JP2007534657A - ベンゾ［ｄ］イソオキサゾール阻害剤 - Google Patents
ベンゾ［ｄ］イソオキサゾール阻害剤 Download PDFInfo
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- JP2007534657A JP2007534657A JP2006547443A JP2006547443A JP2007534657A JP 2007534657 A JP2007534657 A JP 2007534657A JP 2006547443 A JP2006547443 A JP 2006547443A JP 2006547443 A JP2006547443 A JP 2006547443A JP 2007534657 A JP2007534657 A JP 2007534657A
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- hydrogen atom
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- alkyl
- serine
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Classifications
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
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| US53297803P | 2003-12-29 | 2003-12-29 | |
| PCT/US2004/043547 WO2005066143A2 (en) | 2003-12-29 | 2004-12-28 | Benzo[d]isoxazol-3-ol daao inhibitors |
Publications (2)
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| JP2007534657A true JP2007534657A (ja) | 2007-11-29 |
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|---|---|
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| EP (1) | EP1711478A2 (enExample) |
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| CN (3) | CN101798291A (enExample) |
| AU (1) | AU2004312511A1 (enExample) |
| BR (1) | BRPI0417910A (enExample) |
| CA (1) | CA2552098A1 (enExample) |
| CZ (1) | CZ2006426A3 (enExample) |
| IL (1) | IL176607A0 (enExample) |
| NZ (1) | NZ548213A (enExample) |
| PL (1) | PL380766A1 (enExample) |
| RU (1) | RU2384574C2 (enExample) |
| WO (1) | WO2005066143A2 (enExample) |
| ZA (1) | ZA200605384B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016517866A (ja) * | 2014-03-24 | 2016-06-20 | カオシュン・チャン・グン・メモリアル・ホスピタル | 認知症または軽度認知障害を予防または治療する組成物を製造するための安息香酸塩の使用 |
| JP2017190341A (ja) * | 2017-07-26 | 2017-10-19 | カオシュン・チャン・グン・メモリアル・ホスピタル | 認知症または軽度認知障害を予防または治療する組成物を製造するための安息香酸塩の使用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2004312530A1 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole DAAO inhibitors |
| CA2472806A1 (en) | 2004-05-18 | 2005-11-18 | Petro-Canada | Compositions and methods for treating turf insect pests and diseases such as fungal infestations |
| JP2009500425A (ja) | 2005-07-06 | 2009-01-08 | セプラコア インコーポレーテッド | エスゾピクロン及びトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−ｎ−メチル−１−ナフタレンアミン又はトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−１−ナフタレンアミンの組み合わせ、並びに閉経期並びに気分、不安、及び認知障害の治療方法 |
| BRPI0706365A2 (pt) | 2006-01-06 | 2011-03-22 | Sepracor Inc | Cicloalquilaminas como inibidores da recaptação de monoamina |
| NZ569608A (en) * | 2006-01-06 | 2011-09-30 | Sepracor Inc | Tetralone-based monoamine reuptake inhibitors |
| EP1988085B8 (en) | 2006-02-21 | 2015-01-28 | Toyama Chemical Co., Ltd. | Process for production of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl]propionate ester and intermediate for the process |
| DK2816024T3 (en) | 2006-03-31 | 2017-10-30 | Sunovion Pharmaceuticals Inc | CHIRALE AMINER |
| US7884124B2 (en) * | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| US20080082066A1 (en) * | 2006-10-02 | 2008-04-03 | Weyerhaeuser Co. | Crosslinked carboxyalkyl cellulose fibers having non-permanent and temporary crosslinks |
| US9357768B2 (en) | 2006-10-05 | 2016-06-07 | Suncor Energy Inc. | Herbicidal composition with increased herbicidal efficacy |
