JP2009539833A5 - - Google Patents
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- Publication number
- JP2009539833A5 JP2009539833A5 JP2009514233A JP2009514233A JP2009539833A5 JP 2009539833 A5 JP2009539833 A5 JP 2009539833A5 JP 2009514233 A JP2009514233 A JP 2009514233A JP 2009514233 A JP2009514233 A JP 2009514233A JP 2009539833 A5 JP2009539833 A5 JP 2009539833A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- heteroaryl
- heterocycloalkyl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 158
- 125000003545 alkoxy group Chemical group 0.000 claims 143
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 48
- 229910052739 hydrogen Inorganic materials 0.000 claims 47
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 46
- 239000001257 hydrogen Substances 0.000 claims 45
- 125000001072 heteroaryl group Chemical group 0.000 claims 44
- 150000002431 hydrogen Chemical class 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 30
- 125000003118 aryl group Chemical group 0.000 claims 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims 30
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical class 0.000 claims 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 24
- 125000004104 aryloxy group Chemical group 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 18
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 12
- PBVFROWIWWGIFK-UHFFFAOYSA-N fluoromethyl-(2-hydroxyethyl)-dimethylazanium Chemical compound FC[N+](C)(C)CCO PBVFROWIWWGIFK-UHFFFAOYSA-N 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000002947 alkylene group Chemical group 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- -1 methoxy, ethoxy, isopropoxy Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- FFXWWOUMOYWKDS-HNNXBMFYSA-N (3s)-n-ethyl-3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]pyrrolidine-1-carboxamide Chemical compound C1N(C(=O)NCC)CC[C@@H]1N1CCC(N2C(NC3=CC=CC=C32)=O)CC1 FFXWWOUMOYWKDS-HNNXBMFYSA-N 0.000 claims 1
- IESXAYQMUSOGKX-FQEVSTJZSA-N 1-[1-[(3s)-1-[3-(2-oxopyrrolidin-1-yl)propanoyl]pyrrolidin-3-yl]piperidin-4-yl]-3h-indol-2-one Chemical compound C([C@H](CC1)N2CCC(CC2)N2C3=CC=CC=C3CC2=O)N1C(=O)CCN1CCCC1=O IESXAYQMUSOGKX-FQEVSTJZSA-N 0.000 claims 1
- DMQNYYUSRGZMNA-IBGZPJMESA-N 1-methyl-3-[1-[(3s)-1-[3-(2-oxopyrrolidin-1-yl)propanoyl]pyrrolidin-3-yl]piperidin-4-yl]benzimidazol-2-one Chemical compound C([C@@H](C1)N2CCC(CC2)N2C3=CC=CC=C3N(C2=O)C)CN1C(=O)CCN1CCCC1=O DMQNYYUSRGZMNA-IBGZPJMESA-N 0.000 claims 1
- WQMADGKABXWRPB-UHFFFAOYSA-N 3-[1-(1-butanoylpyrrolidin-3-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1N(C(=O)CCC)CCC1N1CCC(N2C(NC3=CC=CC=C32)=O)CC1 WQMADGKABXWRPB-UHFFFAOYSA-N 0.000 claims 1
- WGYJSEHXGADBCK-KRWDZBQOSA-N 3-[1-[(3s)-1-(1-methylpyrrole-2-carbonyl)pyrrolidin-3-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound CN1C=CC=C1C(=O)N1C[C@@H](N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CC1 WGYJSEHXGADBCK-KRWDZBQOSA-N 0.000 claims 1
- KIKVFRJEORTHAK-SFHVURJKSA-N 3-[1-[(3s)-1-(cyclopentanecarbonyl)pyrrolidin-3-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C([C@H](CC1)N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)N1C(=O)C1CCCC1 KIKVFRJEORTHAK-SFHVURJKSA-N 0.000 claims 1
- JNOJPZRLZGKCBU-LPHOPBHVSA-N 3-[1-[(3s)-1-[(2s)-oxolane-2-carbonyl]pyrrolidin-3-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C([C@H](CC1)N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)N1C(=O)[C@@H]1CCCO1 JNOJPZRLZGKCBU-LPHOPBHVSA-N 0.000 claims 1
