JP2008509910A5 - - Google Patents
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- Publication number
- JP2008509910A5 JP2008509910A5 JP2007525719A JP2007525719A JP2008509910A5 JP 2008509910 A5 JP2008509910 A5 JP 2008509910A5 JP 2007525719 A JP2007525719 A JP 2007525719A JP 2007525719 A JP2007525719 A JP 2007525719A JP 2008509910 A5 JP2008509910 A5 JP 2008509910A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidin
- carboxamide
- sulfonyl
- alkyl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims 93
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 91
- 125000000753 cycloalkyl group Chemical group 0.000 claims 80
- 125000003118 aryl group Chemical group 0.000 claims 73
- 125000001072 heteroaryl group Chemical group 0.000 claims 72
- 150000001875 compounds Chemical class 0.000 claims 48
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 42
- -1 nitro, cyano, amino Chemical group 0.000 claims 42
- 229910052799 carbon Inorganic materials 0.000 claims 41
- 125000003710 aryl alkyl group Chemical group 0.000 claims 40
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 38
- 125000005843 halogen group Chemical group 0.000 claims 36
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 30
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 30
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 30
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 17
- 150000001721 carbon Chemical group 0.000 claims 14
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 12
- 125000005466 alkylenyl group Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 11
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 238000007363 ring formation reaction Methods 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- WIBPFEGXBHVRFS-DLEWZHQMSA-N 4-hydroxy-n-[(3s)-1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C(C(F)(F)F)C=N1 WIBPFEGXBHVRFS-DLEWZHQMSA-N 0.000 claims 2
- NDOWOPYBXPNQJB-AAWLYWHWSA-N 6-[(3s)-3-[(4-hydroxyadamantane-1-carbonyl)amino]piperidin-1-yl]-n,n-dimethylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)N(C)C)=CC=C1N1C[C@@H](NC(=O)C23CC4CC(CC(C4O)C3)C2)CCC1 NDOWOPYBXPNQJB-AAWLYWHWSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- CKBZJTAMRPPVSR-UHFFFAOYSA-N adamantane-1-carboxamide Chemical compound C1C(C2)CC3CC2CC1(C(=O)N)C3 CKBZJTAMRPPVSR-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims 2
- HBMJKFXARKXJCY-ULQDDVLXSA-N (1s,3s)-n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3-methoxycyclohexane-1-carboxamide Chemical compound C1[C@@H](OC)CCC[C@@H]1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)CCC1 HBMJKFXARKXJCY-ULQDDVLXSA-N 0.000 claims 1
- JZEMBSQXWNRRTE-ULQDDVLXSA-N (1s,5s)-3-hydroxy-n-[(3s)-1-(2-methylphenyl)sulfonylpiperidin-3-yl]-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=CC=CC=C1C JZEMBSQXWNRRTE-ULQDDVLXSA-N 0.000 claims 1
