.63 (d, J=8.7 Hz, 1H), 7.44 (d, J=3.0 Hz, 1H), 6.59 (d, J=3.0 Hz, 1H), 4.29-4.14 (2m, 1H, ratio 1:0.54, mixture of rotamers), 3.92-3.80 (m, 4H), 3.00-2.90 (2s, 3H, ratio 1:0.54, mixture of rotamers), 2.22-1.41 (m, 8H), 0.99 (2t, J=7.6 Hz, 3H, ratio 1:0.54, mixture of rotamers);

2,N-dimethyl-4-(1-methyl-1H-indol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A119)

(250) ##STR00126##

(251) LC/MS: M+H=418; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 7.85 (s, 1H), 7.91-7.74 (2d, J=9.1 Hz, 1H, ratio 2:1, mixture of rotamers), 7.58 (s, 1H), 7.55-7.45 (m, 3H), 7.35 (d, J=3.1 Hz, 1H), 7.24-7.06 (2d, J=7.8 Hz, 1H, ratio 2:1, mixture of rotamers), 6.48 (d, J=2.8 Hz, 1H), 4.95-3.85 (2m, 2H, ratio 1:1, mixture of rotamers), 4.10-3.75 (2m, 1H, ratio 2:1, mixture of rotamers), 3.82 (s, 3H), 2.96-2.70 (2s, 3H, ratio 2:1, mixture of rotamers), 2.25 (s, 3H), 2.19-1.41 (m, 8H), 1.08-0.92 (2t, J=7.6 Hz, 3H, ratio 2:1, mixture of rotamers);

4-(1H-indol-5-yl)-2,N-dimethyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A120)

(252) ##STR00127##

(253) LC/MS: M+H=404; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 10.87 (s, 1H), 7.82 (s, 1H), 7.53 (d, J=1.8 Hz, 1H), 7.49 (dd, J=7.7, 2.0 Hz, 2H), 7.46 (d, J=8.4 Hz, 1H), 7.39 (dd, J=8.4, 1.8 Hz, 1H), 7.32 (t, J=2.8 Hz, 1H), 7.13 (d, J=7.8 Hz, 1H), 6.52-6.41 (m, 1H), 4.70-3.66 (m, 2H), 2.84 (s, 3H), 2.26 (s, 3H), 2.13-1.48 (m, 8H), 0.99 (t, J=7.6 Hz, 3H);

4-(7-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A121)

(254) ##STR00128##

(255) LC/MS: M+H=408; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 11.66 (s, 1H), 7.81 (d, J=7.3 Hz, 1H), 7.77-7.70 (m, 3H), 7.47-7.36 (m, 3H), 7.29 (dd, J=12.8, 1.4 Hz, 1H), 6.59 (td, J=3.2, 1.8 Hz, 1H), 4.87-3.64 (m, 2H), 2.89 (s, 3H), 2.18-1.92 (m, 3H), 1.92-1.40 (m, 5H), 0.98 (t, J=7.6 Hz, 3H);

4-(6-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A122)

(256) ##STR00129##

(257) LC/MS: M+H=408; .sup.1H NMR (600 MHz, DMSO-d.sub.6) [ppm] 11.21 (s, 1H), 7.82 (d, J=7.2 Hz, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.60 (dd, J=8.3, 1.8 Hz, 2H), 7.47-7.40 (m, 2H), 7.38 (dd, J=3.1, 2.4 Hz, 1H), 7.29 (br d, J=11.7 Hz, 1H), 6.53-6.45 (m, 1H), 5.09-3.61 (m, 2H), 2.89 (s, 3H), 2.18-1.93 (m, 3H), 1.93-1.42 (m, 5H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-4-(1-methyl-1H-benzimidazol-2-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A123)

(258) ##STR00130##

(259) LC/MS: M+H=405; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 7.94 (d, J=8.2 Hz, 2H), 7.85 (d, J=7.2 Hz, 1H), 7.75-7.68 (m, 1H), 7.65 (dt, J=8.1, 0.8 Hz, 1H), 7.63-7.48 (m, 2H), 7.38-7.23 (m, 2H), 5.14-3.71 (m, 5H), 2.92 (s, 3H), 2.25-1.38 (m, 8H), 0.99 (t, J=7.6 Hz, 3H);

3,N-dimethyl-4-(4-methyl-1H-indazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A124)

(260) ##STR00131##

(261) LC/MS: M+H=419; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 13.09 (s, 1H), 8.17 (s, 1H), 7.86 (d, J=7.2 Hz, 1H), 7.42 (d, J=8.5 Hz, 1H), 7.31 (s, 1H), 7.27-7.20 (m, 1H), 7.18 (d, J=7.7 Hz, 1H), 7.09 (d, J=8.5 Hz, 1H), 5.02-3.76 (m, 2H), 2.90 (s, 3H), 2.28 (s, 3H), 2.18-1.95 (m, 6H), 1.91-1.46 (m, 5H), 1.00 (t, J=7.6 Hz, 3H);

