JP2009539831A5 - - Google Patents
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- JP2009539831A5 JP2009539831A5 JP2009514231A JP2009514231A JP2009539831A5 JP 2009539831 A5 JP2009539831 A5 JP 2009539831A5 JP 2009514231 A JP2009514231 A JP 2009514231A JP 2009514231 A JP2009514231 A JP 2009514231A JP 2009539831 A5 JP2009539831 A5 JP 2009539831A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- piperidyl
- benzimidazol
- hexahydro
- alkoxy
- 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.)
- Ceased
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- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- -1 4-heptyl Chemical group 0.000 claims description 16
- SXVOJMDLKZHJBL-ROUUACIJSA-N ethyl 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)OCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SXVOJMDLKZHJBL-ROUUACIJSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 89
- 150000001875 compounds Chemical class 0.000 claims 41
- 150000003839 salts Chemical class 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000002393 azetidinyl group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 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 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 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
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- LCIHDOOZKXOYAA-RTBURBONSA-N (3ar,7ar)-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-RTBURBONSA-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
- HFTYBVTZIUWPKC-NHCUHLMSSA-N (3ar,7ar)-3-[1-[1-(cyclopentanecarbonyl)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)C1CCCC1 HFTYBVTZIUWPKC-NHCUHLMSSA-N 0.000 claims 1
- ACVMDJFCEPWEDE-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(cyclopropanecarbonyl)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)C1CC1 ACVMDJFCEPWEDE-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
- CNPPMLHQUZNOFF-YKSBVNFPSA-N (3ar,7as)-1-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 CNPPMLHQUZNOFF-YKSBVNFPSA-N 0.000 claims 1
- 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 1
- 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 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
- 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 1
- 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 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
- 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
- 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
- SFKZMNQERBDWTD-OALUTQOASA-N (3as,7as)-3-[1-[1-(2-methylpropanoyl)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)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SFKZMNQERBDWTD-OALUTQOASA-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
- CLOVXUMUVUNELE-OALUTQOASA-N (3as,7as)-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-OALUTQOASA-N 0.000 claims 1
- GDPVOBYRPRZLFB-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylbutanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 GDPVOBYRPRZLFB-PMACEKPBSA-N 0.000 claims 1
- YGSAIPMMUUNJAB-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylfuran-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=COC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1C YGSAIPMMUUNJAB-PMACEKPBSA-N 0.000 claims 1
- SHQRUJGLGJBNCK-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylthiophene-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)=C1C SHQRUJGLGJBNCK-PMACEKPBSA-N 0.000 claims 1
- CVOKURJIAZYYGI-GOTSBHOMSA-N (3as,7as)-3-[1-[1-(4-methoxybenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CVOKURJIAZYYGI-GOTSBHOMSA-N 0.000 claims 1
- WAVRRRRZOHOAAA-PMACEKPBSA-N (3as,7as)-3-[1-[1-(cyclobutanecarbonyl)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)C1CCC1 WAVRRRRZOHOAAA-PMACEKPBSA-N 0.000 claims 1
- RIUYKDFTYOCUAI-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(cyclohexanecarbonyl)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)C1CCCCC1 RIUYKDFTYOCUAI-VXKWHMMOSA-N 0.000 claims 1
