CA2654138A1 - Novel compounds - Google Patents

Info

Publication number

CA2654138A1

CA2654138A1 CA002654138A CA2654138A CA2654138A1 CA 2654138 A1 CA2654138 A1 CA 2654138A1 CA 002654138 A CA002654138 A CA 002654138A CA 2654138 A CA2654138 A CA 2654138A CA 2654138 A1 CA2654138 A1 CA 2654138A1

Authority

CA

Canada

Prior art keywords

6alkyl

3alkyl

piperidyl

compound

hydrogen

Prior art date

2006-06-09

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 266
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 208000002193 Pain Diseases 0.000 claims abstract description 21
• 230000036407 pain Effects 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• -1 C2-9heteroaryl Chemical group 0.000 claims description 177
• 239000000203 mixture Substances 0.000 claims description 143
• 229910052739 hydrogen Inorganic materials 0.000 claims description 130
• 239000001257 hydrogen Substances 0.000 claims description 127
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 126
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
• 229910052736 halogen Inorganic materials 0.000 claims description 75
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 73
• 150000002367 halogens Chemical class 0.000 claims description 73
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 57
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 47
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 36
• 229910052740 iodine Inorganic materials 0.000 claims description 36
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
• 125000002393 azetidinyl group Chemical group 0.000 claims description 26
• 125000002541 furyl group Chemical group 0.000 claims description 26
• 238000000034 method Methods 0.000 claims description 26
• 125000002757 morpholinyl group Chemical group 0.000 claims description 25
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 25
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 25
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000001544 thienyl group Chemical group 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
• RWIIUBCMPVZLBA-UHFFFAOYSA-N 1,3,3a,4,5,6,7,7a-octahydrobenzimidazol-2-one Chemical compound C1CCCC2NC(=O)NC21 RWIIUBCMPVZLBA-UHFFFAOYSA-N 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 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 description 15
• 239000003814 drug Substances 0.000 claims description 15
• 241001465754 Metazoa Species 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 10
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 10
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 10
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• YKYIFBPVNIHHID-HOTGVXAUSA-N (3as,7as)-3-(1-piperidin-4-ylpiperidin-4-yl)-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2NC1=O)C(CC1)CCN1C1CCNCC1 YKYIFBPVNIHHID-HOTGVXAUSA-N 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 208000019901 Anxiety disease Diseases 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• DBWUZUSWJDAQMD-YADHBBJMSA-N (3as,7ar)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-YADHBBJMSA-N 0.000 claims description 2
• FMQGKZLVPYCWGW-PMACEKPBSA-N (3as,7as)-1-[1-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N(C)[C@H]3CCCC[C@@H]32)=O)=C1OC FMQGKZLVPYCWGW-PMACEKPBSA-N 0.000 claims description 2
• JRWADFLOEGGLNP-VXKWHMMOSA-N (3as,7as)-1-methyl-3-[1-[1-[3-(2-oxopyrrolidin-1-yl)propanoyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)CCN1CCCC1=O JRWADFLOEGGLNP-VXKWHMMOSA-N 0.000 claims description 2
• 230000036506 anxiety Effects 0.000 claims description 2
• CAILALCZTOOPJY-SFTDATJTSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3-prop-2-enyl-3a,4,5,6,7,7a-hexahydrobenzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N(CC=C)[C@H]3CCCC[C@@H]32)=O)CC1 CAILALCZTOOPJY-SFTDATJTSA-N 0.000 claims description 2
• ZWZHLKCQSCOKOI-SFTDATJTSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3-propan-2-yl-3a,4,5,6,7,7a-hexahydrobenzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N(C(C)C)[C@H]3CCCC[C@@H]32)=O)CC1 ZWZHLKCQSCOKOI-SFTDATJTSA-N 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• NBIGYGVWMVQMFP-OALUTQOASA-N tert-butyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 NBIGYGVWMVQMFP-OALUTQOASA-N 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 119
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 19
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 8
• 125000005843 halogen group Chemical group 0.000 claims 2
• DBWUZUSWJDAQMD-FGZHOGPDSA-N (3ar,7ar)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-FGZHOGPDSA-N 0.000 claims 1
• LUDJURAMNWXMQL-DHIUTWEWSA-N (3ar,7ar)-3-[1-[1-(2,6-dimethylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC(C)=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 LUDJURAMNWXMQL-DHIUTWEWSA-N 0.000 claims 1
