Use of pyrimidine 3-oxide derivatives for slowing down hair loss

Details Use of pyrimidine 3-oxide derivatives for slowing down hair loss Use of pyrimidine 3-oxide derivatives for slowing down hair loss

1993-01-19

1994-07-12

Prescott, Arthur C.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514256, 514272, 514320, 424 70, A61K 706, A61K 31505, A01N 4354

Patent

active

053289145

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to the use of pyrimidine 3-oxide derivatives for slowing down hair loss and to the compositions containing these derivatives and intended for topical application to the scalp.
Compounds which are effective for the treatment of hair loss without, however, exhibiting side effects which could be inconvenient during prolonged application have been sought for many years.
Mucopolysaccharide-based compositions which are used for slowing down hair loss are particularly known.
The applicant company has discovered new pyrimidine 3-oxide derivatives which are particularly effective for slowing down hair loss. In particular, it has observed an increase in the number of hairs in the anagen phase or in the growth phase and a decrease in the number of hairs in the telogen phase or in the terminal phase of the hair. The increase in the ratio of the number of hairs in the anagen phase to the number of hairs in the telogen phase is an indication of the effect of these compounds on the treatment of hair loss. Moreover, these compounds have the advantage of not having side effects which may be inconvenient during prolonged application.
The subject of the invention is the use of pyrimidine 3-oxide derivatives for slowing down hair loss.
Another subject of the invention consists of the topical compositions intended for use in slowing down hair loss.
Other subjects of the invention will become apparent on reading the following description and examples.
The compounds used in conformity with the invention for slowing down hair loss are of the general formula: ##STR2## in which: R.sub.1 denotes a methyl or NHR.sub.4 group in which R.sub.4 denotes a C.sub.1 -C.sub.4 alkyl group or a hydrogen atom; meaning as above; R.sub.2 may also denote methyl when R.sub.1 denotes methyl; when R.sub.1 denotes NH.sub.2, R.sub.2 cannot be hydrogen; optionally carry: -C.sub.4 alkoxy groups;
An alkyl group preferably denotes, in conformity with the invention, a methyl or ethyl group, the alkoxy group preferably denotes methoxy or ethoxy, the halogen atoms preferably denote chlorine or bromine.
The preferred compounds which may be used in conformity with the invention are the compounds corresponding to the formula (I) in which R.sub.1 denotes amino, R.sub.2 denotes amino and R.sub.3 denotes hydrogen or alternatively R.sub.1 denotes amino, R.sub.2 denotes amino and R.sub.3 denotes chlorine.
The compounds corresponding to the general formula (I) can also be obtained for example by hydrogenolysis, in the presence of palladium on charcoal, of compounds corresponding to the formula (II) which is defined below, in which Z denotes a halogen atom and preferably chlorine or bromine.
The reduction is performed according to the conventional method described in the literature (D. J. Brown, The pyrimidines, supplement II, Vol. 16, chapter X, page 360, Interscience Pub. 1985; Cowden and Waring, Aust. J. Chem. 94, 1539 (1981) according to the following reaction scheme: ##STR3##
The compounds of formula (I) can also be used in the form of their physiologically acceptable acid additional salts such as the salts of sulfuric, hydrochloric, phosphoric, acetic, benzoic, salicylic, glycolic, aceturic, succinic, nicotinic, tartaric, maleic, pamoic [sic], methanesulfonic, picric and lactic acid, of amino acids and more particularly of aceturic acid.
These compounds are generally used for the treatment of hair loss in compositions which can be provided in the form of a lotion, shampoo, gel, foam, emulsion, vesicular dispersion, soap, spray or aerosol foam.
The compositions intended for topical application are essentially characterized in that they contain, in a physiologically acceptable medium appropriate for topical application, at least one compound Corresponding to the formula (I) or one of its acid addition salts defined above.
The compound of formula (I) is present in proportions of between 0.1 and 10% by weight and preferably between 0.2 and 5% by weight relative to the total weight of the composition.
The physiologically acceptable medium

REFERENCES:
patent: 4973474 (1990-11-01), Hocquaux et al.
Interscience Pub., Supplement II, vol. 16, Chapter X, p. 360, 1985.
Aust. J. Chem., 34, 1539, 1981.

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