CA2671321A1 - Means for improving cognitive functions and memory based on hydrogenated pyrido (4,3-b) indoles (variants), pharmacological means based thereon and method for the use thereof - Google Patents
Means for improving cognitive functions and memory based on hydrogenated pyrido (4,3-b) indoles (variants), pharmacological means based thereon and method for the use thereof Download PDFInfo
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- CA2671321A1 CA2671321A1 CA002671321A CA2671321A CA2671321A1 CA 2671321 A1 CA2671321 A1 CA 2671321A1 CA 002671321 A CA002671321 A CA 002671321A CA 2671321 A CA2671321 A CA 2671321A CA 2671321 A1 CA2671321 A1 CA 2671321A1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2006142521/15A RU2334514C1 (ru) | 2006-12-01 | 2006-12-01 | СРЕДСТВО ДЛЯ УЛУЧШЕНИЯ КОГНИТИВНЫХ ФУНКЦИЙ И ПАМЯТИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО (4,3-b) ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| RU2006142521 | 2006-12-01 | ||
| PCT/US2007/024623 WO2008069963A1 (en) | 2006-12-01 | 2007-11-30 | Means for improving cognitive functions and memory based on hydrogenated pyrido (4,3-b) indoles (variants), pharmacological means based thereon and method for the use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2671321A1 true CA2671321A1 (en) | 2008-06-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002671321A Abandoned CA2671321A1 (en) | 2006-12-01 | 2007-11-30 | Means for improving cognitive functions and memory based on hydrogenated pyrido (4,3-b) indoles (variants), pharmacological means based thereon and method for the use thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100286188A1 (OSRAM) |
| EP (1) | EP2101579A4 (OSRAM) |
| JP (1) | JP2010511616A (OSRAM) |
| AU (1) | AU2007328323A1 (OSRAM) |
| CA (1) | CA2671321A1 (OSRAM) |
| RU (1) | RU2334514C1 (OSRAM) |
| WO (1) | WO2008069963A1 (OSRAM) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090130105A (ko) * | 2007-04-05 | 2009-12-17 | 알라 캠, 엘엘씨 | 치환된 2,3,4,5-테트라히드로-1ｈ-피리도［4,3-ｂ］ 인돌, 그 제조방법 및 용도 |
| JP2010540439A (ja) | 2007-09-20 | 2010-12-24 | ディー２イー，エルエルシー | 神経保護性の及び認知を向上させる性質を備えた水素化されたピリド［４，３−ｂ］インドール類のフッ素を含有する誘導体、調製するための工程、並びに使用 |
| RU2007139634A (ru) | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| RU2544856C2 (ru) * | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| PE20091820A1 (es) | 2008-03-24 | 2009-12-10 | Medivation Technologies Inc | Compuestos heterociclicos con uniones puente y metodos para usarlos |
| EP2280968A2 (en) | 2008-03-24 | 2011-02-09 | Medivation Technologies, Inc. | Pyrido [3, 4-b]indoles and methods of use |
| JP5551708B2 (ja) | 2008-10-31 | 2014-07-16 | メディベイション テクノロジーズ， インコーポレイテッド | アゼピノ［４，５−ｂ］インドール化合物およびその使用方法 |
| US8907097B2 (en) | 2008-10-31 | 2014-12-09 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles containing rigid moieties |
| US9125898B2 (en) * | 2008-11-14 | 2015-09-08 | Neurotune Ag | Acetam derivatives for pain relief |
| KR20110132564A (ko) * | 2009-02-11 | 2011-12-08 | 선오비온 파마슈티컬스 인코포레이티드 | 히스타민 ｈ3 역 작용제 및 길항제, 및 이의 사용 방법 |
| EP2236160A3 (en) * | 2009-03-31 | 2011-12-14 | Sanovel Ilac Sanayi ve Ticaret A.S. | Modified release dimebolin formulations |
| EP2236159A3 (en) * | 2009-03-31 | 2011-12-07 | Sanovel Ilac Sanayi ve Ticaret A.S. | Modified release dimebolin compositions |
| WO2010115342A1 (zh) * | 2009-04-10 | 2010-10-14 | 中国人民解放军军事医学科学院毒物药物研究所 | 含有四氢吡啶[4，3-b]吲哚衍生物的缓释组合物及该衍生物的制备方法 |
| TR200903014A1 (tr) * | 2009-04-17 | 2010-11-22 | Sanovel İlaç San. Ve Ti̇c. A.Ş. | Oral yolla dağılan dimebolin bileşimleri. |
| EP2424364A4 (en) | 2009-04-29 | 2012-12-19 | Medivation Technologies Inc | PYRIDO [4.3-B] INDOLES AND METHODS OF USE |
| US8741919B2 (en) | 2009-04-29 | 2014-06-03 | Medivation Technologies, Inc. | Pyrido[4,3-B]indoles and methods of use |
| EP2475664A2 (en) * | 2009-09-11 | 2012-07-18 | Sunovion Pharmaceuticals Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| WO2011038163A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[3,4-b]indoles and methods of use |
| BR112012006648A2 (pt) * | 2009-09-23 | 2019-09-24 | Medivation Neurology Inc | composto,método de tratamento de um distúrbio cognitivo, distúrbio psicótico, distúrbio mediado por neurotransmissor ou um distúrbio neuronal, composição farmacêutica e kit |
| CA2775328A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[4,3-b]indoles and methods of use |