5-(1-methyl-1H-indol-5-yl)-pyrazine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A125)

(262) ##STR00132##

(263) LC/MS: M+H=406; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 9.20 (d, J=1.5 Hz, 1H), 8.78 (d, J=1.3 Hz, 1H), 8.43 (d, J=1.3 Hz, 1H), 8.02 (dd, J=8.7, 1.7 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.56-7.46 (m, 1H), 7.38 (d, J=3.1 Hz, 1H), 6.58 (d, J=3.1 Hz, 1H), 4.72-3.91 (m, 2H), 3.86 (s, 3H), 2.99 (s, 3H), 2.26-1.46 (m, 8H), 1.03 (t, J=7.6 Hz, 3H);

N-methyl-4-(4-methyl-1H-indazol-5-yl)-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A126)

(264) ##STR00133##

(265) LC/MS: M+H=405; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 13.10 (s, 1H), 8.20 (s, 1H), 7.85 (d, J=7.3 Hz, 1H), 7.54-7.34 (m, 5H), 7.27 (d, J=8.6 Hz, 1H), 5.12-3.67 (m, 2H), 2.91 (s, 3H), 2.52 (s, 3H), 2.07 (q, J=7.6 Hz, 2H), 1.95-1.14 (m, 6H), 1.00 (t, J=7.6 Hz, 3H);

4-(6-fluoro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A127)

(266) ##STR00134##

(267) LC/MS: M+H=410; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.23 (d, J=8.4 Hz, 2H), 7.87 (dd, J=8.8, 5.0 Hz, 1H), 7.83 (dd, J=8.4, 2.5 Hz, 2H), 7.66-7.51 (m, 2H), 7.32 (ddd, J=10.0, 8.8, 2.5 Hz, 1H), 5.09-3.61 (4m, mixture of rotamers, ratio 2:1, 2H), 2.89 (s, 3H), 2.22-1.37 (m, 8H), 0.98 (t, J=7.6 Hz, 3H);

4-(6-chloro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A128)

(268) ##STR00135##

(269) LC/MS: M+H=426; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 8.24 (d, J=8.4 Hz, 2H), 8.04 (d, J=1.8 Hz, 1H), 7.86 (d, J=8.6 Hz, 1H), 7.83 (d, J=6.8 Hz, 1H), 7.65-7.54 (m, 2H), 7.49 (dd, J=8.5, 2.0 Hz, 1H), 4.97-4.67, 4.25-3.70 (2m, 2H, ratio 1:2 mixture of rotamers), 2.89 (br. s, 3H), 2.26-1.39 (m, 8H), 0.98 (t, J=7.6 Hz, 3H);

N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-(1H-pyrrolo[3,2-b]pyridin-5-yl)-benzamide (A129)

(270) ##STR00136##

(271) LC/MS: M+H=391; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 12.17 (br s, 1H), 8.33 (d, J=8.4 Hz, 1H), 8.20-8.07 (m, 2H), 8.02 (s, 1H), 7.91 (d, J=8.5 Hz, 1H), 7.84 (t, J=6.8 Hz, 1H), 7.57 (d, J=7.8 Hz, 2H), 6.78 (s, 1H), 4.23-3.77 (br m, 2H), 2.91 (s, 3H), 2.21-1.39 (m, 8H), 0.99 (t, J=7.6 Hz, 3H);

4-(3-aminomethyl-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A130)

(272) ##STR00137##

(273) LC/MS: M+H=419; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 10.98 (s, 1H), 7.98 (s, 1H), 7.84 (d, J=7.3 Hz, 1H), 7.77 (d, J=8.3 Hz, 2H), 7.55-7.35 (m, 3H), 7.32 (d, J=1.9 Hz, 1H), 4.00 (s, 2H), 3.97-3.81, 3.72-3.07 (2m, 2H), 2.90 (s, 3H), 2.15-2.01 (m, 3H), 1.92-1.67 (m, 3H), 1.66-1.42 (m, 2H), 0.99 (t, J=7.6 Hz, 3H);

5-(1H-indol-5-yl)-pyrimidine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A131)

(274) ##STR00138##

(275) LC/MS: M+H=392; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.04 (s, 1H), 9.13 (s, 2H), 8.00 (s, 1H), 7.72-7.43 (m, 3H), 7.38 (t, J=2.8 Hz, 1H), 6.53 (t, J=2.5 Hz, 1H), 4.98-4.67, 4.29-3.65 (2m, 2H, ratio=1:2, mixture of rotamers), 2.99-2.65 (m, 3H), 2.27-1.44 (m, 8H), 1.00 (t, J=7.6 Hz, 3H);