| US20090099248A1 (en) * | 2007-01-18 | 2009-04-16 | Sepracor Inc. | Inhibitors of d-amino acid oxidase |
| US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| AU2008259841B2 (en) | 2007-05-31 | 2015-02-05 | Sunovion Pharmaceuticals Inc. | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
| ES2619731T3 (es) | 2008-06-26 | 2017-06-26 | Suncor Energy Inc. | Formulación fungicida para hierba de césped mejorada con pigmento |
| WO2010017418A1 (en) * | 2008-08-07 | 2010-02-11 | Sepracor Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| EP2389187B1 (en) | 2009-01-20 | 2016-11-16 | Los Angeles Biomedical Research Institute at Harbor-UCLA Medical Center | Sorbic and benzoic acid and derivatives thereof enhance the activity of a neuropharmaceutical |
| WO2011017634A2 (en) * | 2009-08-07 | 2011-02-10 | Sepracore Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| AU2011301171C1 (en) | 2010-09-09 | 2015-09-10 | Nutrien Ag Solutions (Canada) Inc. | Synergistic paraffinic oil and boscalid fungicides |
| AU2012381990B2 (en) | 2012-06-04 | 2017-02-23 | Nutrien Ag Solutions (Canada) Inc. | Formulations containing paraffinic oil and anti-settling agent |
| WO2014025993A1 (en) | 2012-08-08 | 2014-02-13 | The Johns Hopkins University | Inhibitors of d-amino acid oxidase |
| US9265458B2 (en) | 2012-12-04 | 2016-02-23 | Sync-Think, Inc. | Application of smooth pursuit cognitive testing paradigms to clinical drug development |
| US9380976B2 (en) | 2013-03-11 | 2016-07-05 | Sync-Think, Inc. | Optical neuroinformatics |
| CN103435561B (zh) * | 2013-08-19 | 2016-08-10 | 上海交通大学 | 一种新型d-氨基酸氧化酶抑制剂及其制备和应用 |
| CN105801511B (zh) * | 2016-04-22 | 2018-01-02 | 山西大学 | 一种1,2‑苯并异恶唑啉‑3‑酮的制备方法 |
| US11008277B2 (en) | 2016-06-13 | 2021-05-18 | Syneurx International (Taiwan) Corp. | Co-crystals of sodium benzoate and uses thereof |
| US10815184B2 (en) | 2016-06-13 | 2020-10-27 | Syneurx International (Taiwan) Corp. | Co-crystals of lithium benzoate and uses thereof |
| CA2938096C (en) | 2016-08-04 | 2019-02-26 | Suncor Energy Inc. | Stabilized emulsions |
| US11369579B2 (en) | 2016-10-24 | 2022-06-28 | Syneurx International (Taiwan) Corp. | Polymorphic forms of sodium benzoate and uses thereof |
| US10336679B2 (en) | 2016-10-24 | 2019-07-02 | Syneurx International (Taiwan) Corp. | Polymorphic forms of sodium benzoate and uses thereof |
| WO2019043635A1 (en) | 2017-09-01 | 2019-03-07 | Richter Gedeon Nyrt. | COMPOUNDS INHIBITING THE ACTIVITY OF D-AMINO ACID OXIDASE |
| US10336724B2 (en) * | 2017-10-18 | 2019-07-02 | Syneurx International (Taiwan) Corp. | D-amino acid oxidase inhibitors and therapeutic uses thereof |
| US10098861B1 (en) | 2017-10-24 | 2018-10-16 | Syneurx International (Taiwan) Corp. | Pharmaceutical composition comprising sodium benzoate compound and clozapine, and uses thereof |
| WO2020150831A1 (en) | 2019-01-25 | 2020-07-30 | Suncor Energy Inc. | Photosensitizer compounds, methods of manufacture and application to plants |
| CN113677204B (zh) | 2019-02-15 | 2024-03-05 | 桑科能源股份有限公司 | 原卟啉ix衍生物改善植物健康的用途 |
| CN117362246B (zh) * | 2023-12-04 | 2024-03-12 | 烟台海川化学制品有限公司 | 一种3-苯基-1,4,2-二恶唑-5-酮的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58177915A (ja) * | 1982-04-12 | 1983-10-18 | Green Cross Corp:The | 抗血栓剤 |
