JP2009539831A - 疼痛、アルツハイマー病および統合失調症の治療に有効なムスカリン受容体アゴニスト - Google Patents
疼痛、アルツハイマー病および統合失調症の治療に有効なムスカリン受容体アゴニスト Download PDFInfo
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- JP2009539831A JP2009539831A JP2009514231A JP2009514231A JP2009539831A JP 2009539831 A JP2009539831 A JP 2009539831A JP 2009514231 A JP2009514231 A JP 2009514231A JP 2009514231 A JP2009514231 A JP 2009514231A JP 2009539831 A JP2009539831 A JP 2009539831A
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- Prior art keywords
- alkyl
- alkoxy
- cycloalkyl
- piperidyl
- benzimidazol
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 30
- 208000002193 Pain Diseases 0.000 title claims abstract description 22
- 230000036407 pain Effects 0.000 title claims abstract description 14
- 208000024827 Alzheimer disease Diseases 0.000 title claims description 8
- 201000000980 schizophrenia Diseases 0.000 title claims description 8
- 239000000472 muscarinic agonist Substances 0.000 title description 3
- 229940121743 Muscarinic receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 240
- 239000000203 mixture Substances 0.000 claims abstract description 115
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 366
- 125000003545 alkoxy group Chemical group 0.000 claims description 193
- -1 4-heptyl Chemical group 0.000 claims description 142
- 229910052739 hydrogen Inorganic materials 0.000 claims description 127
- 239000001257 hydrogen Substances 0.000 claims description 127
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 125
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 80
- 150000002367 halogens Chemical class 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 62
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 40
- 125000003282 alkyl amino group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 33
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 31
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
- 125000003386 piperidinyl group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000002393 azetidinyl group Chemical group 0.000 claims description 27
- 125000002541 furyl group Chemical group 0.000 claims description 26
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 125000002757 morpholinyl 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 239000003814 drug Substances 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 18
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 14
- 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 13
- 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 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
- 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 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 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 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 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 3
- 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 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 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 description 2
- 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 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
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 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
- 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
- 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
- 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
- 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
- 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
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- 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
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- 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
- 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
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- HLDOBAJLRANBAC-LCLZZFPVSA-N C1(CCCC1)C(=O)N1CCC(CC1)N1CCC(CC1)N1C(N[C@H]2[C@H]1CCCC2)=O.C(CC)C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]1[C@H]2CCCC1)=O Chemical compound C1(CCCC1)C(=O)N1CCC(CC1)N1CCC(CC1)N1C(N[C@H]2[C@H]1CCCC2)=O.C(CC)C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]1[C@H]2CCCC1)=O HLDOBAJLRANBAC-LCLZZFPVSA-N 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 246
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- 239000000243 solution Substances 0.000 description 65
- 238000002360 preparation method Methods 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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)
| Publication Number | Publication Date |
|---|---|
| JP2009539831A true JP2009539831A (ja) | 2009-11-19 |
| JP2009539831A5 JP2009539831A5 (cg-RX-API-DMAC7.html) | 2010-07-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009514231A Ceased JP2009539831A (ja) | 2006-06-09 | 2007-06-08 | 疼痛、アルツハイマー病および統合失調症の治療に有効なムスカリン受容体アゴニスト |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010539151A (ja) * | 2007-09-11 | 2010-12-16 | アストラゼネカ・アクチエボラーグ | ムスカリン受容体のアゴニストとしてのピペリジン誘導体 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200815405A (en) * | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| US20090221567A1 (en) * | 2008-02-28 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof 177 |
| 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 |
| CA2753205A1 (en) * | 2009-02-19 | 2010-08-26 | Vanderbilt University | Amidobipiperidinecarboxylate m1 allosteric agonists, analogs and derivatives thereof, and methods of making and using same |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| RU2013114771A (ru) * | 2010-09-03 | 2014-10-10 | Янссен Фармацевтика Нв | Диамиды азетидинила как ингибиторы моноацилглицерол липазы |
| ES2694299T3 (es) | 2013-02-07 | 2018-12-19 | Heptares Therapeutics Limited | Carboxilatos de piperidin-1-ilo y azepin-1-ilo como agonistas del receptor muscarínico M4 |
| WO2019195751A1 (en) * | 2018-04-06 | 2019-10-10 | Aquinox Pharmaceuticals (Canada) Inc. | Indene derivatives useful in treating pain and inflammation |
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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 MX MX2008015136A patent/MX2008015136A/es not_active Application Discontinuation
- 2007-06-08 KR KR1020097000417A patent/KR20090018210A/ko not_active Withdrawn
- 2007-06-08 AU AU2007256012A patent/AU2007256012A1/en not_active Abandoned
- 2007-06-08 RU RU2008147542/04A patent/RU2008147542A/ru not_active Application Discontinuation
- 2007-06-08 WO PCT/SE2007/000554 patent/WO2007142583A1/en not_active Ceased
- 2007-06-08 JP JP2009514231A patent/JP2009539831A/ja not_active Ceased
- 2007-06-08 CN CNA2007800295059A patent/CN101501025A/zh active Pending
- 2007-06-08 US US11/760,011 patent/US7956069B2/en not_active Expired - Fee Related
- 2007-06-08 CA CA002654138A patent/CA2654138A1/en not_active Abandoned
- 2007-06-08 AR ARP070102507A patent/AR061305A1/es not_active Application Discontinuation
- 2007-06-08 EP EP07748217A patent/EP2035411A1/en not_active Withdrawn
- 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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| WO1997016192A1 (en) * | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Muscarine antagonists |
| US5756508A (en) * | 1995-10-31 | 1998-05-26 | Merck & Co., Inc. | Muscarine antagonists |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010539151A (ja) * | 2007-09-11 | 2010-12-16 | アストラゼネカ・アクチエボラーグ | ムスカリン受容体のアゴニストとしてのピペリジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| UY30397A1 (es) | 2008-01-31 |
| BRPI0712331A2 (pt) | 2012-04-03 |
| US7956069B2 (en) | 2011-06-07 |
| EP2035411A1 (en) | 2009-03-18 |
| WO2007142583A1 (en) | 2007-12-13 |
| CN101501025A (zh) | 2009-08-05 |
| SA07280303B1 (ar) | 2011-02-23 |
| TW200813018A (en) | 2008-03-16 |
| NO20085270L (no) | 2009-01-07 |
| CA2654138A1 (en) | 2007-12-13 |
| AU2007256012A1 (en) | 2007-12-13 |
| IL195431A0 (en) | 2009-08-03 |
| AR061305A1 (es) | 2008-08-20 |
| RU2008147542A (ru) | 2010-07-20 |
| MX2008015136A (es) | 2008-12-10 |
| US20070287695A1 (en) | 2007-12-13 |
| KR20090018210A (ko) | 2009-02-19 |
| ECSP088966A (es) | 2009-01-30 |
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