JP2012509940A5 - - Google Patents
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- Publication number
- JP2012509940A5 JP2012509940A5 JP2011538682A JP2011538682A JP2012509940A5 JP 2012509940 A5 JP2012509940 A5 JP 2012509940A5 JP 2011538682 A JP2011538682 A JP 2011538682A JP 2011538682 A JP2011538682 A JP 2011538682A JP 2012509940 A5 JP2012509940 A5 JP 2012509940A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrol
- octahydrocyclopenta
- trifluoromethyl
- methyl
- phenyl
- 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.)
- Pending
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- -1 nitro, oxo, phenyl Chemical group 0.000 claims 217
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 213
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 140
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 111
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 95
- 229910052739 hydrogen Inorganic materials 0.000 claims 61
- 239000001257 hydrogen Substances 0.000 claims 61
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 49
- 125000003118 aryl group Chemical group 0.000 claims 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims 34
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 29
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical group 0.000 claims 20
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 229960004295 valine Drugs 0.000 claims 7
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- GPYTYOMSQHBYTK-LURJTMIESA-N (2s)-2-azaniumyl-2,3-dimethylbutanoate Chemical compound CC(C)[C@](C)([NH3+])C([O-])=O GPYTYOMSQHBYTK-LURJTMIESA-N 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- QCIGLPLDNRDLQQ-UHFFFAOYSA-N butan-2-ylcarbamic acid Chemical compound CCC(C)NC(O)=O QCIGLPLDNRDLQQ-UHFFFAOYSA-N 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- HZMVPSHLMIQQNX-UHFFFAOYSA-N pentan-2-yl carbamate Chemical compound CCCC(C)OC(N)=O HZMVPSHLMIQQNX-UHFFFAOYSA-N 0.000 claims 3
- NPDWHDXPQPMHJR-UHFFFAOYSA-N pentan-2-ylcarbamic acid Chemical compound CCCC(C)NC(O)=O NPDWHDXPQPMHJR-UHFFFAOYSA-N 0.000 claims 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- WAUGGYPDCQZJKK-UHFFFAOYSA-N 1h-pyrrol-3-amine Chemical compound NC=1C=CNC=1 WAUGGYPDCQZJKK-UHFFFAOYSA-N 0.000 claims 2
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical group FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- VGEIIVMUMFPNKY-SAJDGTNDSA-N (2S)-N-[(3aR,4S,6aS)-2-[[3-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-amino-4-methyl-2-methylsulfonylpentanamide Chemical compound CS(=O)(=O)[C@@](N)(CC(C)C)C(=O)N[C@H]1CC[C@@H]2CN(C[C@@H]21)CC1=CC(=CC=C1)C(F)(F)F VGEIIVMUMFPNKY-SAJDGTNDSA-N 0.000 claims 1
- VGEIIVMUMFPNKY-SFFNPBHPSA-N (2S)-N-[(3aS,4R,6aR)-2-[[3-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-amino-4-methyl-2-methylsulfonylpentanamide Chemical compound CS(=O)(=O)[C@@](N)(CC(C)C)C(=O)N[C@@H]1CC[C@H]2CN(C[C@H]21)CC1=CC(=CC=C1)C(F)(F)F VGEIIVMUMFPNKY-SFFNPBHPSA-N 0.000 claims 1