5-(1H-indol-5-yl)-pyrazine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A132)

(276) ##STR00139##

(277) LC/MS: M+H=392; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.07 (s, 1H), 9.15 (d, J=1.5 Hz, 1H), 8.75 (d, J=1.3 Hz, 1H), 8.39 (s, 1H), 7.92 (dd, J=8.6, 1.7 Hz, 1H), 7.71-7.43 (m, 2H), 7.43-7.28 (m, 1H), 6.65-6.47 (m, 1H), 4.80-4.07, 4.07-3.85 (2m, 2H), 2.96 (s, 3H), 2.20-1.48 (m, 8H), 1.00 (t, J=7.6 Hz, 3H);

5-(1-methyl-1H-indol-5-yl)-pyrimidine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A133)

(278) ##STR00140##

(279) LC/MS: M+H=406; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 9.14 (s, 1H), 8.00 (s, 1H), 7.69-7.43 (m, 3H), 7.36 (d, J=3.1 Hz, 1H), 6.53 (d, J=3.1 Hz, 1H), 5.04-4.55, 4.27-3.95, 3.95-3.67 (3m, 2H, ratio=1:2, mixture of rotamers), 3.83 (s, 3H), 2.99-2.54 (m, 3H), 2.30-1.35 (m, 8H), 1.00 (t, J=7.5 Hz, 3H);

6-(7-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A134)

(280) ##STR00141##

(281) LC/MS: M+H=409; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.69 (s, 1H), 8.56 (s, 8H), 8.15 (s, 1H), 7.99 (d, J=8.2 Hz, 1H), 7.83-7.72 (m, 1H), 7.68 (d, J=13.1 Hz, 1H), 7.40 (t, J=2.7 Hz, 1H), 6.61-6.54 (m, 1H), 5.06-4.41, 4.36-3.60 (2m, 2H), 2.85 (s, 3H), 2.19-1.34 (m, 8H), 0.92 (t, J=7.6 Hz, 3H);

6-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A135)

(282) ##STR00142##

(283) LC/MS: M+H=409; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.31 (s, 1H), 8.75-8.54 (m, 1H), 7.97-7.81 (m, 2H), 7.81-7.72 (m, 1H), 7.62-7.49 (m, 1H), 7.47-7.38 (m, 1H), 7.36 (d, J=8.5 Hz, 1H), 6.67-6.51 (m, 1H), 4.54-4.34 (m, 1H), 4.06-3.86 (m, 1H), 2.95 (s, 3H), 2.23-1.49 (m, 8H), 1.03 (t, J=7.6 Hz, 3H);

6-(7-fluoro-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A136)

(284) ##STR00143##

(285) LC/MS: M+H=410; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm] 11.90 (s, 1H), 8.40 (dd, J=8.9, 5.2 Hz, 1H), 8.31 (s, 1H), 7.97-7.74 (m, 3H), 7.53 (t, J=2.7 Hz, 1H), 6.81-6.58 (m, 1H), 5.07-3.75 (4m, ratio 1:2, mixture of rotamers, 2H), 2.97 (s, 3H), 2.22-1.39 (m, 8H), 0.99 (t, J=7.6 Hz, 3H);

6-(4-fluoro-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A137)

(286) ##STR00144##

(287) LC/MS: M+H=410; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.39 (s, 1H), 8.13 (dd, J=8.8, 1.8 Hz, 1H), 7.85-7.73 (m, 2H), 7.51 (br s, 1H), 7.45-7.31 (m, 2H), 6.74-6.50 (m, 1H), 4.97-3.77 (br m, 2H), 2.99 (s, 3H), 2.30-1.44 (m, 8H), 1.00 (t, J=7.6 Hz, 3H);

(S)-tetrahydro-furan-2-carboxylic acid ((1S,3R)-3-{[4-(6-chloro-benzooxazol-2-yl)-benzoyl]-methyl-amino}-cyclopentyl)-amide (A138)

(288) ##STR00145##

(289) LC/MS: M+H=468; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 8.25 (d, J=8.3 Hz, 2H), 7.95 (d, J=2.0 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.51 (br s, 1H), 7.48 (dd, J=8.5, 2.0 Hz, 1H), 4.34 (br s, 1H), 4.24-4.12 (m, 1H), 4.09-3.85 (m, 2H), 3.85-3.72 (m, 1H), 2.93 (s, 3H), 2.19-1.99 (m, 2H), 1.97-1.71 (m, 7H), 1.71-1.49 (m, 1H);

2-(1H-indol-5-yl)-pyrimidine-5-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A139)

