US2009257977A1PendingUtilityA1
Novel tetrahydropyridothiophenes
Est. expiryMay 25, 2025(expired)· nominal 20-yr term from priority
A61P 43/00A61P 35/00C07D 495/04A61P 31/18
57
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Claims
Abstract
Compounds of a certain formula (I), in which Ra and Rb have the meanings indicated in the description, are novel effective compounds with anti-proliferative and apoptosis inducing activity.
Claims
exact text as granted — not AI-modified1 - 21 . (canceled)
22 . A method for treating a (hyper)proliferative disease of benign or malignant behaviour and/or disorder responsive to the induction of apoptosis in a patient, comprising administering to said patient in need thereof a therapeutically effective amount of a compound of formula I
wherein
Ra is —C(O)R1,
R1 is 1-4C-alkyl, 1-4C-alkyl substituted by Raa, or 2-4C-alkyl substituted by Rab and Rac on different carbon atoms,
Rb is -T-Q,
T is 1-6C-alkylene or 3-7C-cycloalkylene,
Q is substituted by Rba and Rbb and Rbc, and is phenyl, Raa is selected from the group consisting of:
3-7C-cycloalkyl, halogen, trifluoromethyl, cyano, hydroxyl, Har, morpholino, —C(O)R2, —C(O)OR3, —C(O)N(R4)R5, —N(R6)C(O)R7, —OC(O)R8, completely or predominantly fluorine-substituted 1-4C-alkoxy, and —OR9,
wherein said Har is optionally substituted by one or two substituents independently selected from R10,
R2, R3, R4, R5, R6, R7 and R8 are the same or different and are independently selected from the group consisting of:
hydrogen and 1-4C-alkyl,
R9 is selected from the group consisting of:
1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl-1-4C-alkyl, pyridyl-1-4C-alkyl, and (1-4C-alkoxy-2-4C-alkoxy)-2-4C-alkyl,
Har is bonded to the parent molecular group via a ring carbon or a ring nitrogen atom, and is a 5-membered monocyclic unsaturated, aromatic heteroaryl ring comprising at least one heteroatom independently selected from the group consisting of nitrogen, oxygen and sulphur,
or
Har is bonded to the parent molecular group via a ring carbon atom, and is a 6-membered monocyclic unsaturated, aromatic heteroaryl ring comprising one or two nitrogen atoms,
or
Har is bonded to the parent molecular group via a ring carbon or a ring nitrogen atom, and is a 9- or 10-membered fused bicyclic unsaturated, aromatic heteroaryl ring comprising one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulphur,
each R10 is the same or different and is each independently selected from the group consisting of:
1-4C-alkyl, halogen and 1-4C-alkoxy,
Rab is hydroxyl,
Rac is hydroxyl,
or Rab and Rac bonded to adjacent carbon atoms form together an 1-2C-alkylenedioxy bridge which is optionally substituted by one or two substituents independently selected from the group consisting of fluorine and methyl,
or Rab and Rac bonded to carbon atoms two bonds distant from each other form together a methylenedioxy bridge which is optionally substituted by one or two substituents independently selected from the group consisting of fluorine and methyl,
Rba is selected from the group consisting of:
1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkyl-1-4C-alkoxy, 1-4C-alkoxy-2-4C-alkoxy, phenyl-1-4C-alkoxy, cyano-1-4C-alkoxy, 3-6C-alkinyloxy, nitro, and completely and predominantly fluorine-substituted 1-4C-alkoxy,
Rbb is selected from the group consisting of:
hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, and 1-4C-alkoxy,
Rbc is selected from the group consisting of:
hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, and 1-4C-alkoxy,
or Rbb and Rbc bounded in ortho position to each other form together an 1-2C-alkylenedioxy bridge, or a completely or partially fluorine-substituted 1-2C-alkylenedioxy bridge,
or a salt thereof.
23 . The method according to claim 22 , wherein the disease or disorder is cancer, or a malignant or benign neoplasia.