• CDHZCKYVYJFWIQ-FGZHOGPDSA-N (3ar,7ar)-3-[1-[1-(2-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound COC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 CDHZCKYVYJFWIQ-FGZHOGPDSA-N 0.000 claims 1
• CEEPQONDLRSWHP-DHIUTWEWSA-N (3ar,7ar)-3-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 CEEPQONDLRSWHP-DHIUTWEWSA-N 0.000 claims 1
• CLOVXUMUVUNELE-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)=C1OC CLOVXUMUVUNELE-RTBURBONSA-N 0.000 claims 1
• GNIWETLLWMGHQG-NHCUHLMSSA-N (3ar,7ar)-3-[1-[1-[3-(2-oxopyrrolidin-1-yl)propanoyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)CCN1CCCC1=O GNIWETLLWMGHQG-NHCUHLMSSA-N 0.000 claims 1
• OFMSVAGCJZSCGP-PMACEKPBSA-N (3as,7as)-1-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)C1CC1 OFMSVAGCJZSCGP-PMACEKPBSA-N 0.000 claims 1
• RZUTVWOSQTVGCZ-ZEQRLZLVSA-N (3as,7as)-1-methyl-3-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)C1=CC=CC=C1C RZUTVWOSQTVGCZ-ZEQRLZLVSA-N 0.000 claims 1
• DBWUZUSWJDAQMD-VXKWHMMOSA-N (3as,7as)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-VXKWHMMOSA-N 0.000 claims 1
• LCIHDOOZKXOYAA-OALUTQOASA-N (3as,7as)-3-[1-(1-butanoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 LCIHDOOZKXOYAA-OALUTQOASA-N 0.000 claims 1
• JZIXKCQWMXAZJQ-SFTDATJTSA-N (3as,7as)-3-[1-[1-(1,5-dimethylpyrrole-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CN1C(C)=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 JZIXKCQWMXAZJQ-SFTDATJTSA-N 0.000 claims 1
• TXOFDYDHTGBFSI-OALUTQOASA-N (3as,7as)-3-[1-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1(C)CC1 TXOFDYDHTGBFSI-OALUTQOASA-N 0.000 claims 1
• CLYBZACMYSDIOQ-PMACEKPBSA-N (3as,7as)-3-[1-[1-(1-methylpyrrole-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CN1C=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CLYBZACMYSDIOQ-PMACEKPBSA-N 0.000 claims 1
• YUOPUHPAOHYNNR-FQECFTEESA-N (3as,7as)-3-[1-[1-(2,2-difluorocyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound FC1(F)CC1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 YUOPUHPAOHYNNR-FQECFTEESA-N 0.000 claims 1
• SWJGZBJNGIXQFY-OALUTQOASA-N (3as,7as)-3-[1-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)C(C)(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SWJGZBJNGIXQFY-OALUTQOASA-N 0.000 claims 1
• YWVMEPZGGSIFLO-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(2,3-dihydro-1-benzofuran-7-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC2=C1OCC2 YWVMEPZGGSIFLO-GOTSBHOMSA-N 0.000 claims 1
• LUDJURAMNWXMQL-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(2,6-dimethylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC(C)=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 LUDJURAMNWXMQL-GOTSBHOMSA-N 0.000 claims 1
• KBLTWAQGHCHBCP-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(2-chlorobenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound ClC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 KBLTWAQGHCHBCP-VXKWHMMOSA-N 0.000 claims 1
• HGQNZTNYMPWMTA-NSOVKSMOSA-N (3as,7as)-3-[1-[1-(2-cyclohexylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C1CCCCC1 HGQNZTNYMPWMTA-NSOVKSMOSA-N 0.000 claims 1
• BKDCFHZJHGPZAG-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(2-fluorobenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound FC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 BKDCFHZJHGPZAG-VXKWHMMOSA-N 0.000 claims 1
• CDHZCKYVYJFWIQ-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(2-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound COC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CDHZCKYVYJFWIQ-VXKWHMMOSA-N 0.000 claims 1
• CEEPQONDLRSWHP-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CEEPQONDLRSWHP-GOTSBHOMSA-N 0.000 claims 1
• JNVGUNGAJYNXKS-YIGDWTTGSA-N (3as,7as)-3-[1-[1-(2-methylcyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1CC1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 JNVGUNGAJYNXKS-YIGDWTTGSA-N 0.000 claims 1
• JYCQGNFNEBGBNB-AHWVRZQESA-N (3as,7as)-3-[1-[1-(2-morpholin-4-ylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1N1CCOCC1 JYCQGNFNEBGBNB-AHWVRZQESA-N 0.000 claims 1
• WDPWCQKKCSYSFN-NSOVKSMOSA-N (3as,7as)-3-[1-[1-(2-phenylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C1=CC=CC=C1 WDPWCQKKCSYSFN-NSOVKSMOSA-N 0.000 claims 1
• CYEFUBXMFRJDMS-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(2-propylpentanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)C(CCC)CCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CYEFUBXMFRJDMS-GOTSBHOMSA-N 0.000 claims 1
• FZOZQNJAAVKVOT-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(3-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound COC1=CC=CC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1 FZOZQNJAAVKVOT-GOTSBHOMSA-N 0.000 claims 1
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