(290) ##STR00146##

(291) LC/MS: M+H=392; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.07 (s, 1H), 8.81 (s, 2H), 8.75-8.61 (m, 1H), 8.22 (dd, J=8.6, 1.7 Hz, 1H), 7.61-7.42 (m, 2H), 7.36 (t, J=2.8 Hz, 1H), 6.56 (ddd, J=3.0, 1.9, 0.9 Hz, 1H), 4.55-4.30 (m, 1H), 4.08-3.88 (m, 1H), 2.95 (s, 3H), 2.17-1.49 (m, 8H), 1.00 (t, J=7.6 Hz, 3H);

5-fluoro-6-(1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A140)

(292) ##STR00147##

(293) LC/MS: M+H=409; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.03 (s, 1H), 8.55-8.43 (m, 1H), 8.20 (s, 1H), 7.76 (dt, J=8.6, 1.5 Hz, 1H), 7.72 (dd, J=11.9, 1.8 Hz, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.36 (t, J=2.8 Hz, 1H), 6.60-6.46 (m, 1H), 4.40 (br s, 1H), 4.04-3.89 (m, 1H), 2.93 (s, 3H), 2.06 (q, J=7.6 Hz, 2H), 1.90-1.49 (m, 6H), 1.00 (t, J=7.6 Hz, 3H);

6-(7-fluoro-1H-indol-5-yl)-4,N-dimethyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A141)

(294) ##STR00148##

(295) LC/MS: M+H=423; .sup.1H NMR (400 MHz, 363 K, DMSO-d.sub.6) [ppm] 11.44 (s, 1H), 8.33 (s, 1H), 8.14 (s, 1H), 7.85 (s, 1H), 7.67 (dd, J=13.2, 1.4 Hz, 1H), 7.49 (br d, J=5.3 Hz, 1H), 7.39 (t, J=2.8 Hz, 1H), 6.68-6.50 (m, 1H), 4.80-3.45 (m, 2H), 2.88 (br s, 3H), 2.28 (s, 3H), 2.13-1.47 (m, 8H), 0.99 (t, J=7.6 Hz, 3H);

5-fluoro-6-(7-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A142)

(296) ##STR00149##

(297) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

5-fluoro-6-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A143)

(298) ##STR00150##

(299) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-imidazo[1,2-a]pyridin-6-yl-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A144)

(300) ##STR00151##

(301) LC/MS: M+H=392; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(7-fluoro-2,3-dihydro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A145)

(302) ##STR00152##

(303) LC/MS: M+H=411; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(4-fluoro-1H-indol-5-yl)-4,N-dimethyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A146)

(304) ##STR00153##

(305) LC/MS: M+H=423; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(3,3-difluoro-2-oxo-2,3-dihydro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A147)

(306) ##STR00154##

(307) LC/MS: M+H=443; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

5-(6-chloro-benzoxazol-2-yl)-pyrazine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A148)

(308) ##STR00155##

(309) LC/MS: M+H=428; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

5-(6-chloro-benzoxazol-2-yl)-pyrimidine-2-carboxylic acid methyl-{(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)-amino]-cyclopentyl}-amide (A149)

(310) ##STR00156##

(311) LC/MS: M+H=470; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(4-methyl-1H-indol-5-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A150)

(312) ##STR00157##

(313) LC/MS: M+H=406; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

3-fluoro-4-(4-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A151)

(314) ##STR00158##

(315) LC/MS: M+H=426; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

4-(3-aminomethyl-1-methyl-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-benzamide (A152)

(316) ##STR00159##

(317) LC/MS: M+H=433; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(6-chloro-benzoxazol-2-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A153)

(318) ##STR00160##

(319) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(6-chloro-benzoxazol-2-yl)-N-methyl-N-{(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)-amino]-cyclopentyl}-nicotinamide (A154)

(320) ##STR00161##

(321) LC/MS: M+H=469; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(6-chloro-benzoxazol-2-yl)-pyridazine-3-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A155)

(322) ##STR00162##

(323) LC/MS: M+H=428; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

5-(6-chloro-benzoxazol-2-yl)-pyrimidine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A156)

(324) ##STR00163##

(325) LC/MS: M+H=428; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(7-fluoro-1H-indol-6-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A157)

(326) ##STR00164##

(327) LC/MS: M+H=409; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

6-(6-chloro-1,3-benzoxazol-2-yl)-N-methyl-N-[(1R,3S)-3-[[(2S)-tetrahydrofuran-2-carbonyl]amino]cyclopentyl]pyridazine-3-carboxamide (A158)

(328) ##STR00165##

(329) LC/MS: M+H=470; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

5-(6-chloro-benzoxazol-2-yl)-pyrazine-2-carboxylic acid methyl-{(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)-amino]-cyclopentyl}-amide (A159)

(330) ##STR00166##

(331) LC/MS: M+H=470; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

5-{2-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-phenyl}-1H-indole-3-carboxylic acid amide (A160)

(332) ##STR00167##

(333) LC/MS: M+H=451; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

3-fluoro-5-(7-fluoro-1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A161)

(334) ##STR00168##

(335) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

3-fluoro-5-(4-fluoro-1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A162)

(336) ##STR00169##

(337) LC/MS: M+H=427; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm]

3-fluoro-5-(1H-indol-5-yl)-pyridine-2-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A163)

(338) ##STR00170##

(339) LC/MS: M+H=409; .sup.1H NMR (400 MHz, DMSO-d.sub.6) [ppm].