24 . The method according to claim 22 , wherein the disease or disorder is benign hypoplasia, benign hypoplasia of the prostate (“BPH”) or colon epithelium, psoriasias, glomerulonephritis, osteoarthritis, a malignant neoplasia, a solid or hematological tumor, a tumor of the breast, bladder, bone, brain, central or peripheral nervus system, colon, endocrine glands, thyroid gland, adrenal cortex, esophagus, endometrium, germ cells, head and neck, kidney, liver, lung, larynx, hypopharynx, mesothelioma, sarcoma, ovary, pancreas, prostate, rectum, renal, small intestine, soft tissue, testis, stomach, skin, ureter, vagina or vulva, Retinomblastoma, Wilms tumor, leukemia, lymphoma, non-Hodgkins disease, chronic or acute myeloid leukemia (CML I AML), acute lymphoblastic leukemia (ALL), Hodgkins disease, multiple myeloma, T-cell lymphoma, myelodysplastic syndrome, plasma cell neoplasia, paraneoplastic syndrome, a cancer of unknown primary site or an AIDS related malignancy.
25 . The method according to claim 22 , wherein the compound is one of the formulae Ia, Ib, Ic, Id and Id′
wherein
Ra is —C(O)R1,
R1 is 1-4C-alkyl, 1-4C-alkyl substituted by Raa, or 2-4C-alkyl substituted by Rab and Rac on different carbon atoms,
Q is substituted by Rba and Rbb and Rbc, and is phenyl,
Raa is selected from the group consisting of:
hydroxyl, Har, morpholino, —C(O)R2, —C(O)OR3, —C(O)N(R4)R5, —N(R6)C(O)R7, —OC(O)R8, and —OR9,
wherein said Har is optionally substituted by one or two substituents independently selected from R10,
R2, R3, R4, R5, R6, R7 and R8 are the same or different and are independently selected from the group consisting of:
hydrogen and 1-4C-alkyl,
R9 is selected from the group consisting of:
1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl-1-4C-alkyl, pyridyl-1-4C-alkyl, and (1-4C-alkoxy-2-4C-alkoxy)-2-4C-alkyl,
Har is bonded to the parent molecular group via a ring carbon or a ring nitrogen atom, and is a 5-membered monocyclic unsaturated, aromatic heteroaryl ring comprising at least one heteroatom independently selected from the group consisting of nitrogen, oxygen and sulphur, or
Har is bonded to the parent molecular group via a ring carbon atom, and is a 6-membered monocyclic unsaturated, aromatic heteroaryl ring comprising one or two nitrogen atoms,
each R10 is the same or different and is each independently selected from the group consisting of: 1-4C-alkyl, halogen and 1-4C-alkoxy,
Rab is hydroxyl,
Rac is hydroxyl,
or Rab and Rac bonded to adjacent carbon atoms form together a dimethylmethylenedioxy bridge,
Rba is selected from the group consisting of:
1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkyl-1-4C-alkoxy, cyano-2-4C-alkoxy, 3-5C-alkinyloxy, nitro, and completely and predominantly fluorine-substituted 1-4C-alkoxy,
Rbb is selected from the group consisting of:
hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, and 1-4C-alkoxy,
Rbc is selected from the group consisting of:
hydrogen, halogen, and 1-4C-alkoxy,
or Rbb and Rbc bounded in ortho position to each other form together a methylenedioxy, ethylenedioxy, difluoromethylenedioxy or tetrafluoroethylenedioxy bridge,
or a salt thereof.
26 . The method according to claim 22 , wherein the compound is one of the formulae Ia, Ib, Ic, Id and Id′
wherein
Ra is —C(O)R1,
R1 is 1-4C-alkyl, or 1-4C-alkyl substituted by Raa, or 3-4C-alkyl substituted by Rab and Rac on different carbon atoms,
Q is substituted by Rba and Rbb and Rbc, and is phenyl,
Raa is selected from the group consisting of:
hydroxyl, Har, morpholino, —C(O)R2, —C(O)OR3, —C(O)N(R4)R5, —N(R6)C(O)R7, —OC(O)R8, and —OR9,
wherein said Har is optionally substituted by one or two substituents independently selected from R10,
R2, R3, R4, R5, R6, R7 and R8 are the same or different and are independently selected from the group consisting of:
hydrogen and 1-4C-alkyl,
R9 is selected from the group consisting of:
1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl-1-4C-alkyl, pyridyl-1-4C-alkyl, and (1-4C-alkoxy-2-4C-alkoxy)-2-4C-alkyl,
Har is bonded to the parent molecular group via a ring carbon or a ring nitrogen atom, and is imidazolyl, pyrazolyl or triazolyl,
or
Har is bonded to the parent molecular group via a ring carbon atom, and is pyridinyl, pyrazinyl or pyrimidinyl,
each R10 is the same or different and is each independently selected from the group consisting of: 1-4C-alkyl and 1-4C-alkoxy,
Rab is hydroxyl,
Rac is hydroxyl,
or Rab and Rac bonded to adjacent carbon atoms form together a dimethylmethylenedioxy bridge,
Rba is selected from the group consisting of:
1-4C-alkoxy, and completely and predominantly fluorine-substituted 1-4C-alkoxy,
Rbb is selected from the group consisting of:
hydrogen, 1-4C-alkyl, and 1-4C-alkoxy,
Rbc is selected from the group consisting of:
hydrogen, and halogen,
or Rbb and Rbc bounded in ortho position to each other form together a methylenedioxy, ethylenedioxy, difluoromethylenedioxy or tetrafluoroethylenedioxy bridge,
or a salt thereof.
27 . The method according to claim 22 , wherein the compound is one of the formulae Ia, Ib and Ic
wherein
Ra is —C(O)R1,
R1 is 1-4C-alkyl,
or
R1 is 1-4C-alkyl which is substituted by Raa, in which
Raa is pyridyl, pyrimidinyl, R101- and/or R102-substituted pyridyl, or R101- and/or R102-substituted pyrimidinyl,
or
R1 is 1-4C-alkyl which is substituted by Raa, in which
Raa is 1N-(1-4C-alkyl)-imidazolyl, 1N-(1-4C-alkyl)-pyrazolyl, R101-substituted 1N-(1-4C-alkyl)-imidazolyl, or R101-substituted 1N-(1-4C-alkyl)-pyrazolyl,
or
R1 is 1-4C-alkyl which is substituted by Raa, in which
Raa is 1N—(H)-imidazolyl, 1N—(H)-pyrazolyl, R101-substituted 1N—(H)-imidazolyl, or R101-substituted 1N—(H)-pyrazolyl,
or
R1 is 3-4C-alkyl which is substituted by Rab and Rac on different carbon atoms, in which
Rab is hydroxyl,
Rac is hydroxyl,
or Rab and Rac bonded to adjacent carbon atoms form together a dimethylmethylenedioxy bridge,
or
R1 is 1-4C-alkyl which is substituted by Raa, in which
Raa is —C(O)OR3,
or
R1 is 1-4C-alkyl which is substituted by Raa, in which
Raa is hydroxyl, morpholino, —OC(O)R8, or —OR9,
or
R1 is 1-4C-alkyl which is substituted by Raa, in which
Raa is imidazol-1-yl, pyrazol-1-yl, mono- or di-(R101)-substituted imidazol-1-yl, or mono- or di-(R101)-substituted pyrazol-1-yl, and
Q is substituted by Rba and Rbb and Rbc, and is phenyl,
R3 is selected from the group consisting of:
hydrogen, and 1-4C-alkyl,
R8 is 1-4C-alkyl,
R9 is selected from the group consisting of:
1-4C-alkyl, phenyl-1-2C-alkyl, 1-2C-alkoxy-2-3C-alkyl, and (1-2C-alkoxy-2-3C-alkoxy)-2-3C-alkyl,
R101 is 1-4C-alkyl,
R102 is 1-4C-alkoxy, or 1-4C-alkyl,
Rba is selected from the group consisting of:
methoxy, ethoxy, trifluoromethoxy, and difluoromethoxy,
Rbb is selected from the group consisting of:
hydrogen, methyl, ethyl, methoxy, and ethoxy,
Rbc is hydrogen;
or a salt thereof.