- WBDDYONKZYZOSB-ULQDDVLXSA-N (1s,5s)-3-hydroxy-n-[(3s)-1-(3-methylphenyl)sulfonylpiperidin-3-yl]-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=CC=CC(C)=C1 WBDDYONKZYZOSB-ULQDDVLXSA-N 0.000 claims 1
- VJWNPYKUQXHHCR-FHWLQOOXSA-N (1s,5s)-3-hydroxy-n-[(3s)-1-naphthalen-1-ylsulfonylpiperidin-3-yl]-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C1=CC=C2C(S(=O)(=O)N3CCC[C@@H](C3)NC(=O)N3[C@@]4([H])CC[C@]3(CC(O)C4)[H])=CC=CC2=C1 VJWNPYKUQXHHCR-FHWLQOOXSA-N 0.000 claims 1
- ASAPBYZPKFYEIU-XIRDDKMYSA-N (1s,5s)-3-hydroxy-n-[(3s)-1-phenylpiperidin-3-yl]-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1C1=CC=CC=C1 ASAPBYZPKFYEIU-XIRDDKMYSA-N 0.000 claims 1
- GGMSNUXBMQOSBQ-IHRRRGAJSA-N (1s,5s)-n-[(3s)-1-(2,6-dichlorophenyl)sulfonylpiperidin-3-yl]-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=C(Cl)C=CC=C1Cl GGMSNUXBMQOSBQ-IHRRRGAJSA-N 0.000 claims 1
- MOYLUNFMRGWTBH-KKUMJFAQSA-N (1s,5s)-n-[(3s)-1-(2-fluorophenyl)sulfonylpiperidin-3-yl]-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=CC=CC=C1F MOYLUNFMRGWTBH-KKUMJFAQSA-N 0.000 claims 1
- TXALXNUTVKQOED-IHRRRGAJSA-N (1s,5s)-n-[(3s)-1-(3-chloro-2-fluorophenyl)sulfonylpiperidin-3-yl]-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=CC=CC(Cl)=C1F TXALXNUTVKQOED-IHRRRGAJSA-N 0.000 claims 1
- PIFSJOREBLLQLH-JYJNAYRXSA-N (1s,5s)-n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=CC=CC(Cl)=C1C PIFSJOREBLLQLH-JYJNAYRXSA-N 0.000 claims 1
- HYFVAXHYVKAJPP-JYJNAYRXSA-N (1s,5s)-n-[(3s)-1-(3-chlorophenyl)sulfonylpiperidin-3-yl]-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2[C@@]3([H])CC[C@]2(CC(O)C3)[H])CCN1S(=O)(=O)C1=CC=CC(Cl)=C1 HYFVAXHYVKAJPP-JYJNAYRXSA-N 0.000 claims 1
- IDYPIUNVAHYFBL-SQVUVWECSA-N (3s)-3-[(4-hydroxyadamantane-1-carbonyl)amino]-n-phenylpiperidine-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(=O)NC1=CC=CC=C1 IDYPIUNVAHYFBL-SQVUVWECSA-N 0.000 claims 1
- GTYBIGUTVHNATR-KRWDZBQOSA-N 1-methyl-n-[(3s)-1-phenylpiperidin-3-yl]indole-2-carboxamide Chemical compound C([C@@H](C1)NC(=O)C=2N(C3=CC=CC=C3C=2)C)CCN1C1=CC=CC=C1 GTYBIGUTVHNATR-KRWDZBQOSA-N 0.000 claims 1
- VAJHMBLRNPFMLL-UHFFFAOYSA-N 1-piperidin-3-ylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1CNCCC1 VAJHMBLRNPFMLL-UHFFFAOYSA-N 0.000 claims 1
- LGBKGSGPEFVJQI-KRWDZBQOSA-N 2-(2-methyl-1h-indol-3-yl)-n-[(3s)-1-phenylpiperidin-3-yl]acetamide Chemical compound C([C@@H](C1)NC(=O)CC=2C3=CC=CC=C3NC=2C)CCN1C1=CC=CC=C1 LGBKGSGPEFVJQI-KRWDZBQOSA-N 0.000 claims 1
- QBZIHVNYTCBHHN-AWEZNQCLSA-N 2-chloro-n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]benzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C(=CC=CC=2)Cl)CCC1 QBZIHVNYTCBHHN-AWEZNQCLSA-N 0.000 claims 1
- AEYSYIHTLODAAB-INIZCTEOSA-N 2-methyl-n-[(3s)-1-phenylpiperidin-3-yl]benzamide Chemical compound CC1=CC=CC=C1C(=O)N[C@@H]1CN(C=2C=CC=CC=2)CCC1 AEYSYIHTLODAAB-INIZCTEOSA-N 0.000 claims 1
- AADQBFFNDZHLGI-SFHVURJKSA-N 2-methyl-n-[(3s)-1-phenylpiperidin-3-yl]quinoline-3-carboxamide Chemical compound C([C@@H](C1)NC(=O)C2=CC3=CC=CC=C3N=C2C)CCN1C1=CC=CC=C1 AADQBFFNDZHLGI-SFHVURJKSA-N 0.000 claims 1