- JAUFMQYUBYKIEE-SFHVURJKSA-N 3-[1-[(3s)-1-[3-(2-oxopyrrolidin-1-yl)propanoyl]pyrrolidin-3-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C([C@H](CC1)N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)N1C(=O)CCN1CCCC1=O JAUFMQYUBYKIEE-SFHVURJKSA-N 0.000 claims 1
- XEUDQGUHTWLHKW-IBGZPJMESA-N 3-[1-[(3s)-1-[4-(2-oxopyrrolidin-1-yl)butanoyl]pyrrolidin-3-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C([C@H](CC1)N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)N1C(=O)CCCN1CCCC1=O XEUDQGUHTWLHKW-IBGZPJMESA-N 0.000 claims 1
- VTIHIQFWUKTACE-UHFFFAOYSA-N 3-[1-[1-(3-methylbutanoyl)pyrrolidin-3-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1N(C(=O)CC(C)C)CCC1N1CCC(N2C(NC3=CC=CC=C32)=O)CC1 VTIHIQFWUKTACE-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- HPTPNUOHRVVTRL-UHFFFAOYSA-N benzyl 3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]pyrrolidine-1-carboxylate Chemical compound C1CC(N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CN1C(=O)OCC1=CC=CC=C1 HPTPNUOHRVVTRL-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- HXYQHTSHRKZZEB-UHFFFAOYSA-N ethyl 3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1N1CCC(N2C(NC3=CC=CC=C32)=O)CC1 HXYQHTSHRKZZEB-UHFFFAOYSA-N 0.000 claims 1
- CYPTXTYYWOUWKO-UHFFFAOYSA-N ethyl 3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1N1CCC(N2C(NC3=CC(Cl)=CC=C32)=O)CC1 CYPTXTYYWOUWKO-UHFFFAOYSA-N 0.000 claims 1
- CQQOKEJUCXUWAA-UHFFFAOYSA-N ethyl 3-[4-(benzotriazol-1-yl)piperidin-1-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1N1CCC(N2C3=CC=CC=C3N=N2)CC1 CQQOKEJUCXUWAA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 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 1
- VKQFQFLXAGPJKI-UHFFFAOYSA-N tert-butyl 3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1N1CCC(N2C(NC3=CC=CC=C32)=O)CC1 VKQFQFLXAGPJKI-UHFFFAOYSA-N 0.000 claims 1
- 0 CC(CC(C1)[*@@](C([*@@](C=N)C2=CC=*)=O)C2=CC=C**)(*(C(CC2)C*2C(P)=O)C1(N)O)N Chemical compound CC(CC(C1)[*@@](C([*@@](C=N)C2=CC=*)=O)C2=CC=C**)(*(C(CC2)C*2C(P)=O)C1(N)O)N 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81220806P | 2006-06-09 | 2006-06-09 | |
| PCT/SE2007/000556 WO2007142585A1 (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 |
|---|---|
| JP2009539833A JP2009539833A (ja) | 2009-11-19 |
| JP2009539833A5 true JP2009539833A5 (https=) | 2010-07-29 |
Family
ID=38801729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009514233A Pending JP2009539833A (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 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20100173935A1 (https=) |
| EP (1) | EP2035412A4 (https=) |
| JP (1) | JP2009539833A (https=) |
| KR (1) | KR20090016636A (https=) |
| CN (1) | CN101501024A (https=) |
| AR (1) | AR061306A1 (https=) |
| AU (1) | AU2007256014B2 (https=) |
| BR (1) | BRPI0712415A2 (https=) |
| CA (1) | CA2654147A1 (https=) |
| EC (1) | ECSP088967A (https=) |
| IL (1) | IL195427A0 (https=) |
| MX (1) | MX2008015155A (https=) |
| NO (1) | NO20085271L (https=) |
| RU (1) | RU2008147543A (https=) |
| TW (1) | TW200815405A (https=) |
| UY (1) | UY30393A1 (https=) |
| WO (1) | WO2007142585A1 (https=) |
| ZA (1) | ZA200809976B (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200813018A (en) * | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| TW201322983A (zh) * | 2007-08-31 | 2013-06-16 | Purdue Pharma Lp | 經取代之喹□啉型哌啶化合物及其用途 |
| 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 |
| CN102105465B (zh) | 2008-07-21 | 2015-03-11 | 普渡制药公司 | 取代的喹喔啉型桥连哌啶化合物及其用途 |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| WO2012020813A1 (ja) * | 2010-08-10 | 2012-02-16 | 大日本住友製薬株式会社 | 縮環ピロリジン誘導体 |