- AFYSEMLDHWBGBG-LUKWVAJMSA-N (2r)-n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@H](CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AFYSEMLDHWBGBG-LUKWVAJMSA-N 0.000 claims 1
- ZIIGNHNCZKJHGP-GFRNBQLOSA-N (2r)-n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@H](C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZIIGNHNCZKJHGP-GFRNBQLOSA-N 0.000 claims 1
- ZHCVAQPWDAYWNI-OLKYXYMISA-N (2r)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3,3-dimethyl-2-phenylbutanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@H](C(C)(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZHCVAQPWDAYWNI-OLKYXYMISA-N 0.000 claims 1
- XGHGKVOKFBNHFC-QCSYZSNVSA-N (2s)-n-[(3ar,4s,6as)-2-[3-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C[C@@H]3[C@@H](NC(=O)[C@H]4NCCCC4)CC[C@@H]3C2)=C1 XGHGKVOKFBNHFC-QCSYZSNVSA-N 0.000 claims 1
- VFMZAEZBXACMRF-QKDIEKDRSA-N (2s)-n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-[4-(2-methylpropyl)phenyl]propanamide Chemical compound C1=CC(CC(C)C)=CC=C1[C@H](C)C(=O)N[C@@H]1[C@H]2CN(CC=3C=CC=CC=3)C[C@H]2CC1 VFMZAEZBXACMRF-QKDIEKDRSA-N 0.000 claims 1
- AFYSEMLDHWBGBG-LDVJMBRRSA-N (2s)-n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@@H](CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AFYSEMLDHWBGBG-LDVJMBRRSA-N 0.000 claims 1
- ZIIGNHNCZKJHGP-XGARDCMYSA-N (2s)-n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@@H](C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZIIGNHNCZKJHGP-XGARDCMYSA-N 0.000 claims 1
- JIJXKKFQLDKTJP-LIRZEXBASA-N (2s)-n-[(3as,4r,6ar)-2-(4-fluorophenyl)sulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 JIJXKKFQLDKTJP-LIRZEXBASA-N 0.000 claims 1
- WQZWOLQTLQNVGD-OTGYPNLISA-N (2s)-n-[(3as,4r,6ar)-2-[(1s)-1-phenylethyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C1([C@H](C)N2C[C@@H]3CC[C@H]([C@@H]3C2)NC(=O)[C@@H](CC)C=2C=CC=CC=2)=CC=CC=C1 WQZWOLQTLQNVGD-OTGYPNLISA-N 0.000 claims 1
- PJQNPTHRIJPDSO-AITUJVMLSA-N (2s)-n-[(3as,4r,6ar)-2-[(4-fluorophenyl)methyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1CN1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 PJQNPTHRIJPDSO-AITUJVMLSA-N 0.000 claims 1
- XGHGKVOKFBNHFC-LIRZEXBASA-N (2s)-n-[(3as,4r,6ar)-2-[3-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C[C@H]3[C@H](NC(=O)[C@H]4NCCCC4)CC[C@H]3C2)=C1 XGHGKVOKFBNHFC-LIRZEXBASA-N 0.000 claims 1
- XHAOOIHWQCRONK-LIRZEXBASA-N (2s)-n-[(3as,4r,6ar)-2-[4-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 XHAOOIHWQCRONK-LIRZEXBASA-N 0.000 claims 1
- XBKSTLUJFXKPCT-AITUJVMLSA-N (2s)-n-[(3as,4r,6ar)-2-[[4-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 XBKSTLUJFXKPCT-AITUJVMLSA-N 0.000 claims 1
- AFYSEMLDHWBGBG-MYDTUXCISA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AFYSEMLDHWBGBG-MYDTUXCISA-N 0.000 claims 1
- ZIIGNHNCZKJHGP-GUGJDKNPSA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-phenylpropanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZIIGNHNCZKJHGP-GUGJDKNPSA-N 0.000 claims 1
