NZ583823A - Furazanes for enhancing glutamatergic synaptic responses - Google Patents
Furazanes for enhancing glutamatergic synaptic responsesInfo
- Publication number
- NZ583823A NZ583823A NZ583823A NZ58382308A NZ583823A NZ 583823 A NZ583823 A NZ 583823A NZ 583823 A NZ583823 A NZ 583823A NZ 58382308 A NZ58382308 A NZ 58382308A NZ 583823 A NZ583823 A NZ 583823A
- Authority
- NZ
- New Zealand
- Prior art keywords
- substituted
- compound according
- medicament
- branched
- treatment
- Prior art date
Links
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
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Applications Claiming Priority (2)
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| US96436207P | 2007-08-10 | 2007-08-10 | |
| PCT/US2008/009508 WO2009023126A2 (en) | 2007-08-10 | 2008-08-08 | Bicyclic amides for enhancing glutamatergic synaptic responses |
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| NZ583823A NZ583823A (en) | 2007-08-10 | 2008-08-08 | Furazanes for enhancing glutamatergic synaptic responses |
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| WO2008085506A1 (en) | 2007-01-03 | 2008-07-17 | Cortex Pharmaceuticals, Inc. | 3-substituted-[1,2,3]-benzotriazinone compound for enhancing glutamatergic synaptic responses |
| WO2008143963A1 (en) | 2007-05-17 | 2008-11-27 | Cortex Pharmaceuticals, Inc. | Di-substituted amides for enhancing glutamatergic synaptic responses |
| US8119632B2 (en) | 2007-08-10 | 2012-02-21 | Cortex Pharmaceuticals, Inc. | Bicyclic amide derivatives for enhancing glutamatergic synaptic responses |
| BRPI0823262A2 (pt) | 2007-08-10 | 2013-09-24 | Cortex Pharma Inc | mÉtodo de tratamento de depressço respiratària e uso de um composto na fabricaÇço de um medicamento para o tratamento de depressço respiratària |
| WO2010087980A2 (en) * | 2009-02-02 | 2010-08-05 | Cortex Pharmaceuticals, Inc. | Bicyclic amide derivatives for the treatment of respiratory depression |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| RU2014136339A (ru) | 2012-02-07 | 2016-03-27 | Иолас Терапьютикс, Инк. | Замещенные пролины/пиперидины как антагонисты орексиновых рецепторов |
| EP3180332B1 (en) | 2014-08-13 | 2021-10-27 | Eolas Therapeutics Inc. | Difluoropyrrolidines as orexin receptor modulators |
| US9739787B2 (en) | 2015-09-01 | 2017-08-22 | Abdulmohsen Ebrahim Alterki | Method for diagnosing sleep apnea by measuring adipsin and betatrophin levels |
| KR102738491B1 (ko) | 2016-02-12 | 2024-12-03 | 아스트라제네카 아베 | 오렉신 수용체 조정제로서의 할로-치환된 피페리딘 |
| WO2018009256A1 (en) | 2016-03-29 | 2018-01-11 | Respirerx Pharmaceuticals, Inc. | Compositions and methods for treating attention deficit disorders |
| US12187737B2 (en) | 2019-06-04 | 2025-01-07 | Hager Biosciences, Llc | Imidazolo derivatives, compositions and methods as orexin antagonists |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3723436A (en) * | 1971-02-25 | 1973-03-27 | Sun Oil Co | Process for aromatic lactams |
| FR2597103B1 (fr) * | 1986-04-15 | 1988-12-16 | Provesan Sa | Procede de preparation de derives d'oxazinobenzothiazine 6,6-dioxyde |
| ES2174851T3 (es) * | 1992-07-24 | 2002-11-16 | Univ California | Farmacos que aumentan las respuestas sinapticas mediadas por receptores ampa. |
| US20020099050A1 (en) | 1993-07-23 | 2002-07-25 | Lynch Gary S. | Drugs that enhance synaptic responses mediated by AMPA receptors |
| US5650409A (en) * | 1995-06-02 | 1997-07-22 | Cortex Pharmaceuticals, Inc. | Benzoyl piperidines/pyrrolidines for enhancing synaptic response |
| US5736543A (en) * | 1996-04-03 | 1998-04-07 | The Regents Of The University Of California | Benzoxazines for enhancing synaptic response |
| US6030968A (en) * | 1996-09-17 | 2000-02-29 | The Regents Of The University Of California | Positive AMPA receptor modulation to enhance brain neurotrophic factor expression |
| US6110935A (en) * | 1997-02-13 | 2000-08-29 | The Regents Of The University Of California | Benzofurazan compounds for enhancing glutamatergic synaptic responses |
| BR9814106A (pt) | 1997-10-27 | 2000-10-03 | Cortex Pharma Inc | Processo para tratar da esquizofrenia em um indivìduo, e, conjunto |
| US5985871A (en) | 1997-12-24 | 1999-11-16 | Cortex Pharmaceuticals, Inc. | Benzoxazine compounds for enhancing synaptic response |
| HUP0101280A3 (en) | 1998-02-18 | 2003-02-28 | Neurosearch As | Positive ampa receptor modulator compounds and their use |
| US6713474B2 (en) | 1998-09-18 | 2004-03-30 | Abbott Gmbh & Co. Kg | Pyrrolopyrimidines as therapeutic agents |
| US6303542B1 (en) * | 2000-08-18 | 2001-10-16 | Rohm And Haas Company | Herbicidal 3-substituted-phenyl-1,2,3-benzotriazin-4-ones |
| PA8535601A1 (es) * | 2000-12-21 | 2002-11-28 | Pfizer | Derivados benzimidazol y piridilimidazol como ligandos para gabaa |
| AUPS255202A0 (en) | 2002-05-27 | 2002-06-13 | Monash University | Agents and methods for the treatment of disorders associated with motor neuron degeneration |
| WO2004089416A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Combination of an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent |
| US20050085446A1 (en) | 2003-04-14 | 2005-04-21 | Babu M.K. M. | Fluoroquinolone formulations and methods of making and using the same |
| GB0317482D0 (en) * | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
| CN1897950A (zh) * | 2003-10-14 | 2007-01-17 | 惠氏公司 | 稠合芳基和杂芳基衍生物及其使用方法 |
| US8039468B2 (en) | 2006-08-31 | 2011-10-18 | The Governors Of The University Of Alberta | Method of inhibition of respiratory depression using positive allosteric AMPA receptor modulators |
| NZ578290A (en) * | 2007-01-03 | 2012-03-30 | Cortex Pharma Inc | 3-substituted-[1,2,3]benzotriazinone compounds for enhancing glutamatergic synaptic responses |
| WO2008085506A1 (en) | 2007-01-03 | 2008-07-17 | Cortex Pharmaceuticals, Inc. | 3-substituted-[1,2,3]-benzotriazinone compound for enhancing glutamatergic synaptic responses |
| WO2008143963A1 (en) * | 2007-05-17 | 2008-11-27 | Cortex Pharmaceuticals, Inc. | Di-substituted amides for enhancing glutamatergic synaptic responses |
| BRPI0823262A2 (pt) | 2007-08-10 | 2013-09-24 | Cortex Pharma Inc | mÉtodo de tratamento de depressço respiratària e uso de um composto na fabricaÇço de um medicamento para o tratamento de depressço respiratària |
| KR20100063087A (ko) | 2007-09-20 | 2010-06-10 | 코텍스 파마슈티칼스, 인크. | 글루타메이트 시냅스 반응 향상을 위한 3-치환된 1,2,3-트리아진-4-온 및 3-치환된 1,3-피리미디논 |
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