KR20040047877A - 무스카린 제제로서 벤즈이미다졸리디논 유도체 - Google Patents
무스카린 제제로서 벤즈이미다졸리디논 유도체 Download PDFInfo
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- KR20040047877A KR20040047877A KR10-2004-7004720A KR20047004720A KR20040047877A KR 20040047877 A KR20040047877 A KR 20040047877A KR 20047004720 A KR20047004720 A KR 20047004720A KR 20040047877 A KR20040047877 A KR 20040047877A
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- South Korea
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- optionally substituted
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- cycloalkyl
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Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32675401P | 2001-10-02 | 2001-10-02 | |
| US60/326,754 | 2001-10-02 | ||
| PCT/US2002/031308 WO2003028650A2 (en) | 2001-10-02 | 2002-09-30 | Benzimidazolidinone derivatives as muscarinic agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020067025160A Division KR100809569B1 (ko) | 2001-10-02 | 2002-09-30 | 무스카린 제제로서 벤즈이미다졸리디논 유도체 |
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| KR1020067025160A Expired - Fee Related KR100809569B1 (ko) | 2001-10-02 | 2002-09-30 | 무스카린 제제로서 벤즈이미다졸리디논 유도체 |
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| KR1020067025160A Expired - Fee Related KR100809569B1 (ko) | 2001-10-02 | 2002-09-30 | 무스카린 제제로서 벤즈이미다졸리디논 유도체 |
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| EP (1) | EP1432420B1 (https=) |
| JP (1) | JP4347047B2 (https=) |
| KR (2) | KR20040047877A (https=) |
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| AR (1) | AR036716A1 (https=) |
| AT (1) | ATE516030T1 (https=) |
| AU (1) | AU2002327810B2 (https=) |
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| CA (1) | CA2457647A1 (https=) |
| MX (1) | MXPA04003103A (https=) |
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| RU (1) | RU2288919C2 (https=) |
| TW (1) | TWI310034B (https=) |
| WO (1) | WO2003028650A2 (https=) |
| ZA (1) | ZA200402609B (https=) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004089942A2 (en) * | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| US6951849B2 (en) * | 2001-10-02 | 2005-10-04 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| BR0213611A (pt) * | 2001-10-02 | 2005-12-20 | Acadia Pharm Inc | Composto, composição farmacêutica, seus usos, método para aumentar a atividade de um receptor colinérgico, métodos para tratamento ou prevenção de distúrbio mental, dor, pressão intraocular aumentada e progressão ou formação de placas amilóides |
| CN100522976C (zh) * | 2002-05-07 | 2009-08-05 | 神经研究公司 | 氮杂环乙炔基衍生物 |
| NZ542690A (en) * | 2003-03-28 | 2009-04-30 | Acadia Pharm Inc | Muscarinic M1 receptor agonists for pain management |
| US7157471B2 (en) * | 2003-08-25 | 2007-01-02 | Boehringer Ingelheim International Gmbh | Haloalkyl- and piperidine-substituted benzimidazole-derivatives |
| AR045843A1 (es) * | 2003-10-03 | 2005-11-16 | Solvay Pharm Bv | Derivados de bencimidazolonas y quinazolinonas sustituidas con hidronopol como agonistas en receptores orl 1 humanos |
| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| WO2007036711A1 (en) * | 2005-09-30 | 2007-04-05 | Glaxo Group Limited | BENZIMIDAZOLONES WHICH HAVE ACTIVITY AT Ml RECEPTOR |
| US8283364B2 (en) * | 2005-09-30 | 2012-10-09 | Glaxo Group Limited | Compounds which have activity at M1 receptor and their uses in medicine |
| WO2007036718A2 (en) * | 2005-09-30 | 2007-04-05 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| CN101374836A (zh) * | 2005-12-27 | 2009-02-25 | 托莱多大学 | 毒蕈碱激动剂及其使用方法 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| GB0607949D0 (en) * | 2006-04-21 | 2006-05-31 | Minster Res The Ltd | Mono and combination therapy |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| JP2009536667A (ja) | 2006-05-09 | 2009-10-15 | ブレインセルス,インコーポレイティド | 5ht受容体介在性の神経新生 |
| TW200813018A (en) * | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| AU2007292848A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| AR063275A1 (es) * | 2006-10-12 | 2009-01-14 | Epix Delaware Inc | Compuestos de carboxamida, una composicion farmaceutica que los comprende y su uso en la preparacion de un medicamento para el tratamiento de enfermedades mediadas por la activacion de ccr2. |
