KR100845450B1 - 약학적 제형물로서의 세로토닌 아고니스트 (5에이치티2)및 안타고니스트 (5에이치티6) 의 새로운 조합 - Google Patents
약학적 제형물로서의 세로토닌 아고니스트 (5에이치티2)및 안타고니스트 (5에이치티6) 의 새로운 조합 Download PDFInfo
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- KR100845450B1 KR100845450B1 KR1020037000321A KR20037000321A KR100845450B1 KR 100845450 B1 KR100845450 B1 KR 100845450B1 KR 1020037000321 A KR1020037000321 A KR 1020037000321A KR 20037000321 A KR20037000321 A KR 20037000321A KR 100845450 B1 KR100845450 B1 KR 100845450B1
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| SE0002754-0 | 2000-07-21 | ||
| SE0002754A SE0002754D0 (sv) | 2000-07-21 | 2000-07-21 | New pharmaceutical combination formulation and method of treatment with the combination |
| PCT/SE2001/001651 WO2002008178A1 (en) | 2000-07-21 | 2001-07-19 | New combination of serotonin agonist (5ht2) and antagonist (5ht6)as pharmaceutical formulation |
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| KR20030036599A KR20030036599A (ko) | 2003-05-09 |
| KR100845450B1 true KR100845450B1 (ko) | 2008-07-10 |
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| KR (1) | KR100845450B1 (ru) |
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| PL (1) | PL360309A1 (ru) |
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| EP2298738B1 (en) * | 2000-11-02 | 2012-09-19 | Wyeth LLC | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| US7034029B2 (en) | 2000-11-02 | 2006-04-25 | Wyeth | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| CA2450245A1 (en) | 2001-06-15 | 2002-12-27 | F. Hoffmann-La Roche Ag | 4-piperazinylindole derivatives with 5-ht6 receptor affinity |
| CN1321110C (zh) * | 2001-06-15 | 2007-06-13 | 弗·哈夫曼-拉罗切有限公司 | 具有5－ht6受体亲和力的4－哌嗪基吲哚衍生物 |
| US6825198B2 (en) | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
| GB0202679D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| DE60321558D1 (de) | 2002-03-27 | 2008-07-24 | Glaxo Group Ltd | Chinolinderivate und deren verwendung als 5-ht6 liganden |
| CL2004000826A1 (es) * | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| KR101157272B1 (ko) | 2003-07-22 | 2012-06-15 | 아레나 파마슈티칼스, 인크. | 5?ｈｔ2ａ 세로토닌 수용체의 조절자로서 이와 관련된질환의 예방 및 치료에 유용한 디아릴 및 아릴헤테로아릴우레아 유도체 |
| WO2006022420A1 (ja) | 2004-08-25 | 2006-03-02 | Takeda Pharmaceutical Company Limited | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| US7713954B2 (en) | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
| US20100048713A1 (en) * | 2006-01-06 | 2010-02-25 | Aarhus Universitet | Compounds acting on the serotonin transporter |
| EP2742936A1 (en) | 2006-05-16 | 2014-06-18 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| WO2007149728A2 (en) * | 2006-06-20 | 2007-12-27 | Alcon Research, Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| EP2020230B1 (en) * | 2007-08-01 | 2011-01-19 | Laboratorios del Dr. Esteve S.A. | Combination of at least two 5-HT6-Ligands |
| US20100266504A1 (en) | 2007-11-15 | 2010-10-21 | Takahiro Matsumoto | Condensed pyridine derivative and use thereof |
| US9084742B2 (en) | 2007-12-12 | 2015-07-21 | Axovant Sciences Ltd. | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-Quinoline |
| US20110021538A1 (en) | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| UA100192C2 (en) | 2008-11-11 | 2012-11-26 | УАЙТ ЭлЭлСи | 1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands |
| CA2765239C (en) | 2009-06-15 | 2018-08-07 | Takeda Pharmaceutical Company Limited | Pyrazinooxazepine derivatives |
| US20120253036A1 (en) | 2009-12-11 | 2012-10-04 | Yukinori Nagakura | Agent for treating fibromyalgia |
| WO2016201373A1 (en) | 2015-06-12 | 2016-12-15 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of rem sleep behavior disorder |
| MX391031B (es) | 2015-07-15 | 2025-03-21 | Axovant Sciences Gmbh | Derivados de diaril y arilheteroaril urea como moduladores del receptor de serotonina 5-ht2a útiles para la profilaxis y el tratamiento de alucinaciones asociadas con una enfermedad neurodegenerativa. |
| CN107628981B (zh) * | 2017-10-31 | 2019-07-30 | 威海市妇女儿童医院 | 一种肉桂酰基吲哚啉化合物及其制备青光眼药物的应用 |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
| CN111269165A (zh) * | 2018-12-05 | 2020-06-12 | 中国科学院大连化学物理研究所 | 一种3-芳基磺酰基吲哚衍生物的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998027081A1 (en) * | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
| WO2000012510A1 (en) * | 1998-09-01 | 2000-03-09 | Vernalis Research Limited | Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9803411D0 (en) * | 1998-02-18 | 1998-04-15 | Smithkline Beecham Plc | Novel compounds |
| US6100291A (en) * | 1998-03-16 | 2000-08-08 | Allelix Biopharmaceuticals Inc. | Pyrrolidine-indole compounds having 5-HT6 affinity |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
-
2000
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2001
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- 2001-07-19 YU YU2603A patent/YU2603A/sh unknown
- 2001-07-19 WO PCT/SE2001/001651 patent/WO2002008178A1/en active IP Right Grant
- 2001-07-19 CA CA002411192A patent/CA2411192A1/en not_active Abandoned
- 2001-07-19 HU HU0301346A patent/HUP0301346A3/hu unknown
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- 2001-07-19 KR KR1020037000321A patent/KR100845450B1/ko not_active Expired - Fee Related
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- 2001-07-19 EA EA200300183A patent/EA006604B1/ru not_active IP Right Cessation
- 2001-07-19 JP JP2002514087A patent/JP2004504376A/ja not_active Withdrawn
- 2001-07-19 EP EP01961472A patent/EP1301476A1/en not_active Withdrawn
- 2001-07-19 AU AU2001282734A patent/AU2001282734B2/en not_active Ceased
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- 2001-07-19 PL PL36030901A patent/PL360309A1/xx not_active Application Discontinuation
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998027081A1 (en) * | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
| WO2000012510A1 (en) * | 1998-09-01 | 2000-03-09 | Vernalis Research Limited | Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030036599A (ko) | 2003-05-09 |
| IL154057A0 (en) | 2003-07-31 |
| EA200300183A1 (ru) | 2003-08-28 |
| HK1057536A1 (en) | 2004-04-08 |
| HUP0301346A2 (hu) | 2003-08-28 |
| MXPA03000548A (es) | 2004-04-05 |
| AU8273401A (en) | 2002-02-05 |
| BR0112661A (pt) | 2003-06-24 |
| JP2004504376A (ja) | 2004-02-12 |
| HUP0301346A3 (en) | 2005-05-30 |
| CN1221254C (zh) | 2005-10-05 |
| CA2411192A1 (en) | 2002-01-31 |
| PL360309A1 (en) | 2004-09-06 |
| ZA200210234B (en) | 2004-03-18 |
| CN1443162A (zh) | 2003-09-17 |
| AU2001282734B2 (en) | 2006-10-12 |
| EA006604B1 (ru) | 2006-02-24 |
| WO2002008178A1 (en) | 2002-01-31 |
| YU2603A (sh) | 2006-05-25 |
| SE0002754D0 (sv) | 2000-07-21 |
| NZ523216A (en) | 2005-05-27 |
| NO20030304D0 (no) | 2003-01-20 |
| NO20030304L (no) | 2003-03-12 |
| EP1301476A1 (en) | 2003-04-16 |
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