EXAMPLE 18

4-benzoxazol-2-yl-N-methyl-N-((1R,3R)-3-propionylamino-cyclopentyl)-benzamide (A165)

(340) ##STR00171##

(341) a) Treatment of (1R,3R)-3-(tert-butoxycarbonyl-methyl-amino)-cyclopentanecarboxylic acid with diphenylphosphorylazide (DPPA) as described above in example 1a leads to [(1R,3R)-3-(tert-butoxycarbonyl-methyl-amino)-cyclopentyl]-carbamic acid benzyl ester as colorless resin; LC/MS: M+H-t-BuOCO=249.

(342) b) Starting with [(1R,3R)-3-(tert-butoxycarbonyl-methyl-amino)-cyclopentyl]-carbamic acid benzyl ester and following the reaction sequence 17a)-17c) as described above in example 17 leads to N-((1R,3R)-3-amino-cyclopentyl)-4-benzoxazol-2-yl-N-methyl-benzamide as a white solid; MS: M+HNH.sub.3=319.

(343) c) Treatment of N-((1R,3R)-3-amino-cyclopentyl)-4-benzoxazol-2-yl-N-methyl-benzamide with propionyl chloride as described above in example 1c leads to 4-benzoxazol-2-yl-N-methyl-N-((1R,3R)-3-propionylamino-cyclopentyl)-benzamide (A165); LC/MS: M+H=392; .sup.1H NMR (500 MHz, DMSO-d.sub.6) [ppm] 8.26 (d, J=8.3 Hz, 2H), 7.83 (ddd, J=12.7, 7.3, 1.8 Hz, 2H), 7.69-7.52 (m, 3H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 5.05, 4.14 (2br.s, 2H, ratio=1:1.8 mixture of rotamers), 2.86 (s, 3H), 2.17-1.77 (m, 5H), 1.77-1.52 (m, 2H), 1.49-1.24 (m, 1H), 1.13-0.74 (m, 3H).

(344) The following compounds are prepared analogously:

N-((1R,3R)-3-acetylamino-cyclopentyl)-4-benzooxazol-2-yl-N-methyl-benzamide (A166)

(345) ##STR00172##

(346) LC/MS: M+H=378; .sup.1H NMR (500 MHz, DMSO-d.sub.6): [ppm] 8.26 (d, J=8.2 Hz, 2H), 7.93, 7.74 (2br.s, 1H, ratio=1:1.8 mixture of rotamers; NH), 7.88-7.78 (m, 2H), 7.59 (d, J=6.3 Hz, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 5.05, 4.13 (2br.s, 2H, ratio=1:1.8 mixture of rotamers), 2.85 (br. s, 3H), 2.12-1.21 (m, 9H);

4-benzoxazol-2-yl-N-methyl-N-((1R,3R)-3-phenylacetylamino-cyclopentyl)-benzamide (A167)

(347) ##STR00173##

(348) LC/MS: M+H=454; .sup.1H NMR (500 MHz, DMSO-d.sub.6): [ppm] 8.26 (d, J=8.2 Hz, 2H), 7.95 (s, 1H; NH), 7.87-7.80 (m, 2H), 7.59 (d, J=6.3 Hz, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 7.35-7.09 (m, 5H), 5.07, 4.13 (2br.s, 2H, ratio=1:1.8 mixture of rotamers), 3.28 (br. s, 2H), 2.85 (s, 3H), 2.12-1.24 (m, 6H);

4-benzoxazol-2-yl-N-methyl-N-[(1R,3R)-3-((R)-3-methyl-pentanoylamino)-cyclopentyl]-benzamide (A168)

(349) ##STR00174##

(350) LC/MS: M+H=434; .sup.1H NMR (500 MHz, DMSO-d.sub.6): [ppm] 8.25 (d, J=8.4 Hz, 2H), 7.88-7.76 (m, 2H), 7.64 (br. s, 1H; NH), 7.59 (br.s, 2H), 7.45 (pd, J=7.4, 1.4 Hz, 2H), 5.06, 4.13 (2br.s, 2H, ratio=1:1.8 mixture of rotamers) 2.86 (br. s, 3H), 2.15-1.53 (m, 8H), 1.50-0.97 (m, 3H), 0.95-0.62 (m, 6H);