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims 1
- GYKQAEVWTBOURF-COIXEQEXSA-N 3-hydroxy-n-[(3s)-1-phenylpiperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C4)(C3)O)CCN1C1=CC=CC=C1 GYKQAEVWTBOURF-COIXEQEXSA-N 0.000 claims 1
- FCFIXEBRGSUTSF-ZBZISHEGSA-N 3-hydroxy-n-[(3s)-1-quinolin-8-ylsulfonylpiperidin-3-yl]-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C1=CN=C2C(S(=O)(=O)N3CCC[C@@H](C3)NC(=O)N3C4CCC3CC(C4)O)=CC=CC2=C1 FCFIXEBRGSUTSF-ZBZISHEGSA-N 0.000 claims 1
- KBJPKLYWRUZXIX-INIZCTEOSA-N 3-methoxy-n-[(3s)-1-phenylpiperidin-3-yl]benzamide Chemical compound COC1=CC=CC(C(=O)N[C@@H]2CN(CCC2)C=2C=CC=CC=2)=C1 KBJPKLYWRUZXIX-INIZCTEOSA-N 0.000 claims 1
- FNLZUKQTESIVSF-MPIHSMFISA-N 4-hydroxy-4-methyl-n-[(3s)-1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4(O)C)CCN1C1=CC=C(C(F)(F)F)C=N1 FNLZUKQTESIVSF-MPIHSMFISA-N 0.000 claims 1
- XXCHHLLNAPPEBQ-PGSCBNACSA-N 4-hydroxy-n-[(3s)-1-(1,3-thiazol-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=NC=CS1 XXCHHLLNAPPEBQ-PGSCBNACSA-N 0.000 claims 1
- WEFYWVGCCAMTHK-SAJIZACHSA-N 4-hydroxy-n-[(3s)-1-(4-methoxypyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound COC1=CC=NC(N2C[C@H](CCC2)NC(=O)C23CC4CC(CC(C4O)C3)C2)=C1 WEFYWVGCCAMTHK-SAJIZACHSA-N 0.000 claims 1
- BRYIPAGWSUPGMD-JZNKNQBLSA-N 4-hydroxy-n-[(3s)-1-(4-methylpyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound CC1=CC=NC(N2C[C@H](CCC2)NC(=O)C23CC4CC(CC(C4O)C3)C2)=C1 BRYIPAGWSUPGMD-JZNKNQBLSA-N 0.000 claims 1
- KMILPSIBKREGPZ-QQHNZBQLSA-N 4-hydroxy-n-[(3s)-1-(4-phenylmethoxyphenyl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1OCC1=CC=CC=C1 KMILPSIBKREGPZ-QQHNZBQLSA-N 0.000 claims 1
- TZIWVBRTWBIOTK-XTYDGOQYSA-N 4-hydroxy-n-[(3s)-1-(4-pyridin-2-ylphenyl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1C1=CC=CC=N1 TZIWVBRTWBIOTK-XTYDGOQYSA-N 0.000 claims 1
- IFFMLAZNWYYKDQ-WZGQANMZSA-N 4-hydroxy-n-[(3s)-1-(4-pyridin-3-ylphenyl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1C1=CC=CN=C1 IFFMLAZNWYYKDQ-WZGQANMZSA-N 0.000 claims 1
- MBFBHMQUUMIXSG-WZGQANMZSA-N 4-hydroxy-n-[(3s)-1-(4-pyridin-4-ylphenyl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1C1=CC=NC=C1 MBFBHMQUUMIXSG-WZGQANMZSA-N 0.000 claims 1
- QBSIFYKNJYUQFB-JZNKNQBLSA-N 4-hydroxy-n-[(3s)-1-(5-methylpyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound N1=CC(C)=CC=C1N1C[C@@H](NC(=O)C23CC4CC(CC(C4O)C3)C2)CCC1 QBSIFYKNJYUQFB-JZNKNQBLSA-N 0.000 claims 1
- OZOSGKMKCRYBME-VUWWJUAFSA-N 4-hydroxy-n-[(3s)-1-(5-nitropyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C([N+]([O-])=O)C=N1 OZOSGKMKCRYBME-VUWWJUAFSA-N 0.000 claims 1
- PFSNYQKUETWVLH-WSDZPULKSA-N 4-hydroxy-n-[(3s)-1-(5-pyridin-4-ylpyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(N=C1)=CC=C1C1=CC=NC=C1 PFSNYQKUETWVLH-WSDZPULKSA-N 0.000 claims 1
