CA2679882C - Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof - Google Patents
Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof Download PDFInfo
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- CA2679882C CA2679882C CA2679882A CA2679882A CA2679882C CA 2679882 C CA2679882 C CA 2679882C CA 2679882 A CA2679882 A CA 2679882A CA 2679882 A CA2679882 A CA 2679882A CA 2679882 C CA2679882 C CA 2679882C
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- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- A—HUMAN NECESSITIES
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- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US90596307P | 2007-03-08 | 2007-03-08 | |
| US60/905,963 | 2007-03-08 | ||
| PCT/US2008/003092 WO2008112164A2 (en) | 2007-03-08 | 2008-03-07 | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
Publications (2)
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| CA2679882C true CA2679882C (en) | 2015-12-29 |
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| AU (1) | AU2008226947B2 (enExample) |
| CA (1) | CA2679882C (enExample) |
| WO (1) | WO2008112164A2 (enExample) |
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| WO2008112164A2 (en) | 2007-03-08 | 2008-09-18 | The Board Of Trustees Of The Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| WO2010028175A1 (en) | 2008-09-08 | 2010-03-11 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase activity and methods of use thereof |
| JP2012506856A (ja) * | 2008-10-28 | 2012-03-22 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼのモジュレーターおよびその使用方法 |
| WO2012082862A2 (en) * | 2010-12-14 | 2012-06-21 | Beth Israel Deaconess Medical Center | Androgen receptor inhibitors and methods of use thereof |
| WO2012149106A1 (en) | 2011-04-29 | 2012-11-01 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
| TWI567061B (zh) | 2011-07-01 | 2017-01-21 | 吉李德科學股份有限公司 | 用於治療成癮之化合物 |
| US9545393B2 (en) * | 2012-08-24 | 2017-01-17 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions for treating pain |
| KR20150135332A (ko) * | 2013-03-14 | 2015-12-02 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 | 미토콘드리아 알데히드 탈수소효소-2 조절인자들 및 이들의 사용 방법 |
| CN103191103A (zh) * | 2013-04-15 | 2013-07-10 | 中南大学 | 乙醛脱氢酶激活物alda-1的合成方法及其用途 |
| CN103923077B (zh) * | 2013-07-05 | 2016-03-02 | 高尔医药科技(上海)有限公司 | 两种乙醛脱氢酶激动剂、其制备方法及用途 |
| JP6261278B2 (ja) * | 2013-10-16 | 2018-01-17 | 国立大学法人広島大学 | アルデヒドデヒドロゲナーゼの活性を増強するための医薬組成物 |
| WO2015084731A1 (en) * | 2013-12-02 | 2015-06-11 | The Board Of Trustees Of The Leland Stanford Junior University | Aldehyde dehydrogenase inhibitors and methods of use thereof |
| DK3107899T3 (da) * | 2014-02-19 | 2020-11-16 | Aviv Therapeutics Inc | Mitokondriel aldehyddehydrogenase 2 (aldh2)-bindende polycykliske amider og anvendelse deraf til cancerbehandling |
| FR3054564B1 (fr) * | 2016-07-28 | 2018-08-31 | Advanced Biodesign | Substrat specifique d'une isoenzyme de l'aldh |
| WO2019098288A1 (ja) * | 2017-11-15 | 2019-05-23 | 学校法人 慶應義塾 | 抗腫瘍剤及び配合剤 |
| CA3085992A1 (en) | 2018-01-31 | 2019-08-08 | Eisai R&D Management Co., Ltd. | Aldh2 activator |
| CN114149386A (zh) * | 2018-06-04 | 2022-03-08 | 中国人民解放军第二军医大学 | 芳基戊二烯酰胺类醛脱氢酶抑制剂、其合成方法及用途 |
| CN111909138A (zh) * | 2019-05-09 | 2020-11-10 | 上海仕谱生物科技有限公司 | 抑制tdg活性的化合物 |