6-(3-fluoro-1H-indol-5-yl)-N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-nicotinamide (A169)

(351) ##STR00175##

(352) LC/MS: M+H=408; .sup.1H NMR (400 MHz, DMSO-d.sub.6, 90 C.): [ppm] 10.75 (s, 1H), 8.63 (s, 1H), 8.29 (s, 1H), 8.01 (d, J=8.2 Hz, 1H), 7.96 (d, J=8.7 Hz, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.60-7.50 (m, 1H), 7.47 (d, J=8.5 Hz, 1H), 7.29 (s, 1H), 4.52-4.27 (m, 1H), 4.07-3.87 (m, 1H), 2.94 (s, 3H), 2.23-1.46 (m, 8H), 1.02 (t, J=7.5 Hz, 3H);

2-(1H-indol-5-yl)-thiazole-5-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A170)

(353) ##STR00176##

(354) LC/MS: M+H=396; .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363 K): [ppm] 11.16 (s, 1H), 8.26-8.17 (m, 1H), 8.06 (s, 1H), 7.74 (dd, J=8.5, 1.8 Hz, 1H), 7.62-7.47 (m, 2H), 7.41 (t, J=2.8 Hz, 1H), 6.62-6.53 (m, 1H), 4.77-4.59 (m, 1H), 4.10-3.93 (m, 1H), 3.06 (s, 3H), 2.25-2.01 (m, 3H), 1.94-1.80 (m, 3H), 1.71-1.53 (m, 2H), 1.04 (t, J=7.6 Hz, 3H);

7-fluoro-5-{4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-phenyl}-1H-indole-3-carboxylic acid amide (A171)

(355) ##STR00177##

(356) LC/MS: M+H=450; .sup.1H NMR (400 MHz, DMSO-d.sub.6, 90 C.): [ppm] 11.90 (s, 1H), 8.28 (d, J=1.3 Hz, 1H), 8.08 (s, 1H), 7.73 (d, J=8.3 Hz, 2H), 7.57-7.48 (m, 1H), 7.44 (d, J=8.3 Hz, 2H), 7.32 (dd, J=12.7 Hz, 1.4 Hz, 1H), 6.94 (s, 2H), 4.52-4.32 (m, 1H), 4.03-3.87 (m, 1H), 2.91 (s, 3H), 2.18-1.96 (m, 3H), 1.93-1.72 (m, 3H), 1.72-1.45 (m, 2H), 1.02 (t, J=7.6 Hz, 3H);

7-fluoro-5-{2-fluoro-4-[methyl-((1R,3S)-3-propionylamino-cyclopentyl)-carbamoyl]-phenyl}-1H-indole-3-carboxylic acid amide (A172)

(357) ##STR00178##

(358) LC/MS: M+H=468; .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363 K): [ppm] 11.96 (s, 1H), 8.38-8.17 (m, 1H), 8.11 (d, J=2.9 Hz, 1H), 7.62 (t, J=7.9 Hz, 1H), 7.53 (d, J=7.3 Hz, 1H), 7.34-7.24 (m, 2H), 7.21 (dt, J=12.4, 1.5 Hz, 1H), 6.95 (s, 2H), 4.53-4.29 (m, 1H), 4.03-3.85 (m, 1H), 2.92 (s, 3H), 2.19-2.02 (m, 3H), 1.92-1.73 (m, 3H), 1.72-1.48 (m, 2H), 1.03 (t, J=7.6 Hz, 3H);

2-(1H-indol-5-yl)-4-methyl-thiazole-5-carboxylic acid methyl-((1R,3S)-3-propionylamino-cyclopentyl)-amide (A173)

(359) ##STR00179##

(360) LC/MS: M+H=410; .sup.1H NMR (500 MHz, DMSO-d.sub.6): [ppm] 11.36 (s, 1H), 8.15 (d, J=1.5 Hz, 1H), 7.81, 7.76 (2d, J=7.2 Hz, 6.9 Hz, 2H, ratio 1:6.5 mixture of rotamers), 7.68 (dd, J=8.5, 1.7 Hz, 1H), 7.48 (d, J=8.5 Hz, 1H), 7.45-7.38 (m, 1H), 6.62-6.49 (m, 1H), 4.73-4.56, 4.56-4.35, 4.23-4.09, 4.02-3.90 (4m, 2H, ratio 1:6.5 mixture of rotamers), 2.92, 2.88 (2s, 3H, ratio 1:6.5 mixture of rotamers), 2.36 (s, 3H), 2.16-1.45 (m, 8H), 0.98, 0.94 (2t, J=7.6 Hz, 3H, ratio 1:6.5 mixture of rotamers);