- ZHCVAQPWDAYWNI-KEZOAJOQSA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3,3-dimethyl-2-phenylbutanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](C(C)(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZHCVAQPWDAYWNI-KEZOAJOQSA-N 0.000 claims 1
- NUBHGCWUZZYQCT-AFXVXQJMSA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-morpholin-4-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(CC=4C=CC=CC=4)C[C@@H]3CC2)CCOCC1 NUBHGCWUZZYQCT-AFXVXQJMSA-N 0.000 claims 1
- DFHVCZMXZUUYEF-KEZOAJOQSA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-piperidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(CC=4C=CC=CC=4)C[C@@H]3CC2)CCCCC1 DFHVCZMXZUUYEF-KEZOAJOQSA-N 0.000 claims 1
- MMAPUUNPFVWZNT-AFXVXQJMSA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(CC=4C=CC=CC=4)C[C@@H]3CC2)CCCC1 MMAPUUNPFVWZNT-AFXVXQJMSA-N 0.000 claims 1
- FDNJHAFULMBTQR-MANSERQUSA-N (2s)-n-[(3as,4r,6ar)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@H]2NCCCC2)N1CC1=CC=CC=C1 FDNJHAFULMBTQR-MANSERQUSA-N 0.000 claims 1
- QOBBCGKBMUMPEY-AITUJVMLSA-N (2s)-n-[(3as,4r,6ar)-2-cyclopropylsulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(C[C@@H]3CC2)S(=O)(=O)C2CC2)CCCC1 QOBBCGKBMUMPEY-AITUJVMLSA-N 0.000 claims 1
- UEDWLWBUBRWATL-HZMVEIRTSA-N (2s)-n-[(3as,4r,6ar)-2-methylsulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(C[C@@H]3CC2)S(C)(=O)=O)CCCC1 UEDWLWBUBRWATL-HZMVEIRTSA-N 0.000 claims 1
- DGNINGBAZJPLSW-INWMFGNUSA-N (3ar,4s,6as)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-n,n-diethyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-amine Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)N(CC)CC)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl DGNINGBAZJPLSW-INWMFGNUSA-N 0.000 claims 1
- XKAWHGWXUGNVQR-WPGHFRTFSA-N (3ar,4s,6as)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-n-[5-(trifluoromethyl)pyridin-2-yl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1N[C@@H]1[C@H]2CN(S(=O)(=O)C=3C(=CC(=CC=3)C(F)(F)F)Cl)C[C@H]2CC1 XKAWHGWXUGNVQR-WPGHFRTFSA-N 0.000 claims 1
- RXWBIZNXTMGFAV-OSMZGAPFSA-N (3ar,4s,6as)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-n-ethyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-amine Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NCC)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl RXWBIZNXTMGFAV-OSMZGAPFSA-N 0.000 claims 1
- BPRGUKOJPVNZHW-ZLDLUXBVSA-N (3ar,4s,6as)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-n-propan-2-yl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-amine Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(C)C)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl BPRGUKOJPVNZHW-ZLDLUXBVSA-N 0.000 claims 1
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- GOCBIHNWMDBMGM-RAMLRSSZSA-N n-[(3ar,4s,6as)-2-[3-(2-methylphenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC=C1C GOCBIHNWMDBMGM-RAMLRSSZSA-N 0.000 claims 1
- YDWIXNYGPSXIRF-UZGMISGMSA-N n-[(3ar,4s,6as)-2-[3-(3-chlorophenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(Cl)=C1 YDWIXNYGPSXIRF-UZGMISGMSA-N 0.000 claims 1
- BFMZOFRSTNVLKU-UZGMISGMSA-N n-[(3ar,4s,6as)-2-[3-(3-fluorophenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(F)=C1 BFMZOFRSTNVLKU-UZGMISGMSA-N 0.000 claims 1