- OWJMWYFPUJOXJH-SAJIZACHSA-N 4-hydroxy-n-[(3s)-1-(6-methoxypyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound COC1=CC=CC(N2C[C@H](CCC2)NC(=O)C23CC4CC(CC(C4O)C3)C2)=N1 OWJMWYFPUJOXJH-SAJIZACHSA-N 0.000 claims 1
- FLTGFYDNYMEHJS-JZNKNQBLSA-N 4-hydroxy-n-[(3s)-1-(6-methylpyridin-2-yl)piperidin-3-yl]adamantane-1-carboxamide Chemical compound CC1=CC=CC(N2C[C@H](CCC2)NC(=O)C23CC4CC(CC(C4O)C3)C2)=N1 FLTGFYDNYMEHJS-JZNKNQBLSA-N 0.000 claims 1
- NRWXZJMDXJVCCH-RDFRHQLHSA-N 4-hydroxy-n-[(3s)-1-[4-(2-oxopyrrolidin-1-yl)phenyl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1N1CCCC1=O NRWXZJMDXJVCCH-RDFRHQLHSA-N 0.000 claims 1
- XENFGAJIOPLGJB-SAJIZACHSA-N 4-hydroxy-n-[(3s)-1-[4-(trifluoromethoxy)phenyl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C(OC(F)(F)F)C=C1 XENFGAJIOPLGJB-SAJIZACHSA-N 0.000 claims 1
- IWNZPENYIFKXMJ-KPKOXSBOSA-N 4-hydroxy-n-[(3s)-1-[4-(trifluoromethyl)phenyl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C(C(F)(F)F)C=C1 IWNZPENYIFKXMJ-KPKOXSBOSA-N 0.000 claims 1
- JRAOQJXBQOAXDO-VDWHLCGGSA-N 4-hydroxy-n-[(3s)-1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=NC=CC(C(F)(F)F)=N1 JRAOQJXBQOAXDO-VDWHLCGGSA-N 0.000 claims 1
- GKUDNBINYRIKII-APGZODFYSA-N 4-hydroxy-n-[(3s)-1-[5-(4-methoxyphenyl)pyridin-2-yl]piperidin-3-yl]adamantane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2C[C@H](CCC2)NC(=O)C23CC4CC(CC(C4O)C3)C2)N=C1 GKUDNBINYRIKII-APGZODFYSA-N 0.000 claims 1
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- HSAKVFPHMDNCQB-SFHVURJKSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-1-phenylcyclopropane-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2(CC2)C=2C=CC=CC=2)CCC1 HSAKVFPHMDNCQB-SFHVURJKSA-N 0.000 claims 1
- KDMHXWIJBQDJJR-ZDUSSCGKSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2,2-dimethylpropanamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C(C)(C)C)CCC1 KDMHXWIJBQDJJR-ZDUSSCGKSA-N 0.000 claims 1
- FHLTZIXRAFGTIK-QFIPXVFZSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2,2-diphenylacetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1 FHLTZIXRAFGTIK-QFIPXVFZSA-N 0.000 claims 1
- PMIWERGHLVMAJD-AWEZNQCLSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2,5-difluorobenzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C(=CC=C(F)C=2)F)CCC1 PMIWERGHLVMAJD-AWEZNQCLSA-N 0.000 claims 1
- FJDCIZHQAKEYDJ-ZDUSSCGKSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2,6-difluorobenzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C(=CC=CC=2F)F)CCC1 FJDCIZHQAKEYDJ-ZDUSSCGKSA-N 0.000 claims 1
- KTWVABVXUSXGEF-HNNXBMFYSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)CCC1 KTWVABVXUSXGEF-HNNXBMFYSA-N 0.000 claims 1
- DZPCSARWOSUSEN-INIZCTEOSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)CCC1 DZPCSARWOSUSEN-INIZCTEOSA-N 0.000 claims 1
- OHCTZUGHAGXFDY-ZDUSSCGKSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2-methylpropanamide Chemical compound C1[C@@H](NC(=O)C(C)C)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1C OHCTZUGHAGXFDY-ZDUSSCGKSA-N 0.000 claims 1