(S)-tetrahydro-furan-2-carboxylic acid ((1S,3R)-3-{-([4-(5-chloro-benzoxazol-2-yl)-benzoyl]-methyl-amino}-cyclopentyl)-amide (A174)

(361) ##STR00180##

(362) LC/MS: M+H=468; .sup.1H NMR (400 MHz, DMSO-d.sub.6, 363 K): [ppm] 8.24 (d, J=8.3 Hz, 2H), 7.88 (d, J=2.1 Hz, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.57 (d, J=8.3 Hz, 2H), 7.52-7.43 (m, 2H), 4.33 (m, 1H), 4.15 (dd, J=8.1, 5.4 Hz, 1H), 4.05-3.93 (m, 1H), 3.93-3.81 (m, 1H), 3.81-3.69 (m, 1H), 2.90 (s, 3H), 2.16-1.96 (m, 2H), 1.94-1.70 (m, 7H), 1.67-1.54 (m, 1H);

(S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4-benzoxazol-2-yl-2-fluoro-benzoyl)-methyl-amino]-cyclopentyl}-amide (A175)

(363) ##STR00181##

(364) LC/MS: M+H=451; .sup.1H NMR (400 MHz, DMSO-d.sub.6): [ppm] 8.16-7.99 (m, 2H), 7.93-7.71 (m, 3H), 7.65, 7.59 (2t, 2J=7.4 Hz, 1H, 1:1,9 mixture of rotamers), 7.54-7.40 (m, 2H), 4.98-3.82 (m, 4H), 3.81-3.69 (m, 1H), 2.97, 2.82 (2s, 3H, ratio 1:1,9 mixture of rotamers), 2.20-1.41 (m, 10H);

5-(6-chloro-benzoxazol-2-yl)-3-fluoro-pyridine-2-carboxylic acid methyl-{(1R,3S)-3-[((S)-tetrahydro-furan-2-carbonyl)-amino]-cyclopentyl}-amide (A176)

(365) ##STR00182##

(366) LC/MS: M+H=487.2/489.2 (single Cl isotopy, relative peak intensity ratio 100:43);

(S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4-benzoxazol-2-yl-3-methoxy-benzoyl)-methyl-amino]-cyclopentyl}-amide (A177)

(367) ##STR00183##

(368) LC/MS: M+H=464;

(S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(4-benzooxazol-2-yl-3-fluoro-benzoyl)-methyl-amino]-cyclopentyl}-amide (A178)

(369) ##STR00184##

(370) LC/MS: M+H=451; .sup.1H NMR (400 MHz, DMSO-d.sub.6): [ppm] 8.16-7.99 (m, 2H), 7.93-7.71 (m, 3H), 7.65, 7.59 (2t, 2J=7.4 Hz, 1H, 1:1,9 mixture of rotamers), 7.54-7.40 (m, 2H), 4.98-3.82 (m, 4H), 3.81-3.69 (m, 1H), 2.97, 2.82 (2s, 3H, ratio 1:1,9 mixture of rotamers), 2.20-1.41 (m, 10H);

N-methyl-N-((1R,3S)-3-propionylamino-cyclopentyl)-4-(1H-pyrrolo[2,3-c]pyridin-5-yl)-benzamide (A179)

(371) ##STR00185##

(372) LC/MS: M+H=391;

(S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(3-fluoro-4-oxazolo[4,5-b]pyridin-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-amide (A180)

(373) ##STR00186##

(374) LC/MS: M+H=453;

(S)-tetrahydro-furan-2-carboxylic acid {(1S,3R)-3-[(2-fluoro-4-oxazolo[4,5-b]pyridin-2-yl-benzoyl)-methyl-amino]-cyclopentyl}-amide (A181)

(375) ##STR00187##

(376) LC/MS: M+H=453;

(S)-tetrahydro-furan-2-carboxylic acid ((1S,3R)-3-{[4-(4-fluoro-benzooxazol-2-yl)-benzoyl]-methyl-amino}-cyclopentyl)-amide (A182)

(377) ##STR00188##

(378) LC/MS: M+H=452;

N-methyl-4-[3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indol-5-yl]-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A183)

(379) ##STR00189##

4-[6-fluoro-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indol-5-yl]-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A184)

(380) ##STR00190##

(2S)N-[(1S,3R)-3-[[4-(4-cyano-1,3-benzoxazol-2-yl)benzoyl]-methyl-amino]cyclopentyl]tetrahydrofuran-2-carboxamide (A185)

(381) ##STR00191##

(2S)N-[(1S,3R)-3-[[4-(1,3-benzoxazol-2-yl)benzoyl]-ethyl-amino]cyclopentyl]-tetrahydrofuran-2-carboxamide (A186)

