JP2016515526A5 - - Google Patents
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- JP2016515526A5 JP2016515526A5 JP2016503224A JP2016503224A JP2016515526A5 JP 2016515526 A5 JP2016515526 A5 JP 2016515526A5 JP 2016503224 A JP2016503224 A JP 2016503224A JP 2016503224 A JP2016503224 A JP 2016503224A JP 2016515526 A5 JP2016515526 A5 JP 2016515526A5
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Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2610152C (en) | 2005-06-01 | 2018-04-10 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| EA019675B1 (ru) | 2006-02-22 | 2014-05-30 | Эдисон Фармасьютикалз, Инк. | Редокс-активные терапевтические средства для лечения митохондриальных заболеваний и модуляции биомаркера коэнзима q |
| EP3018122B1 (en) | 2007-11-06 | 2018-10-10 | BioElectron Technology Corporation | 4-(p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| CA2708961C (en) | 2008-01-08 | 2017-03-28 | Ptc Therapeutics, Inc. | (het)aryl-p-quinone derivatives for treatment of mitochondrial diseases |
| BRPI0918139B1 (pt) | 2008-09-10 | 2024-04-30 | Ptc Therapeutics, Inc | Composição, alimento medicinal ou funcional, suplemento alimentar ou dietético para tratamento de distúrbios de desenvolvimento pervasivos com terapêuticos redox-ativos |
| CN102264730B (zh) | 2008-10-28 | 2016-04-13 | 爱迪生药物公司 | 用于生产生育三烯酚及衍生物的方法 |
| JP2012525399A (ja) | 2009-04-28 | 2012-10-22 | エジソン ファーマシューティカルズ， インコーポレイテッド | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
| WO2012174286A1 (en) | 2011-06-14 | 2012-12-20 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ， インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| US9670170B2 (en) | 2013-03-15 | 2017-06-06 | Bioelectron Technology Corporation | Resorufin derivatives for treatment of oxidative stress disorders |
| US9868711B2 (en) | 2013-03-15 | 2018-01-16 | Bioelectron Technology Corporation | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| WO2016100579A1 (en) | 2014-12-16 | 2016-06-23 | Edison Pharmaceuticals, Inc., | Polymorphic and amorphous forms of (r)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| WO2017106786A1 (en) | 2015-12-16 | 2017-06-22 | Bioelectron Technology Corporation | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| CN113024369A (zh) | 2015-12-17 | 2021-06-25 | Ptc医疗公司 | 用于治疗氧化应急障碍的化合物 |
| JP2018083799A (ja) | 2016-11-15 | 2018-05-31 | バイオエレクトロン テクノロジー コーポレイション | ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩 |
| JP7586815B2 (ja) | 2018-10-17 | 2024-11-19 | ピーティーシー セラピューティクス， インコーポレイテッド | α－シヌクレイノパチー、タウオパチー、および他の障害を抑制および処置するための２，３，５－トリメチル－６－ノニルシクロヘキサ－２，５－ジエン－１，４－ジオン |
| IL291898A (en) | 2019-10-04 | 2022-06-01 | Stealth Biotherapeutics Inc | Quinone-, hydroquinone- and naphthoquinone-analogues of vatiquinone for treatment of mitochondrial disorder diseases |
| WO2021202986A1 (en) | 2020-04-03 | 2021-10-07 | Stealth Biotherapeutics Corp | Compositions and methods for the prevention and/or treatment of mitochondrial disease, including friedreich's ataxia |
| CN118175991A (zh) | 2021-07-08 | 2024-06-11 | Ptc医疗公司 | 包含2,3,5-三甲基-6-壬基环己-2,5-二烯-1,4-二酮的药物组合物 |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL81264A (en) * | 1986-01-30 | 1990-11-05 | Takeda Chemical Industries Ltd | Quinone derivatives,their production and pharmaceutical compositions containing them |
| US5229385A (en) * | 1986-01-30 | 1993-07-20 | Takeda Chemical Industries, Ltd. | Quinone derivatives, their production and use |
| JPS62223150A (ja) * | 1986-02-12 | 1987-10-01 | Otsuka Pharmaceut Co Ltd | １，４−ベンゾキノン誘導体 |
| JP3042547B2 (ja) * | 1990-05-11 | 2000-05-15 | サントリー株式会社 | ベンゾフラン誘導体及びそれを含む虚血による器質性又は機能性障害治療剤 |
| EP0560568A3 (en) | 1992-03-13 | 1994-06-29 | Takeda Chemical Industries Ltd | Hydroquinone derivatives and intermediates for production thereof |
| US6133278A (en) | 1994-08-12 | 2000-10-17 | Takeda Chemical Industries, Ltd. | Use of quinone and hydroquinone derivatives for the treatment of cachexia |
| WO1996041626A1 (en) | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
| JPH0959258A (ja) * | 1995-08-11 | 1997-03-04 | Ono Pharmaceut Co Ltd | グアニジル誘導体 |
| JPH09221471A (ja) | 1995-12-15 | 1997-08-26 | Takeda Chem Ind Ltd | キノン誘導体の製造法および中間体 |
| DE69709069T2 (de) | 1996-02-13 | 2002-07-04 | G.D. Searle & Co., Chicago | Zusammensetzungen mit immunosuppressiven wirkungen, welche 5-lipoxygenase-inhibitoren und cyclooxygenase-2-inhibitoren enthalten |
| US7034054B2 (en) | 2000-12-15 | 2006-04-25 | Galileo Pharmaceuticals, Inc. | Methods for the prevention and treatment of cerebral ischemia using non-alpha tocopherols |
| DE10121252A1 (de) | 2001-04-30 | 2002-11-07 | Christos C Zouboulis | Behandlung der Akne |
| NZ513547A (en) | 2001-08-13 | 2002-09-27 | Antipodean Biotechnology Ltd | Synthesis of triphenylphosphonium quinols (e.g. mitoquinol) and/or quinones (e.g. mitoquinone) |
| GB0204232D0 (en) | 2002-02-22 | 2002-04-10 | Isis Innovation | Assay |
| EP1378753B1 (en) | 2002-07-01 | 2006-05-31 | Santhera Pharmaceuticals (Schweiz) GmbH | A screening method and compounds for treating Friedreich Ataxia |
| WO2004042353A2 (en) | 2002-10-30 | 2004-05-21 | Galileo Pharmaceuticals, Inc. | Identifying therapeutic compounds based on their physical-chemical properties |
| CA2580584C (en) | 2003-09-19 | 2015-07-28 | Galileo Pharmaceuticals, Inc. | Use of alpha-tocotrienol for treatment of mitochondrial diseases |
| US7067659B2 (en) | 2004-04-23 | 2006-06-27 | Duke University | Reactive oxygen generating enzyme inhibitor with nitric oxide bioactivity and uses thereof |
| US20090111837A1 (en) | 2005-03-01 | 2009-04-30 | Peter Cox | Use of pde7 inhibitors for the treatment of neuropathic pain |
| CA2610152C (en) | 2005-06-01 | 2018-04-10 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| EP1947942B1 (en) | 2005-08-18 | 2015-07-29 | Accelalox, Inc. | Methods for bone treatment by modulating an arachidonic acid metabolic or signaling pathway |
| ES2823728T3 (es) | 2005-09-15 | 2021-05-10 | Ptc Therapeutics Inc | Variantes de cola de agentes terapéuticos con actividad redox para el tratamiento de enfermedades mitocondriales y otras afecciones y la modulación de biomarcadores de energía |
| EA019675B1 (ru) | 2006-02-22 | 2014-05-30 | Эдисон Фармасьютикалз, Инк. | Редокс-активные терапевтические средства для лечения митохондриальных заболеваний и модуляции биомаркера коэнзима q |
| EP3018122B1 (en) * | 2007-11-06 | 2018-10-10 | BioElectron Technology Corporation | 4-(p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| CA2708961C (en) | 2008-01-08 | 2017-03-28 | Ptc Therapeutics, Inc. | (het)aryl-p-quinone derivatives for treatment of mitochondrial diseases |
| WO2009105723A2 (en) | 2008-02-22 | 2009-08-27 | Accelalox, Inc. | Novel methods for bone treatment by modulating an arachidonic acid metabolic or signaling pathway |
| WO2009111543A2 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | Treatment of hearing and balance impairments with redox-active therapeutics |
| WO2009111576A2 (en) * | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| WO2009158348A1 (en) * | 2008-06-25 | 2009-12-30 | Edison Pharmaceuticals, Inc. | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| PE20110368A1 (es) * | 2008-08-18 | 2011-06-13 | Univ Yale | Moduladores de mif |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| BRPI0918139B1 (pt) | 2008-09-10 | 2024-04-30 | Ptc Therapeutics, Inc | Composição, alimento medicinal ou funcional, suplemento alimentar ou dietético para tratamento de distúrbios de desenvolvimento pervasivos com terapêuticos redox-ativos |
| CA2740773A1 (en) | 2008-10-14 | 2010-04-22 | Edison Pharmaceuticals, Inc. | Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells |
| CN102264730B (zh) | 2008-10-28 | 2016-04-13 | 爱迪生药物公司 | 用于生产生育三烯酚及衍生物的方法 |
| JP2012525399A (ja) | 2009-04-28 | 2012-10-22 | エジソン ファーマシューティカルズ， インコーポレイテッド | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
| MX2011011310A (es) | 2009-04-28 | 2011-11-18 | Edison Pharmaceuticals Inc | Formulacion de tocotrienol quinonas para el tratamiento de enfermedades oftalmicas. |
| SI2470168T1 (en) | 2009-08-26 | 2018-05-31 | Bioelectron Technology Corporation | Procedures for the prevention and treatment of brain ischemia |
| EP2519232A1 (en) | 2009-12-31 | 2012-11-07 | Edison Pharmaceuticals, Inc. | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| CN102985083A (zh) | 2010-04-27 | 2013-03-20 | 爱迪生药物公司 | 治疗眼科疾病的醌类的制剂 |
| SG187744A1 (en) | 2010-08-06 | 2013-03-28 | Edison Pharmaceuticals Inc | Treatment of mitochondrial diseases with naphthoquinones |
| WO2012022467A2 (en) * | 2010-08-16 | 2012-02-23 | Santhera Pharmaceuticals (Schweiz) Ag | Novel benzoquinone derivatives and use thereof as modulators of mitochondrial function |
| WO2012047664A1 (en) | 2010-09-27 | 2012-04-12 | Sutter West Bay Hospital D/B/A California Pacific Medical Center | Anti-pecam therapy, compositions, methods, and uses |
| WO2012174286A1 (en) | 2011-06-14 | 2012-12-20 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| WO2013006737A1 (en) | 2011-07-06 | 2013-01-10 | Edison Pharmaceuticals, Inc. | Treatment of methylmalonic aciduria, isovaleric aciduria, and other organic acidurias with tocotrienol quinones |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ， インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| DK2825208T3 (en) | 2012-03-14 | 2017-09-11 | Levicept Ltd | P75NTR-NEUROTROPHIN BINDING PROTEIN FOR THERAPEUTIC USE |
| WO2014031586A2 (en) | 2012-08-20 | 2014-02-27 | Tallikut Pharmaceuticals, Inc. | Methods for treating cardiovascular diseases |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| US9868711B2 (en) | 2013-03-15 | 2018-01-16 | Bioelectron Technology Corporation | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| US20140275045A1 (en) | 2013-03-15 | 2014-09-18 | Edison Pharmaceuticals, Inc. | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | Resorufin derivatives for treatment of oxidative stress disorders |
| US9670170B2 (en) | 2013-03-15 | 2017-06-06 | Bioelectron Technology Corporation | Resorufin derivatives for treatment of oxidative stress disorders |
| US20160115141A1 (en) | 2013-05-31 | 2016-04-28 | Edison Pharmaceuticals, Inc. | Carboxylic acid derivatives for treatment of oxidative stress disorders |
-
2014
- 2014-03-14 CA CA2906145A patent/CA2906145A1/en not_active Abandoned
- 2014-03-14 HK HK16108427.8A patent/HK1220451A1/zh unknown
- 2014-03-14 US US14/776,678 patent/US10189830B2/en not_active Expired - Fee Related
- 2014-03-14 JP JP2016503224A patent/JP2016515526A/ja not_active Ceased
- 2014-03-14 WO PCT/US2014/029806 patent/WO2014145116A2/en not_active Ceased
- 2014-03-14 EP EP14720006.7A patent/EP2970158B1/en not_active Not-in-force
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