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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- A—HUMAN NECESSITIES
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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
- A61P9/04—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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| PCT/US2008/003092 WO2008112164A2 (en) | 2007-03-08 | 2008-03-07 | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
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| WO (1) | WO2008112164A2 (Direct) |
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| US8354435B2 (en) | 2008-09-08 | 2013-01-15 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase activity and methods of use thereof |
| US8389522B2 (en) | 2008-10-28 | 2013-03-05 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
| WO2012082862A2 (en) * | 2010-12-14 | 2012-06-21 | Beth Israel Deaconess Medical Center | Androgen receptor inhibitors and methods of use thereof |
| US10457659B2 (en) | 2011-04-29 | 2019-10-29 | 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 |
| EP2887968A2 (en) * | 2012-08-24 | 2015-07-01 | The Board of Trustees of the Leland Stanford Junior University | Methods and compositions for treating pain |
| US9670162B2 (en) | 2013-03-14 | 2017-06-06 | The Board Of Trustees Of The Leland Stanford Junio | Mitochondrial aldehyde dehyrogenase-2 modulators and methods of use thereof |
| 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 |
| US9879036B2 (en) | 2014-02-19 | 2018-01-30 | Aviv Therapeutics, Inc. | Mitochondrial aldehyde dehydrogenase-2 binding compounds and methods of use thereof |
| 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 |
| BR112020014237A2 (pt) | 2018-01-31 | 2020-12-08 | Eisai R&D Management Co., Ltd. | Ativador de aldh2 |
| CN108864034A (zh) * | 2018-06-04 | 2018-11-23 | 中国人民解放军第二军医大学 | 酰胺类醛脱氢酶激动剂、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 |
| WO2020237172A1 (en) * | 2019-05-23 | 2020-11-26 | Xinova, LLC | Compositions and methods for the treatment and mitigation of alcohol-induced skin flushing |
| EP4238964A4 (en) | 2020-11-02 | 2024-10-02 | Alchemedicine, Inc. | COMPOUND, ALDEHYDE DEHYDROGENASE 2 ACTIVATOR, PHARMACEUTICAL COMPOSITION, AND TREATMENT AND/OR PREVENTION MEDICATION |
| KR20250005979A (ko) | 2022-04-22 | 2025-01-10 | 앨커메디신, 인크. | 화합물, 알데히드데히드로게나아제2 활성화제, 의약 조성물, 그리고 치료 및/또는 예방약 |
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 |
| DE69631347T2 (de) | 1995-09-15 | 2004-10-07 | Upjohn Co | Aminoaryl oxazolidinone n-oxide |
| 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 |
| WO1999023063A1 (en) | 1997-10-31 | 1999-05-14 | Aventis Pharma Limited | Substituted anilides |
| US6121471A (en) | 1997-12-22 | 2000-09-19 | Eli Lilly And Company | Catalyst and method for amide formation |
| CA2328413A1 (en) * | 1998-04-20 | 1999-10-28 | Fujisawa Pharmaceutical Co., Ltd. | Anthranilic acid derivatives as inhibitors of the cgmp-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 |
| WO2001032928A2 (en) * | 1999-11-05 | 2001-05-10 | Phase-1 Molecular Toxicology | Methods of determining individual hypersensitivity to an agent |
| WO2001079489A2 (en) | 2000-04-18 | 2001-10-25 | 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 |
| CN1237061C (zh) | 2000-09-15 | 2006-01-18 | 阿诺麦德股份有限公司 | 结合趋化因子受体的杂环化合物 |
| 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 |
| JP4448902B2 (ja) | 2001-06-08 | 2010-04-14 | 株式会社医薬分子設計研究所 | スルホンアミド誘導体 |
| EP1438973A4 (en) * | 2001-10-05 | 2005-07-13 | Ono Pharmaceutical Co | MEANS FOR THE TREATMENT OF STRESS-RELATED DISEASES WITH MITOCHONDRIENE 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 |
| EA200400724A1 (ru) | 2002-01-31 | 2004-12-30 | Пфайзер Продактс Инк. | Метаболиты (3-{[(4-трет-бутилбензил)-(пиридин-3-сульфонил)амино]метил}фенокси)уксусной кислоты |
