CA1173028A - Quinone derivatives, their production and use - Google Patents

Quinone derivatives, their production and use

Info

Publication number
CA1173028A
CA1173028A CA000360089A CA360089A CA1173028A CA 1173028 A CA1173028 A CA 1173028A CA 000360089 A CA000360089 A CA 000360089A CA 360089 A CA360089 A CA 360089A CA 1173028 A CA1173028 A CA 1173028A
Authority
CA
Canada
Prior art keywords
compound
methoxy
amino
mono
alkylamino
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
Application number
CA000360089A
Other languages
English (en)
French (fr)
Inventor
Shinji Terao
Mitsuru Shiraishi
Kaneyoshi Kato
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
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 Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Application granted granted Critical
Publication of CA1173028A publication Critical patent/CA1173028A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40Acylated substituent nitrogen atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10Antioedematous agents; Diuretics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/30Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C243/32Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C66/00Quinone carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D257/00Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04Five-membered rings
    • C07D257/06Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28Nitrogen atoms
    • C07D295/32Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58Radicals substituted by nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biochemistry (AREA)
  • Cardiology (AREA)
  • Pulmonology (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Pain & Pain Management (AREA)
  • Biotechnology (AREA)
  • Immunology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA000360089A 1979-08-12 1980-09-11 Quinone derivatives, their production and use Expired CA1173028A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP117771/1979 1979-08-12
JP11777179A JPS5640651A (en) 1979-09-12 1979-09-12 Quinone compound and its preparation

Publications (1)

Publication Number Publication Date
CA1173028A true CA1173028A (en) 1984-08-21

Family

ID=14719910

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000360089A Expired CA1173028A (en) 1979-08-12 1980-09-11 Quinone derivatives, their production and use

Country Status (5)

Country Link
US (1) US4388312A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0025692B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JPS5640651A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA1173028A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE3061226D1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

