GB1449027A - Vitamin a acid amides - Google Patents

Vitamin a acid amides

Info

Publication number
GB1449027A
GB1449027A GB5900873A GB5900873A GB1449027A GB 1449027 A GB1449027 A GB 1449027A GB 5900873 A GB5900873 A GB 5900873A GB 5900873 A GB5900873 A GB 5900873A GB 1449027 A GB1449027 A GB 1449027A
Authority
GB
United Kingdom
Prior art keywords
vitamin
acid
acid amides
amides
chloroaniline
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
GB5900873A
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 GB1449027A publication Critical patent/GB1449027A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1449027 Vitamin A-acid amides BASF AG 20 Dec 1973 [3 Jan 1973] 59008/73 Heading C2V Vitamin A-acid amides have the formula where R<SP>1</SP> is hydrogen and R<SP>2</SP> is alkyl of more than 10 carbon atoms, naphthyl, cycloalkyl, polycycloalkyl or substituted phenyl, or R<SP>1</SP> is alkyl and R<SP>2</SP> is a cycloaliphatic ring or R<SP>1</SP> and R<SP>2</SP> together with the nitrogen atom form a ring which may contain a further hetero-atom. The amides are obtained by reacting a functional derivative of vitamin A-acid with an amine of formula In examples vitamin A-acid chloride is reacted with morpholine, piperidine, cyclopropylamine, 1-adamantylamine, stearylamine, N-propyl-N cyclohexylamine, N - butyl - N - cyclohexylamine, p-naphthylamine, 3,4-dimethylaniline, p - fluoroaniline, m - nitroaniline, 2 - methylaniline, aniline - 4 - carboxylic acid ethyl ester, 2-methoxyaniline, p-ethoxyaniline, m-chloroaniline and p-chloroaniline.
GB5900873A 1973-01-03 1973-12-20 Vitamin a acid amides Expired GB1449027A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2300107A DE2300107C2 (en) 1973-01-03 1973-01-03 Vitamin A acid anilide-4-carboxylic acid ethyl ester, process for its production and preparations containing it

Publications (1)

Publication Number Publication Date
GB1449027A true GB1449027A (en) 1976-09-08

Family

ID=5868192

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5900873A Expired GB1449027A (en) 1973-01-03 1973-12-20 Vitamin a acid amides

Country Status (6)

Country Link
AT (1) AT331426B (en)
BE (1) BE809367A (en)
CH (1) CH582139A5 (en)
DE (1) DE2300107C2 (en)
FR (1) FR2212135B1 (en)
GB (1) GB1449027A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1390343A1 (en) * 2001-05-29 2004-02-25 Chebigen Co., Ltd. Novel retinoid derivatives and methods for producing said compounds and an anti-cancer pharmaceutical composition comprising said compounds
WO2006005455A2 (en) * 2004-07-09 2006-01-19 Dsm Ip Assets B.V. Amino, amino acid or peptide conjugates of retinoic acid
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
CN110831586A (en) * 2017-05-23 2020-02-21 密执安大学评议会 Dimethyl-nonatetraenyl-trimethyl-cyclohexyl compound and application thereof
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 (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4310546A (en) * 1978-07-31 1982-01-12 Johnson & Johnson Novel retinoids and their use in preventing carcinogenesis
DE2843915A1 (en) * 1978-10-07 1980-04-24 Basf Ag N-BENZOYL RETINYLAMINE
DE2843811A1 (en) * 1978-10-07 1980-04-24 Basf Ag RETINIC ACID AND 7,8-DEHYDRO RETINIC ACID-N- (CARBOXY) -PHENYLAMIDE
DE3002545A1 (en) * 1980-01-25 1981-07-30 Basf Ag, 6700 Ludwigshafen 5-AMINO-TETRAZOLE DERIVATIVES OF RETINIC ACIDS, THEIR PRODUCTION AND THE PHARMACEUTICAL PREPARATIONS CONTAINING THEM
US4642318A (en) * 1982-11-17 1987-02-10 Klaus Wolff Method for decreasing radiation load in PUVA therapy
US4743400A (en) * 1986-09-22 1988-05-10 Mcneilab, Inc. Process for preparing retinoyl chlorides
DE4011056A1 (en) * 1989-04-05 1990-10-11 Gradinger F Hermes Pharma New N-retinoyl-L-thiazolidine-4-carboxylic acid derivs. - for treating neoplastic and mucosal diseases, esp. gastro-intestinal ulcers and new intermediates
DE19523079A1 (en) * 1995-06-26 1997-01-02 Basf Ag Esters and amides of 9 (Z) -retinoic acid
WO2003003987A2 (en) * 2001-07-06 2003-01-16 The Ohio State University Research Foundation Solid phase synthesis of arylretinamides
US7566808B2 (en) * 2004-02-17 2009-07-28 President And Fellows Of Harvard College Management of ophthalmologic disorders, including macular degeneration

