US3689667A - C22 acid and its salts to promote wound healing - Google Patents

C22 acid and its salts to promote wound healing Download PDF

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Publication number
US3689667A
US3689667A US49505A US3689667DA US3689667A US 3689667 A US3689667 A US 3689667A US 49505 A US49505 A US 49505A US 3689667D A US3689667D A US 3689667DA US 3689667 A US3689667 A US 3689667A
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US
United States
Prior art keywords
acid
salts
wound
healing
wound healing
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Expired - Lifetime
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US49505A
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English (en)
Inventor
Kwan-Hua Lee
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University of California Berkeley
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University of California Berkeley
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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
    • 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

Definitions

  • wound as used in this application means any topical lesion such as a surgical incision, accidental wound or ulcer.
  • Aspirin inhibits both features.
  • the healing inhibitory action of aspirin and other inflammatory agents has been demonstrated.
  • Vitamin A increases mucopolysaccharide synthesis and it also causes inflammation.
  • Retinoic acid the acid form of vitamin A
  • its salts also have been found active compounds in promoting healing.
  • Topical application of retinoic acid or its salts reverses the healing retardation action caused by oral administration of sodium salicylate, prednisone and other inflammatory agents and topical application of salicylic acid or hydrocortisone.
  • Topical application of retinoic acid and its salts promotes skin wound healing in rats and human beings.
  • hydrocortisone, prednisone and salicylic acid are very commonly used. Hydrocortisone and salicylic acid preparations for topic uses are quite popular. Whitfield Ointment, USP, contains 3% salicylic acid.
  • Prednisone is a potent synthetic analogue of cortisone which is only used orally. It has been used in a large variety of diseases and it is not uncommonly used on surgical patients to reduce edema or inflammation. Corticosteroids are used in organ-transplant surgery to suppress immunological response. Sodium salicylate has been employed in the symptomatic therapy of acute rheumatic fever for many decades. Oftentimes it is still the drug of choice in many incidences.
  • C22 acid and its salts have been found to promote wound healing. This is true both of animals which have not been otherwise treated and also true of animals which have been treated with antiinflammatory agents such as a salicylate, hydrocortisone, prednisone, indomethacin, mefenamic acid and the like. These compounds normally retard healing and C22 acid and its salts has been found to reverse this action.
  • the C22 acid namely 2,6,6-trimethyl-l-(10'-carboxy-3',7'-dimethyldeca-l ',3,5',7',9',-pentaenyl)- cyclohex-l-ene acid is a novel compound and can be made as follows:
  • Suitable oil carriers include physiologically acceptable oils in which the acid is soluble such as isopropyl myristate, corn oil, cotton seed oil and the like. Powder can be prepared utilizing the C22 acid crystals by grinding the crystals with a suitable inert carrier such as talc. C22 acid or its salts can be combined with any of the usual ointment bases used in pharmacy.
  • One suitable base is known as NIB (non-ionic base) developed by the University of California School of Pharmacy having the following approximate composition:
  • retinoic acid and C22 is the acid of the present.
  • This method involves subcutaneous implantation of cotton-pellets and measuring the size of the. granuloma induced after a few days.
  • Anti-inflammatory agents reduce the size or weight of granuloma as compared with that of the control.
  • Those compound derivatives which promote healing increase the size or weight of the granuloma.
  • the cotton-pellet implanted on the right side con tains the compound under test and the cotton-pellet implanted on the left side serves as the control.
  • a wound healing composition comprising an effective amount of a compound selected from 2,6,6,- trimethyll 10'-carboxy-3 7-dimethyldeca-l 3 5,7', 9',-pentaenyl)-cyclohex-l-ene acid and its salts in a physiologically acceptable topical carrier selected from the group consisting of an oil, an ointment or a powder.
  • a method of healing a wound comprising applying to said wound site a composition of claim 1 containing about 1% of the acid or its salt.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US49505A 1970-06-24 1970-06-24 C22 acid and its salts to promote wound healing Expired - Lifetime US3689667A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US4950570A 1970-06-24 1970-06-24

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US3689667A true US3689667A (en) 1972-09-05

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US49505A Expired - Lifetime US3689667A (en) 1970-06-24 1970-06-24 C22 acid and its salts to promote wound healing

Country Status (2)

