CA2906154A1 - Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders - Google Patents

Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders Download PDF

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Publication number
CA2906154A1
CA2906154A1 CA2906154A CA2906154A CA2906154A1 CA 2906154 A1 CA2906154 A1 CA 2906154A1 CA 2906154 A CA2906154 A CA 2906154A CA 2906154 A CA2906154 A CA 2906154A CA 2906154 A1 CA2906154 A1 CA 2906154A1
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CA
Canada
Prior art keywords
alkyl
compound
group
disorder
deficiency
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.)
Abandoned
Application number
CA2906154A
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English (en)
French (fr)
Inventor
Andrew W. Hinman
Dana Davis
William D. Shrader
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bioelectron Technology Corp
Original Assignee
Edison Phamaceuticals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Edison Phamaceuticals Inc filed Critical Edison Phamaceuticals Inc
Publication of CA2906154A1 publication Critical patent/CA2906154A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P27/16—Otologicals
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/46—Phenazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychology (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Obesity (AREA)
  • Toxicology (AREA)
  • Biochemistry (AREA)
  • Vascular Medicine (AREA)
  • Endocrinology (AREA)
  • Hospice & Palliative Care (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
CA2906154A 2013-03-15 2014-03-14 Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders Abandoned CA2906154A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13/838,372 US20140275045A1 (en) 2013-03-15 2013-03-15 Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders
US13/838,372 2013-03-15
PCT/US2014/029811 WO2014145119A1 (en) 2013-03-15 2014-03-14 Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders

Publications (1)

Publication Number Publication Date
CA2906154A1 true CA2906154A1 (en) 2014-09-18

Family

ID=50680171

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2906154A Abandoned CA2906154A1 (en) 2013-03-15 2014-03-14 Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders

Country Status (6)

Country Link
US (1) US20140275045A1 (enExample)
EP (1) EP2970151A1 (enExample)
JP (1) JP2016514697A (enExample)
CA (1) CA2906154A1 (enExample)
HK (1) HK1220450A1 (enExample)
WO (1) WO2014145119A1 (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA035619B1 (ru) 2005-06-01 2020-07-16 ПиТиСи ТЕРАПЬЮТИКС, ИНК. Композиции для использования в способе лечения митохондриальных нарушений
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
EP2344142B1 (en) 2008-09-10 2024-06-26 PTC Therapeutics, Inc. Treatment of pervasive developmental disorders with redox-active therapeutics
WO2010051277A1 (en) 2008-10-28 2010-05-06 Edison Pharmaceuticals, Inc. Process for the production of alpha-tocotrienol and derivatives
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
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
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
CA2976776C (en) * 2015-02-17 2023-06-20 Arizona Board Of Regents On Behalf Of Arizona State University Phenothiazine analogues as mitochondrial therapeutic agents
CA2976937C (en) 2015-02-17 2023-04-04 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
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
US11390605B2 (en) 2016-08-25 2022-07-19 Arizona Board Of Regents On Behalf Of Arizona State University Substituted pyrimidine compounds as multifunctional radical quenchers and their uses
WO2018039487A1 (en) * 2016-08-25 2018-03-01 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
US12570622B2 (en) 2016-08-25 2026-03-10 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
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
JP6958860B2 (ja) 2017-11-07 2021-11-02 学校法人自治医科大学 ミトコンドリアの機能障害の改善剤、及びミトコンドリアの機能障害に起因する疾患又は症状の予防又は治療薬、並びにそれらの用途
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
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

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE840115L (en) * 1983-01-21 1984-07-21 Merck Frosst Canada Inc Phenothiazine derivatives and analogs
US4667032A (en) * 1983-01-21 1987-05-19 Merck Frosst Canada, Inc. Phenothiazone derivatives and analogs
US4548927A (en) * 1983-05-25 1985-10-22 Eaton John W Method and agents for raising animal tolerance to oxidant stress-inducing antibiotics
JPS60209520A (ja) * 1984-03-19 1985-10-22 メルク　エンド　カムパニー　インコーポレーテツド リポキシゲナーゼ阻害剤の細胞保護的使用
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
DE60211875T2 (de) 2002-07-01 2006-10-26 Santhera Pharmaceuticals (Schweiz) Ag Screeningverfahren und Verbindungen zur Behandlung von Friedreich ataxia
WO2012138713A2 (en) * 2011-04-04 2012-10-11 Arizona Board Of Regents, A Body Corporate Of The State Of Arizona, Acting For And On Behalf Of Arizona State University Multifunctional radical quenchers for the treatment of mitochondrial dysfunction

Also Published As

Publication number Publication date
EP2970151A1 (en) 2016-01-20
WO2014145119A1 (en) 2014-09-18
US20140275045A1 (en) 2014-09-18
JP2016514697A (ja) 2016-05-23
HK1220450A1 (zh) 2017-05-05

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