Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1985-12-05
1990-05-29
Siegel, Alan
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5142375, 514252, 514255, 514256, 514544, 514568, 514617, 5142315, 549 77, 549 79, 544146, 544176, 544379, 544391, 560 8, 562405, 564161, A61K 3138, C07D33322
Patent
active
049296353
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new derivatives of 4-vinyl benzoic acid which have an activity on growth and the differentiation of biological tissues and which may be used in therapeutics for the treatment of acne, psoriasis, disorders of keratinization, in certain forms of cancer and as healing agents, particularly in the ocular field.
Vitamin A is essential for certain functions such as vision, growth and reproduction. It plays an important part in the control of growth and of the differentiation of epithelial tissues. Vitamin A deficiency causes a cutaneous hyperkeratosis and a keratinizing metaplasia of the mucous membranes.
Although the mode of action of the retinoids (analogs of Vitamin A) is still poorly understood, it has been shown:
that they slow down growth and the development of precancerous and cancerous cells;
that they possess an anti-inflammatory effect and can take part in the mechanism of healing by acting at the level of protein synthesis indispensable to the process of tissure repair.
The retinoids are used as therapeutic agents for the treatment of acute acne and psoriasis, as well as disorders of keratinization. However, although very effective, these products have the major drawback of showing side effects which are not negligible: hypervitaminosis-A, toxicity, irritation.
In FR-A-2 422 620, derivatives of stilbene are described showing certain analogy in structure and activity with the retinoids.
The object of the present invention is to provide new compounds which link with the receptor of retinoic acid (C.R.A.B.P.) at the tissue level and show a therapeutic interest similar to the retinoids without having the toxic effects thereof, particularly in the ocular field.
Thus the present invention relates to compounds of the formula (I) ##STR2## in which: R.sub.1 represents a methyl group; -C.sub.4 alkyl group, a 5-11 membered monocyclic heteroaromatic group containing one or two heteroatoms selected from nitrogen, oxygen and sulfur, of such a heteroaromatic group substituted by a C.sub.1 -C.sub.4 alkyl group; ##STR3## in which R.sub.3 and R.sub.4 represent, independently from one another, a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or amino (C.sub.1 -C.sub.6 alkyl) or R.sub.3 and R.sub.4 form, with the nitrogen atom to which they are attached, a 5-8 membered heterocyclic group, saturated or not, and which can contain another heteroatom selected from nitrogen, oxygen and sulfur; a C.sub.1 -C.sub.4 alkoxy group; a group of formula --O--Ar, Ar having the above-given meanings; an aminoalkoxy group of the formula ##STR4## in which R.sub.5 and R.sub.6 represent, independently from one another, a C.sub.1 -C.sub.4 alkyl group and n=1 to 4; and their pharmaceutically acceptable salts.
The present invention relates also to therapeutic compositions containing, as active ingredient, a compound of formula (I) or one of its pharmaceutically acceptable salts.
By the term "pharmaceutically acceptable salts", are meant the addition salts which are formed by the compounds of formula (I) having a basic group with pharmaceutically acceptable acids, as well as the salts which are formed by the compounds of formula (I) having an acid group with pharmaceutically acceptable bases.
"Addition salts with pharmaceutically acceptable acids" means the salts which give the biological properties of free bases, without having an undesirable effect. These salts may be particularly those formed with inorganic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid; acid metallic salts, such as disodium orthophosphate, and monopotassium sulfate, and organic acids, such as formic acid, acetic acid, propionic acid, glycolic acid, oxalic acid, fumaric acid, lactic acid, succinic acid, tartaric acid and pamoic acid.
In the same way, "salts with pharmaceutically acceptable bases" means salts which do not modify the biological properties of the free acids. These salts may be particularly those formed withh inorganic bases, such as sodium hydroxide, potassium hydroxide, lithium hydr
REFERENCES:
patent: Re27031 (1971-01-01), Okubo
patent: 4723028 (1988-02-01), Shudo
Alazet Alain
Bonne Claude
Coquelet Claude
Roussillon Samia
Sincholle Daniel
Laboratoires Chauvin-Blache
Siegel Alan
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