- DEWZDZQKZHTKMB-RAMLRSSZSA-N n-[(3ar,4s,6as)-2-[3-(3-methylphenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(C)=C1 DEWZDZQKZHTKMB-RAMLRSSZSA-N 0.000 claims 1
- RNDDOHQGBFHRRD-PLFRKVQXSA-N n-[(3ar,4s,6as)-2-[3-(4-tert-butylphenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=C(C(C)(C)C)C=C1 RNDDOHQGBFHRRD-PLFRKVQXSA-N 0.000 claims 1
- NDMXQOUDOHEXMV-UZGMISGMSA-N n-[(3ar,4s,6as)-2-[3-[3-(trifluoromethyl)phenyl]propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(C(F)(F)F)=C1 NDMXQOUDOHEXMV-UZGMISGMSA-N 0.000 claims 1
- VTWSFYYTEQRDKR-UZGMISGMSA-N n-[(3ar,4s,6as)-2-[3-[4-(trifluoromethyl)phenyl]propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=C(C(F)(F)F)C=C1 VTWSFYYTEQRDKR-UZGMISGMSA-N 0.000 claims 1
- LIDPUHPUOYOHKJ-HOMPBRHSSA-N n-[(3ar,4s,6as)-2-[4,4-bis(4-fluorophenyl)butyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 LIDPUHPUOYOHKJ-HOMPBRHSSA-N 0.000 claims 1
- SYQKRALDUSLNEI-COXVUDFISA-N n-[(3ar,4s,6as)-2-[4-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)N[C@@H]1[C@H]2CN(S(=O)(=O)C=3C=CC(=CC=3)C(F)(F)F)C[C@H]2CC1 SYQKRALDUSLNEI-COXVUDFISA-N 0.000 claims 1
- GOVBSNDWEVMCCG-JLSDUUJJSA-N n-[(3ar,4s,6as)-2-[4-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-n-methyl-2-nitrobenzenesulfonamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)N(C)S(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 GOVBSNDWEVMCCG-JLSDUUJJSA-N 0.000 claims 1
- HAGVAOVIOPYLKI-BYKNITIXSA-N n-[(3ar,4s,6as)-2-[5,5-bis(4-fluorophenyl)pentyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 HAGVAOVIOPYLKI-BYKNITIXSA-N 0.000 claims 1
- BRFLFYAITKCSIZ-GYGZHRCXSA-N n-[(3ar,4s,6as)-2-[6,6-bis(4-fluorophenyl)hexyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BRFLFYAITKCSIZ-GYGZHRCXSA-N 0.000 claims 1
- CCFLIQFJRUCFCB-KBMXLJTQSA-N n-[(3ar,4s,6as)-2-[6-(trifluoromethyl)pyridin-2-yl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)N[C@@H]1[C@H]2CN(C=3N=C(C=CC=3)C(F)(F)F)C[C@H]2CC1 CCFLIQFJRUCFCB-KBMXLJTQSA-N 0.000 claims 1
- WRHXIEPCASAPCY-ZRSRXCJOSA-N n-[(3ar,4s,6as)-2-[[2-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1C(F)(F)F WRHXIEPCASAPCY-ZRSRXCJOSA-N 0.000 claims 1
- DYRMMCRLIMMOJL-LSSMUYGWSA-N n-[(3ar,4s,6as)-2-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=C(C(F)(F)F)C(F)=C1 DYRMMCRLIMMOJL-LSSMUYGWSA-N 0.000 claims 1
- FBUNVEFOYSAPBM-LSSMUYGWSA-N n-[(3ar,4s,6as)-2-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=C(F)C(C(F)(F)F)=C1 FBUNVEFOYSAPBM-LSSMUYGWSA-N 0.000 claims 1
- NATSUVQXKCVDKZ-ZFSMBLLKSA-N n-[(3ar,4s,6as)-2-benzoyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1 NATSUVQXKCVDKZ-ZFSMBLLKSA-N 0.000 claims 1
- NWOTVJCUJHEELF-VJTSUQJLSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-1-phenylcyclohexane-1-carboxamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C2(CCCCC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 NWOTVJCUJHEELF-VJTSUQJLSA-N 0.000 claims 1