- VELFSPBJIRDVDE-FQEVSTJZSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-2-phenylbenzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)CCC1 VELFSPBJIRDVDE-FQEVSTJZSA-N 0.000 claims 1
- NNGKRAUGLCIFMO-INIZCTEOSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3,5-difluorobenzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C=C(F)C=C(F)C=2)CCC1 NNGKRAUGLCIFMO-INIZCTEOSA-N 0.000 claims 1
- ZXGVLXZPUVIDQB-INIZCTEOSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3-fluorobenzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C=C(F)C=CC=2)CCC1 ZXGVLXZPUVIDQB-INIZCTEOSA-N 0.000 claims 1
- SCPYCOFWEXCVIN-INIZCTEOSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)N[C@@H]2CN(CCC2)S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=C1 SCPYCOFWEXCVIN-INIZCTEOSA-N 0.000 claims 1
- HBMJKFXARKXJCY-CGZBRXJRSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3-methoxycyclohexane-1-carboxamide Chemical compound C1C(OC)CCCC1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)CCC1 HBMJKFXARKXJCY-CGZBRXJRSA-N 0.000 claims 1
- OHSDLXPQANOPBO-FQEVSTJZSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-3-phenoxybenzamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C=C(OC=3C=CC=CC=3)C=CC=2)CCC1 OHSDLXPQANOPBO-FQEVSTJZSA-N 0.000 claims 1
- XARYBFRJEMGMEL-PCKAHOCUSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-4-hydroxycyclohexane-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCC(O)CC2)CCC1 XARYBFRJEMGMEL-PCKAHOCUSA-N 0.000 claims 1
- YJCNOXVAXNOQJF-INIZCTEOSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)CCC1 YJCNOXVAXNOQJF-INIZCTEOSA-N 0.000 claims 1
- IQHPEWAXJXALRO-CGZBRXJRSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-4-methoxycyclohexane-1-carboxamide Chemical compound C1CC(OC)CCC1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)CCC1 IQHPEWAXJXALRO-CGZBRXJRSA-N 0.000 claims 1
- UKVFXTDHRXZJOV-HJGBXLFDSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]adamantane-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C23CC4CC(CC(C4)C2)C3)CCC1 UKVFXTDHRXZJOV-HJGBXLFDSA-N 0.000 claims 1
- LZRXVDBXYVQQRI-KRWDZBQOSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]cycloheptanecarboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCCC2)CCC1 LZRXVDBXYVQQRI-KRWDZBQOSA-N 0.000 claims 1
- LQLARWNDHJSQPI-HNNXBMFYSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]cyclopentanecarboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCC2)CCC1 LQLARWNDHJSQPI-HNNXBMFYSA-N 0.000 claims 1
- WATIJJUUTCNXSX-AWEZNQCLSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]morpholine-4-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)N2CCOCC2)CCC1 WATIJJUUTCNXSX-AWEZNQCLSA-N 0.000 claims 1
- NYCQNXOIOSIUGL-SFHVURJKSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]naphthalene-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C3=CC=CC=C3C=CC=2)CCC1 NYCQNXOIOSIUGL-SFHVURJKSA-N 0.000 claims 1
