DE69516903T2 - Retinoid trienverbindungen und verfahren - Google Patents

Retinoid trienverbindungen und verfahren

Info

Publication number
DE69516903T2
DE69516903T2 DE69516903T DE69516903T DE69516903T2 DE 69516903 T2 DE69516903 T2 DE 69516903T2 DE 69516903 T DE69516903 T DE 69516903T DE 69516903 T DE69516903 T DE 69516903T DE 69516903 T2 DE69516903 T2 DE 69516903T2
Authority
DE
Germany
Prior art keywords
retinoid
triene
connections
compounds
receptors
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
Application number
DE69516903T
Other languages
English (en)
Other versions
DE69516903D1 (de
Inventor
F Boehm
Lin Zhang
L Bennani
M Nadzan
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.)
Ligand Pharmaceuticals Inc
Original Assignee
Ligand Pharmaceuticals 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
Priority claimed from US08/480,127 external-priority patent/US5721103A/en
Application filed by Ligand Pharmaceuticals Inc filed Critical Ligand Pharmaceuticals Inc
Application granted granted Critical
Publication of DE69516903D1 publication Critical patent/DE69516903D1/de
Publication of DE69516903T2 publication Critical patent/DE69516903T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Nutrition Science (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Immunology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
DE69516903T 1994-12-30 1995-12-21 Retinoid trienverbindungen und verfahren Expired - Fee Related DE69516903T2 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US36661394A 1994-12-30 1994-12-30
US08/480,127 US5721103A (en) 1994-12-30 1995-06-07 Trienoic retinoid compounds and methods
US08/481,877 US6083977A (en) 1994-12-30 1995-06-07 Trienoic retinoid compounds and methods
PCT/US1995/016695 WO1996020913A1 (en) 1994-12-30 1995-12-21 Novel trienoic retinoid compounds and methods

Publications (2)

Publication Number Publication Date
DE69516903D1 DE69516903D1 (de) 2000-06-15
DE69516903T2 true DE69516903T2 (de) 2000-10-26

Family

ID=27408763

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69516903T Expired - Fee Related DE69516903T2 (de) 1994-12-30 1995-12-21 Retinoid trienverbindungen und verfahren

Country Status (14)