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1297730A (en) * 1960-11-04 1962-07-06 Hoffmann La Roche Cosmetic preparation
CH529742A (en) * 1970-02-02 1972-10-31 Hoffmann La Roche Process for the production of vitamin A acid amides

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1390343A4 (en) * 2001-05-29 2005-06-22 Chebigen Co Ltd Novel retinoid derivatives and methods for producing said compounds and an anti-cancer pharmaceutical composition comprising said compounds
US7166744B2 (en) 2001-05-29 2007-01-23 Chebigen Co., Ltd. Retinoid derivatives and methods for producing said compounds and anti-cancer pharmaceutical composition comprising said compounds
EP1390343A1 (en) * 2001-05-29 2004-02-25 Chebigen Co., Ltd. Novel retinoid derivatives and methods for producing said compounds and an anti-cancer pharmaceutical composition comprising said compounds
US8962691B2 (en) 2003-03-14 2015-02-24 University Of Washington Retinoid replacements and opsin agonists and methods for the use thereof
US10238610B2 (en) 2003-03-14 2019-03-26 University Of Washington Retinoid replacements and opsin agonists and methods for the use thereof
US9907762B2 (en) 2003-03-14 2018-03-06 University Of Washington Stabilized mutant opsin proteins
US9149446B2 (en) 2003-03-14 2015-10-06 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
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
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
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
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
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
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
CN102976937B (en) * 2004-06-18 2016-12-21 华盛顿大学 For treating retinoid and the using method thereof of visual disorder
WO2006005455A3 (en) * 2004-07-09 2008-02-07 Dsm Ip Assets Bv Amino, amino acid or peptide conjugates of retinoic acid
WO2006005455A2 (en) * 2004-07-09 2006-01-19 Dsm Ip Assets B.V. Amino, amino acid or peptide conjugates of retinoic acid
CN101048375B (en) * 2004-07-09 2012-12-05 帝斯曼知识产权资产管理有限公司 Amino, amino acid or peptide conjugates of retinoic acid
US9233091B2 (en) 2008-02-11 2016-01-12 University Of Washington Methods for the treatment and prevention of age-related retinal dysfunction
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
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
CN110831586A (en) * 2017-05-23 2020-02-21 密执安大学评议会 Dimethyl-nonatetraenyl-trimethyl-cyclohexyl compound and application thereof
CN110831586B (en) * 2017-05-23 2023-06-13 密执安大学评议会 Dimethyl-nonyltetraalkenyl-trimethyl-cyclohexyl compounds and uses thereof

Also Published As

Publication number Publication date
FR2212135B1 (en) 1976-05-14
BE809367A (en) 1974-07-03
CH582139A5 (en) 1976-11-30
AT331426B (en) 1976-08-25
ATA1974A (en) 1975-11-15
DE2300107A1 (en) 1974-07-11
FR2212135A1 (en) 1974-07-26
DE2300107C2 (en) 1982-03-11

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Legal Events

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