| TW202110437A (zh) * | 2019-05-23 | 2021-03-16 | 美商希諾瓦有限責任公司 | 用於酒精誘發之皮膚潮紅之治療及緩解的組成物及方法 |
| CN116348449B (zh) | 2020-11-02 | 2026-03-13 | 亚克医药株式会社 | 化合物、乙醛脱氢酶2激活剂、医药组合物、以及治疗及/或预防药 |
| EP4512468A4 (en) | 2022-04-22 | 2026-04-08 | Alchemedicine Inc | COMPOUND, ALDHEHYDE DEHYDROGENASE 2 ACTIVATOR, PHARMACEUTICAL COMPOSITION AND TREATMENT AND/OR PREVENTIVE MEDICINE |
Family Cites Families (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2319808A (en) | 1939-08-31 | 1943-05-25 | Squibb & Sons Inc | Sterol derivatives and process for producing same |
| JPH01203351A (ja) | 1988-02-05 | 1989-08-16 | Mitsui Petrochem Ind Ltd | １，４−ジヒドロキシナフタレン誘導体および医薬 |
| JPH023351A (ja) | 1988-06-16 | 1990-01-08 | Oki Electric Ind Co Ltd | 印刷装置 |
| US4861891A (en) | 1988-08-31 | 1989-08-29 | Pfizer Inc. | Antidepressant N-substituted nicotinamide compounds |
| JPH03184973A (ja) | 1989-12-14 | 1991-08-12 | Rooman Kogyo:Kk | 放射線障害防護剤 |
| US5260323A (en) | 1990-06-28 | 1993-11-09 | Hoechst Aktiengesellschaft | 2,4- and 2,5-substituted pyridine-N-oxides, processes for their preparation and their use |
| DE4201047A1 (de) * | 1992-01-17 | 1993-07-22 | Bayer Ag | Substituierte isoxazolcarbonsaeureamide |
| US5272137A (en) * | 1992-02-14 | 1993-12-21 | Mcneil-Pfc, Inc. | Aqueous pharmaceutical suspension for pharmaceutical actives |
| JP2994182B2 (ja) | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
| JP3833281B2 (ja) | 1995-02-03 | 2006-10-11 | 日本曹達株式会社 | ２，６−ジクロロイソニコチン酸ベンジルアミド誘導体及び植物病害防除剤 |
| US6277985B1 (en) | 1995-09-15 | 2001-08-21 | Pharmacia & Upjohn Company | Aminoaryl oxazolidinone N-oxides |
| US6072050A (en) | 1996-06-11 | 2000-06-06 | Pioneer Hi-Bred International, Inc. | Synthetic promoters |
| FR2751645B1 (fr) | 1996-07-29 | 1998-12-24 | Sanofi Sa | Amines pour la fabrication de medicaments destines a empecher la proliferation de cellules tumorales |
| DK1027328T3 (da) | 1997-10-31 | 2006-11-13 | Aventis Pharma Ltd | Substituerede anilider |
| EP1045835A1 (en) | 1997-12-22 | 2000-10-25 | Eli Lilly And Company | Catalyst and method for amide formation |
| DE69906059D1 (de) * | 1998-04-20 | 2003-04-24 | Fujisawa Pharmaceutical Co | Anthranilsäurederivate als inhibitoren der c-gmp-phosphodiesterase |
| AR019190A1 (es) | 1998-07-08 | 2001-12-26 | Sod Conseils Rech Applic | Derivados de 2-aminopiridinas, productos intermedios para su preparacion, medicamentos y composiciones farmaceuticas que los contienen y su uso para preparar medicamentos |
| US6780883B2 (en) | 1998-11-05 | 2004-08-24 | Warner-Lambert Company | Amide inhibitors of microsomal triglyceride transfer protein |
| CA2352144A1 (en) | 1998-11-25 | 2000-06-02 | Yissum Research Development Company Of The Hebrew University In Jerusale M | Scavenger compounds |
| GB9919558D0 (en) | 1999-08-18 | 1999-10-20 | Hoechst Schering Agrevo Gmbh | Fungicidal compounds |
| AU1466001A (en) * | 1999-11-05 | 2001-05-14 | Phase-1 Molecular Toxicology | Methods of determining individual hypersensitivity to an agent |
| EP1402026A2 (en) | 2000-04-18 | 2004-03-31 | Millennium Pharmaceuticals, Inc. | 39228, a human alcohol dehydrogenase and uses therefor |