| US4738709A (en) * | 1985-01-10 | 1988-04-19 | Ppg Industries, Inc. | Herbicidally active substituted benzisoxazoles |
| JPH0477476A (ja) * | 1990-07-19 | 1992-03-11 | Sankyo Co Ltd | 抗潰瘍剤 |
| CA2146755A1 (en) * | 1992-10-28 | 1994-05-11 | Kenji Takeda | Novel 1,2-benzoisoxazole derivative or its salt and brain-protecting agent comprising the same |
| ES2208690T3 (es) * | 1994-08-30 | 2004-06-16 | Sankyo Company Limited | Isoxazol. |
| US5484763A (en) * | 1995-02-10 | 1996-01-16 | American Cyanamid Company | Substituted benzisoxazole and benzisothiazole herbicidal agents |
| US5620997A (en) * | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| DE19960917A1 (de) * | 1999-12-17 | 2001-06-21 | Bayer Ag | Neue 3-Oxo-2,1-benzisoxazol-1(3H)-carboxamide zur Behandlung von ZNS-Erkrankungen |
| JP2001247462A (ja) * | 2000-03-07 | 2001-09-11 | Otsuka Pharmaceut Co Ltd | ウレアーゼ阻害剤 |
| CA2559105A1 (en) | 2004-03-16 | 2005-09-29 | Janssen Pharmaceutica N.V. | Benzisoxazoles |
-
2004
- 2004-12-28 CN CN201010150424A patent/CN101798291A/zh active Pending
- 2004-12-28 NZ NZ548213A patent/NZ548213A/en unknown
- 2004-12-28 JP JP2006547443A patent/JP2007534657A/ja active Pending
- 2004-12-28 BR BRPI0417910-2A patent/BRPI0417910A/pt not_active Application Discontinuation
- 2004-12-28 CA CA002552098A patent/CA2552098A1/en not_active Abandoned
- 2004-12-28 CZ CZ20060426A patent/CZ2006426A3/cs unknown
- 2004-12-28 PL PL380766A patent/PL380766A1/pl not_active Application Discontinuation
- 2004-12-28 RU RU2006127436/04A patent/RU2384574C2/ru not_active IP Right Cessation
- 2004-12-28 WO PCT/US2004/043547 patent/WO2005066143A2/en not_active Ceased
- 2004-12-28 ZA ZA200605384A patent/ZA200605384B/en unknown
- 2004-12-28 US US11/024,151 patent/US7166725B2/en not_active Expired - Lifetime
- 2004-12-28 CN CN2010105590539A patent/CN102010382A/zh active Pending
- 2004-12-28 CN CN2004800422050A patent/CN1922157B/zh not_active Expired - Fee Related
- 2004-12-28 EP EP04815603A patent/EP1711478A2/en not_active Withdrawn
- 2004-12-28 AU AU2004312511A patent/AU2004312511A1/en not_active Abandoned
- 2004-12-28 KR KR1020067015383A patent/KR20060128978A/ko not_active Ceased
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016517866A (ja) * | 2014-03-24 | 2016-06-20 | カオシュン・チャン・グン・メモリアル・ホスピタル | 認知症または軽度認知障害を予防または治療する組成物を製造するための安息香酸塩の使用 |
| JP2017190341A (ja) * | 2017-07-26 | 2017-10-19 | カオシュン・チャン・グン・メモリアル・ホスピタル | 認知症または軽度認知障害を予防または治療する組成物を製造するための安息香酸塩の使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060128978A (ko) | 2006-12-14 |
| US20050143434A1 (en) | 2005-06-30 |
| RU2384574C2 (ru) | 2010-03-20 |
| US7166725B2 (en) | 2007-01-23 |
| CN102010382A (zh) | 2011-04-13 |
| WO2005066143A3 (en) | 2005-10-20 |
| CN1922157A (zh) | 2007-02-28 |
| IL176607A0 (en) | 2006-10-31 |
| NZ548213A (en) | 2010-05-28 |
| ZA200605384B (en) | 2007-10-31 |
| BRPI0417910A (pt) | 2007-04-10 |
| CZ2006426A3 (cs) | 2006-10-11 |
| CN101798291A (zh) | 2010-08-11 |
| PL380766A1 (pl) | 2007-03-19 |
| EP1711478A2 (en) | 2006-10-18 |
| RU2006127436A (ru) | 2008-02-10 |
| CA2552098A1 (en) | 2005-07-21 |
| CN1922157B (zh) | 2011-01-12 |
| AU2004312511A1 (en) | 2005-07-21 |
| WO2005066143A2 (en) | 2005-07-21 |
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