Country Link
EP (1) EP0800503B1 (de)
JP (1) JP4001913B2 (de)
CN (1) CN1121374C (de)
AT (1) ATE192731T1 (de)
AU (1) AU712187B2 (de)
CA (1) CA2208981C (de)
DE (1) DE69516903T2 (de)
DK (1) DK0800503T3 (de)
ES (1) ES2148593T3 (de)
GR (1) GR3033676T3 (de)
MX (1) MX9704878A (de)
NO (1) NO310408B1 (de)
PT (1) PT800503E (de)
WO (1) WO1996020913A1 (de)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7115728B1 (en) 1995-01-30 2006-10-03 Ligand Pharmaceutical Incorporated Human peroxisome proliferator activated receptor γ
AU7074496A (en) 1995-09-18 1997-04-09 Ligand Pharmaceuticals Incorporated Ppar gamma antagonists for treating obesity
JPH10158192A (ja) * 1996-10-03 1998-06-16 Eisai Co Ltd 移植片対宿主疾患（ｇｖｈｄ）の治療および臓器移植時の移植片拒絶反応抑制のための医薬組成物
EP1093362A1 (de) 1998-06-12 2001-04-25 Ligand Pharmaceuticals Incorporated Verwendung von rxr modulatoren zur behandlung von anti-östrogen-resistent brustkrebs
AU9556298A (en) * 1998-11-03 2000-05-22 Ligand Pharmaceuticals Incorporated Trienoic retinoid compounds as retinoic acid receptor antagonists
US6326397B1 (en) 1998-11-10 2001-12-04 Hoffman-La Roche Inc. Retinoid antagonists and use thereof
WO2000035856A1 (en) 1998-12-17 2000-06-22 F. Hoffmann-La Roche Ag 7-aryl-6(z)heptatrienoic acid retinamides as apoptosis inducing compounds and their use as anti-cancer agents
FR2787789B1 (fr) 1998-12-29 2002-06-14 Lipha Benzopyranes et benzoxepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparations
ATE266616T1 (de) * 1999-03-08 2004-05-15 Basilea Pharmaceutica Ag Retinoid antagonisten und ihre verwendung
TW550264B (en) 1999-04-07 2003-09-01 Sankyo Co Amine derivated compounds and the pharmaceutical compositions thereof
HUP0202814A3 (en) 1999-08-27 2003-11-28 Ligand Pharmaceuticals Inc San Androgen receptor modulator compounds and methods for their preparation and pharmaceutical compositions containing them and their use
WO2001016133A2 (en) 1999-08-27 2001-03-08 Ligand Pharmaceuticals Incorporated 8-substituted-6-trifluoromethyl-9-pyrido[3,2-g]quinoline compounds as androgen receptor modulators
US6566372B1 (en) 1999-08-27 2003-05-20 Ligand Pharmaceuticals Incorporated Bicyclic androgen and progesterone receptor modulator compounds and methods
US6593493B1 (en) * 1999-09-14 2003-07-15 Ligand Pharmaceuticals, Inc. RXR modulators with improved pharmacologic profile
DE122008000018I1 (de) 2000-01-21 2008-08-14 Novartis Pharma Ag Zusammensetzungen bestehend aus Dipeptidylpeptidase-IV Inhibitoren und Antidiabetica
US20050163801A1 (en) * 2001-12-14 2005-07-28 Kyowa Engineering Co., Ltd. Method of inducing apoptosis and compositions therefor
JP5877466B2 (ja) * 2012-02-29 2016-03-08 国立大学法人 岡山大学 テルペノイド由来レチノイド化合物
KR101556439B1 (ko) 2013-07-01 2015-10-15 서울대학교산학협력단 미토콘드리아 역행성 신호 경로와 관련된 ＲＸＲα의 기능 및 용도
WO2015059632A1 (en) 2013-10-23 2015-04-30 Acadia Pharmaceuticals Inc. Treatment of a neurodegenerative disease or disorder
CN103759895B (zh) * 2013-11-26 2016-03-23 四川蓝讯宝迩电子科技有限公司 气体减压阀进气端的装配测试基台
US20230132366A9 (en) 2018-11-26 2023-04-27 Denali Therapeutics Inc. Methods for treating dysregulated lipid metabolism

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3845089A (en) * 1972-07-27 1974-10-29 Zoecon Corp Phenylheptadienoates
US3882157A (en) * 1972-07-27 1975-05-06 Zoecon Corp Thiolesters of phenylheptadienoic acids
LU77254A1 (de) * 1977-05-04 1979-01-18
FR2719041B1 (fr) * 1994-04-26 1996-05-31 Cird Galderma Nouveaux composés polyéniques, compositions pharmaceutiques et cosmétiques les contenant et utilisations.

Also Published As

Publication number Publication date
EP0800503B1 (de) 2000-05-10
CN1220656A (zh) 1999-06-23
EP0800503A1 (de) 1997-10-15
PT800503E (pt) 2000-11-30
JPH10511948A (ja) 1998-11-17
ES2148593T3 (es) 2000-10-16
GR3033676T3 (en) 2000-10-31
CA2208981A1 (en) 1996-07-11
JP4001913B2 (ja) 2007-10-31
NO973017D0 (no) 1997-06-27
WO1996020913A1 (en) 1996-07-11
NO973017L (no) 1997-08-28
AU712187B2 (en) 1999-10-28
DE69516903D1 (de) 2000-06-15
CN1121374C (zh) 2003-09-17
MX9704878A (es) 1997-11-29
ATE192731T1 (de) 2000-05-15
DK0800503T3 (da) 2000-08-07
AU4643096A (en) 1996-07-24
NO310408B1 (no) 2001-07-02
CA2208981C (en) 2008-08-26

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