- HFTYBVTZIUWPKC-SFTDATJTSA-N (3as,7as)-3-[1-[1-(cyclopentanecarbonyl)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)C1CCCC1 HFTYBVTZIUWPKC-SFTDATJTSA-N 0.000 claims 1
- ACVMDJFCEPWEDE-OALUTQOASA-N (3as,7as)-3-[1-[1-(cyclopropanecarbonyl)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)C1CC1 ACVMDJFCEPWEDE-OALUTQOASA-N 0.000 claims 1
- DFSPYDUYYXGDBM-DQEYMECFSA-N (3as,7as)-3-[1-[1-(quinoline-4-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CC=C2C(C(N3CCC(CC3)N3CCC(CC3)N3C(N[C@H]4CCCC[C@@H]43)=O)=O)=CC=NC2=C1 DFSPYDUYYXGDBM-DQEYMECFSA-N 0.000 claims 1
- JVFARHQUXPIWSC-OALUTQOASA-N (3as,7as)-3-[1-[1-(thiophene-2-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=CS1 JVFARHQUXPIWSC-OALUTQOASA-N 0.000 claims 1
- KNGBCSZKNUYXJV-ROUUACIJSA-N (3as,7as)-3-[1-[1-[1-(trifluoromethyl)cyclopropanecarbonyl]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(F)(F)F)CC1 KNGBCSZKNUYXJV-ROUUACIJSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 1
- 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 1
- IWVLXAWCUVLTGS-GOTSBHOMSA-N 2-[4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carbonyl]benzonitrile Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C#N IWVLXAWCUVLTGS-GOTSBHOMSA-N 0.000 claims 1
- XGGBTENKEWPYIR-ROUUACIJSA-N 2-fluoroethyl 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)OCCF)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 XGGBTENKEWPYIR-ROUUACIJSA-N 0.000 claims 1
- BIUQRDFLGXLVOH-PMACEKPBSA-N 2-methylpropyl 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)OCC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 BIUQRDFLGXLVOH-PMACEKPBSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- SXVOJMDLKZHJBL-QZTJIDSGSA-N ethyl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 SXVOJMDLKZHJBL-QZTJIDSGSA-N 0.000 claims 1
- SXVOJMDLKZHJBL-MSOLQXFVSA-N ethyl 4-[4-[(3ar,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)OCC)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 SXVOJMDLKZHJBL-MSOLQXFVSA-N 0.000 claims 1
- SXVOJMDLKZHJBL-ZWKOTPCHSA-N ethyl 4-[4-[(3as,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@H]32)=O)CC1 SXVOJMDLKZHJBL-ZWKOTPCHSA-N 0.000 claims 1
- 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 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- DCAUAGVMSPDZLB-IRXDYDNUSA-N methyl 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)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 DCAUAGVMSPDZLB-IRXDYDNUSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- MTVKPGFOMDTATR-OALUTQOASA-N prop-1-en-2-yl 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)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 MTVKPGFOMDTATR-OALUTQOASA-N 0.000 claims 1
- PYJAXKIMFNHYSK-RTBURBONSA-N propan-2-yl 4-[4-[(3ar,7ar)-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)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 PYJAXKIMFNHYSK-RTBURBONSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-MOPGFXCFSA-N propan-2-yl 4-[4-[(3ar,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)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 PYJAXKIMFNHYSK-MOPGFXCFSA-N 0.000 claims 1
- ATDYFOLFOQOQHV-XLIONFOSSA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 ATDYFOLFOQOQHV-XLIONFOSSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-RBUKOAKNSA-N propan-2-yl 4-[4-[(3as,7ar)-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)CCC1N1CCC(N2C(N[C@H]3CCCC[C@H]32)=O)CC1 PYJAXKIMFNHYSK-RBUKOAKNSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-OALUTQOASA-N propan-2-yl 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)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 PYJAXKIMFNHYSK-OALUTQOASA-N 0.000 claims 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 0 CC(CCN(C)C(*)=O)N(CC1)CCC1N(C1C(*2)CCCC1)C2=O Chemical compound CC(CCN(C)C(*)=O)N(CC1)CCC1N(C1C(*2)CCCC1)C2=O 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