- MASLRAWNNPKERH-HJNYFJLDSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-1-phenylcyclopropane-1-carboxamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C2(CC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 MASLRAWNNPKERH-HJNYFJLDSA-N 0.000 claims 1
- IQEVAHZYBSUYPP-RZFJZAQRSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,2-bis(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C(=O)N[C@@H]1[C@H]2CN(CC=3C=CC=CC=3)C[C@H]2CC1 IQEVAHZYBSUYPP-RZFJZAQRSA-N 0.000 claims 1
- USIBBSAAJMNUPN-ZNZIZOMTSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CCCCC2)C2CCCCC2)N1CC1=CC=CC=C1 USIBBSAAJMNUPN-ZNZIZOMTSA-N 0.000 claims 1
- KQQJEVURYCVLGV-LBSFNXSNSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,3-diphenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(CC=2C=CC=CC=2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 KQQJEVURYCVLGV-LBSFNXSNSA-N 0.000 claims 1
- MMRDVXCWKZHBDM-JDMZLTFJSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-(4-chlorophenyl)-3-methylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC(Cl)=CC=2)N1CC1=CC=CC=C1 MMRDVXCWKZHBDM-JDMZLTFJSA-N 0.000 claims 1
- STTSBVHXFVXHRR-JDMZLTFJSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-(4-hydroxyphenyl)-3-methylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC(O)=CC=2)N1CC1=CC=CC=C1 STTSBVHXFVXHRR-JDMZLTFJSA-N 0.000 claims 1
- JYMDHABUCGOMGF-JJZURMAISA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-benzyl-3,3-dimethylbutanamide Chemical compound N([C@@H]1[C@H]2CN(CC=3C=CC=CC=3)C[C@H]2CC1)C(=O)C(C(C)(C)C)CC1=CC=CC=C1 JYMDHABUCGOMGF-JJZURMAISA-N 0.000 claims 1
- JEXAZUMKXNHAFK-XXRNLSRLSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-cyclobutyl-2-phenylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CCC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 JEXAZUMKXNHAFK-XXRNLSRLSA-N 0.000 claims 1
- BDECLCVAQQPYIA-VHNWMKGBSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-cyclopentyl-2-phenylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CCCC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 BDECLCVAQQPYIA-VHNWMKGBSA-N 0.000 claims 1
- WJJWYFRYFSYNPN-XDXUOVRZSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-cyclopropyl-2-phenylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 WJJWYFRYFSYNPN-XDXUOVRZSA-N 0.000 claims 1
- ZOWLHDAHUAMRTQ-HJNYFJLDSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-methyl-2-phenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C)(C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZOWLHDAHUAMRTQ-HJNYFJLDSA-N 0.000 claims 1
- GGTHRHXEGUHINV-NSGAJXJNSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2-methyl-3-phenylpropanamide Chemical compound N([C@@H]1[C@H]2CN(CC=3C=CC=CC=3)C[C@H]2CC1)C(=O)C(C)CC1=CC=CC=C1 GGTHRHXEGUHINV-NSGAJXJNSA-N 0.000 claims 1
- ZHCVAQPWDAYWNI-XDXUOVRZSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3,3-dimethyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZHCVAQPWDAYWNI-XDXUOVRZSA-N 0.000 claims 1