28 . The method according to claim 22 , wherein the compound is one of the formulae Ia, Ib and Ic
wherein
Ra is —C(O)R1,
R1 is methyl, ethyl or propyl,
or
R1 is (Raa)-methyl, 2-(Raa)-ethyl, or 3-(Raa)-propyl, in which
Raa is pyridyl, pyrimidinyl, methyl-substituted pyridyl, or methoxy-substituted pyridyl,
or
R1 is (Raa)-methyl, 2-(Raa)-ethyl, or 3-(Raa)-propyl, in which
Raa is 1N-methyl-imidazolyl,
or
R1 is 2,3-dihydroxy-propyl,
or
R1 is (Raa)-methyl, 2-(Raa)-ethyl, or 3-(Raa)-propyl, in which
Raa is carboxyl, methoxycarbonyl, hydroxyl, methylcarbonyloxy, methoxy, ethoxy, benzyloxy, or 2-methoxyethoxy,
or
R1 is (Raa)-methyl, 2-(Raa)-ethyl, or 3-(Raa)-propyl, in which
Raa is imidazol-1-yl, or mono- or di-methyl-substituted imidazol-1-yl;
Q is 2-(Rba)-phenyl, 3-(Rba)-phenyl, 2-(Rba)-3-(Rbb)-phenyl, 2-(Rba)-5-(Rbb)-phenyl, 2-(Rba)-6-(Rbb)-phenyl, 2-(Rbb)-3-(Rba)-phenyl or 2-(Rbb)-5-(Rba)-phenyl,
Rba is selected from the group consisting of:
methoxy and ethoxy,
Rbb is selected from the group consisting of:
methyl and methoxy;
or a salt thereof.
29 . The method according to claim 22 , wherein the compound is one of the formulae Ia, Ib and Ic
wherein
Ra is —C(O)R1,
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is pyridyl,
or
R1 is (Raa)-methyl, in which
Raa is 1N-methyl-imidazolyl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is hydroxyl or methoxy,
or
R1 is (2-methoxyethoxy)-methyl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is imidazol-1-yl, or mono- or di-methyl-substituted imidazol-1-yl;
Q is 2-(Rba)-phenyl, 3-(Rba)-phenyl, 2-(Rba)-3-(Rbb)-phenyl, 2-(Rba)-5-(Rbb)-phenyl, 2-(Rba)-6-(Rbb)-phenyl, 2-(Rbb)-3-(Rba)-phenyl or 2-(Rbb)-5-(Rba)-phenyl,
Rba is selected from the group consisting of:
methoxy and ethoxy,
Rbb is methyl;
or a salt thereof.
30 . The method according to claim 22 , wherein the compound is one of the formulae Ia, lb and Ic
wherein
Ra is —C(O)R1,
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl,
or
R1 is (Raa)-methyl, in which
Raa is 1-methyl-imidazol-2-yl or 1-methyl-imidazol-5-yl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is hydroxyl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is imidazol-1-yl, 2-methyl-imidazol-1-yl, 4-methyl-imidazol-1-yl or 2,4-dimethyl-imidazol-1-yl;
Q is 2-methoxyphenyl,
or
Q is 2-ethoxyphenyl,
or
Q is 3-methoxyphenyl,
or
Q is 3-ethoxyphenyl,
or
Q is 2-(Rba)-3-(Rbb)-phenyl, in which
Rba is methoxy or ethoxy,
Rbb is methyl,
or
Q is 2-(Rba)-5-(Rbb)-phenyl, in which
Rba is methoxy or ethoxy,
Rbb is methyl;
or a salt thereof.