| RU2428185C1 (ru) * | 2009-12-29 | 2011-09-10 | Учреждение Российской Академии Наук Институт Физиологически Активных Веществ Ран (Ифав Ран) | ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ ДЛЯ ЛЕЧЕНИЯ НЕЙРОДЕГЕНЕРАТИВНЫХ ЗАБОЛЕВАНИЙ НА ОСНОВЕ ГИДРИРОВАННОГО ПИРИДО(4,3-b)ИНДОЛА, СПОСОБ ЕЕ ПОЛУЧЕНИЯ И ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕЕ ОСНОВЕ |
| US9193728B2 (en) | 2010-02-18 | 2015-11-24 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
| US9040519B2 (en) | 2010-02-18 | 2015-05-26 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
| WO2011103433A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| WO2011103430A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| WO2012016708A1 (en) | 2010-08-06 | 2012-02-09 | Ratiopharm Gmbh | Oral dosage form comprising dimebolin and donepezil |
| WO2012016707A2 (en) * | 2010-08-06 | 2012-02-09 | Ratiopharm Gmbh | Oral dosage form for the modified release of dimebolin |
| US9199985B2 (en) | 2011-02-18 | 2015-12-01 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| US9434747B2 (en) | 2011-02-18 | 2016-09-06 | Medivation Technologies, Inc. | Methods of treating diabetes |
| WO2012154261A1 (en) | 2011-02-18 | 2012-11-15 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| US9035056B2 (en) | 2011-02-18 | 2015-05-19 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| RU2482843C2 (ru) * | 2011-05-23 | 2013-05-27 | Федеральное Медико-Биологическое Агентство Федеральное Государственное Учреждение Научно-исследовательский институт детских инфекций | Способ реабилитации неврологических нарушений у детей при нейроинфекциях |
| RU2477131C1 (ru) * | 2012-01-17 | 2013-03-10 | Алиса Владимировна Алесенко | СРЕДСТВО ДЛЯ НЕЙТРАЛИЗАЦИИ ТОКСИЧЕСКОГО ДЕЙСТВИЯ ФАКТОРА НЕКРОЗА ОПУХОЛИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО (4,3-b) ИНДОЛОВ, ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЛЕЧЕНИЯ АУТОИММУННЫХ ЗАБОЛЕВАНИЙ НА ОСНОВЕ НЕЙТРАЛИЗАЦИИ ТОКСИЧЕСКОГО ДЕЙСТВИЯ ФАКТОРА НЕКРОЗА ОПУХОЛИ |
| DE102012003065A1 (de) * | 2012-02-13 | 2013-08-14 | Friedrich-Schiller-Universität Jena | Neue bivalente Gammacarbolinderivate sowie deren Herstellung und Verwendung als Antidementiva |
| RU2672728C1 (ru) * | 2017-09-19 | 2018-11-19 | Игорь Анатольевич Помыткин | Холиновые соли фумаровой кислоты |
Family Cites Families (6)
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| RU2140417C1 (ru) * | 1995-10-17 | 1999-10-27 | Институт физиологически активных веществ РАН | Производные гидрированных пиридо(4,3-b)индолов, способы их получения, фармацевтическая композиция и способ лечения |
| RU2106864C1 (ru) * | 1995-10-23 | 1998-03-20 | Николай Серафимович Зефиров | Средство для лечения болезни альцгеймера |
| RU2283108C2 (ru) * | 2003-12-08 | 2006-09-10 | Сергей Олегович Бачурин | ГЕРОПРОТЕКТОР НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b) ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| AU2005315319B2 (en) * | 2004-12-17 | 2011-07-07 | Glenmark Pharmaceuticals S.A. | Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders |
| AU2007309390A1 (en) * | 2006-10-27 | 2008-05-02 | Medivation Neurology, Inc. | Methods and combination therapies for treating Alzheimer's disease |
| AU2008257152A1 (en) * | 2007-05-25 | 2008-12-04 | Medivation Neurology, Inc. | Methods and compositions for stimulating cells |
-
2006
- 2006-12-01 RU RU2006142521/15A patent/RU2334514C1/ru not_active IP Right Cessation
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2007
- 2007-11-30 CA CA002671321A patent/CA2671321A1/en not_active Abandoned
- 2007-11-30 JP JP2009539340A patent/JP2010511616A/ja active Pending
- 2007-11-30 US US12/517,191 patent/US20100286188A1/en not_active Abandoned
- 2007-11-30 AU AU2007328323A patent/AU2007328323A1/en not_active Abandoned
- 2007-11-30 EP EP07862370A patent/EP2101579A4/en not_active Withdrawn
- 2007-11-30 WO PCT/US2007/024623 patent/WO2008069963A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007328323A1 (en) | 2008-06-12 |
| RU2334514C1 (ru) | 2008-09-27 |
| JP2010511616A (ja) | 2010-04-15 |
| US20100286188A1 (en) | 2010-11-11 |
| EP2101579A1 (en) | 2009-09-23 |
| WO2008069963A1 (en) | 2008-06-12 |
| RU2006142521A (ru) | 2008-06-20 |
| EP2101579A4 (en) | 2011-05-18 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20131202 |