- AEHLVQDFIMVPSJ-VHNWMKGBSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-ethyl-2-phenylpentanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(CC)CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AEHLVQDFIMVPSJ-VHNWMKGBSA-N 0.000 claims 1
- HEVYJRZHYSRHDM-XDXUOVRZSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 HEVYJRZHYSRHDM-XDXUOVRZSA-N 0.000 claims 1
- PDFATPKTQIBOSI-AABGKKOBSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-propan-2-ylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C(C)C)N1CC1=CC=CC=C1 PDFATPKTQIBOSI-AABGKKOBSA-N 0.000 claims 1
- IHQZJMDOKJOKIE-SQNIBIBYSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)CC(C)C)N1CC1=CC=CC=C1 IHQZJMDOKJOKIE-SQNIBIBYSA-N 0.000 claims 1
- CNBIUZXLXDADDC-XXRNLSRLSA-N n-[(3ar,4s,6as)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-n,3-dimethyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)N(C)C(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 CNBIUZXLXDADDC-XXRNLSRLSA-N 0.000 claims 1
- BGZOADFLQOFKNC-KKSQLVLISA-N n-[(3ar,4s,6as)-2-methyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound N([C@@H]1[C@H]2CN(C)C[C@H]2CC1)C(=O)C(C(C)C)C1=CC=CC=C1 BGZOADFLQOFKNC-KKSQLVLISA-N 0.000 claims 1
- LCHOSRIKTHYCQA-IPMKNSEASA-N n-[(3as,4r,6ar)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound N([C@H]1[C@@H]2CNC[C@@H]2CC1)C(=O)C(C1CCCCC1)C1CCCCC1 LCHOSRIKTHYCQA-IPMKNSEASA-N 0.000 claims 1
- WNPKHVYUJWDHTA-HEAIWMBWSA-N n-[(3as,4r,6ar)-2-(3,3-diphenylpropyl)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)C(C2CCCCC2)C2CCCCC2)N1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 WNPKHVYUJWDHTA-HEAIWMBWSA-N 0.000 claims 1
- NAHLNYDVBZOUFA-BKKFENPESA-N n-[(3as,4r,6ar)-2-[(2r)-2-(dimethylamino)-4-methylpentanoyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound N([C@@H]1CC[C@H]2CN(C[C@H]21)C(=O)[C@H](N(C)C)CC(C)C)C(=O)C(C1CCCCC1)C1CCCCC1 NAHLNYDVBZOUFA-BKKFENPESA-N 0.000 claims 1
- SIYCCBZZNCPXKJ-AQEWBBHDSA-N n-[(3as,4r,6ar)-2-[3,3-bis(4-fluorophenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCN1C[C@H]2[C@H](NC(=O)C(C3CCCCC3)C3CCCCC3)CC[C@H]2C1 SIYCCBZZNCPXKJ-AQEWBBHDSA-N 0.000 claims 1
- FLWIQOZBJZNRSS-KGJXQKDRSA-N n-[(3as,4r,6ar)-2-[4,4-bis(4-fluorophenyl)butyl]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1C[C@H]2[C@H](NC(=O)C(C3CCCCC3)C3CCCCC3)CC[C@H]2C1 FLWIQOZBJZNRSS-KGJXQKDRSA-N 0.000 claims 1
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| US11799508P | 2008-11-26 | 2008-11-26 | |
| US61/117,995 | 2008-11-26 | ||
| PCT/US2009/065847 WO2010062927A2 (en) | 2008-11-26 | 2009-11-25 | Novel substituted octahydrocyclopenta(c)pyrrol-4-amines as calcium channel blockers |
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| JP2012509940A JP2012509940A (ja) | 2012-04-26 |
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| US (1) | US8129417B2 (OSRAM) |
| EP (1) | EP2367790A2 (OSRAM) |
| JP (1) | JP2012509940A (OSRAM) |
| KR (1) | KR20110091784A (OSRAM) |
| CN (1) | CN102292319A (OSRAM) |
| AR (1) | AR074226A1 (OSRAM) |
| AU (1) | AU2009319796A1 (OSRAM) |
| BR (1) | BRPI0921184A2 (OSRAM) |
| CA (1) | CA2742350A1 (OSRAM) |
| CL (1) | CL2011001176A1 (OSRAM) |