| JP2010539218A (ja) * | 2007-09-20 | 2010-12-16 | グラクソ グループ リミテッド | M1受容体にて活性を有する化合物および医薬としてのそれらの使用 |
| GB0718415D0 (en) * | 2007-09-20 | 2007-10-31 | Glaxo Group Ltd | Compounds |
| WO2009037294A1 (en) * | 2007-09-20 | 2009-03-26 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| BRPI0820701A2 (pt) | 2007-12-11 | 2015-06-16 | Cytopathfinder Inc | Composto de carboxamida e seu uso como agonistas do receptor de quimiocina |
| WO2009140483A1 (en) | 2008-05-15 | 2009-11-19 | University Of Toledo | Muscarinic agonists as cognitive enhancers |
| US20100158829A1 (en) * | 2008-12-24 | 2010-06-24 | Conopco, Inc., D/B/A Unilever | Method and Composition for Color Modulation |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| WO2010129843A1 (en) * | 2009-05-08 | 2010-11-11 | Cytopathfinder, Inc. | Dihydronaphthyridinyl and related compounds for use in treating ophthalmological disorders |
| MY170236A (en) | 2010-10-06 | 2019-07-11 | Glaxosmithkline Llc | Benzimidazole derivatives as pi3 kinase inhibitors |
| US9549928B2 (en) | 2011-04-29 | 2017-01-24 | The University Of Toledo | Muscarinic agonists as enhancers of cognitive flexibility |
| JP6393524B2 (ja) * | 2014-06-05 | 2018-09-19 | ロート製薬株式会社 | 保湿剤 |
| WO2016022644A1 (en) * | 2014-08-06 | 2016-02-11 | Merck Sharp & Dohme Corp. | Heterocyclic cgrp receptor antagonists |
| PL3325444T3 (pl) | 2015-07-20 | 2021-12-06 | Acadia Pharmaceuticals Inc. | Sposoby wytwarzania N-(4-fluorobenzylo)-N-(1-metylopiperydyn-4-ylo)-N'-(4-(2-metylopropyloksy)fenylometylo)karbamidu oraz jego soli winianowej i postaci polimorficznej C |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| US20190117636A1 (en) * | 2016-03-29 | 2019-04-25 | Acadia Pharmaceuticals Inc. | 5-ht2a serotonin receptor inverse agonists or antagonists for use in reducing amyloid-beta peptides and accumulation of amyloid plaques |
| EP3558311A1 (en) | 2016-12-20 | 2019-10-30 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of alzheimer's disease psychosis |
| WO2018200977A1 (en) | 2017-04-28 | 2018-11-01 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| WO2019046167A1 (en) | 2017-08-30 | 2019-03-07 | Acadia Pharmaceuticals Inc. | PIMAVANSERIN FORMULATIONS |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CR20220565A (es) | 2020-05-06 | 2023-01-13 | Merck Sharp & Dohme Llc | Inhibidores de il4i1 y métodos de uso |
| WO2023114224A1 (en) | 2021-12-13 | 2023-06-22 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
| WO2024138108A2 (en) * | 2022-12-22 | 2024-06-27 | University Of Florida Research Foundation, Incorporated | Metabolically stable sigma receptor ligands |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH407121A (de) | 1962-03-30 | 1966-02-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| US4371388A (en) * | 1980-01-25 | 1983-02-01 | Monsanto Company | 3-Substituted aminoalkyl-2-benzothiazolinones as plant growth regulants |
| US4254127A (en) * | 1980-04-03 | 1981-03-03 | Janssen Pharmaceutica, N.V. | 1,3-Dihydro-1-[(1-piperidinyl)alkyl]-2H-benzimidazol-2-one derivatives |
| US4943580A (en) * | 1987-03-09 | 1990-07-24 | Janssen Pharmaceutica N.V. | Anti-histaminic benzimidazole, imidazopyridine and purine derivatives |
| GB8718345D0 (en) * | 1987-08-03 | 1987-09-09 | Fordonal Sa | N-substituted benzamides |
| US4861889A (en) * | 1988-03-14 | 1989-08-29 | Hoechst-Roussel Pharmaceuticals, Inc. | 3-(2,3,4,5,6-pentafluorophenoxy)-8-azabicyclo[3.2.1]octanes |
| IL110298A (en) | 1993-07-13 | 1999-04-11 | Brann Mark Robert | Identification of ligands by selective amplification of cells transfected with receptors |
| JP3916093B2 (ja) | 1993-09-17 | 2007-05-16 | 杏林製薬株式会社 | 光学活性イミダゾリジノン誘導体とその製造方法 |
| JP3916092B2 (ja) | 1993-09-17 | 2007-05-16 | 杏林製薬株式会社 | イミダゾリジノン誘導体とその酸付加塩及び老年性痴呆症の治療薬 |
| 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 |
| EP0816362A4 (en) * | 1995-03-22 | 1998-07-08 | Taisho Pharmaceutical Co Ltd | Thiazole derivatives |
| US5756508A (en) | 1995-10-31 | 1998-05-26 | Merck & Co., Inc. | Muscarine antagonists |
