TW200804355A - Compounds which have activity at M1 receptor and their uses in medicine - Google Patents
Compounds which have activity at M1 receptor and their uses in medicine Download PDFInfo
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- TW200804355A TW200804355A TW095135888A TW95135888A TW200804355A TW 200804355 A TW200804355 A TW 200804355A TW 095135888 A TW095135888 A TW 095135888A TW 95135888 A TW95135888 A TW 95135888A TW 200804355 A TW200804355 A TW 200804355A
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Landscapes
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- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0519949.2A GB0519949D0 (en) | 2005-09-30 | 2005-09-30 | Compounds |
| GB0602856A GB0602856D0 (en) | 2006-02-13 | 2006-02-13 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200804355A true TW200804355A (en) | 2008-01-16 |
Family
ID=37635729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095135888A TW200804355A (en) | 2005-09-30 | 2006-09-28 | Compounds which have activity at M1 receptor and their uses in medicine |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8288412B2 (enExample) |
| EP (1) | EP1960389B1 (enExample) |
| JP (1) | JP5209481B2 (enExample) |
| AR (1) | AR055667A1 (enExample) |
| ES (1) | ES2391107T3 (enExample) |
| PE (1) | PE20070586A1 (enExample) |
| TW (1) | TW200804355A (enExample) |
| WO (1) | WO2007036718A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1960389B1 (en) | 2005-09-30 | 2012-08-15 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| KR101374458B1 (ko) * | 2005-09-30 | 2014-03-17 | 글락소 그룹 리미티드 | M1 수용체에서 활성을 갖는 화합물 및 그의 의약적 용도 |
| JP5209479B2 (ja) * | 2005-09-30 | 2013-06-12 | 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ベンゾイミダゾロン類 |
| GB0605784D0 (en) * | 2006-03-22 | 2006-05-03 | Glaxo Group Ltd | Compounds |
| GB0706164D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706170D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706174D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706165D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0718415D0 (en) * | 2007-09-20 | 2007-10-31 | Glaxo Group Ltd | Compounds |
| 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 |
| GB0817982D0 (en) | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| US20100278835A1 (en) | 2009-03-10 | 2010-11-04 | Astrazeneca Uk Limited | Novel compounds 660 |
| US20180250270A1 (en) | 2015-09-11 | 2018-09-06 | Chase Pharmaceuticals Corporation | Muscarinic combination and its use for combating hypocholinergic disorders of the central nervous system |
| CN106316864A (zh) * | 2016-08-22 | 2017-01-11 | 苏州天马精细化学品股份有限公司 | 4‑甲基‑3‑三氟甲基苯胺的制备方法 |
| CN111848406B (zh) * | 2019-04-26 | 2022-03-29 | 沈阳中化农药化工研发有限公司 | 一种2-氯-4-氟-5-硝基苯甲醛的制备方法 |
| CN113637001A (zh) * | 2021-08-09 | 2021-11-12 | 安康市农业科学研究院 | 一种氟哌利多中间体的合成方法 |
| EP4447953A1 (en) | 2021-12-13 | 2024-10-23 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161645A (en) * | 1962-12-18 | 1964-12-15 | Res Lab Dr C Janssen N V | 1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds |
| US3989707A (en) * | 1974-06-21 | 1976-11-02 | Janssen Pharmaceutica N.V. | Benzimidazolinone derivatives |
| US4292321A (en) * | 1979-05-24 | 1981-09-29 | Warner-Lambert Company | 1,3,8-Triazaspirodecane-4-ones, pharmaceutical compositions thereof and method of use thereof |
| US4411904A (en) * | 1981-05-29 | 1983-10-25 | Warner-Lambert Company | Diphenylpropanamines, compositions thereof and use thereof |
| DE3124366A1 (de) * | 1981-06-20 | 1982-12-30 | Hoechst Ag, 6000 Frankfurt | N-oxacyclyl-alkylpiperidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und deren verwendung |
| DE4040300A1 (de) | 1990-12-17 | 1992-07-02 | Leifeld Gmbh & Co | Drueckmaschine mit wenigstens einem rollenhalter |
| 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 |
| US5691323A (en) * | 1995-05-12 | 1997-11-25 | Merck & Co., Inc. | Muscarine antagonists |
| US5574044A (en) * | 1994-10-27 | 1996-11-12 | Merck & Co., Inc. | Muscarine antagonists |
| CA2200468A1 (en) | 1994-10-27 | 1996-05-09 | Wayne J. Thompson | Muscarine antagonists |
| AU7478396A (en) | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Muscarine agonists |
| US5718912A (en) * | 1996-10-28 | 1998-02-17 | Merck & Co., Inc. | Muscarine agonists |
