CA2729227C - 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases - Google Patents
2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases Download PDFInfo
- Publication number
- CA2729227C CA2729227C CA2729227A CA2729227A CA2729227C CA 2729227 C CA2729227 C CA 2729227C CA 2729227 A CA2729227 A CA 2729227A CA 2729227 A CA2729227 A CA 2729227A CA 2729227 C CA2729227 C CA 2729227C
- Authority
- CA
- Canada
- Prior art keywords
- dione
- diene
- ylamino
- ethyl
- disorder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- 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
-
- A—HUMAN NECESSITIES
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/02—Quinones with monocyclic quinoid structure
- C07C50/04—Benzoquinones, i.e. C6H4O2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Biochemistry (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Toxicology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13316908P | 2008-06-25 | 2008-06-25 | |
| US61/133,169 | 2008-06-25 | ||
| PCT/US2009/048308 WO2009158348A1 (en) | 2008-06-25 | 2009-06-23 | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2729227A1 CA2729227A1 (en) | 2009-12-30 |
| CA2729227C true CA2729227C (en) | 2018-05-22 |
Family
ID=41444902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2729227A Expired - Fee Related CA2729227C (en) | 2008-06-25 | 2009-06-23 | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8716486B2 (enExample) |
| EP (1) | EP2303824B1 (enExample) |
| JP (1) | JP5798481B2 (enExample) |
| CA (1) | CA2729227C (enExample) |
| WO (1) | WO2009158348A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005033092A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| EA035619B1 (ru) | 2005-06-01 | 2020-07-16 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Композиции для использования в способе лечения митохондриальных нарушений |
| EP1986636B1 (en) | 2006-02-22 | 2013-04-24 | Edison Pharmaceuticals, Inc. | Phenol and 1,4-benzoquinone derivatives for use in the treatment of mitochondrial diseases |
| EA200900582A1 (ru) | 2006-10-20 | 2009-08-28 | Общество С Ограниченной Ответственностью "Митотехнология" | Фармацевтические композиции для профилактики и лечения глазных патологий |
| EP2095713A1 (en) | 2006-10-20 | 2009-09-02 | Limited Liability Company "Mitotechnology" | Composition for regenerating and stimulating growth of plants and for adapting plants to different stress factors |
| EP2145623A4 (en) | 2007-01-29 | 2010-10-27 | Ltd Liability Company Mitotech | PHARMACEUTICAL AND COSMETIC COMPOSITIONS FOR ACCELERATING THE PROCESS OF WOUND HEALING AND OTHER SURFACE INJURIES |
| WO2008127138A1 (fr) | 2007-04-11 | 2008-10-23 | Limited Liability Company 'mitotechnology' | Composition visant à ralentir le vieillissement et à allonger la durée de vie de l'organisme et utilisation de cette composition |
| US8518915B2 (en) | 2007-06-29 | 2013-08-27 | Mitotech Sa | Use of mitochondrially-addressed compounds for preventing and treating cardiovascular diseases |
| PL2220030T3 (pl) | 2007-11-06 | 2016-07-29 | Bioelectron Tech Corp | Pochodne 4-(p-chinonylo)-2-hydroksybutanamidu do leczenia chorób mitochondrialnych |
| EP2237664A4 (en) | 2008-01-08 | 2013-05-22 | Edison Pharmaceuticals Inc | (HET) ARYL-p-CHINONE DERIVATIVES FOR THE TREATMENT OF OCHONDRIAL DISEASES |
| WO2009111576A2 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| EP2303824B1 (en) * | 2008-06-25 | 2015-03-25 | Edison Pharmaceuticals, Inc. | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| EP2344142B1 (en) | 2008-09-10 | 2024-06-26 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| 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 |
| WO2010051277A1 (en) | 2008-10-28 | 2010-05-06 | Edison Pharmaceuticals, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| US9308214B2 (en) | 2008-11-12 | 2016-04-12 | Mitotech S.A. | Method for moderately increasing the proton conductivity of biological membranes with the aid of mitochondria-targeted delocalized cations |
| CA2777479C (en) | 2009-04-28 | 2017-10-17 | Ptc Therapeutics, Inc. | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
| EA025414B1 (ru) | 2009-06-10 | 2016-12-30 | Общество С Ограниченной Ответственностью "Митотех" | Фармацевтическая композиция для применения в медицинской и ветеринарной офтальмологии |
| NO2470168T3 (enExample) * | 2009-08-26 | 2018-06-30 | ||
| MX2012005356A (es) | 2009-11-13 | 2013-01-29 | Obschestvo S Ogranichennoi Otvetstvennostyu Mitotekh | Substancias farmaceuticas basadas en antioxidantes dirigidos a mitocondria. |