| AU7528696A (en) | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Muscarine antagonists |
| AU7478396A (en) | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Muscarine agonists |
| WO1997016187A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Muscarine antagonists |
| US5718912A (en) | 1996-10-28 | 1998-02-17 | Merck & Co., Inc. | Muscarine agonists |
| AU2307999A (en) | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| US6569956B1 (en) * | 1999-12-22 | 2003-05-27 | Basf Corporation | Hyperbranched polyol macromolecule, method of making same, and coating composition including same |
| RU2002126554A (ru) * | 2000-03-06 | 2004-03-20 | Акадиа Фармасьютикалз, Инк. (Us) | Азациклические соединения для применения при лечении опосредованных серотонином заболеваний |
| AR028385A1 (es) | 2000-04-28 | 2003-05-07 | Acadia Pharm Inc | Agonistas muscarinicos |
| US6586435B2 (en) | 2000-09-19 | 2003-07-01 | Boehringer Ingelheim Pharma Kg | Benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors |
| JP5062939B2 (ja) | 2000-09-19 | 2012-10-31 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | セロトニン受容体及びドーパミン受容体にアフィニティーを示す新規n,n’−二置換ベンゾイミダゾロン誘導体 |
| US6951849B2 (en) * | 2001-10-02 | 2005-10-04 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| BR0213611A (pt) * | 2001-10-02 | 2005-12-20 | Acadia Pharm Inc | Composto, composição farmacêutica, seus usos, método para aumentar a atividade de um receptor colinérgico, métodos para tratamento ou prevenção de distúrbio mental, dor, pressão intraocular aumentada e progressão ou formação de placas amilóides |
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2002
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- 2002-09-30 JP JP2003531986A patent/JP4347047B2/ja not_active Expired - Fee Related
- 2002-09-30 US US10/262,517 patent/US7087593B2/en not_active Expired - Fee Related
- 2002-09-30 MX MXPA04003103A patent/MXPA04003103A/es active IP Right Grant
- 2002-09-30 TW TW091122574A patent/TWI310034B/zh not_active IP Right Cessation
- 2002-09-30 AU AU2002327810A patent/AU2002327810B2/en not_active Ceased
- 2002-09-30 NZ NZ531550A patent/NZ531550A/en not_active IP Right Cessation
- 2002-09-30 KR KR10-2004-7004720A patent/KR20040047877A/ko not_active Ceased
- 2002-09-30 CA CA002457647A patent/CA2457647A1/en not_active Abandoned
- 2002-09-30 RU RU2004113451/04A patent/RU2288919C2/ru not_active IP Right Cessation
- 2002-09-30 CN CNA028194446A patent/CN1561212A/zh active Pending
- 2002-09-30 WO PCT/US2002/031308 patent/WO2003028650A2/en not_active Ceased
- 2002-09-30 KR KR1020067025160A patent/KR100809569B1/ko not_active Expired - Fee Related
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2007
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- 2007-11-27 US US11/945,857 patent/US20080070948A1/en not_active Abandoned
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2010
- 2010-05-07 US US12/776,096 patent/US20100216840A1/en not_active Abandoned
Also Published As
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|---|---|
| ZA200402609B (en) | 2005-05-09 |
| AR036716A1 (es) | 2004-09-29 |
| MXPA04003103A (es) | 2004-07-27 |
| AU2002327810B2 (en) | 2006-11-02 |
| US20030100545A1 (en) | 2003-05-29 |
| NO20041317L (no) | 2004-06-29 |
| WO2003028650A3 (en) | 2003-06-19 |
| NZ531550A (en) | 2006-12-22 |
| EP1432420B1 (en) | 2011-07-13 |
| US20060205785A1 (en) | 2006-09-14 |
| TWI310034B (en) | 2009-05-21 |
| JP4347047B2 (ja) | 2009-10-21 |
| JP2005510473A (ja) | 2005-04-21 |
| KR100809569B1 (ko) | 2008-03-04 |
| CN1561212A (zh) | 2005-01-05 |
| ATE516030T1 (de) | 2011-07-15 |
| US7273857B2 (en) | 2007-09-25 |
| RU2288919C2 (ru) | 2006-12-10 |
| US20100216840A1 (en) | 2010-08-26 |
| KR20060130271A (ko) | 2006-12-18 |
| CA2457647A1 (en) | 2003-04-10 |
| EP1432420A2 (en) | 2004-06-30 |
| WO2003028650A2 (en) | 2003-04-10 |
| EP1432420A4 (en) | 2005-11-09 |
| US20060258707A1 (en) | 2006-11-16 |
| RU2004113451A (ru) | 2005-09-10 |
| US20080070948A1 (en) | 2008-03-20 |
| US7087593B2 (en) | 2006-08-08 |
| US20080009520A1 (en) | 2008-01-10 |
| BR0213611A (pt) | 2005-12-20 |
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