N-acylglutamine derivatives and cosmetic compositions

Details N-acylglutamine derivatives and cosmetic compositions N-acylglutamine derivatives and cosmetic compositions

1994-07-27

1995-11-21

Venkat, Jyothsna

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

424 59, 424401, 514844, 514847, 549406, 552544, 560142, 560145, A61K 706, C07D31120, C07C 6900

Patent

active

054684749

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to N-acylglutamine derivatives and to cosmetics and hair growth stimulants containing the N-acylglutamine derivatives.


PRIOR ART

Japanese Published Unexamined Patent Application No. 20438/78 discloses cosmetics containing esters of N-acylamino acids, and Japanese Published Unexamined Patent Application No. 223206/91 (corresponding to U.S. Pat. No. 5,112,613) discloses cosmetics containing N-acylglutamine (NAG).
NAG is stable but is poorly compatible with oily bases, and emulsion in cosmetics is often unstable to lower the viscosity of cosmetics containing NAG. Therefore, kinds of cosmetics containing NAG and the amounts of NAG contained in cosmetics are limited.
The object of the present invention is to provide N-acylglutamine derivatives which are more compatible with oily bases than NAG and are therefore stable in cosmetics and hair growth stimulants to have good skin-moisturizing activity in cosmetics and hair growth-stimulative effect in hair growth stimulants.


DISCLOSURE OF THE INVENTION

The present invention relates to N-acylglutamine derivatives represented by formula (I): ##STR2## wherein R.sup.1 represents an alkyl having 12 to 22 carbon atoms, an alkenyl having 12 to 22 carbon atoms, ##STR3##
wherein R.sup.3 represents an alkyl having 1 to 6 carbon atoms; and
R.sup.2 represents an alkyl having 1 to 6 carbon atoms.
The present invention also relates to cosmetics and hair growth stimulants containing the N-acylglutamine derivatives.
The alkyl having 1 to 6 carbon atoms for the definitions of R.sup.2 and R.sup.3 is a linear or branched alkyl including methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl and hexyl groups. The alkyl having 12 to 22 carbon atoms for the definition of R.sup.1 is a linear or branched alkyl group including dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, isostearyl, myristyl, octadecyl, nonadecyl, eicosanyl, henicosanyl and docosanyl groups. The alkenyl having 12 to 22 carbon atoms is a linear or branched alkenyl group including oleyl, dodecenyl, elaidyl, linoleyl and linolenyl groups.
Compounds represented by formulae (I) , (II) , (III), . . . are hereinafter referred to as Compound (I), Compound (II), Compound (III), . . . , respectively.
Methods for producing Compounds (I) are mentioned below. ##STR4##
wherein R.sup.1 and R.sup.2 have the same meanings as defined above; and P represents a protective group for the amino group.
As the protective group for the amino group, t-butoxycarbonyl group, benzyloxycarbonyl group, etc. are used.
Compound (IV) may be obtained by reacting Compound (II) with 0.8 to 2 equivalents of Compound (III) in a solvent in the presence of a condensing agent such as dicyclohexylcarbodiimide, at a temperature from -80.degree. C. to 40.degree. C. for 30 minutes to 2 days.
As the reaction solvent, tetrahydrofuran (THF), dioxane, dimethylformamide (DMF), dimethylsulfoxide (DMSO), etc. are used.
Compound (I) may be obtained by removing the amino-protective group of Compound (IV) in a solvent by trifluoroacetic acid (TFA), catalytic reduction, etc., followed by acylating it with an acid anhydride such as acetic anhydride, or with an acid halide such as acetyl chloride at 0.degree. to 80.degree. C for 30 minutes to 2 days. The abovementioned solvents may be used as the reaction solvent.
Compound (II), the starting material, may be obtained by introducing the above-mentioned protective group into a commercially available L-glutamine by a conventional method, or a commercial product of Compound (II) may be used. ##STR5##
wherein R.sup.1 and R.sup.2 have the same meanings as defined above; and X represents a halogen atom.
The halogen atom includes chlorine atom, iodine atom and bromine atom.
Compound (I) may be obtained by reacting an N-acylglutamine with 0.8 to 2 equivalents of Compound (V) in the presence of a base such as sodium hydride, cesium fluoride, triethanolamine and cesium carbonate, if necessary.
As the reaction solvent, DMF, THF, DMSO, dioxane, etc. are used. Th

REFERENCES:
patent: 3969087 (1976-07-01), Saito et al.
patent: 3979449 (1976-09-01), Hirsbrunner et al.
patent: 4760095 (1988-07-01), Djerassi et al.
patent: 5112613 (1992-05-01), Honda et al.
patent: 5153340 (1992-10-01), Ichikawa et al.

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