| WO2002020500A2 (en) | 2000-09-01 | 2002-03-14 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| NZ524421A (en) | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| WO2002053544A1 (en) | 2000-12-29 | 2002-07-11 | Darwin Discovery Ltd. | Pharmaceutical uses and synthesis of nicotinanilide-n-oxides |
| DOP2002000332A (es) | 2001-02-14 | 2002-08-30 | Warner Lambert Co | Inhibidores de piridina de metaloproteinasas de la matriz |
| US6678516B2 (en) | 2001-05-21 | 2004-01-13 | Nokia Corporation | Method, system, and apparatus for providing services in a privacy enabled mobile and Ubicom environment |
| EP1402890B1 (en) | 2001-06-08 | 2008-01-09 | Institute of Medicinal Molecular Design, Inc. | Sulfonamide derivatives |
| WO2003030937A1 (en) * | 2001-10-05 | 2003-04-17 | Ono Pharmaceutical Co., Ltd. | Remedies for stress diseases comprising mitochondrial benzodiazepine receptor antagonists |
| DE10149674A1 (de) | 2001-10-09 | 2003-04-24 | Apogepha Arzneimittel Gmbh | Orale Darreichungsformen für Propiverin oder seinen pharmazeutisch annehmbaren Salzen mit verlängerter Wirkstoffreisetzung |
| US20030100034A1 (en) | 2001-10-16 | 2003-05-29 | Millennium Pharmaceuticals, Inc. | 9136, a human aldehyde dehydrogenase family member and uses therefor |
| PY0300568A (es) | 2002-01-31 | 2004-10-01 | Pfizer Prod Inc | Metabolitos del acido(3-{[4-terc-butilbencil)-(piridin-3-sulfonil)amino]metil}fenoxi)acetico |
| GB2403474B (en) | 2002-04-18 | 2006-10-11 | Inst Med Molecular Design Inc | Amide derivatives |
| GB0215650D0 (en) * | 2002-07-05 | 2002-08-14 | Cyclacel Ltd | Bisarylsufonamide compounds |
| RU2357962C2 (ru) | 2002-09-06 | 2009-06-10 | Элан Фармасьютикалз, Инк. | Пролекарственные производные 1,3-диамино-2-гидроксипропана |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| EP1402887A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | New compounds for the inhibition of undesired cell proliferation and use thereof |
| US7135575B2 (en) | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| US7022850B2 (en) | 2003-05-22 | 2006-04-04 | Bristol-Myers Squibb Co. | Bicyclicpyrimidones and their use to treat diseases |
| JP4359754B2 (ja) | 2003-07-03 | 2009-11-04 | 三菱瓦斯化学株式会社 | 基板の洗浄剤 |
| WO2005007889A1 (en) | 2003-07-21 | 2005-01-27 | Oncotherapy Science, Inc. | Method for diagnosing colorectal cancers |
| WO2005011561A2 (en) | 2003-08-04 | 2005-02-10 | Labcoat, Ltd. | Stent coating apparatus and method |
| GB0318814D0 (en) | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
| FR2861071B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
| FR2861074B1 (fr) | 2003-10-17 | 2006-04-07 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| WO2005057213A1 (en) | 2003-12-09 | 2005-06-23 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions for modulating mitochondrial aldehyde dehydrogenase-2 |
| US20080021083A1 (en) * | 2004-03-03 | 2008-01-24 | Daley Thomas E | 4-Methylpyrazole Formulations for Inhibiting Ethanol Intolerance |
| EP1750719A2 (en) * | 2004-05-19 | 2007-02-14 | Boehringer Ingelheim International GmbH | Treatment of diseases associated with altered level of amyloid beta peptides |
| CN1749415A (zh) * | 2004-09-15 | 2006-03-22 | 上海人类基因组研究中心 | 硝酸甘油治疗急性心绞痛疗效检测方法和试剂盒 |
| ATE538124T1 (de) | 2004-11-12 | 2012-01-15 | Bristol Myers Squibb Co | Imidazokondensierte tricyclische verbindungen auf thiazoloä4,5-büpyridin-basis und pharmazeutische zusammensetzungen damit |
