Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1999-03-23
2000-08-15
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514561, 514562, 560 57, 562473, 562474, 424401, 424 47, 424101, 424443, 564161, 564162, 564163, 564180, A61K 31015, A61K 3119, A61K 31215, A61K 702, C07C 6976
Patent
active
061037621
DESCRIPTION:
BRIEF SUMMARY
The invention relates, as novel and useful industrial products, to biaromatic compounds in which the aromatic nuclei are connected by a propynylene or allenylene divalent radical. 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 a marked activity in the fields of cell differentiation and proliferation, and they find applications more particularly in the topical and systemic treatment of dermatological conditions linked to a keratinization disorder, dermatological conditions (and the like) with an inflammatory and/or immunoallergic component, and dermal or epidermal proliferation, whether benign or malignant. These compounds can, in addition, be used in the treatment of degenerative diseases of the connective tissue, for combating skin ageing, whether photoinduced or chronologic, and treating cicatrization disorders. Furthermore, they find an application in the ophthalmological field, in particular in the treatment of corneopathies.
It is also possible to use the compounds according to the invention in cosmetic compositions for body and hair hygiene.
EP-661,258 has already disclosed biaromatic compounds, the aromatic nuclei of which are connected by a propynylene divalent radical, as substances which are active in pharmaceutical or cosmetic compositions.
The compounds according to EP-661,258 correspond to the following general formula: ##STR2## in which: Ar is an aromatic divalent radical optionally substituted by an R.sub.5 radical or a heteroaromatic divalent radical optionally substituted by an R.sub.6 radical when the heteroatom is nitrogen, --COR.sub.7 or --S(O).sub.t R.sub.9, t being 0, 1 or 2, --SR.sub.6, optionally substituted by methyl groups and/or optionally interrupted by an oxygen or sulphur atom, ##STR3## or --OR.sub.8, R.sub.8 represents H, C.sub.1 -C.sub.20 alkyl, which can be linear or branched, alkenyl, mono- or polyhydroxyalkyl, optionally substituted aryl or aralkyl, or a sugar or amino acid or peptide residue, substituted aryl or a sugar, amino acid or peptide residue or R and R', taken together, form a heterocycle, and has the formula: ##STR4## in which: R.sub.10 represents H, lower alkyl or --OR.sub.6, represents a carboxylic acid functional group, and the optical and geometrical isomers of these said compounds.
The compounds according to the present invention, with respect to those of EP-661,258, are essentially distinguished in that the --X--Ar--R.sub.1 substituent is at the ortho position with respect to the R.sub.2 radical or to the 5- or 6-membered ring when R.sub.2 and R.sub.3 are taken together, whereas, in EP-661,258, the --X--Ar--R.sub.1 substituent is found at the meta position.
This is because it has been found, unexpectedly and surprisingly, that this modification in structure makes it possible to significantly increase the pharmaceutical and cosmetic properties thereof and, in addition, to decrease certain side effects thereof.
The subject-matter of the present invention is therefore novel compounds which can be represented by the following general formula: ##STR5## in which: Ar represents a radical chosen from the following formulae (a) to (c): ##STR6## Z being an oxygen or sulphur atom, R.sub.1 represents --CH.sub.3, --CH.sub.2 --O--R.sub.6, --OR.sub.6 or --COR.sub.7, the latter case, R.sub.4 represents linear or branched C.sub.1 -C.sub.20 alkyl and is at the ortho or meta position with respect to the X--Ar bond, optionally substituted by at least one methyl and/or optionally interrupted by an oxygen or sulphur atom, alkyl, --OR.sub.8, a polyether radical or aryl, or an --OR.sub.8 radical, ##STR7## or --OR.sub.10, R.sub.8 represents H, lower alkyl or --COR.sub.9, branched, alkenyl, mono- or polyhydroxyalkyl, optionally substituted aryl or aralkyl, or a sugar residue, substituted aryl, or an amino acid or sugar residue or, taken together with the nitrogen atom, form a heterocycle, has the formula: ##ST
REFERENCES:
patent: 5468879 (1995-11-01), Chandraratna
patent: 5677451 (1997-10-01), Chandraratna
patent: 5716624 (1998-02-01), Bernardon
Hiroyuki Kagechika et al.: "Retinobenzoic Acids 2." Journal of Medicinal Chemistry., vol. 32, 1989, pp. 834-840, XP000569639 Washington US see p. 834--p. 840; figure 1; table II.
Caplus 83:147317, Abstract DE2453357, Siegrist Adolf et al., May 22, 1975.
Bernardon Jean-Michel
Trouille Simon
Desai Rita
Galderma Research & Development
Rotman Alan L.
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