| US5977134A (en) * | 1996-12-05 | 1999-11-02 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US6465484B1 (en) * | 1997-09-26 | 2002-10-15 | Merck & Co., Inc. | Angiogenesis inhibitors |
| US6162804A (en) * | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| AU2307999A (en) | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| US6699880B1 (en) * | 1999-10-13 | 2004-03-02 | Banyu Pharmaceutical Co., Ltd. | Substituted imidazolidinone derivatives |
| SE9904652D0 (sv) * | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
| EP1263754A1 (en) * | 2000-02-01 | 2002-12-11 | Millennium Pharmaceuticals, Inc. | INDALONE AND BENZIMIDAZOLONE INHIBITORS OF FACTOR Xa |
| DE60235274D1 (de) * | 2001-04-18 | 2010-03-18 | Euro Celtique Sa | Octahydrobenzimidazolon-Verbindungen als Analgetika |
| EP1386920A4 (en) * | 2001-04-20 | 2005-09-14 | Banyu Pharma Co Ltd | benzimidazolone derivatives |
| US6951849B2 (en) * | 2001-10-02 | 2005-10-04 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| WO2004089942A2 (en) | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| TWI310034B (en) * | 2001-10-02 | 2009-05-21 | Acadia Pharmaceuticais Inc | Benzimidazolidinone derivatives as muscarinic agents |
| US7244744B2 (en) * | 2001-11-01 | 2007-07-17 | Icagen, Inc. | Piperidines |
| PT1491212E (pt) | 2002-03-29 | 2012-11-16 | Mitsubishi Tanabe Pharma Corp | Medicamento para distúrbios de sono |
| WO2003105781A2 (en) | 2002-06-17 | 2003-12-24 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| BR0317230A (pt) | 2002-12-13 | 2005-10-25 | Smithkline Beecham Corp | Composto, composição, métodos de antagonizar uma atividade do receptor de quimiocina ccr-5, e de tratar uma infecção viral em um paciente, e, uso de um composto |
| JP2006528186A (ja) * | 2003-07-23 | 2006-12-14 | ワイス | 5−ヒドロキシトリプタミン−6リガンドとしてのスルホニルジヒドロベンゾイミダゾロン化合物 |
| DK1664036T3 (da) | 2003-09-03 | 2012-02-13 | Pfizer | Benzimidazolonforbindelser med 5-HT4-receptoragonistisk virkning |
| BRPI0517925A (pt) * | 2004-11-02 | 2008-10-21 | Pfizer | derivados de sulfonil benzimidazol |
| US7300947B2 (en) * | 2005-07-13 | 2007-11-27 | Banyu Pharmaceutical Co., Ltd. | N-dihydroxyalkyl-substituted 2-oxo-imidazole derivatives |
| KR101374458B1 (ko) | 2005-09-30 | 2014-03-17 | 글락소 그룹 리미티드 | M1 수용체에서 활성을 갖는 화합물 및 그의 의약적 용도 |
| EP1960389B1 (en) | 2005-09-30 | 2012-08-15 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| JP5209479B2 (ja) * | 2005-09-30 | 2013-06-12 | 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ベンゾイミダゾロン類 |
| EP2068673A2 (en) | 2006-09-08 | 2009-06-17 | The Gillette Company | Toothbrush with multiple bristle states |
| GB0706188D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706187D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706170D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706164D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706167D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706190D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706189D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706174D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706168D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706173D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| GB0706165D0 (en) | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
-
2006
- 2006-09-27 EP EP06794587A patent/EP1960389B1/en active Active
- 2006-09-27 US US12/088,451 patent/US8288412B2/en not_active Expired - Fee Related
- 2006-09-27 ES ES06794587T patent/ES2391107T3/es active Active
- 2006-09-27 JP JP2008532868A patent/JP5209481B2/ja not_active Expired - Fee Related
- 2006-09-27 WO PCT/GB2006/003595 patent/WO2007036718A2/en not_active Ceased
- 2006-09-28 AR ARP060104267A patent/AR055667A1/es not_active Application Discontinuation
- 2006-09-28 PE PE2006001184A patent/PE20070586A1/es not_active Application Discontinuation
- 2006-09-28 TW TW095135888A patent/TW200804355A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1960389A2 (en) | 2008-08-27 |
| WO2007036718A3 (en) | 2007-05-31 |
| AR055667A1 (es) | 2007-08-29 |
| PE20070586A1 (es) | 2007-06-16 |
| EP1960389B1 (en) | 2012-08-15 |
| JP2009510041A (ja) | 2009-03-12 |
| US20080293770A1 (en) | 2008-11-27 |
| JP5209481B2 (ja) | 2013-06-12 |
| ES2391107T3 (es) | 2012-11-21 |
| US8288412B2 (en) | 2012-10-16 |
| WO2007036718A2 (en) | 2007-04-05 |
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