(382) ##STR00192##

4-(3-cyano-6-fluoro-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A187)

(383) ##STR00193##

N-ethyl-4-(1H-indol-5-yl)-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]-benzamide (A188)

(384) ##STR00194##

4-(3-cyano-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A189)

(385) ##STR00195##

6-(6-fluoro-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)cyclopentyl]-pyridine-3-carboxamide (A190)

(386) ##STR00196##

N-methyl-N-[(1R,3S)-3-(propanoylamino)cyclopentyl]-4-[4-(trifluoromethyl)-1H-indol-5-yl]benzamide (A191)

(387) ##STR00197##

4-(5-fluoro-1-methyl-indazol-4-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A192)

(388) ##STR00198##

4-(5-fluoro-1-methyl-indol-4-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A193)

(389) ##STR00199##

4-(5-fluoro-1H-indol-4-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A194)

(390) ##STR00200##

(2S)N-[(1S,3R)-3-[Methyl-(4-oxazolo[4,5-b]pyridin-2-ylbenzoyl)amino]cyclopentyl]tetrahydrofuran-2-carboxamide (A195)

(391) ##STR00201##

(2S)N-[(1S,3R)-3-[[4-(6-chlorooxazolo[4,5-b]pyridin-2-yl)benzoyl]-methyl-amino]cyclopentyl]tetrahydrofuran-2-carboxamide (A196)

(392) ##STR00202##

(2S)N-[(1S,3R)-3-[(4-furo[3,2-b]pyridin-2-ylbenzoyl)-methyl-amino]cyclopentyl]tetrahydrofuran-2-carboxamide (A197)

(393) ##STR00203##

4-(4-cyano-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A198)

(394) ##STR00204##

4-[3-(cyanomethyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]benzamide (A199)

(395) ##STR00205##

6-(3-cyano-6-fluoro-1H-indol-5-yl)-N-methyl-N-[(1R,3S)-3-(propanoylamino)-cyclopentyl]pyridine-3-carboxamide (A200)

(396) ##STR00206##

7-(1,3-benzoxazol-2-yl)-N-methyl-N-[(1R,3S)-3-[[(2S)-tetrahydrofuran-2-carbonyl]amino]cyclopentyl]-3H-benzimidazole-4-carboxamide (A201)

(397) ##STR00207##
Pharmacological Data

(398) TABLE-US-00001 TABLE 2 Inhibition of FASN of some representative compounds of the formula I Compound IC.sub.50 FASN No. (enzyme assay) A1 A A2 A A3 A A4 A A5 A A6 A A7 A A8 A A9 A A10 A A11 C A12 A A13 A A14 A A15 A A16 A A17 A A18 A A19 A A20 B A21 A A22 B A23 A A24 A A25 B A26 A A27 A A28 A29 A A30 A A31 A A32 B A33 A A34 A A35 A A36 B A37 A A38 B A39 B A40 A A41 A A42 C A43 B A44 A A45 C A46 A A47 C A48 C A49 A A50 B A51 A A52 A A53 A A54 B A55 C A56 A A57 A A58 A A59 A A60 A A61 C A62 B A63 A A64 A A65 A A66 A A67 A A68 A A69 A A70 A A71 A A72 A A73 A A74 A A75 A A76 A A77 A A78 A A79 A A80 A A81 A A82 A A83 A A84 A A85 A A86 A A87 A A88 A A89 B A90 A A91 A A92 A A93 A A94 A A95 A A96 B A97 A A98 A A99 A A99a A A100 A A101 A A102 A A103 B A104 A A105 A A106 A A107 A A108 A A109 A A110 A A111 A A112 A A113 A A114 A A115 A A116 A A117 A A118 A A119 A A120 A A121 A A122 A A123 A A124 A A125 A A126 A A127 A A128 A A129 A A130 A A131 A A132 A A133 A A134 B A135 A A136 B A137 A A138 A A139 A A140 A A141 B A142 B A143 A A144 A A145 B A146 A A147 C A148 B A149 B A150 A A151 A A152 A A153 A A154 A A155 C A156 C A157 A A158 B A159 A A160 A A165 C A166 C A167 C A168 C A169 A A170 A A171 A A172 B A173 A A174 A A175 A A176 IC.sub.50: <0.3 M = A 0.3-3 M = B 3-50 M = C

(399) The compounds shown in Table 2 are particularly preferred compounds according to the invention.

(400) The following examples relate to medicaments:

Example A

Injection Vials

(401) 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

(402) 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

(403) 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

(404) 500 mg of an active ingredient of the formula I are mixed with 99.5 g of Vaseline under aseptic conditions.

Example E

Tablets

(405) 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

(406) 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

(407) 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

(408) 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.