| CO (1) | CO6382118A2 (OSRAM) |
| CR (1) | CR20110304A (OSRAM) |
| EC (1) | ECSP11011160A (OSRAM) |
| IL (1) | IL212484A0 (OSRAM) |
| MX (1) | MX2011005537A (OSRAM) |
| NZ (1) | NZ592507A (OSRAM) |
| PA (1) | PA8850301A1 (OSRAM) |
| PE (1) | PE20110833A1 (OSRAM) |
| RU (1) | RU2011126215A (OSRAM) |
| TW (1) | TW201028378A (OSRAM) |
| UY (1) | UY32261A (OSRAM) |
| WO (1) | WO2010062927A2 (OSRAM) |
| ZA (1) | ZA201103538B (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR074226A1 (es) | 2008-11-26 | 2010-12-29 | Abbott Lab | Octahidrociclopenta[c]pirrol-4-aminas sustituidas como bloqueantes de los canales de calcio, composiciones farmaceuticas que las comprenden y el uso de las mismas para el tratamiento del dolor. |
| US8211933B2 (en) * | 2008-12-12 | 2012-07-03 | Vanderbilt University | 3.3.0 bicyclic GlyT1 inhibitors and methods of making and using same |
| WO2011115813A1 (en) * | 2010-03-18 | 2011-09-22 | Abbott Laboratories | Lactam acetamides as calcium channel blockers |
| WO2011149995A1 (en) * | 2010-05-25 | 2011-12-01 | Abbott Laboratories | Novel substituted octahydrocyclopenta [c]pyrrol-4-amines as calcium channel blockers |
| US8796470B2 (en) | 2010-05-25 | 2014-08-05 | Abbvie Inc. | Substituted octahydrocyclopenta[c]pyrroles as calcium channel modulators |
| FR2976285B1 (fr) * | 2011-06-08 | 2013-05-24 | Servier Lab | Procede de synthese et forme cristalline du chlorhydrate de 4-{3-[cis-hexahydrocypenta[c]pyrrol-2(1h)-yl]propoxy}benzamide ainsi que les compositions pharmaceutiques qui la contiennent |
| WO2013049164A1 (en) | 2011-09-29 | 2013-04-04 | Abbvie Inc. | SUBSTITUTED OCTAHYDROPYRROLO[1,2-a]PYRAZINES AS CALCIUM CHANNEL BLOCKERS |
| WO2013049174A1 (en) | 2011-09-29 | 2013-04-04 | Abbvie Inc. | Substituted octahydropyrrolo[1,2-a]pyrazine sulfonamides as calcium channel blockers |
| KR20150093237A (ko) | 2012-12-12 | 2015-08-17 | 애브비 인코포레이티드 | 통증 치료시 칼슘 채널 차단제로서 유용한 디아제핀 유도체 |
| WO2017063563A1 (zh) * | 2015-10-13 | 2017-04-20 | 四川海思科制药有限公司 | 一种八氢环戊烷并[c]吡咯衍生物及其制备方法和在医药上的用途 |
| CN118684652A (zh) * | 2017-09-11 | 2024-09-24 | 克鲁松制药公司 | SHP2的八氢环戊二烯并[c]吡咯别构抑制剂 |
| US12054500B2 (en) | 2018-03-05 | 2024-08-06 | Arcus Biosciences, Inc. | Arginase inhibitors |
| AU2020480829A1 (en) | 2020-12-07 | 2023-07-20 | Kimberly-Clark Worldwide, Inc. | Methods and consumer products for detecting a metabolite |
| WO2022211060A1 (ja) | 2021-04-01 | 2022-10-06 | 小野薬品工業株式会社 | Ａｂｈｄ６アンタゴニスト |
| KR20240046089A (ko) | 2022-09-30 | 2024-04-08 | 오노 야꾸힝 고교 가부시키가이샤 | Abhd6 길항제를 함유하는 약학 조성물 |
| JP7852604B2 (ja) * | 2022-09-30 | 2026-04-28 | 小野薬品工業株式会社 | Ａｂｈｄ６アンタゴニストを含有する医薬組成物 |
| TW202421635A (zh) | 2022-09-30 | 2024-06-01 | 日商小野藥品工業股份有限公司 | Abhd6拮抗劑 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0278659A (ja) | 1988-09-12 | 1990-03-19 | Shionogi & Co Ltd | アザビシクロアルカン類化合物 |
| DE60011755T2 (de) * | 1999-04-07 | 2005-06-30 | The University Of Virginia Patent Foundation | Calciumkanalblocker als antikrebsmittel |
| US8163769B2 (en) * | 2002-03-12 | 2012-04-24 | Abbott Laboratories | Antibacterial compounds |
