Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1998-01-26
2000-11-14
Oazi, Sabiha
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562492, 564171, 560 59, 514557, 514568, 514570, 514588, 514598, C07C 6300, C07C 6976, A61K 3119, A61K 3117
Patent
active
061472557
DESCRIPTION:
BRIEF SUMMARY
The invention relates to bicyclic aromatic compounds as novel and useful industrial products. It also relates to the use of these novel compounds in pharmaceutical compositions intended for use in human or veterinary medicine, or alternatively in cosmetic compositions.
The compounds according to the invention have pronounced activity in the fields of cell differentiation and cell proliferation, and find applications more particularly in the topical and systemic treatment of dermatological complaints associated with a disorder of keratinization, dermatological (or other) complaints with an inflammatory and/or immunoallergic component, and dermal or epidermal proliferations, these being either benign or malignant. These compounds may also be used in the treatment of degenerative diseases of connective tissue, for combating both light-induced and chronological ageing of the skin and for treating disorders of cicatrization. They moreover find an application in the ophthalmological field, in particular in the treatment of corneopathies.
The compounds according to the invention may also be used in cosmetic compositions for body and hair hygiene.
The compounds according to the invention may be represented by the general formula (I) below: ##STR2## in which: R.sub.1 represents (i) the --CH.sub.3 radical ##STR3## R.sub.5 and R.sub.7 having the meaning given below, X represents ##STR4## R.sub.8 and R.sub.9 having the meanings given below R.sub.2 and R.sub.3, which may be identical or different, represent carbon attached to the phenyl radical is substituted with at least two carbon atoms, the adjacent aromatic ring a 5- or 6-membered ring optionally substituted with methyl groups and/or optionally interrupted by an oxygen or sulphur atom, have the meanings (i), (iii) and (iv) mentioned above, hydrogen atom, a halogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms or a radical --OR.sub.5, --COR.sub.10 ##STR5## R' and R" having the meaning given below, (d) a radical --OR.sub.11 hydrogen atom or a lower alkyl radical, having from 1 to 20 carbon atoms, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, a sugar residue or an amino acid or peptide residue,
R' and R", which may be identical or different, represent a hydrogen atom, a lower alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl radical or an amino acid or sugar residue, or alternatively, taken together form a heterocycle.
The invention is also directed towards the salts of the compounds of formula (I) when R.sub.1 represents a carboxylic acid function and the geometrical and optical isomers of the said compounds of formula (I).
When the compounds according to the invention are in the form of salts, they are preferably salts of an alkali metal or alkaline-earth metal, or alternatively of zinc or of an organic amine.
According to the present invention, the term lower alkyl radical is understood to refer to a radical having from 1 to 12, preferably from 1 to 9, carbon atoms, advantageously the methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, nonyl, decyl and dodecyl radicals.
The expression linear alkyl radical having from 1 to 20 carbon atoms is understood to refer in particular to the methyl, ethyl, propyl, pentyl, hexyl, octyl, decyl, dodecyl, hexadecyl and octadecyl radicals.
The expression branched alkyl radical having from 1 to 20 carbon atoms is understood to refer in particular to the 2-ethylhexyl, 2-methylbutyl, 2-methylpentyl, 1-methylhexyl and 3-methylheptyl radicals.
Among the alkyl radicals having at least 3 carbon atoms, where the carbon attached to the phenyl radical is substituted with at least two carbon atoms, mention may be made of the tert-butyl, isopropyl, 1,1-dimethylhexyl and 1,1-dimethyldecyl radical. Preferably, these radicals have not more than 20 carbon atoms, even more preferably not more than 12 carbon atoms. Advantageously, the radical (ii) is the tert-butyl radical.
Among the monohydroxyalkyl ra
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patent: 5763487 (1998-06-01), Bernardon
patent: 5766610 (1998-06-01), Bernardon
Chemical Abstracts, vol. 80, No. 7, Feb. 18, 1974, XP002020611.
Chemical Abstracts, vol. 80, No 19, May 13, 1974, XP002020612.
Chemical Abstracts, vol. 108, No. 4, 1975, XP002020610 (in German).
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Franke et al. (CA 77:126263 abstract of DE 2162571), 1972.
Teufel et al. (CA 80:133005 abstract of DE 2240440), 1972.
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Hanaoka et al. (CA 124:55583 abstract of JP 07252192), 1995.
Centre International de Recherches Dermatologiques Galderma
Oazi Sabiha
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