Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-08-23
2002-08-20
Hartley, Michael G. (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S210010, C514S228800, C424S401000
Reexamination Certificate
active
06436920
ABSTRACT:
TECHNICAL FIELD
The present invention relates to wrinkling modifiers and anti-aging cosmetic compositions, and more particularly to anti-aging cosmetic compositions which are excellent in the effects of suppressing wrinkling and of removing or smoothing wrinkles.
BACKGROUND ART
It is a significant concern of, particularly, women to maintain the healthy and beautiful skin. However, the condition of the skin is always affected by factors such as humidity, ultraviolet rays, cosmetic compositions, aging, diseases, stress and eating habits. As the result thereof, various skin troubles such as the decrement of various functions of the skin and the aging of the skin occur. Of these, wrinkles occur due to dermal aging by aging, light aging by exposure to sunbeam, or the like. More specifically, cells f or producing fibers of the dermis are made small and lessened by exposure to sunbeam or with the increase in age. In particular, collagen fibers are lost to a great extent, and so the skin is aged by degeneration of the dermis, reduction of subcutaneous adipose tissue and the like, which forms the cause of wrinkling, relaxation, and loss of resilience.
Various compositions and methods have heretofore been proposed for preventing or treating the aging effects such as wrinkling [Japanese Patent Application Laid-Open Nos. 185005/1987, 502546/1987, 72157/1990, 288822/1990 and 41419/1995, Japanese Patent Application Laid-Open (KOHYO) No. 510542/1994 (through PCT route), etc.]. However, all of these proposals have not been fully satisfactory in the effect of modifying wrinkling (or preventing wrinkling and removing wrinkles). There has thus been a demand for development of cosmetic skin care compositions excellent in the effect of modifying wrinkling.
It is an object of the present invention to provide wrinkling modifiers and anti-aging cosmetic compositions which can solve the above-described problems, are excellent in the effects of suppressing wrinkling without impairing normal dermatophysiology and removing wrinkles, and give users a pleasant feeling upon use.
DISCLOSURE OF THE INVENTION
In view of the foregoing circumstances, the present inventors have carried out an extensive investigation with a view toward achieving the above object. As a result, it has been found that guanidine derivatives having a specific structure or acid-addition salts thereof are excellent in the effect of modifying wrinkling and give users a pleasant feeling upon use, thus leading to completion of the present invention.
According to the present invention, there are thus provided a wrinkling modifier and an anti-aging cosmetic composition, each comprising a guanidine derivative represented by the following general formula (1):
wherein
is a heterocyclic group selected from azetidine, pyrrolidine, piperidine, piperazine or morpholine, and R
1
and R
2
are the same or different from each other and independently a hydrogen atom, or an alkyl, hydroxyl, hydroxyalkyl, carboxyl, carboxyalkyl or amidino group, or a salt thereof.
According to the present invention, there is also provided a cosmetic skin care composition comprising the wrinkling modifier (1) and a synthetic sphingosine derivative represented by the following general formula (2):
wherein R
3
is a linear, branched or cyclic, saturated or unsaturated hydrocarbon group having 4 to 40 carbon atoms, R
4
, R
5
, R
6
, R
7
and R
8
are independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, which may be substituted by at least one hydroxyl group, and X and Y are independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which may contain at least one oxygen atom in its structure.
BEST MODE FOR CARRYING OUT THE INVENTION
Among the heterocyclic groups represented by
in the general formula (1) which represents the guanidine derivatives or the salts thereof used in the present invention, pyrrolidine, piperidine, piperazine and morpholine are preferred. The alkyl groups represented by R
1
and R
2
include linear or branched alkyl groups having 1 to 6 carbon atoms. Of these, alkyl groups having 1 to 4 carbon atoms are preferred. Specific examples of the alkyl groups include methyl, ethyl, n-propyl and isopropyl groups. Of these, methyl group is particularly preferred. The hydroxyalkyl groups include hydroxyalkyl groups having 1 to 6 carbon atoms, and hydroxyalkyl groups having 1 to 4 carbon atoms are preferred. Specific examples of the hydroxyalkyl groups include hydroxymethyl, hydroxyethyl and hydroxypropyl groups, with the hydroxymethyl and hydroxyethyl groups being particularly preferred. The carboxyalkyl groups include carboxyalkyl groups having 2 to 7 carbon atoms, and carboxyalkyl groups having 2 to 5 carbon atoms are preferred. Specific examples of the carboxyalkyl groups include carboxymethyl, carboxyethyl, carboxypropyl and carboxybutyl groups, with the carboxymethyl and carboxyethyl groups being particularly preferred.
R
1
and R
2
may be the same or different from each other and be an optional combination of 2 groups.
Stereoisomers exist in the guanidine derivatives (1) because of the presence of asymmetric carbon atoms. In the present invention, all these stereoisomers and mixtures thereof may be used.
Specific examples of the guanidine derivatives (1) include N-amidinoproline, 2-hydroxymethyl-1-pyrrolidine-carboxamidine, 3-hydroxy-1-pyrrolidinecarboxamidine, N-amidinoaziridine-2-carboxylic acid, N-amidino-2-piperidinecarboxylic acid, N-amidino-3-piperidine-carboxylic acid, N-amidino-4-piperidinecarboxylic acid, N-amidino-4-piperidinepropionic acid, pyrrolidine-carboxamidine, piperidinecarboxamidine, 2-methyl-piperidinecarboxamidine, 3-methylpiperidinecarboxamidine, 4-methylpiperidinecarboxamidine, 2-methylmorpholine-carboxamidine, 3-methylmorpholinecarboxamidine, N-methyl-piperazinecarboxamidine, N-2-hydroxyethylpiperazine-carboxamidine and piperazinecarboxamidine.
An acid for forming salts of the guanidine derivatives (1) may be either an organic acid or an inorganic acid. Examples thereof include monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, acrylic acid, methacrylic acid, crotonic acid, isocrotonic acid, phenylacetic acid, cinnamic acid, benzoic acid, sorbic acid, nicotinic acid, urocanic acid and pyrrolidone-carboxylic acid; dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, cork acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, phthalic acid and terephthalic acid; hydroxy acids such as glycolic acid, lactic acid, malic acid, tartaric acid, citric acid and o-, m- or p-hydroxybenzoic acid; amino acids such as glycine, alanine, &bgr;-alanine, valine, leucine, phenylalanine, tyrosine, serine, threonine, methionine, cysteine, cystine, proline, hydroxyproline, pipecolic acid, triptophan, aspartic acid, asparagin, glutamic acid, glutamine, lysine, histidine, ornithine, arginine and aminobenzoic acid; lower alkyl-sulfonic acids such as methanesulfonic acid and trifluoro-methanesulfonic acid; arylsulfonic acids such as benzene-sulfonic acid and p-toluenesulfonic acid; hydrohalogenic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydriodic acid; and inorganic acids such as perchloric acid, sulfuric acid, nitric acacia, phosphoric acid and carbonic acid.
The guanidine derivatives (1) or the salts thereof can be obtained in accordance with, for example, a preparation process represented by the following reaction scheme:
wherein
R
1
and R
2
have the same meanings defined above.
More specifically, a cyclic amine derivative (3) is reacted with a guanidylating reagent, whereby a guanidine derivative (1) or a salt thereof can be obtained.
Examples of the guanidylating reagent include known guanidylating reagents such as cyanamides, S-alkyl-isothioureas, O-alkylisoureas, aminoiminomethanesulfonic acid, 3,5-dimethyl-1-guanyl
Fujimura Tsutomu
Ito Noriko
Nagai Minoru
Ono Toshiya
Takema Yoshinori
Hartley Michael G.
Kao Corporation
Willia Michael A.
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