| US7888374B2 (en) | 2005-01-28 | 2011-02-15 | Abbott Laboratories | Inhibitors of c-jun N-terminal kinases |
| DOP2006000051A (es) | 2005-02-24 | 2006-08-31 | Lilly Co Eli | Inhibidores de vegf-r2 y métodos |
| GEP20115230B (en) | 2005-09-23 | 2011-06-10 | Pfizer Prod Inc | Pyridinaminosulfonyl substituted benzamides as inhibitors of cytochrome p450 3a4 |
| WO2007075783A2 (en) | 2005-12-22 | 2007-07-05 | Wyeth | Substituted isoquinoline-1,3(2h,4h)-diones, 1-thioxo-1,4-dihydro-2h-isoquinoline-3-ones and 1,4-dihydro-3(2h)-isoquinolones and use thereof as kinase inhibitor |
| CA2644369A1 (en) | 2006-03-28 | 2007-10-04 | Novartis Ag | Amide derivatives and their application for the treatment of g protein related diseases |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| US20080003585A1 (en) | 2006-06-29 | 2008-01-03 | Bio-Rad Laboratories, Inc., A Corporation Of The State Of Delaware | Purification and amplification of nucleic acids in a microfluidic device |
| RU2008151762A (ru) | 2006-07-27 | 2010-06-27 | Си Ви Терапьютикс, Инк. (Us) | Adlh-2 ингибиторы для лечения аддикции |
| PE20080906A1 (es) | 2006-08-17 | 2008-07-05 | Kemia Inc | Derivados heteroarilo como inhibidores de citocina |
| EP2064187A2 (en) * | 2006-08-25 | 2009-06-03 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| DE602006021591D1 (de) | 2006-12-11 | 2011-06-09 | Genetics Co Inc | Aromatische 1,4-DI-Carboxylamide und deren Verwendung |
| CN101611007A (zh) | 2006-12-20 | 2009-12-23 | 先灵公司 | 新颖的jnk抑制剂 |
| WO2008103354A2 (en) | 2007-02-20 | 2008-08-28 | Cropsolution, Inc. | Modulators of acetyl-coenzyme a carboxylase and methods of use thereof |
| EP2131654A4 (en) * | 2007-03-02 | 2011-02-02 | Merck Sharp & Dohme | Bipyridine-carboxamide-orexin receptor Antagonist |
| WO2008112164A2 (en) | 2007-03-08 | 2008-09-18 | The Board Of Trustees Of The Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| US8742123B2 (en) | 2008-06-04 | 2014-06-03 | Taimed Biologics, Inc. | HIV integrase inhibitors from pyridoxine |
| WO2009156484A2 (en) | 2008-06-27 | 2009-12-30 | Novartis Ag | Organic compounds |
| WO2010028175A1 (en) * | 2008-09-08 | 2010-03-11 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase activity and methods of use thereof |
| JP2012506856A (ja) | 2008-10-28 | 2012-03-22 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼのモジュレーターおよびその使用方法 |
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2014
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Also Published As
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| KR20090117950A (ko) | 2009-11-16 |
| EP2126574A2 (en) | 2009-12-02 |
| JP2015061836A (ja) | 2015-04-02 |
| EP2126574B1 (en) | 2015-12-23 |
| US20120010248A1 (en) | 2012-01-12 |
| CN101669030B (zh) | 2016-01-13 |
| WO2008112164A2 (en) | 2008-09-18 |
| AU2008226947A1 (en) | 2008-09-18 |
| EP2126574A4 (en) | 2012-02-22 |
| CA2679882A1 (en) | 2008-09-18 |
| JP2010523476A (ja) | 2010-07-15 |
| US20110105602A2 (en) | 2011-05-05 |
| WO2008112164A3 (en) | 2008-11-13 |
| US20150105456A1 (en) | 2015-04-16 |
| US9315484B2 (en) | 2016-04-19 |
| US9102651B2 (en) | 2015-08-11 |
| AU2008226947B2 (en) | 2014-07-17 |
| US20090082431A1 (en) | 2009-03-26 |
| CN101669030A (zh) | 2010-03-10 |
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