| AU2003231370A1 (en) | 2002-04-18 | 2003-10-27 | Institute Of Medicinal Molecular Design. Inc. | Amide derivatives |
| GB0215650D0 (en) * | 2002-07-05 | 2002-08-14 | Cyclacel Ltd | Bisarylsufonamide compounds |
| US7294642B2 (en) | 2002-09-06 | 2007-11-13 | Elan Pharmaceuticals, Inc. | 1,3-Diamino-2-hydroxypropane pro-drug derivatives |
| EP1402887A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | New compounds for the inhibition of undesired cell proliferation and use thereof |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| 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 |
| 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 |
| 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 |
| EP1702213A4 (en) * | 2003-12-09 | 2007-07-18 | Univ Leland Stanford Junior | METHOD 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 |
| WO2005110422A2 (en) * | 2004-05-19 | 2005-11-24 | 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 |
| WO2006053120A1 (en) | 2004-11-12 | 2006-05-18 | Bristol-Myers Squibb Company | IMIDAZO-FUSED THIAZOLO[4,5-b]PYRIDINE BASED TRICYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME |
| 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 |
| NZ566136A (en) | 2005-09-23 | 2010-04-30 | Pfizer Prod Inc | Pyridinaminosulfonyl substituted benzamides as inhibitors of cytochrome p450 3a4 (cyp3a4) |
| CN101356159A (zh) | 2005-12-22 | 2009-01-28 | 惠氏公司 | 经取代异喹啉-1,3(2h,4h)-二酮类、1-硫代-1,4-二氢-2h-异喹啉-3-酮类和1,4-二氢-3(2h)-异喹啉酮类以及其作为激酶抑制剂的用途 |
| US20100261758A1 (en) | 2006-03-28 | 2010-10-14 | Novartis Ag | Heterocyclic amides for use as pharmaceuticals |
| US8158617B2 (en) | 2006-05-16 | 2012-04-17 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| 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 |
| MX2008015765A (es) | 2006-07-27 | 2009-03-26 | Cv Therapeutics Inc | Inhibidores de aldh-2 en el tratamiento de adiccion. |
| 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 |
| WO2008082487A2 (en) | 2006-12-20 | 2008-07-10 | Schering Corporation | Novel jnk inhibitors |
| US20080200461A1 (en) | 2007-02-20 | 2008-08-21 | Cropsolution, Inc. | Modulators of acetyl-coenzyme a carboxylase and methods of use thereof |
| WO2008108991A1 (en) * | 2007-03-02 | 2008-09-12 | Merck & Co., Inc. | Bipyridine carboxamide orexin receptor antagonists |
| JP2010523476A (ja) | 2007-03-08 | 2010-07-15 | ザ ボード オブ トラスティーズ オブ ザ リーランド スタンフォード ジュニア ユニバーシティ | ミトコンドリアアルデヒドデヒドロゲナーゼ−２モジュレーター及びその使用方法 |
| JP2011507910A (ja) | 2007-12-21 | 2011-03-10 | ユニバーシティー オブ ロチェスター | 真核生物の寿命を変更するための方法 |
| CA2726742A1 (en) | 2008-06-04 | 2009-12-10 | Brent Stranix | Hiv integrase inhibitors from pyridoxine |
| WO2009156484A2 (en) | 2008-06-27 | 2009-12-30 | Novartis Ag | Organic compounds |
| US8354435B2 (en) * | 2008-09-08 | 2013-01-15 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase activity and methods of use thereof |
| US8389522B2 (en) * | 2008-10-28 | 2013-03-05 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
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| AU2008226947A1 (en) | 2008-09-18 |
| KR20090117950A (ko) | 2009-11-16 |
| US20120010248A1 (en) | 2012-01-12 |
| JP2015061836A (ja) | 2015-04-02 |
| JP2010523476A (ja) | 2010-07-15 |
| EP2126574B1 (en) | 2015-12-23 |
| EP2126574A4 (en) | 2012-02-22 |
| WO2008112164A2 (en) | 2008-09-18 |
| CA2679882A1 (en) | 2008-09-18 |
| US9315484B2 (en) | 2016-04-19 |
| AU2008226947B2 (en) | 2014-07-17 |
| CN101669030A (zh) | 2010-03-10 |
| CN101669030B (zh) | 2016-01-13 |
| EP2126574A2 (en) | 2009-12-02 |
| US20090082431A1 (en) | 2009-03-26 |
| US9102651B2 (en) | 2015-08-11 |
| US20110105602A2 (en) | 2011-05-05 |
| WO2008112164A3 (en) | 2008-11-13 |
| US20150105456A1 (en) | 2015-04-16 |
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