Arene-carboxylic acid derivatives as antiseborrheic additives fo

Details Arene-carboxylic acid derivatives as antiseborrheic additives fo Arene-carboxylic acid derivatives as antiseborrheic additives fo

1982-11-15

1985-10-08

Marantz, Sidney

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Amphoteric or zwitterionic surfactant containing

514532, 424DIG4, A61K 706, A61K 31235

Patent

active

045459843

DESCRIPTION:

BRIEF SUMMARY
The subject of the invention are topical cosmetic preparations for the improvement of the oily and unesthetic appearance of hair and skin, especially for the treatment of very oily hair.
The excessive secretion of the seborrheic glands of the scalp gives the hair an oily appearance which is generally considered unesthetic. Consequently, many attempts were made to restore a healthy appearance to the hair by adjusting the secretion of the seborrheic glands to their normal level with suitable preparations. Oral preparations containing cysteamine derivatives were recommended for the treatment of seborrhea in the DE-OS No. 1667902. Shampoos with sulfur, mercury or tar additives were used to treat seborrhea of the hair on the head. It was observed that the extended use of these well-known products frequently led to side effects without producing actually satisfactory results with regard to efficacy or application technological properties. Finally, N,N-diethyl-m-toluamide was recommended as active substance for the treatment of dandruff due to seborrhea in the DE-OS No. 1906665. In the U.S. Pat. No. 3,755,604, phenyl-pentadienoic acids are recommended as agent for the prevention of the production of sebum. But it was found that neither N,N-diethyl-m-toluamide nor phenyl-pentadienoic acid has a satisfactory antiseborrheic effect.
Now, it was observed that topical cosmetic preparations with a content of compounds of the general formula: ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 represent independently of one another a hydrogen atom, an intermediate alkyl group with 3 to 10 carbon atoms, a halogen atom, preferably a chlorine atom, a hydroxy group, an aryl group, an alkoxy group with 1 to 20 carbon atoms substituted, if needed, with aryl, hydroxy, amino, alkoxy as well as aryloxy groups, or a carboxyl group esterified with an intermediate-chain alkyl group with 2 to 12 carbon atoms or an aralkyl group, as well as two of the radicals R.sup.1 --R.sup.3 can represent a naphthalene ring together with the benzene ring, and Y represents an alkoxy group with 1 to 12 carbon atoms or an aralkoxy group, are especially effective in the treatment of seborrheic skin and very oily hair.
The compounds of formula (I) are known from the literature and most of them are commercially available, or their precursors are generally commercially available. When only the arene-carboxylic acids are available as precursors of the compounds, these can be converted into the respective esters by well-known methods of organic chemistry. For the synthesis of the alkoxy-substituted arene-carboxylic acid derivatives, the best approach is the alkylation of arene-carboxylic acid esters containing the phenolic hydroxyl group with suitable alkylating agents. Especially suitable for the introduction of multisubstituted alkoxy groups are epihalohydrins, which are then reacted with different or the same nucleophiles.
Arene-carboxylic acids from which the compounds to be used according to the invention are prepared are, for example: 4-Propyl-, 4-butyl-, 4-tert-butyl-, 4-octyl-, 4-decyl-, 4-phenyl-, 4-methoxy-, 3-methoxy-, 2-methoxy-, 3,4-dimethoxy-, 2,4-dimethoxy-, 3,4,5-trimethoxy-, 2,4,6-trimethoxy-, 4-propoxy-, 4-hexyloxy-, 4-decyloxy-, 4-tetradecyloxy-, 4-benzyloxy-, 4-(3,4-dimethoxybenzyloxy)-, 4-(3-phenoxy-2-hydroxypropoxy)-, 4-(3-(4-methoxyphenoxy)-2-hydroxypropoxy) -, 4-(3-(3,4-dimethoxyphenoxy)2-hydroxy-propoxy)-, 4-(3-(4-chlorophenoxy)-2-hydroxypropoxy)-, 4-(3-(3,4-dichloroanilino)-2-hydroxypropoxy)-, 4-chloro-, 3,4-dichloro-, 2,4-dichloro-, 2,5-dichloro-, 2,4,5-trichloro-, 4-bromo-, 5-chloro-2-methoxy-benzoic acid, phthalic acid, 4,5-dichlorophthalic acid, benzoic acid, .alpha.-naphthoic acid, .beta.-naphthoic acid, isophthalic acid, terephthalic acid.
Suitable alcohol components for the preparation of the arene-carboxylic acid esters to be used according to the invention are, for example: sec-butanol, tert-butanol, pentanol, hexanol, octanol, 2-ethylhexanol, decanol, benzyl alcohol.
The cosmetic agents according to the invention are solutions

REFERENCES:
patent: 3076017 (1963-01-01), Grisley
patent: 3317382 (1967-05-01), Brunner et al.
patent: 3766245 (1973-10-01), Hausermann et al.
patent: 3868406 (1975-02-01), Siddall
patent: 4136165 (1979-01-01), Moller et al.
patent: 4235889 (1980-11-01), Evers

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