| CN103764641B (zh) | 2011-05-06 | 2016-10-26 | 扎夫根股份有限公司 | 部分饱和的三环化合物及其制备和使用方法 |
| JP2015083543A (ja) * | 2012-02-14 | 2015-04-30 | 大日本住友製薬株式会社 | 新規縮環ピロリジン誘導体 |
| US20140171466A1 (en) * | 2012-08-14 | 2014-06-19 | Regents Of The University Of Minnesota | Pain management in sickle cell anemia |
| BR112015006029B1 (pt) | 2012-09-18 | 2022-01-25 | Heptares Therapeutics Limited | Compostos aza bicíclicos como agonistas de receptor m1 muscarínicos, composição farmacêutica compreendendo ditos compostos e uso dos mesmos para tratar um distúrbio cognitivo ou distúrbio psicótico ou para tratar ou reduzir a gravidade de dores agudas, crônicas, neuropáticas ou inflamatórias |
| NZ707773A (en) | 2012-11-05 | 2019-05-31 | Zafgen Inc | Methods of treating liver diseases |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5524326A (en) * | 1993-01-21 | 1996-06-11 | Markowitz; Eli | Interactive game between pet and owner |
| JP2002515008A (ja) * | 1994-10-27 | 2002-05-21 | メルク エンド カンパニー インコーポレーテッド | ムスカリン・アンタゴニスト |
| US5756508A (en) * | 1995-10-31 | 1998-05-26 | Merck & Co., Inc. | Muscarine antagonists |
| AU2307999A (en) * | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| ATE275141T1 (de) * | 1999-10-13 | 2004-09-15 | Banyu Pharma Co Ltd | Substituierte imidazolin-derivate |
| JPWO2002085890A1 (ja) * | 2001-04-20 | 2004-08-12 | 萬有製薬株式会社 | ベンズイミダゾロン誘導体 |
| WO2004089942A2 (en) * | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| JP2005532361A (ja) * | 2002-06-17 | 2005-10-27 | メルク エンド カムパニー インコーポレーテッド | 高眼圧症の治療用の眼科用組成物 |
| WO2004069828A1 (ja) * | 2003-02-04 | 2004-08-19 | Mitsubishi Pharma Corporation | ピペリジン化合物およびその医薬用途 |
| KR100869616B1 (ko) * | 2004-05-12 | 2008-11-21 | 화이자 프로덕츠 인코포레이티드 | 프롤린 유도체 및 그의 다이펩티딜 펩티다제－ｉｖ저해제로서의 용도 |
| AU2005249494A1 (en) * | 2004-05-28 | 2005-12-15 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| TW200815351A (en) * | 2006-05-02 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| TW200813018A (en) * | 2006-06-09 | 2008-03-16 | 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 |
-
2007
- 2007-05-29 TW TW096119136A patent/TW200815405A/zh unknown
- 2007-06-06 UY UY30393A patent/UY30393A1/es unknown
- 2007-06-08 JP JP2009514233A patent/JP2009539833A/ja active Pending
- 2007-06-08 US US12/303,641 patent/US20100173935A1/en not_active Abandoned
- 2007-06-08 RU RU2008147543/04A patent/RU2008147543A/ru not_active Application Discontinuation
- 2007-06-08 KR KR1020097000416A patent/KR20090016636A/ko not_active Withdrawn
- 2007-06-08 AR ARP070102508A patent/AR061306A1/es unknown
- 2007-06-08 WO PCT/SE2007/000556 patent/WO2007142585A1/en not_active Ceased
- 2007-06-08 CA CA002654147A patent/CA2654147A1/en not_active Abandoned
- 2007-06-08 MX MX2008015155A patent/MX2008015155A/es not_active Application Discontinuation
- 2007-06-08 BR BRPI0712415-5A patent/BRPI0712415A2/pt not_active IP Right Cessation
- 2007-06-08 EP EP07748219A patent/EP2035412A4/en not_active Withdrawn
- 2007-06-08 AU AU2007256014A patent/AU2007256014B2/en not_active Expired - Fee Related
- 2007-06-08 CN CNA2007800294554A patent/CN101501024A/zh active Pending
-
2008
- 2008-11-20 IL IL195427A patent/IL195427A0/en unknown
- 2008-11-24 ZA ZA2008/09976A patent/ZA200809976B/en unknown
- 2008-12-12 EC EC2008008967A patent/ECSP088967A/es unknown
- 2008-12-16 NO NO20085271A patent/NO20085271L/no not_active Application Discontinuation
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