BRPI0708843A2 - composto, composiÇço farmacÊutica, e, uso do composto - Google Patents
composto, composiÇço farmacÊutica, e, uso do composto Download PDFInfo
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- BRPI0708843A2 BRPI0708843A2 BRPI0708843-4A BRPI0708843A BRPI0708843A2 BR PI0708843 A2 BRPI0708843 A2 BR PI0708843A2 BR PI0708843 A BRPI0708843 A BR PI0708843A BR PI0708843 A2 BRPI0708843 A2 BR PI0708843A2
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- diaza
- disorder
- disorders
- bicyclo
- pain
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Applications Claiming Priority (3)
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| DKPA200600731 | 2006-05-30 | ||
| DKPA200600731 | 2006-05-30 | ||
| PCT/EP2007/055169 WO2007138038A1 (en) | 2006-05-30 | 2007-05-29 | Novel 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl derivatives and their medical use |
Publications (1)
| Publication Number | Publication Date |
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| BRPI0708843A2 true BRPI0708843A2 (pt) | 2011-06-14 |
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| PT2032575E (pt) | 2006-05-30 | 2010-07-09 | Neurosearch As | NOVO DERIVADO DE 1,4-DIAZA-BICICLO[3,2,2]NONIL-OXADIAZOLILO E A SUA APLICAÃO MéDICA |
| CA2667545A1 (en) * | 2006-10-25 | 2008-05-02 | Neurosearch A/S | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
| US7935695B2 (en) | 2007-08-17 | 2011-05-03 | Neurosearch A/S | 1,4-diaza-bicyclo[3.2.2]nonyl heteroaryl derivatives useful as nicotinic acetylcholine receptor ligands |
| RU2010135037A (ru) | 2008-03-11 | 2012-04-20 | Ньюросерч А/С (DK) | Новые производные, 1,4-диазабицикло[3.2.2]нонилоксадиазолил, полезные в качестве модуляторов никотиновых ацетилхолиновых рецепторов |
| WO2009150138A1 (en) * | 2008-06-10 | 2009-12-17 | Neurosearch A/S | Novel oxadiazolyl-diazabicyclononane derivatives and their medical use |
| WO2010043539A1 (en) * | 2008-10-13 | 2010-04-22 | Neurosearch A/S | Novel oxadiazolyl-diazabicyclononane derivatives and their medical use |
| US20110257161A1 (en) * | 2008-12-04 | 2011-10-20 | Neurosearch A/S | Novel diaza-bicyclononyl-phenyl derivatives and their medical use |
| CN102300574A (zh) | 2009-01-26 | 2011-12-28 | 神经研究公司 | 新的吲哚基-*二唑基-二氮杂二环壬烷衍生物及它们的医药和诊断用途 |
| WO2010086280A1 (en) | 2009-01-27 | 2010-08-05 | Neurosearch A/S | Novel n-oxides of furanyl-oxadiazolyl-diazabicyclononane derivatives and their medical use |
| WO2010086279A1 (en) | 2009-01-27 | 2010-08-05 | Neurosearch A/S | Novel dibenzofuranyl-oxadiazolyl-diazabicyclononane derivatives and their medical use |
| US20120238553A1 (en) * | 2009-01-27 | 2012-09-20 | Neurosearch A/S | Novel benzodioxolyl-oxadiazolyl-diazabicyclononane derivatives and their medical use |
| WO2010130768A1 (en) * | 2009-05-14 | 2010-11-18 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.1]octane derivatives useful as nicotinic acetylcholine receptor modulators |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| US20120288443A1 (en) | 2009-11-11 | 2012-11-15 | Neurosearch A/S | Labelled pyrrolyl-oxadiazolyl-diazabicyclononane derivatives and their use in diagnostic methods |
| EP2513097A1 (en) | 2009-12-18 | 2012-10-24 | NeuroSearch AS | Diazabicyclononyl oxadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
| WO2012139925A1 (en) | 2011-04-15 | 2012-10-18 | Neurosearch A/S | Labelled and un-labelled methyl-pyrrolyl-oxadiazolyl-diazabicyclononane derivatives and their medical use |
| CN111499615B (zh) | 2017-08-04 | 2024-02-02 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| HUE066783T2 (hu) | 2018-04-18 | 2024-09-28 | Constellation Pharmaceuticals Inc | Metil módosító enzimek modulátorai, ezek készítményei és alkalmazásuk |
| CA3100977A1 (en) | 2018-05-21 | 2019-11-28 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| JP2022519294A (ja) * | 2019-02-04 | 2022-03-22 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| CN114007613A (zh) | 2019-02-05 | 2022-02-01 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| JP7603595B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5821371A (en) * | 1994-10-24 | 1998-10-13 | Eli Lilly And Comany | Heterocyclic compounds and their preparation and use |
| FR2809732B1 (fr) | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE |
| FR2809731B1 (fr) | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
| FR2832712B1 (fr) | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(oxadiazol-3-yl)-1,4-diazabicyclo[3.2.2]nonane, leur preparation et leur application en therapeutique |
| FR2832713B1 (fr) | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(1,3,4-thiadiazol-2-yl)-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
| NZ538512A (en) * | 2002-09-30 | 2006-12-22 | Neurosearch As | 1,4-diazabicycloalkane derivatives, their preparation and use in treatment of disorders responsive to modulation of cholmergic and/or monoamine receptors |
| BR0314183A (pt) * | 2002-09-30 | 2005-08-09 | Neurosearch As | Derivados de 1,4-diazabicicloalcano, quaisquer de seus enanciÈmeros ou qualquer mistura de seus enaciÈmeros, ou um seu sal de adição farmaceuticamente aceitável ou um seu n-óxido, composição farmacêutica, uso do dito composto, de qualquer um de seus enanciÈmeros ou de qualquer mistura de seus enanciÈmeros, ou de um seu sal de adição farmaceuticamente aceitável, e, método de tratamento, prevenção ou alìvio de uma doença ou um distúrbio ou condição de um corpo animal vivo |
| AU2003280309A1 (en) * | 2002-11-11 | 2004-06-03 | Neurosearch A/S | 1,4-diazabicyclo (3,2,2)nonane derivatives, preparation and therapeutical use thereof |
| US6996399B2 (en) * | 2003-01-13 | 2006-02-07 | Micrel, Inc. | Wireless device and method using frequency hopping and sweep modes |
| WO2005074940A1 (en) * | 2004-02-04 | 2005-08-18 | Neurosearch A/S | Diazabicyclic aryl derivatives as cholinergic receptor modulators |
| EP1863819B1 (en) | 2005-02-16 | 2011-01-12 | NeuroSearch A/S | Diazabicyclic aryl derivatives and their use as chinolinergic ligands at the nicotinic acetylcholine receptors |
| PT2032575E (pt) | 2006-05-30 | 2010-07-09 | Neurosearch As | NOVO DERIVADO DE 1,4-DIAZA-BICICLO[3,2,2]NONIL-OXADIAZOLILO E A SUA APLICAÃO MéDICA |
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