| US7223754B2 (en) * | 2003-03-10 | 2007-05-29 | Dynogen Pharmaceuticals, Inc. | Thiazolidinone, oxazolidinone, and imidazolone derivatives for treating lower urinary tract and related disorders |
| WO2004083207A1 (en) * | 2003-03-12 | 2004-09-30 | Abbott Laboratories | Naphthyridine derivatives as antibacterial agents |
| US7381738B2 (en) | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7230022B2 (en) * | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| JP2008507543A (ja) * | 2004-07-22 | 2008-03-13 | グラクソ グループ リミテッド | 抗細菌剤 |
| DE102004039789A1 (de) * | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2006113471A2 (en) | 2005-04-19 | 2006-10-26 | Merck & Co., Inc. | N-alkyl-azacycloalkyl nmda/nr2b antagonists |
| CN102239146A (zh) * | 2008-10-02 | 2011-11-09 | 雅培制药有限公司 | 作为钙通道阻断剂的新化合物 |
| AR074226A1 (es) | 2008-11-26 | 2010-12-29 | Abbott Lab | Octahidrociclopenta[c]pirrol-4-aminas sustituidas como bloqueantes de los canales de calcio, composiciones farmaceuticas que las comprenden y el uso de las mismas para el tratamiento del dolor. |
| US8211933B2 (en) * | 2008-12-12 | 2012-07-03 | Vanderbilt University | 3.3.0 bicyclic GlyT1 inhibitors and methods of making and using same |
-
2009
- 2009-11-25 AR ARP090104557A patent/AR074226A1/es not_active Application Discontinuation
- 2009-11-25 RU RU2011126215/04A patent/RU2011126215A/ru not_active Application Discontinuation
- 2009-11-25 CA CA2742350A patent/CA2742350A1/en not_active Abandoned
- 2009-11-25 EP EP09764953A patent/EP2367790A2/en not_active Withdrawn
- 2009-11-25 PA PA20098850301A patent/PA8850301A1/es unknown
- 2009-11-25 BR BRPI0921184A patent/BRPI0921184A2/pt not_active IP Right Cessation
- 2009-11-25 MX MX2011005537A patent/MX2011005537A/es unknown
- 2009-11-25 WO PCT/US2009/065847 patent/WO2010062927A2/en not_active Ceased
- 2009-11-25 NZ NZ592507A patent/NZ592507A/xx not_active IP Right Cessation
- 2009-11-25 TW TW098140141A patent/TW201028378A/zh unknown
- 2009-11-25 AU AU2009319796A patent/AU2009319796A1/en not_active Abandoned
- 2009-11-25 KR KR1020117014731A patent/KR20110091784A/ko not_active Withdrawn
- 2009-11-25 UY UY0001032261A patent/UY32261A/es not_active Application Discontinuation
- 2009-11-25 JP JP2011538682A patent/JP2012509940A/ja active Pending
- 2009-11-25 US US12/625,754 patent/US8129417B2/en not_active Expired - Fee Related
- 2009-11-25 CN CN2009801553748A patent/CN102292319A/zh active Pending
- 2009-11-25 PE PE2011001093A patent/PE20110833A1/es not_active Application Discontinuation
-
2011
- 2011-04-26 IL IL212484A patent/IL212484A0/en unknown
- 2011-05-13 ZA ZA2011/03538A patent/ZA201103538B/en unknown
- 2011-05-19 CL CL2011001176A patent/CL2011001176A1/es unknown
- 2011-05-27 CO CO11065858A patent/CO6382118A2/es not_active Application Discontinuation
- 2011-06-06 CR CR20110304A patent/CR20110304A/es not_active Application Discontinuation
- 2011-06-24 EC EC2011011160A patent/ECSP11011160A/es unknown
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