| WO2011126544A2 (en) * | 2010-03-26 | 2011-10-13 | Wayne State University | Thymoquinone analogs for the treatment of pancreatic cancer |
| AU2011260323A1 (en) * | 2010-06-04 | 2012-11-15 | F. Hoffmann-La Roche Ag | Aminopyrimidine derivatives as LRRK2 modulators |
| KR101566091B1 (ko) | 2010-11-10 | 2015-11-04 | 에프. 호프만-라 로슈 아게 | Lrrk2 조절제로서 피라졸 아미노피리미딘 유도체 |
| ES2704064T3 (es) * | 2011-06-03 | 2019-03-14 | Mitotech Sa | Formulaciones orales de antioxidantes dirigidos mitocondrialmente y su preparación y uso |
| US9464016B2 (en) | 2011-06-14 | 2016-10-11 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| CA2842486C (en) | 2011-07-19 | 2022-09-06 | Edison Pharmaceuticals, Inc. | Methods for oxidation of alpha tocotrienol in the presence of non-alpha tocotrienols |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| JP2016515526A (ja) * | 2013-03-15 | 2016-05-30 | 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 | 酸化ストレス障害の処置のためのアルキル−ヘテロアリール置換されたキノン誘導体 |
| 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 |
| US9670170B2 (en) | 2013-03-15 | 2017-06-06 | Bioelectron Technology Corporation | Resorufin 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 |
| HUE058877T2 (hu) | 2014-12-16 | 2022-09-28 | Ptc Therapeutics Inc | (R)-2-hidroxi-2-metil-4-(2,4,5-trimetil-3,6-dioxociklohexa-1,4-dienil)butánamid polimorf és amorf alakjai |
| JP7117241B2 (ja) | 2015-12-16 | 2022-08-12 | 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 | 混合されたトコール組成物からアルファ-トコトリエノールを富化するための改良された方法 |
| EP3389646A1 (en) | 2015-12-17 | 2018-10-24 | BioElectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| 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 |
| HUE066196T2 (hu) | 2018-10-17 | 2024-07-28 | Ptc Therapeutics Inc | 2,3,5-trimetil-6-nonilciklohexa-2,5-dién-1,4-dion alfa-szinukleinopátiák, tauopátiák és egyéb rendellenességek szuppresszálására és kezelésére |
| IL291898B1 (en) | 2019-10-04 | 2026-06-01 | Stealth Biotherapeutics Inc | Quinone-, hydroquinone-, and naphthoquinone- analogs of quinone for the treatment of mitochondrial disorders |
| CA3176909A1 (en) | 2020-04-03 | 2021-10-07 | Stealth Biotherapeutics Inc. | Compositions and methods for the prevention and/or treatment of mitochondrial disease, including friedreich's ataxia |
| EP4366700A1 (en) | 2021-07-08 | 2024-05-15 | PTC Therapeutics, Inc. | Pharmaceutical compositions comprising 2,3,5-trimethyl-6-nonylcyclohexa-2,5-diene-1,4-dione |
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| JPS5883698A (ja) | 1981-11-13 | 1983-05-19 | Takeda Chem Ind Ltd | キノン化合物およびその製造法 |
| JPS62223150A (ja) * | 1986-02-12 | 1987-10-01 | Otsuka Pharmaceut Co Ltd | 1,4−ベンゾキノン誘導体 |
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| WO2005033092A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| EP1694623A4 (en) * | 2003-12-05 | 2007-01-17 | Zymes Inc | PRACTICAL, COST-EFFECTIVE SYNTHESIS OF UBICHINONES |
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| EA035619B1 (ru) | 2005-06-01 | 2020-07-16 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Композиции для использования в способе лечения митохондриальных нарушений |
| JP2009508867A (ja) | 2005-09-15 | 2009-03-05 | 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 | ミトコンドリア病および関連した様態の治療ならびにエネルギーバイオマーカーの調節のための酸化還元活性治療剤のテイル改変体 |
| EP1986636B1 (en) * | 2006-02-22 | 2013-04-24 | Edison Pharmaceuticals, Inc. | Phenol and 1,4-benzoquinone derivatives for use in the treatment of mitochondrial diseases |
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-
2009
- 2009-06-23 EP EP09770882.0A patent/EP2303824B1/en not_active Not-in-force
- 2009-06-23 WO PCT/US2009/048308 patent/WO2009158348A1/en not_active Ceased
- 2009-06-23 US US12/997,869 patent/US8716486B2/en not_active Expired - Fee Related
- 2009-06-23 CA CA2729227A patent/CA2729227C/en not_active Expired - Fee Related
- 2009-06-23 JP JP2011516536A patent/JP5798481B2/ja not_active Expired - Fee Related
-
2014
- 2014-03-24 US US14/223,932 patent/US9073873B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2303824B1 (en) | 2015-03-25 |
| US9073873B2 (en) | 2015-07-07 |
| EP2303824A1 (en) | 2011-04-06 |
| EP2303824A4 (en) | 2012-05-23 |
| US20110218208A1 (en) | 2011-09-08 |
| US8716486B2 (en) | 2014-05-06 |
| US20140323509A1 (en) | 2014-10-30 |
| WO2009158348A1 (en) | 2009-12-30 |
| JP2011525926A (ja) | 2011-09-29 |
| CA2729227A1 (en) | 2009-12-30 |
| JP5798481B2 (ja) | 2015-10-21 |
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