31 . The method according to claim 22 , wherein the compound is one of the formulae Ia, lb and Ic
wherein
Ra is —C(O)R1,
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is hydroxyl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is imidazol-1-yl;
Q is 2-methoxyphenyl,
or
Q is 2-ethoxyphenyl,
or
Q is 3-methoxyphenyl,
or
Q is 2-(Rba)-5-(Rbb)-phenyl, in which
Rba is methoxy,
Rbb is methyl;
or a salt thereof.
32 . The method according to claim 22 , wherein the compound is one of the formulae Ia and Ic
wherein
Ra is —C(O)R1,
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is pyridyl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is methoxy,
or
R1 is (2-methoxyethoxy)-methyl,
or
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is imidazol-1-yl;
Q is 2-(Rba)-phenyl, 3-(Rba)-phenyl, 2-(Rba)-3-(Rbb)-phenyl, 2-(Rba)-5-(Rbb)-phenyl, 2-(Rba)-6-(Rbb)-phenyl, 2-(Rbb)-3-(Rba)-phenyl or 2-(Rbb)-5-(Rba)-phenyl,
Rba is selected from the group consisting of:
methoxy and ethoxy,
Rbb is methyl;
or a salt thereof.
33 . The method according to claim 22 , wherein the compound is one of the formulae Ia and Ic
wherein
Ra is —C(O)R1,
R1 is (Raa)-methyl, or 2-(Raa)-ethyl, in which
Raa is pyridyl,
or
R1 is 2-(Raa)-ethyl, in which
Raa is imidazol-1-yl;
Q is 2-methoxyphenyl,
or
Q is 2-ethoxyphenyl,
or
Q is 3-methoxyphenyl,
or
Q is 3-ethoxyphenyl,
or
Q is 2-(Rba)-3-(Rbb)-phenyl, in which
Rba is methoxy or ethoxy,
Rbb is methyl,
or
Q is 2-(Rba)-5-(Rbb)-phenyl, in which
Rba is methoxy or ethoxy,
Rbb is methyl;
or a salt thereof.
34 . A method for treating a (hyper)proliferative disease of benign or malignant behaviour and/or disorder responsive to the induction of apoptosis in a patient, comprising administering to said patient in need thereof a therapeutically effective amount of a compound selected from the group consisting of
N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
4-{3-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl}-4-oxo-butyric acid methyl ester,
N-[3-Cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2-methoxy-ethoxy)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
Acetic acid 2-{3-cyano-2-[3-(2-methoxy-phenyl)-propanoylaminol]-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl}-2-oxo-ethyl ester,
N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
4-{3-Cyano-2-[3-(2-ethoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl}-4-oxo-butyric acid methyl ester,
Acetic acid 2-{3-cyano-2-[3-(2-ethoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl}-2-oxo-ethyl ester,
N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-methoxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-methoxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(4-hydroxy-butanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(3-methoxy-phenyl)-propionamide,
N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2-methoxy-ethoxy)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2-methoxy-ethoxy)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-methoxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-[3-Cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methyl-pyridin-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyrimidin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methoxy-pyridin-3-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-[3-Cyano-6-(3-methoxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2,5-dimethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methyl-pyridin-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methoxy-pyridin-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2,5-dimethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methoxy-6-methyl-pyridin-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2,5-dimethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methoxy-pyridin-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methoxy-6-methyl-pyridin-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-(6-Butyryl-3-cyan-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(2,5-dimethoxy-phenyl)-propionamide,
N-[6-(4-Chloro-butanoyl)-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-((RS)-3-imidazol-1-yl-butanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-((RS)-3-imidazol-1-yl-butanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-2-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(2-ethoxy-phenyl)-butyramide,
N-(6-Butyryl-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-3-(2-methoxy-phenyl)-propionamide,
(RS)—N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(2-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[3-(1-methyl-H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(4-methyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[2-(2,4-dimethyl-imidazol-1-yl)-ethanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(4-methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-{3-Cyano-6-[3-(2,4-dimethyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-{3-Cyano-6-[3-(2,4-dimethyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-ethoxy-phenyl)-butyramide,
N-{3-Cyano-6-[3-(2,4-di methyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(3-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(2,4-dimethyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(2,4-dimethyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-ethoxy-phenyl)-propionamide,
N-{3-Cyano-6-[3-(2,4-dimethyl-imidazol-1-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(RS)—N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
(RS)—N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-butyramide,
N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(3-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-phenyl)-propionamide,
N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-ethoxy-phenyl)-propionamide,
N-[3-Cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
N-[3-Cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-propionamide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid {3-cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-methoxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(2-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-pyridin-3-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-pyridin-4-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-pyridin-4-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-pyridin-3-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-pyridin-2-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-imidazol-1-yl-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-imidazol-1-yl-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid {3-cyano-6-[3-(1-methyl-1H-imidazol-2-yl)-propanoyl]-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl}-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-hydroxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2 RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-hydroxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide,
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(3-methoxy-propanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide, and
(1RS,2RS)-2-(3-Methoxy-phenyl)-cyclopropanecarboxylic acid [3-cyano-6-(2-methoxy-ethanoyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl]-amide and salts thereof.
