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GB1526410A - 4-(e)-and 4-(z)-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-nona-2,4,6,8-tetraenecarboxylic acid their derivatives and preparations containing same - Google Patents

4-(e)-and 4-(z)-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-nona-2,4,6,8-tetraenecarboxylic acid their derivatives and preparations containing same

Info

Publication number
GB1526410A
GB1526410A GB49370/75A GB4937075A GB1526410A GB 1526410 A GB1526410 A GB 1526410A GB 49370/75 A GB49370/75 A GB 49370/75A GB 4937075 A GB4937075 A GB 4937075A GB 1526410 A GB1526410 A GB 1526410A
Authority
GB
United Kingdom
Prior art keywords
acid
tetraenecarboxylic
nona
cyclohexen
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
GB49370/75A
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of GB1526410A publication Critical patent/GB1526410A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • C07C403/24—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 six-membered non-aromatic rings, e.g. beta-carotene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/16—Heterocyclic 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
    • C07D295/18—Heterocyclic 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
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • 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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

11-cis-13-Desmethyl vitamin A acid and all-trans-13-desmethyl vitamin A acid are prepared by reacting a compound of the accompanying formula III, in which X<(-)> denotes an organic or inorganic acid radical, with a compound of the accompanying formula IV, in which R<3> denotes hydrogen, alkyl having 1 to 4 carbon atoms, ammonium or an alkali metal ion, in an inert solvent at temperatures from -20 to +30 DEG C in the presence of a base, separating the isomer mixture obtained and hydrolysing the esters obtained before or after separation. The acids thus obtained can be converted on the way into the corresponding esters, amides, azides, hydrazides or anhydrides by means of the acid chlorides. The compounds obtainable according to the invention are distinguished by a cell regeneration-promoting action and are particularly suitable for the treatment of skin diseases and skin injuries.
GB49370/75A 1974-12-03 1975-12-02 4-(e)-and 4-(z)-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-nona-2,4,6,8-tetraenecarboxylic acid their derivatives and preparations containing same Expired GB1526410A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19742456959 DE2456959A1 (en) 1974-12-03 1974-12-03 4- (E) - AND 4- (Z) -7-METHYL-9- (2,6,6TRIMETHYL-1-CYCLOHEXEN-1-YL) -NONA-2,4,6,8TETRAEN CARBONIC ACID, ITS DERIVATIVES AND CONTAINING THEM PREPARATIONS

Publications (1)

Publication Number Publication Date
GB1526410A true GB1526410A (en) 1978-09-27

Family

ID=5932289

Family Applications (1)

Application Number Title Priority Date Filing Date
GB49370/75A Expired GB1526410A (en) 1974-12-03 1975-12-02 4-(e)-and 4-(z)-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-nona-2,4,6,8-tetraenecarboxylic acid their derivatives and preparations containing same

Country Status (7)

Country Link
BE (1) BE835902A (en)
CH (1) CH619211A5 (en)
DE (1) DE2456959A1 (en)
FR (1) FR2293193A1 (en)
GB (1) GB1526410A (en)
SE (1) SE413139B (en)
ZA (1) ZA757545B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5780676A (en) * 1992-04-22 1998-07-14 Ligand Pharmaceuticals Incorporated Compounds having selective activity for Retinoid X Receptors, and means for modulation of processes mediated by Retinoid X Receptors
US5962731A (en) * 1992-04-22 1999-10-05 Ligand Pharmaceuticals Incorporated Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
US7655699B1 (en) 1992-04-22 2010-02-02 Eisai Inc. Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
CN102976937A (en) * 2004-06-18 2013-03-20 华盛顿大学 Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US8962691B2 (en) 2003-03-14 2015-02-24 University Of Washington Retinoid replacements and opsin agonists and methods for the use thereof
US9173856B2 (en) 2010-04-19 2015-11-03 Qlt Inc. Therapeutic regimen and methods for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
US9233091B2 (en) 2008-02-11 2016-01-12 University Of Washington Methods for the treatment and prevention of age-related retinal dysfunction
US10130606B2 (en) 2009-09-15 2018-11-20 Novelion Therapeutics Inc. Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle
US10828267B2 (en) 2012-03-01 2020-11-10 Retinagenix Therapeutics, Inc. Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2843811A1 (en) * 1978-10-07 1980-04-24 Basf Ag RETINIC ACID AND 7,8-DEHYDRO RETINIC ACID-N- (CARBOXY) -PHENYLAMIDE
WO1982002833A1 (en) * 1981-02-17 1982-09-02 Gail Sansone Bazzano The use of retinoids and their derivatives to increase the rate of growth of human scalp hair and to increase the rate of growth of fur in certain fur-bearing animals
DE3280344D1 (en) * 1981-11-09 1991-07-25 Gail S Bazzano USE OF RETINOIDES AND MINOXIDIL (2,4-DIAMINO-6-PIPERIDINO-PYRIMIDINE-3-OXIDE) TO IMPROVE THE GROWTH OF HUMAN HEAD HAIR AND TO TREAT CERTAIN TYPES OF ALOPECIA.
CH651007A5 (en) * 1982-06-24 1985-08-30 Hoffmann La Roche POLYEN CONNECTIONS.
US4539154A (en) * 1983-06-15 1985-09-03 Hoffmann-La Roche Inc. Polyene compounds
US4743400A (en) * 1986-09-22 1988-05-10 Mcneilab, Inc. Process for preparing retinoyl chlorides
DK0678087T3 (en) * 1993-01-11 1999-09-27 Ligand Pharm Inc Compounds with selective activity for retinoid-X receptors and methods for modulating processes mediated by retinoid-X
DE69423911T2 (en) * 1993-12-15 2000-08-03 Avon Products, Inc. NEW RETINOID CONJUGATES FOR THE TREATMENT OF AGE SIGNS OF THE SKIN
US7566808B2 (en) * 2004-02-17 2009-07-28 President And Fellows Of Harvard College Management of ophthalmologic disorders, including macular degeneration

