JP2012533566A - 認識障害処置用のコリンエステラーゼ阻害剤を含む組成物 - Google Patents
認識障害処置用のコリンエステラーゼ阻害剤を含む組成物 Download PDFInfo
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- JP2012533566A JP2012533566A JP2012520814A JP2012520814A JP2012533566A JP 2012533566 A JP2012533566 A JP 2012533566A JP 2012520814 A JP2012520814 A JP 2012520814A JP 2012520814 A JP2012520814 A JP 2012520814A JP 2012533566 A JP2012533566 A JP 2012533566A
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- galantamine
- cholinesterase inhibitor
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| PCT/US2010/042308 WO2011009061A1 (en) | 2009-07-17 | 2010-07-16 | Compositions comprising a cholinesterase inhibitor for treating cognitive disorders |
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| WO2008109610A1 (en) * | 2007-03-06 | 2008-09-12 | Allergan, Inc. | Methods for treating cognitive disorders using 3-aryl-3-hydroxy-2-amino-propionic acid amides, 3-heteroaryl-3-hydroxy-2-amino-propionic acid amides and related compounds |
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| US5A (en) * | 1836-08-10 | Thomas Blanchard | Machine for mortising solid wooden shells of ships' tackle-blocks | |
| US4166452A (en) * | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
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| US5409948A (en) * | 1992-11-23 | 1995-04-25 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Method for treating cognitive disorders with phenserine |
| US20050222123A1 (en) * | 2004-01-27 | 2005-10-06 | North Shore-Long Island Jewish Research Institute | Cholinesterase inhibitors for treating inflammation |
| US20070212253A1 (en) * | 2004-12-21 | 2007-09-13 | Elrod Scott A | Descenting systems and methods |
| PL383715A1 (pl) | 2005-01-26 | 2008-05-12 | Allergan, Inc. | Amidy kwasu 3-arylo-3-hydroksy-2-amino-propionowego, amidy kwasu 3-heteroarylo-3-hydroksy-2-amino-propionowego i ich związki pokrewne posiadające aktywność przeciwbólową i/lub pobudzającą odporność |
| WO2007012154A1 (en) * | 2005-07-27 | 2007-02-01 | Carlos Henrique Horta Lima | Pharmaceutical preparation containing an acetylcholinesterase ihibitor and an antidepressant with 5-ht and alpha-2-adrenoceptor blocking properties. |
| EP2275096A3 (en) * | 2005-08-26 | 2011-07-13 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
| US8173683B2 (en) * | 2007-03-06 | 2012-05-08 | Allergan, Inc. | Methods for treating cognitive disorders |
| WO2008109286A1 (en) * | 2007-03-06 | 2008-09-12 | Allergan, Inc. | Methods for treating cognitive disorders using 1-aryl-1-hydroxy-2,3-diamino-propyl amines, 1-heteroaryl-1-hydroxy-2,3-diamino-propyl amines and related compounds |
| WO2008109287A1 (en) * | 2007-03-06 | 2008-09-12 | Allergan, Inc. | Methods for treating cognitive disorders using 1-benzyl-1-hydroxy-2,3-diamino-propyl amines, 3-benzyl-3-hydroxy-2-amino-propionic acid amides and related compounds |
| CA2693369A1 (en) * | 2007-07-17 | 2009-01-22 | Allergan, Inc. | Methods for treating anxiety |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008109610A1 (en) * | 2007-03-06 | 2008-09-12 | Allergan, Inc. | Methods for treating cognitive disorders using 3-aryl-3-hydroxy-2-amino-propionic acid amides, 3-heteroaryl-3-hydroxy-2-amino-propionic acid amides and related compounds |
Non-Patent Citations (3)
| Title |
|---|
| JPN6014030645; Ｃ． Ｌａｎｎｉ ｅｔ ａｌ．: Ｐｈａｒｍａｃｏｌｏｇｉｃａｌ ｒｅｓｅａｒｃｈ ｖｏｌ．５７, 2008, ｐ．１９６-２１３ * |
| JPN6014030648; Ｄ． Ｂ． Ｈｏｇａｎ ｅｔ ａｌ．: Ａｌｚｈｅｉｍｅｒ'ｓ ＆ Ｄｅｍｅｎｔｉａ ｖｏｌ．３, 2007, ｐ．３５５-３８４ * |
| JPN6014030651; Ｎ． Ｈｅｒｒｍａｎｎ ｅｔ ａｌ．: Ａｌｚｈｅｉｍｅｒ'ｓ ＆ Ｄｅｍｅｎｔｉａ ｖｏｌ．３, 2007, ｐ．３８５-３９７ * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120090029A (ko) | 2012-08-16 |
| US20110015179A1 (en) | 2011-01-20 |
| RU2012103401A (ru) | 2013-08-27 |
| KR101757003B1 (ko) | 2017-07-11 |
| CA2768356A1 (en) | 2011-01-20 |
| US20130040938A1 (en) | 2013-02-14 |
| EP2453890A1 (en) | 2012-05-23 |
| PT2453890T (pt) | 2020-08-25 |
| AU2010273977A1 (en) | 2012-02-02 |
| IN2012DN01209A (enExample) | 2015-04-10 |
| RU2607946C2 (ru) | 2017-01-11 |
| US9492543B2 (en) | 2016-11-15 |
| RU2016151986A (ru) | 2018-12-19 |
| ES2809298T3 (es) | 2021-03-03 |
| CN102497861A (zh) | 2012-06-13 |
| BR112012001047A2 (pt) | 2019-09-24 |
| WO2011009061A1 (en) | 2011-01-20 |
| DK2453890T3 (da) | 2020-08-17 |
| EP2453890B1 (en) | 2020-05-27 |
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