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US (1) US3689667A (fr)
BE (1) BE786497A (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882244A (en) * 1971-12-13 1975-05-06 Univ California Method of treating acne with a c{hd 20 {b acid
US3934028A (en) * 1974-04-22 1976-01-20 The Regents Of The University Of California Acne and psoriasis treatment with retinoic acid analogs
US3966967A (en) * 1973-03-21 1976-06-29 The Regents Of The University Of California Compositions and methods of treating psoriasis with vinyligs of desmethyl retinoic acid
US4021573A (en) * 1974-04-22 1977-05-03 The Regents Of The University Of California Psoriasis treatment with retinoic acid analogs
US4048204A (en) * 1975-11-10 1977-09-13 The Regents Of The University Of California C20 and C22 acids to promote wound healing
US4203969A (en) * 1977-07-06 1980-05-20 Drythanol Limited Dithranol compositions for topical applications
US4551480A (en) * 1983-06-21 1985-11-05 Stiefel Laboratories, Inc. Compositions for the treatment of psoriasis
WO1991005754A3 (fr) * 1989-10-13 1991-11-28 Medafor Derives des alcools gras a longue chaine, leurs applications, notamment en tant que molecules cytotrophiques et cytoprotectrices, et compositions pharmaceutiques les contenant
US6063817A (en) * 1997-02-21 2000-05-16 Bristol-Myers Squibb Company Use of substituted (5,6) dihydronaphthalenyl compounds having retinoid-like activity to prevent or reduce ischemic injury
USRE41134E1 (en) 1989-06-07 2010-02-16 Alyzan, Inc. Slow release vehicles for minimizing skin irritancy of topical compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3026249A (en) * 1960-06-30 1962-03-20 Eastman Kodak Co Preparation of stable aqueous isomeric vitamin a compositions
US3089823A (en) * 1961-09-05 1963-05-14 Eastman Kodak Co Aqueous vitamin a oil emulsion
US3143564A (en) * 1962-01-15 1964-08-04 Sumitomo Chemical Co Method for producing 2-transvitamin a acid

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3026249A (en) * 1960-06-30 1962-03-20 Eastman Kodak Co Preparation of stable aqueous isomeric vitamin a compositions
US3089823A (en) * 1961-09-05 1963-05-14 Eastman Kodak Co Aqueous vitamin a oil emulsion
US3143564A (en) * 1962-01-15 1964-08-04 Sumitomo Chemical Co Method for producing 2-transvitamin a acid

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882244A (en) * 1971-12-13 1975-05-06 Univ California Method of treating acne with a c{hd 20 {b acid
US3966967A (en) * 1973-03-21 1976-06-29 The Regents Of The University Of California Compositions and methods of treating psoriasis with vinyligs of desmethyl retinoic acid
US3934028A (en) * 1974-04-22 1976-01-20 The Regents Of The University Of California Acne and psoriasis treatment with retinoic acid analogs
US4021573A (en) * 1974-04-22 1977-05-03 The Regents Of The University Of California Psoriasis treatment with retinoic acid analogs
US4048204A (en) * 1975-11-10 1977-09-13 The Regents Of The University Of California C20 and C22 acids to promote wound healing
US4203969A (en) * 1977-07-06 1980-05-20 Drythanol Limited Dithranol compositions for topical applications
US4551480A (en) * 1983-06-21 1985-11-05 Stiefel Laboratories, Inc. Compositions for the treatment of psoriasis
USRE41134E1 (en) 1989-06-07 2010-02-16 Alyzan, Inc. Slow release vehicles for minimizing skin irritancy of topical compositions
WO1991005754A3 (fr) * 1989-10-13 1991-11-28 Medafor Derives des alcools gras a longue chaine, leurs applications, notamment en tant que molecules cytotrophiques et cytoprotectrices, et compositions pharmaceutiques les contenant
US5243094A (en) * 1989-10-13 1993-09-07 Medafor Derivatives of long chain fatty alcohols, their uses, particularly as cytotrophic and cytoprotective molecules, and pharmaceutical compositions containing them
US5447959A (en) * 1989-10-13 1995-09-05 Medafor Method of using derivatives of long chain fatty alcohols to treat neuronal degradation
US6063817A (en) * 1997-02-21 2000-05-16 Bristol-Myers Squibb Company Use of substituted (5,6) dihydronaphthalenyl compounds having retinoid-like activity to prevent or reduce ischemic injury

Also Published As

Publication number Publication date
BE786497A (fr) 1972-11-16

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