- XZGYPAGITPOEST-HNNXBMFYSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)N2CCCCC2)CCC1 XZGYPAGITPOEST-HNNXBMFYSA-N 0.000 claims 1
- JTEKRQJIQOPKMB-AWEZNQCLSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]pyridine-2-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2N=CC=CC=2)CCC1 JTEKRQJIQOPKMB-AWEZNQCLSA-N 0.000 claims 1
- AIYXKXZOWLUPHW-HNNXBMFYSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]pyridine-3-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C=NC=CC=2)CCC1 AIYXKXZOWLUPHW-HNNXBMFYSA-N 0.000 claims 1
- LHOOKUQWAHMQFY-HNNXBMFYSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]pyridine-4-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C=2C=CN=CC=2)CCC1 LHOOKUQWAHMQFY-HNNXBMFYSA-N 0.000 claims 1
- ITUCYAGBJDBPRH-AWEZNQCLSA-N n-[(3s)-1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]thiomorpholine-4-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)N2CCSCC2)CCC1 ITUCYAGBJDBPRH-AWEZNQCLSA-N 0.000 claims 1
- BNFCGPJAKOJIQC-AWEZNQCLSA-N n-[(3s)-1-(3-chloro-4-fluorophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=C(Cl)C(F)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 BNFCGPJAKOJIQC-AWEZNQCLSA-N 0.000 claims 1
- KJHWKWXEWOFRNZ-INIZCTEOSA-N n-[(3s)-1-(3-chlorophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound ClC1=CC=CC(S(=O)(=O)N2C[C@H](CCC2)NC(=O)C2CCCCC2)=C1 KJHWKWXEWOFRNZ-INIZCTEOSA-N 0.000 claims 1
- RLKFHAHOZDZWNK-KRWDZBQOSA-N n-[(3s)-1-(3-cyanophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C([C@@H](C1)NC(=O)C2CCCCC2)CCN1S(=O)(=O)C1=CC=CC(C#N)=C1 RLKFHAHOZDZWNK-KRWDZBQOSA-N 0.000 claims 1
- PLASQBGXICVKMB-VUWWJUAFSA-N n-[(3s)-1-(3-fluoropyridin-4-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=NC=C1F PLASQBGXICVKMB-VUWWJUAFSA-N 0.000 claims 1
- HDSGRYWPPYAJEN-KRWDZBQOSA-N n-[(3s)-1-(3-methylphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound CC1=CC=CC(S(=O)(=O)N2C[C@H](CCC2)NC(=O)C2CCCCC2)=C1 HDSGRYWPPYAJEN-KRWDZBQOSA-N 0.000 claims 1
- WREVZAQZAKIMEZ-FQEVSTJZSA-N n-[(3s)-1-(3-phenoxyphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C([C@@H](C1)NC(=O)C2CCCCC2)CCN1S(=O)(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 WREVZAQZAKIMEZ-FQEVSTJZSA-N 0.000 claims 1
- JOEKXZQDLZDNLZ-ZRGNBEGMSA-N n-[(3s)-1-(4-acetamidophenyl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1C[C@@H](NC(=O)C23CC4CC(CC(C4O)C3)C2)CCC1 JOEKXZQDLZDNLZ-ZRGNBEGMSA-N 0.000 claims 1
- VNVFRDSNXQSODV-BSFBHTCNSA-N n-[(3s)-1-(4-acetamidophenyl)piperidin-3-yl]-4-oxoadamantane-1-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1C[C@@H](NC(=O)C23CC4CC(CC(C4=O)C3)C2)CCC1 VNVFRDSNXQSODV-BSFBHTCNSA-N 0.000 claims 1
- QXWLZUPBCIGEBY-SFHVURJKSA-N n-[(3s)-1-(4-acetamidophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 QXWLZUPBCIGEBY-SFHVURJKSA-N 0.000 claims 1
- UCTLDTAUCCGENJ-HNNXBMFYSA-N n-[(3s)-1-(4-chloronaphthalen-1-yl)sulfonylpiperidin-3-yl]-4-hydroxypiperidine-1-carboxamide Chemical compound C1CC(O)CCN1C(=O)N[C@@H]1CN(S(=O)(=O)C=2C3=CC=CC=C3C(Cl)=CC=2)CCC1 UCTLDTAUCCGENJ-HNNXBMFYSA-N 0.000 claims 1
- MQYXYDLLZUTEJI-INIZCTEOSA-N n-[(3s)-1-(4-chlorophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 MQYXYDLLZUTEJI-INIZCTEOSA-N 0.000 claims 1
- BDGUEIZYJMOVJX-VDWHLCGGSA-N n-[(3s)-1-(4-chloropyrimidin-2-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=NC=CC(Cl)=N1 BDGUEIZYJMOVJX-VDWHLCGGSA-N 0.000 claims 1
- YQODQHHRTXXELD-BQOZVKGQSA-N n-[(3s)-1-(4-cyclohexyloxyphenyl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1OC1CCCCC1 YQODQHHRTXXELD-BQOZVKGQSA-N 0.000 claims 1
- KMGHVTXYSASDOO-LKFYMUEESA-N n-[(3s)-1-(4-cyclopentyloxyphenyl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C(C=C1)=CC=C1OC1CCCC1 KMGHVTXYSASDOO-LKFYMUEESA-N 0.000 claims 1
- JOHVYMYHPWMEOL-KRWDZBQOSA-N n-[(3s)-1-(4-fluoro-2-methylphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound CC1=CC(F)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 JOHVYMYHPWMEOL-KRWDZBQOSA-N 0.000 claims 1
- OGEXHBSKUPCAKX-BMWKDGKBSA-N n-[(3s)-1-(4-fluorophenyl)piperidin-3-yl]-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxamide Chemical compound C([C@@H](C1)NC(=O)N2C3CCC2CC(C3)O)CCN1C1=CC=C(F)C=C1 OGEXHBSKUPCAKX-BMWKDGKBSA-N 0.000 claims 1
- JSKCEOFVJFOTEU-INIZCTEOSA-N n-[(3s)-1-(4-fluorophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 JSKCEOFVJFOTEU-INIZCTEOSA-N 0.000 claims 1
- CBEXIZQEWOLTPG-INIZCTEOSA-N n-[(3s)-1-(4-methoxyphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 CBEXIZQEWOLTPG-INIZCTEOSA-N 0.000 claims 1
- USIUGCJHSSLAIM-KRWDZBQOSA-N n-[(3s)-1-(4-methylphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 USIUGCJHSSLAIM-KRWDZBQOSA-N 0.000 claims 1
- IUVMFHMZEHZXIJ-INIZCTEOSA-N n-[(3s)-1-(4-methylsulfonylphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 IUVMFHMZEHZXIJ-INIZCTEOSA-N 0.000 claims 1
- GLJRIJIRSJNNMN-IBGZPJMESA-N n-[(3s)-1-(4-phenoxypyridin-3-yl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C([C@@H](C1)NC(=O)C2CCCCC2)CCN1S(=O)(=O)C1=CN=CC=C1OC1=CC=CC=C1 GLJRIJIRSJNNMN-IBGZPJMESA-N 0.000 claims 1
- LZTAPRVEUJSXKK-IBGZPJMESA-N n-[(3s)-1-(4-propan-2-ylphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 LZTAPRVEUJSXKK-IBGZPJMESA-N 0.000 claims 1
- MPYZEWAKMIQZLX-IBGZPJMESA-N n-[(3s)-1-(4-pyridin-3-yloxyphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C([C@@H](C1)NC(=O)C2CCCCC2)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CN=C1 MPYZEWAKMIQZLX-IBGZPJMESA-N 0.000 claims 1
- LZSXSEPDMPAXKF-IBGZPJMESA-N n-[(3s)-1-(4-pyridin-4-yloxyphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C([C@@H](C1)NC(=O)C2CCCCC2)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=NC=C1 LZSXSEPDMPAXKF-IBGZPJMESA-N 0.000 claims 1
- PMTZXTNHYGEXPW-IBGZPJMESA-N n-[(3s)-1-(4-tert-butylphenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 PMTZXTNHYGEXPW-IBGZPJMESA-N 0.000 claims 1