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5780676A (en) * 1992-04-22 1998-07-14 Ligand Pharmaceuticals Incorporated Compounds having selective activity for Retinoid X Receptors, and means for modulation of processes mediated by Retinoid X Receptors
US5962731A (en) * 1992-04-22 1999-10-05 Ligand Pharmaceuticals Incorporated Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
US6043279A (en) * 1992-04-22 2000-03-28 Ligand Pharmaceuticals, Incorporated Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
US7655699B1 (en) 1992-04-22 2010-02-02 Eisai Inc. Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
US10238610B2 (en) 2003-03-14 2019-03-26 University Of Washington Retinoid replacements and opsin agonists and methods for the use thereof
US8962691B2 (en) 2003-03-14 2015-02-24 University Of Washington Retinoid replacements and opsin agonists and methods for the use thereof
US9149446B2 (en) 2003-03-14 2015-10-06 University Of Washington Stabilized mutant opsin proteins
US9907762B2 (en) 2003-03-14 2018-03-06 University Of Washington Stabilized mutant opsin proteins
US9388130B2 (en) 2004-06-18 2016-07-12 University Of Washington Retinal derivatives and methods for the use thereof for the treatment of visual disorders
CN102976937B (en) * 2004-06-18 2016-12-21 华盛顿大学 For treating retinoid and the using method thereof of visual disorder
CN102976937A (en) * 2004-06-18 2013-03-20 华盛顿大学 Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US10117845B2 (en) 2004-06-18 2018-11-06 University Of Washington Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US9169204B2 (en) 2004-06-18 2015-10-27 University Of Washington Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US9403765B2 (en) 2004-06-18 2016-08-02 University Of Washington Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US9162978B2 (en) 2004-06-18 2015-10-20 University Of Washington Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US9174936B2 (en) 2004-06-18 2015-11-03 University Of Washington Retinal derivatives and methods for the use thereof for the treatment of visual disorders
US9855239B2 (en) 2008-02-11 2018-01-02 University Of Washington Methods for the treatment and prevention of age-related retinal dysfunction
US9408821B2 (en) 2008-02-11 2016-08-09 University Of Washington Methods for the treatment and prevention of age-related retinal dysfunction
US9233091B2 (en) 2008-02-11 2016-01-12 University Of Washington Methods for the treatment and prevention of age-related retinal dysfunction
US10130606B2 (en) 2009-09-15 2018-11-20 Novelion Therapeutics Inc. Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle
US10736865B2 (en) 2009-09-15 2020-08-11 Retinagenix Therapeutics, Inc. Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle
US9987245B2 (en) 2010-04-19 2018-06-05 Novelion Therapeutics Inc. Therapeutic regimen and methods for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
US9173856B2 (en) 2010-04-19 2015-11-03 Qlt Inc. Therapeutic regimen and methods for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
US10828267B2 (en) 2012-03-01 2020-11-10 Retinagenix Therapeutics, Inc. Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency

Also Published As

Publication number Publication date
CH619211A5 (en) 1980-09-15
FR2293193B1 (en) 1979-09-21
SE413139B (en) 1980-04-21
ZA757545B (en) 1976-12-29
DE2456959A1 (en) 1976-06-16
FR2293193A1 (en) 1976-07-02
SE7513080L (en) 1976-06-04
BE835902A (en) 1976-05-25

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee