Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1982-11-15
1985-07-09
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514319, 514330, 514346, 514618, 546226, 546291, 564162, 544158, 548179, 548221, A61K 706, A61K 748
Patent
active
045282862
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. 16 67 092. 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. 19 06 665. 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 represents an aryl radical or a heterocyclic radical, R.sup.2 and R.sup.3 represent independently of one another hydrogen or an alkyl group with 1 to 4 carbon atoms, and Y an alkoxy group with 1 to 12 carbon atoms, an aralkoxy group or an amino group NR.sup.4 R.sup.5 in which R.sup.4 and R.sup.5 stand for hydrogen, an alkyl group with 1-6 carbon atoms, an aryl group or an aralkyl group or they can form a heterocyclic ring together with the nitrogen atom, are especially effective in the treatment of seborrheic skin and very oily hair. R.sup.1 includes radicals of the general formula (II) ##STR3## in which R.sup.6, R.sup.7 and R.sup.8 represent independently of one another a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, a halogen atom (especially Cl), an aryl group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, or an amino group that may also be alkylated or acylated, and two of the radicals R.sup.6 -R.sup.8, which, together with the benzene ring, stand for a naphthalene ring, and includes heterocyclic radicals such as a, if needed substituted, pyridyl, pyrimidyl, benzoxazolyl, benzimidazolyl or benzthiazolyl group.
Most compounds according to Formula (I) are known from the literature and most of them are commercially available. Arene-carboxylic acid derivatives are prepared suitably from the free arene-carboxylic acids, which are converted to esters or amides by a known method, using alcohols or amines. Synthesis of the carboxylic acid derivatives according to Formula (I) is also possible by alkylating the respective mercapto compounds with suitable a-halo-alkanoic acid derivatives.
Arene-carboxylic acids suitable as starting product are, for example: 2-(Phenyl-, 2-chlorophenyl-, 3-chlorophenyl-, 4-chlorphenyl-, 2,4-dichlorophenyl-, 3,4-dichlorophenyl-, 4-hydroxyphenyl-, 2,4-dihydroxyphenyl-, 3,4-dihydroxyphenyl-, 4-aminophenyl-, 4-acetamidophenyl-, 4-tolyl-, .alpha.-naphthyl-, .beta.-naphthyl, 4-methoxyphenyl-, 2,4-dimethoxyphenyl-, 3,4,5-trimethoxyphenyl-, 2,4,6-trichlorophenyl-, benzoxazol-2-yl-, 5-chlorobenzoxazol-2-yl-, 5,7-dichlorobenzoxazol-2-yl, benzothiazol-2-yl-, 5-chlorobenzothiazol-2-yl, benzimidazol-2-yl-, 2-, 3-, 4-pyridyl-, N-oxido-2-pyridyl, 2-pyrimidyl-, 4-pyrimidyl-, 4,6-dihydroxy-2-pyrimidyl-mercapto)-acetic acid, -propionic acid, -butyric acid, -isobutyric acid and -2-ethylbutyric acid.
Suitable as alcohol component for the preparation of the arene-carboxylic esters are, for example, methanol, ethanol, propanol, isopropanol, N-butanol, isobutanol, sec-butanol, tert-butanol, pentanol, hexanol, octanol, 2-ethyl-h
REFERENCES:
Moeller, Chem. Abstracts, vol. 96, No. 5, Abst. No. 40931t, Feb. 1, 1982.
Kuwano et al., Chem. Abstracts, vol. 95, No. 9, Abst. No. 75,381v, Aug. 31, 1981.
Nordmann et al., Chem. Abstracts, vol. 71, No. 19, 91071d, Nov. 10, 1969.
Manoury et al., Chem. Abstracts, vol. 76, No. 5, Abst. No. 24,905u, Jan. 31, 1972.
De Marchi et al., Chem. Abstracts, vol. 68, No. 5, Abst. No. 21633c, Jan. 29, 1968.
Moller Hinrich
Wallat Siegfried
Henkel Kommanditgesellschaft (KGaA)
Littell, Jr. Nelson
Millson Jr. Henry E.
Rotman Alan L.
Szoke Ernest G.
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