- FBJCBWJIAMDPGS-HNNXBMFYSA-N n-[(3s)-1-(5-chloro-2-fluorophenyl)sulfonylpiperidin-3-yl]cyclohexanecarboxamide Chemical compound FC1=CC=C(Cl)C=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 FBJCBWJIAMDPGS-HNNXBMFYSA-N 0.000 claims 1
- HPFRRVHBOPIABW-DLEWZHQMSA-N n-[(3s)-1-(5-chloropyridin-2-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C(Cl)C=N1 HPFRRVHBOPIABW-DLEWZHQMSA-N 0.000 claims 1
- SQSUYCSCEOIDPF-JZNKNQBLSA-N n-[(3s)-1-(5-cyanopyridin-2-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C(C#N)C=N1 SQSUYCSCEOIDPF-JZNKNQBLSA-N 0.000 claims 1
- MSQCBIIQDSNBBZ-URMHCWEBSA-N n-[(3s)-1-(5-ethylpyrimidin-2-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound N1=CC(CC)=CN=C1N1C[C@@H](NC(=O)C23CC4CC(CC(C4O)C3)C2)CCC1 MSQCBIIQDSNBBZ-URMHCWEBSA-N 0.000 claims 1
- SUAYKSZBUAQOQH-DLEWZHQMSA-N n-[(3s)-1-(5-fluoropyridin-2-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=C(F)C=N1 SUAYKSZBUAQOQH-DLEWZHQMSA-N 0.000 claims 1
- PRDCHBWINGQRSV-VUWWJUAFSA-N n-[(3s)-1-(6-fluoropyridin-2-yl)piperidin-3-yl]-4-hydroxyadamantane-1-carboxamide Chemical compound C([C@@H](C1)NC(=O)C23CC4CC(C2)CC(C3)C4O)CCN1C1=CC=CC(F)=N1 PRDCHBWINGQRSV-VUWWJUAFSA-N 0.000 claims 1
- XBVHDCUDBVCAJM-INIZCTEOSA-N n-[(3s)-1-(benzenesulfonyl)piperidin-3-yl]cyclohexanecarboxamide Chemical compound C([C@@H](C1)NC(=O)C2CCCCC2)CCN1S(=O)(=O)C1=CC=CC=C1 XBVHDCUDBVCAJM-INIZCTEOSA-N 0.000 claims 1
- RWLLAVCYAQFHIA-HNNXBMFYSA-N n-[(3s)-1-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]piperidin-3-yl]cyclohexanecarboxamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)N1C[C@@H](NC(=O)C2CCCCC2)CCC1 RWLLAVCYAQFHIA-HNNXBMFYSA-N 0.000 claims 1
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2005
- 2005-08-09 WO PCT/US2005/028201 patent/WO2006020598A2/en not_active Ceased
- 2005-08-09 TW TW094127057A patent/TW200626156A/zh unknown
- 2005-08-09 EP EP05790468A patent/EP1778229A4/en not_active Withdrawn
- 2005-08-09 JP JP2007525719A patent/JP2008509910A/ja not_active Withdrawn
- 2005-08-09 US US11/199,763 patent/US20060122197A1/en not_active Abandoned
- 2005-08-09 AU AU2005273986A patent/AU2005273986A1/en not_active Abandoned
- 2005-08-09 KR KR1020077005642A patent/KR20070050076A/ko not_active Withdrawn
- 2005-08-09 CA CA002575561A patent/CA2575561A1/en not_active Abandoned
- 2005-08-09 MX MX2007001540A patent/MX2007001540A/es not_active Application Discontinuation
- 2005-08-09 CN CNA2005800344287A patent/CN101080226A/zh active Pending
- 2005-08-09 EA EA200700251A patent/EA200700251A1/ru unknown
- 2005-08-09 BR BRPI0514230-0A patent/BRPI0514230A/pt not_active IP Right Cessation
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2007
- 2007-02-05 IL IL181174A patent/IL181174A0/en unknown
- 2007-02-05 CR CR8901A patent/CR8901A/es unknown
- 2007-02-23 NO NO20071048A patent/NO20071048L/no not_active Application Discontinuation
- 2007-03-09 EC EC2007007309A patent/ECSP077309A/es unknown