35 . The method according to claim 34 , wherein the disease or disorder is benign hypoplasia, benign hypoplasia of the prostate (“BPH”) or colon epithelium, psoriasias, glomerulonephritis, osteoarthritis, a malignant neoplasia, a solid or hematological tumor, a tumor of the breast, bladder, bone, brain, central or peripheral nervus system, colon, endocrine glands, thyroid gland, adrenal cortex, esophagus, endometrium, germ cells, head and neck, kidney, liver, lung, larynx, hypopharynx, mesothelioma, sarcoma, ovary, pancreas, prostate, rectum, renal, small intestine, soft tissue, testis, stomach, skin, ureter, vagina or vulva, Retinomblastoma, Wilms tumor, leukemia, lymphoma, non-Hodgkins disease, chronic or acute myeloid leukemia (CML I AML), acute lymphoblastic leukemia (ALL), Hodgkins disease, multiple myeloma, T-cell lymphoma, myelodysplastic syndrome, plasma cell neoplasia, paraneoplastic syndrome, a cancer of unknown primary site or an AIDS related malignancy.
36 . The method according to claim 34 , wherein an enantiomer of a compound according to claim 1 or a salt thereof is administered.
37 . The method according to claim 22 , further comprising administering at least one further anti-cancer agent selected from the group consisting of chemotherapeutic anti-cancer agents and target-specific anti-cancer agents.
38 . The method according to claim 37 , wherein said chemotherapeutic anti-cancer agents are selected from the group consisting of (i) alkylating/carbamylating agents; (ii) platinum derivatives; (iii) antimitotic agents/tubulin inhibitors; (iv) topoisomerase inhibitors; (v) pyrimidine antagonists; (vi) purin antagonists; and (vii) folic acid antagonists.
39 . The method according to claim 37 , wherein said target-specific anti-cancer agents are selected from the group consisting of (i) kinase inhibitors; (ii) proteasome inhibitors; (iii) histone deacetylase inhibitors; (iv) heat shock protein 90 inhibitors; (v) vascular targeting agents, anti-angiogenic drugs and KDR tyrosine kinase inhibitors; (vi) monoclonal antibodies, mutants and conjugates of monoclonal antibodies and antibody fragments; (vii) oligonucleotide based therapeutics; (viii) Toll-like receptor/TLR 9 agonists, TLR 7 agonists and TLR 7/8 agonists; (ix) protease inhibitors; (x) hormonal therapeutics; (xi) aromatase inhibitors; (xii) bleomycin; (xiii) retinoids; (xiv) DNA methyltransferase inhibitors; (xv) alanosine; (xvi) cytokines; (xvii) interferons; (xviii) death receptor agonists; (xix) DR4/5 agonistic antibodies; (xx) FasL; and (xxi) TNF-R agonists.Cited by (0)
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