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| US81220906P | 2006-06-09 | 2006-06-09 | |
| PCT/SE2007/000554 WO2007142583A1 (en) | 2006-06-09 | 2007-06-08 | Muscarinic receptor agonists that are effective in the treatment of pain, alzheimer's disease and schizophrenia. |
Publications (2)
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| JP2009539831A JP2009539831A (ja) | 2009-11-19 |
| JP2009539831A5 true JP2009539831A5 (https=) | 2010-07-22 |
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| EP (1) | EP2035411A1 (https=) |
| JP (1) | JP2009539831A (https=) |
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| CN (1) | CN101501025A (https=) |
| AR (1) | AR061305A1 (https=) |
| AU (1) | AU2007256012A1 (https=) |
| BR (1) | BRPI0712331A2 (https=) |
| CA (1) | CA2654138A1 (https=) |
| EC (1) | ECSP088966A (https=) |
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| NO (1) | NO20085270L (https=) |
| RU (1) | RU2008147542A (https=) |
| SA (1) | SA07280303B1 (https=) |
| TW (1) | TW200813018A (https=) |
| UY (1) | UY30397A1 (https=) |
| WO (1) | WO2007142583A1 (https=) |
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| TW200815405A (en) * | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| US8119661B2 (en) | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| UY31672A1 (es) * | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| US20090221642A1 (en) * | 2008-03-03 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof-176 |
| US20090275574A1 (en) * | 2008-05-05 | 2009-11-05 | Astrazeneca Ab | Novel compounds-300 |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| EP2398320A4 (en) * | 2009-02-19 | 2012-09-19 | Univ Vanderbilt | ALLOSTERIC ANTAGONISTS OF AMIDOBIPIPERIDINECARBOXYLATE M1, ANALOGUES AND DERIVATIVES THEREOF, AND METHODS FOR THEIR MANUFACTURE AND USE |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| CN103068798A (zh) * | 2010-09-03 | 2013-04-24 | 詹森药业有限公司 | 作为单酰甘油脂肪酶抑制剂的二-氮杂环丁烷二酰胺 |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| JP2021526545A (ja) * | 2018-04-06 | 2021-10-07 | アキノックス ファーマシューティカルス（カナダ）インク． | 疼痛及び炎症を治療するのに有用なインデン誘導体 |
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| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| UY31672A1 (es) | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| US20090221642A1 (en) | 2008-03-03 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof-176 |
| US20090275574A1 (en) | 2008-05-05 | 2009-11-05 | Astrazeneca Ab | Novel compounds-300 |
-
2007
- 2007-05-29 TW TW096119135A patent/TW200813018A/zh unknown
- 2007-06-07 UY UY30397A patent/UY30397A1/es unknown
- 2007-06-08 BR BRPI0712331-0A patent/BRPI0712331A2/pt not_active IP Right Cessation
- 2007-06-08 WO PCT/SE2007/000554 patent/WO2007142583A1/en not_active Ceased
- 2007-06-08 AU AU2007256012A patent/AU2007256012A1/en not_active Abandoned
- 2007-06-08 AR ARP070102507A patent/AR061305A1/es not_active Application Discontinuation
- 2007-06-08 KR KR1020097000417A patent/KR20090018210A/ko not_active Withdrawn
- 2007-06-08 JP JP2009514231A patent/JP2009539831A/ja not_active Ceased
- 2007-06-08 CA CA002654138A patent/CA2654138A1/en not_active Abandoned
- 2007-06-08 EP EP07748217A patent/EP2035411A1/en not_active Withdrawn
- 2007-06-08 US US11/760,011 patent/US7956069B2/en not_active Expired - Fee Related
- 2007-06-08 MX MX2008015136A patent/MX2008015136A/es not_active Application Discontinuation
- 2007-06-08 CN CNA2007800295059A patent/CN101501025A/zh active Pending
- 2007-06-08 RU RU2008147542/04A patent/RU2008147542A/ru not_active Application Discontinuation
- 2007-06-09 SA SA7280303A patent/SA07280303B1/ar unknown
-
2008
- 2008-11-20 IL IL195431A patent/IL195431A0/en unknown
- 2008-12-12 EC EC2008008966A patent/ECSP088966A/es unknown
- 2008-12-16 NO NO20085270A patent/NO20085270L/no not_active Application Discontinuation
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