Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-01-26
2000-04-04
Fan, Jane
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514356, 514448, 514569, 562473, 562459, 562475, 560 51, 560 55, 424401, 546322, 546326, 549 71, A61K 3144, C07D21330
Patent
active
060462205
DESCRIPTION:
BRIEF SUMMARY
The invention relates to propynyl or dienyl biaromatic 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 either light-induced or 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 ##STR3## R.sub.5 and R.sub.6 having the meanings given below, X represents a radical of formula: ##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 with 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, 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.6, and R.sub.3 form, with 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, --COR.sub.10 ##STR5## R' and R" having the meaning given below, (d) a radical --OR.sub.11, meaning: a hydrogen atom or a radical --OR.sub.10, or one of them represents a hydrogen atom and the other represents a lower alkyl radical, or, taken together, form a ring --Y--(CH.sub.2).sub.n --Y--, with Y representing an oxygen or sulphur atom and with n equal to 2 or 3, 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, 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 compounds which are intermediates in the synthesis of the compounds of general formula (I), of general formula (II) ##STR6## in which R.sub.1 and Ar have the same meanings as for the general formula (I) and R'.sub.2 and R'.sub.4, which may be identical or different, represent a linear or branched alkyl radical having from 1 to 20 carbon atoms.
The invention is also directed towards the salts of the compounds of formulae (I) and (II) when R.sub.1 represents a carboxylic acid function, and the geometrical and optical isomers of the said compounds of formulae (I) and (II).
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 expression 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
Centre International de Recherches Dermatologiques Galderma
Fan Jane
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