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CA1247632A (en) * 1981-06-19 1988-12-28 Frederick H. Howell Hydroquinones
US4808339A (en) * 1982-04-13 1989-02-28 Takeda Chemical Industries, Ltd. Benzoquinone derivatives
JPS58177934A (ja) * 1982-04-13 1983-10-18 Takeda Chem Ind Ltd ベンゾキノン誘導体
DE3360926D1 (en) * 1982-06-16 1985-11-07 Ciba Geigy Ag Hydroquinone ethers and a process for preparing them
CH661516A5 (de) * 1983-12-08 1987-07-31 Hoffmann La Roche Phenylnonatetraenoylzuckerderivate.
US4849445A (en) * 1983-12-14 1989-07-18 The Upjohn Company Method for treating or preventing deep vein thrombosis using lipoxygenase inhibitors
US4737519A (en) * 1983-12-14 1988-04-12 The Upjohn Company Substituted naphthalenes, indoles, benzofurans, and benzothiophenes as lipoxygenase inhibitors
US4791138A (en) * 1983-12-14 1988-12-13 The Upjohn Company Method for treating or preventing deep vein thrombosis using lipoxygenase inhibitors
JPS6122054A (ja) * 1984-05-09 1986-01-30 Eisai Co Ltd ポリプレニル系化合物
JPS60255749A (ja) * 1984-05-31 1985-12-17 Univ Nagoya キノン誘導体
JPH0610177B2 (ja) * 1985-05-08 1994-02-09 エーザイ株式会社 キノン化合物
US4617311A (en) * 1985-05-17 1986-10-14 Eli Lilly And Company Antiasthmatic method
US4939169A (en) * 1985-09-20 1990-07-03 The Upjohn Company 1,4-naphthalenediol and 1,4-hydroquinone derivatives
JPS63501288A (ja) * 1985-09-20 1988-05-19 ジ・アップジョン・カンパニ− 1,4−ナフタレンジオ−ルおよび1,4−ヒドロキノン誘導体
US4686220A (en) * 1985-12-19 1987-08-11 American Cyanamid Company Substituted 2-[b-substituted-amino)-ethylamino]-1,4-naphthalenediones for treating asthma, allergic diseases and inflammation in warm-blooded animals
ES2037077T3 (es) * 1986-01-28 1993-06-16 Takeda Chemical Industries, Ltd. Metodo para preparar quinona-amidas.
ATE60328T1 (de) * 1986-03-29 1991-02-15 Suntory Ltd Derivate vom benzoquinonylphenylalkansaeure-amid.
JPH062755B2 (ja) * 1987-07-09 1994-01-12 サントリー株式会社 ヒドロキノニルフェニル酪酸アミド誘導体
WO1993002697A1 (en) * 1991-08-08 1993-02-18 Amylin Pharmaceuticals, Inc. Production of peptide amides
DK1888059T3 (en) * 2005-06-01 2015-03-30 Edison Pharmaceuticals Inc Redox-active therapeutic products for the treatment of mitochondrial diseases and other conditions as well as modulation of energy biomarkers
HUE052377T2 (hu) * 2005-09-15 2021-04-28 Ptc Therapeutics Inc Redox-aktív terápiás szerek farokvariánsai mitokondriális betegségek és egyéb állapotok kezelésére és az energia-biomarkerek modulálására
WO2007100652A2 (en) 2006-02-22 2007-09-07 Edison Pharmaceuticals, Inc. Side chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
EP3018122B1 (en) 2007-11-06 2018-10-10 BioElectron Technology Corporation 4-(p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
EP2262508B1 (en) * 2008-03-05 2018-10-03 BioElectron Technology Corporation SUBSTITUTED-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
US8263094B2 (en) * 2008-09-23 2012-09-11 Eastman Chemical Company Esters of 4,5-disubstituted-oxy-2-methyl-3,6-dioxo-cyclohexa-1,4-dienyl alkyl acids and preparation thereof
GB0817528D0 (en) 2008-09-24 2008-10-29 Syntavit As Process
GB2476643B (en) * 2009-12-23 2012-11-14 Haomamedica Ltd 1,4-Dihydro-1,4-dioxonaphtalene derivatives as anticoagulants
GB2476644B (en) * 2009-12-23 2012-11-14 Haomamedica Ltd 1,4-Dihydro-1,4-dioxonaphtalene derivatives for the treatment of osteoporosis
MX357284B (es) * 2011-05-26 2018-07-04 Univ Indiana Res & Tech Corp Compuestos de quinona para tratar enfermedades mediadas por ape1.
WO2012167122A1 (en) 2011-06-03 2012-12-06 Indiana University Research And Technology Corporation Compounds, compositions and methods for treating oxidative dna damage disorders
WO2014039862A1 (en) 2012-09-07 2014-03-13 Edison Pharmaceuticals, Inc. Quinone derivatives for use in the modulation of redox status of individuals
MX2015016014A (es) * 2013-05-31 2016-04-04 Edison Pharmaceuticals Inc Derivados de acido carboxilico para el tratamiento de trastornos por agresion oxidativa.
MX385049B (es) 2014-12-16 2025-03-14 Ptc Therapeutics Inc Formas amorfas y polimorficas de (r)-2-hidroxi-2-metil-4-(2,4,5-trimetil-3,6-dioxociclohexa-1,4-dienil)butanamida.
CN108712903A (zh) 2015-12-17 2018-10-26 生物电子技术有限公司 用于治疗氧化应急障碍的氟烷基、氟代烷氧基、苯氧基、杂芳氧基、烷氧基和胺1,4-苯醌衍生物
KR102742339B1 (ko) 2017-04-21 2024-12-13 유니버시티 오브 타스마니아 치료 화합물 및 방법

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US3562277A (en) * 1967-09-06 1971-02-09 Shulton Inc Ketonic derivatives of phenyl piperazines
US3950418A (en) * 1970-02-02 1976-04-13 Hoffmann-La Roche Inc. Vitamin A acid amides
US3879448A (en) * 1970-02-07 1975-04-22 Takeda Chemical Industries Ltd 4-hexenoic compounds
US3728362A (en) * 1970-02-07 1973-04-17 Takeda Chemical Industries Ltd (3-methyl-5-carboxy-2-pentenyl)quinones
DE2104871A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1970-02-07 1971-08-26
US3875163A (en) * 1972-02-29 1975-04-01 Pierrel Spa Nitrogen containing acyclic isoprenoid compounds
US3957836A (en) * 1973-07-02 1976-05-18 Takeda Chemical Industries, Ltd. Quinone derivatives
CH585709A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1973-08-24 1977-03-15 Hoffmann La Roche
JPS5919930B2 (ja) * 1974-05-02 1984-05-09 武田薬品工業株式会社 キノン酸誘導体の製造法
US4090942A (en) * 1976-05-19 1978-05-23 Gulf Research & Development Company Process for producing benzene

Also Published As

Publication number Publication date
EP0025692A1 (en) 1981-03-25
EP0025692B1 (en) 1982-12-01
JPS5640651A (en) 1981-04-16
US4388312A (en) 1983-06-14
JPS6247176B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1987-10-06
DE3061226D1 (en) 1983-01-05

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