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GB1358469A - Desmethyl retinoic acid homologues - Google Patents

Desmethyl retinoic acid homologues

Info

Publication number
GB1358469A
GB1358469A GB5733272A GB5733272A GB1358469A GB 1358469 A GB1358469 A GB 1358469A GB 5733272 A GB5733272 A GB 5733272A GB 5733272 A GB5733272 A GB 5733272A GB 1358469 A GB1358469 A GB 1358469A
Authority
GB
United Kingdom
Prior art keywords
acid
aldehyde
coor
ene
trimethyl
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
GB5733272A
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.)
University of California
Original Assignee
University of California
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 University of California filed Critical University of California
Publication of GB1358469A publication Critical patent/GB1358469A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • 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
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nutrition Science (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

1358469 Derivatives of desmethyl retenoic acid UNIVERSITY OF CALIFORNIA REGENTS OF 12 Dec 1972 [13 Dec 1971] 57332/72 Headings C2C and C2V 2,6,6 - trimethyl - 1 - (10<SP>1</SP>- carboxydeca 1<SP>1</SP>,3<SP>1</SP>,- 5<SP>1</SP>,7<SP>1</SP>,9<SP>1</SP>-pentaeryl)cyclohex-1-ene is prepared by (a) subjecting #-ionone to a haloform reaction (preferably chloroform) to form 2,6,6-trimethyl- 1-(2<SP>1</SP>-carboxyvinylene)-cyclohexa-1-ene, (b) reducing the acid to the corresponding alcohol (preferably using lithium aluminium hydride in diethyl (ether), (c) oxidizing the alcohol to the corresponding aldehyde (preferably using manganese dioxide), (d) subjecting the aldehyde to a Wittig reaction (preferably in the presence of sodium hydride) using a compound (R 1 O)(R 2 O)- P(O)CH 2 -CH=CH-COOR 3 in which R 1 ,R 2 and R 3 are alkyl or aryl (preferably ethyl) (e) hydrolysing the ester formed to the corresponding acid and repeating the reaction sequence (b) to (e). A modification of this process repeats steps (a) to (c) and subjects the aldehyde to a Wittig reaction using (R 1 O))(R 2 O)P(O)CH 2 - (CH=CH) 3 -COOR 3 and to produce the ester of the decapentaenoic acid directly. 2,6,6-Trimethyl - 1 - (12<SP>1</SP> - carboxydodeca - 1<SP>1</SP>,3<SP>1</SP>,5<SP>1</SP>,7<SP>1</SP>,9<SP>1</SP>,11<SP>1</SP>- hexaenyl)cyclohex-1-ene is prepared from the decapentaenoic acid by repeating steps (b) and (c) and reacting the resulting aldehyde with (R 1 O) (R 2 O)P(O)CH 2 COOR 3 and hydrolysing the resulting ester. The above acids are active in promoting wound-healing and form with a carrier or diluent a pharmaceutical composition which may be administered topically.
GB5733272A 1971-12-13 1972-12-12 Desmethyl retinoic acid homologues Expired GB1358469A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US20762371A 1971-12-13 1971-12-13

Publications (1)

Publication Number Publication Date
GB1358469A true GB1358469A (en) 1974-07-03

Family

ID=22771321

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5733272A Expired GB1358469A (en) 1971-12-13 1972-12-12 Desmethyl retinoic acid homologues

Country Status (9)

Country Link
JP (1) JPS562553B2 (en)
BE (1) BE792645A (en)
CA (1) CA977763A (en)
DE (1) DE2260743C3 (en)
ES (1) ES409551A1 (en)
FR (1) FR2163528B1 (en)
GB (1) GB1358469A (en)
NL (1) NL169467C (en)
SE (1) SE388417B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3443627A1 (en) * 1984-11-29 1986-05-28 USV Pharmaceutical Corp., Tuckahoe, N.Y. Polyolefinic alpha -alkylcarboxylic acids and their derivatives, and pharmaceuticals containing these compounds

Also Published As

Publication number Publication date
SE388417B (en) 1976-10-04
BE792645A (en) 1973-03-30
FR2163528B1 (en) 1976-07-02
JPS4864056A (en) 1973-09-05
FR2163528A1 (en) 1973-07-27
DE2260743B2 (en) 1980-12-18
DE2260743A1 (en) 1973-06-14
NL169467C (en) 1982-07-16
NL169467B (en) 1982-02-16
NL7216913A (en) 1973-06-15
DE2260743C3 (en) 1981-12-24
CA977763A (en) 1975-11-11
AU4993872A (en) 1974-06-13
ES409551A1 (en) 1976-01-01
JPS562553B2 (en) 1981-01-20

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee