ZA200600427B - 1-sulfonylindole derivatives, their preparation and their use as 5-HT6 ligands - Google Patents
1-sulfonylindole derivatives, their preparation and their use as 5-HT6 ligands Download PDFInfo
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- ZA200600427B ZA200600427B ZA200600427A ZA200600427A ZA200600427B ZA 200600427 B ZA200600427 B ZA 200600427B ZA 200600427 A ZA200600427 A ZA 200600427A ZA 200600427 A ZA200600427 A ZA 200600427A ZA 200600427 B ZA200600427 B ZA 200600427B
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- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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Landscapes
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- Nutrition Science (AREA)
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- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200301806A ES2222828B1 (es) | 2003-07-30 | 2003-07-30 | Derivados de 1-sulfonilindoles, su preparacion y su aplicacion como medicamentos. |
Publications (1)
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| ZA200600427B true ZA200600427B (en) | 2007-03-28 |
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| ZA200600427A ZA200600427B (en) | 2003-07-30 | 2004-07-29 | 1-sulfonylindole derivatives, their preparation and their use as 5-HT6 ligands |
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| EP (1) | EP1648443B1 (sl) |
| JP (1) | JP2007500168A (sl) |
| KR (1) | KR20060056347A (sl) |
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| ES2246721B1 (es) * | 2004-08-10 | 2007-03-16 | Laboratorios Del Dr. Esteve, S.A. | Compuestos indolicos sustituidos, su preparacion y su uso como medicamentos. |
| EP1632491A1 (en) * | 2004-08-30 | 2006-03-08 | Laboratorios Del Dr. Esteve, S.A. | Substituted indole compounds and their use as 5-HT6 receptor modulators |
| JP5833804B2 (ja) | 2005-04-13 | 2015-12-16 | ニューラクソン，インコーポレーテッド | Ｎｏｓ阻害活性を有する置換インドール化合物 |
| JP2010519171A (ja) | 2006-02-17 | 2010-06-03 | メモリー・ファーマシューティカルズ・コーポレイション | ５−ｈｔ６受容体親和性を有する化合物 |
| WO2007118314A1 (en) | 2006-04-13 | 2007-10-25 | Neuraxon, Inc. | 1,5 and 3,6- substituted indole compounds having nos inhibitory activity |
| WO2007138611A1 (en) * | 2006-05-30 | 2007-12-06 | Suven Life Sciences Limited | 3-(heterocyclyl)-n-(arylsulfonyl)indole derivatives as functional 5-ht6 ligands |
| ES2398299T3 (es) * | 2006-07-03 | 2013-03-15 | Proximagen Ltd. | Indoles como moduladores de 5-HT6 |
| PT2114878E (pt) * | 2007-01-08 | 2011-03-10 | Suven Life Sciences Ltd | Compostos de 5-(heterociclil)-alquil-n-(arilsulfonil)indol e uso dos mesmos como ligandos de 5-ht6 |
| EP1947085A1 (en) * | 2007-01-19 | 2008-07-23 | Laboratorios del Dr. Esteve S.A. | Substituted indole sulfonamide compounds, their preparation and use as medicaments |
| BRPI0809873A2 (pt) | 2007-05-03 | 2018-11-13 | Suven Life Sciences Ltd | "composto, processo para a preparação do composto, método para o tratamento de uma desordem do sistema nervoso central, composição farmacêutica, uso do composto, método para testar antagonistas e antagonistas com seletividade para o receptor 5-th6 e método de tratamento" |
| ES2359170T3 (es) * | 2007-07-19 | 2011-05-19 | Laboratorios Del Dr. Esteve S.A. | Compuestos tetrahidro-quinolín-sulfonamida sustituidos, su preparación y uso como medicamentos. |
| EP2018861A1 (en) * | 2007-07-26 | 2009-01-28 | Laboratorios del Dr. Esteve S.A. | 5HT6-Ligands such as sulfonamide derivatives in drug-induced weight-gain |
| EP2020230B1 (en) | 2007-08-01 | 2011-01-19 | Laboratorios del Dr. Esteve S.A. | Combination of at least two 5-HT6-Ligands |
| EP2220075A4 (en) | 2007-11-16 | 2012-02-29 | Neuraxon Inc | INDOLE COMPOUNDS AND METHODS FOR TREATING VISCERAL PAIN |
| US8318725B2 (en) | 2008-09-17 | 2012-11-27 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands |
| JP5536781B2 (ja) | 2008-09-17 | 2014-07-02 | スヴェン・ライフ・サイエンシズ・リミテッド | アリールスルホンアミドアミン化合物および５−ｈｔ６リガンドとしてのそれらの使用 |
| CN104276993B (zh) * | 2013-07-12 | 2019-03-15 | 广东东阳光药业有限公司 | 吲哚衍生物及其在药物上的应用 |
| WO2016004882A1 (en) | 2014-07-08 | 2016-01-14 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| CN104529866A (zh) * | 2014-12-12 | 2015-04-22 | 广东东阳光药业有限公司 | 吲哚类衍生物及其在药物上的应用 |
| US20190336585A1 (en) * | 2018-05-03 | 2019-11-07 | John Lawrence Mee | Method for sustainable human cognitive enhancement |
| US20190390193A1 (en) * | 2018-06-23 | 2019-12-26 | John Lawrence Mee | Reversible method for sustainable human cognitive enhancement |
Family Cites Families (8)
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| US5120749A (en) * | 1991-02-20 | 1992-06-09 | Abbott Laboratories | Platelet activating antagonists |
| GB9820113D0 (en) * | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| WO2001012629A1 (en) | 1999-08-12 | 2001-02-22 | Nps Allelix Corp. | Azaindoles having serotonin receptor affinity |
| IL156517A0 (en) * | 2000-12-22 | 2004-01-04 | Wyeth Corp | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
| ES2264994T3 (es) * | 2000-12-22 | 2007-02-01 | Wyeth | Compuestos heterociclilalquilindol o -azaindol como ligandos de 5-hidroxitriptamina-6. |
| BR0206595A (pt) * | 2001-01-30 | 2004-07-13 | Lilly Co Eli | Composto, composição farmacêutica, e uso de um composto |
| JP2005506368A (ja) * | 2001-10-23 | 2005-03-03 | ビオヴィトルム・アクチボラゲット | 肥満の処置におけるまたは食物摂取の減少のためのインドールおよびインドリン誘導体の使用 |
| TW200301251A (en) * | 2001-12-20 | 2003-07-01 | Wyeth Corp | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
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- 2004-07-29 EP EP04763613A patent/EP1648443B1/en active Active
- 2004-07-29 MX MXPA06001229A patent/MXPA06001229A/es active IP Right Grant
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| AR045159A1 (es) | 2005-10-19 |
| US20070060581A1 (en) | 2007-03-15 |
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| JP2007500168A (ja) | 2007-01-11 |
| ES2348621T3 (es) | 2010-12-09 |
| RU2006105782A (ru) | 2007-09-20 |
| EP1648443B1 (en) | 2010-07-14 |
| ES2222828B1 (es) | 2006-04-16 |
| TW200509908A (en) | 2005-03-16 |
| US7655690B2 (en) | 2010-02-02 |
| EP1648443A1 (en) | 2006-04-26 |
| CN1863527A (zh) | 2006-11-15 |
| IL172956A0 (en) | 2006-06-11 |
| DE602004028125D1 (de) | 2010-08-26 |
| BRPI0413062A (pt) | 2006-10-17 |
| ECSP066330A (es) | 2006-08-30 |
| ATE473738T1 (de) | 2010-07-15 |
| AU2004262490A1 (en) | 2005-02-17 |
| MXPA06001229A (es) | 2006-05-15 |
| CA2533996A1 (en) | 2005-02-17 |
| ES2222828A1 (es) | 2005-02-01 |
| KR20060056347A (ko) | 2006-05-24 |
| NO20060342L (no) | 2006-01-23 |
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