Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Reexamination Certificate
2000-10-04
2002-12-03
Jones, Dameron L. (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
C424S401000, C424S078030, C514S554000, C514S627000
Reexamination Certificate
active
06489291
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a topical composition for the skin (hereinafter may be simply referred to as a topical skin composition) exhibiting effects of retarding aging of the skin or rejuvenating the skin and of suppressing hair growth.
2. Background Art
Studies have revealed that aging of the skin is mainly caused by advancing age, drying, oxidation, or sunlight (i.e., UV rays). Aging of the skin is recognized by a decrease in collagen or elastin in the dermis of the skin; a decrease in mucopolysaccharides, including hyaluronic acid; or the presence of cells which are damaged by UV rays.
For the prevention of wrinkle formation, however, sufficient effects have not yet been attained, for example, by a collagen-containing cosmetic composition. In addition, a number of research projects have focused on skin aging caused by exposure to UV rays. However, cosmetic compositions superseding UV absorbing agents or UV protecting agents have not yet been developed.
There is a trend towards a preference for hairless bodies, particularly, hairless arms or legs, for reasons of aesthetic appearance. Various methods have been tried in the pursuit of body hair removal, for example, a mechanical hair-removal method making use of a shaver or hair-tweezers, a method for removing body hair from the hair root by use of a hair removing agent, and a method for removing body hair through chemical action of a hair removing agent.
However, the aforementioned hair removing methods physically or chemically stimulate the skin, and are limited by the unsatisfactory duration of the hairless state. Therefore, there is a need for the development of a method which facilitates removal of body hair.
SUMMARY OF THE INVENTION
In view of the foregoing, an object of the present invention is to provide a topical composition for the skin exhibiting effects with respect to retarding aging of the skin, such as wrinkle formation, or rejuvenating the skin, and of suppressing hair growth.
The present inventors have found that a dipeptide compound having a specific structure or a salt thereof exhibits excellent effects with respect to suppressing wrinkle formation, preventing a reduction in skin elasticity, and suppressing hair growth, and that the compound or the salt is effectively employed in a topical skin composition for retarding aging of the skin or suppressing hair growth.
Accordingly, the present invention provides a topical skin composition comprising a dipeptide compound represented by formula (1) or a salt of the dipeptide:
wherein R
1
represents a hydrogen atom, an alkyl group, an alkanoyl group, or —CH(R
6
)COOR
7
(wherein R
6
represents a hydrogen atom or a lower alkyl group, and R
7
represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, or an aralkyl group);
R
2
represents a hydrogen atom or an alkyl group which may have a substituent;
R
3
represents a lower alkyl group or a phenyl group;
R
4
represents a hydrogen atom or a lower alkyl group, and may form a heterocyclic ring together with R
5
and an adjacent nitrogen atom;
R
5
represents a hydrogen atom, an alkyl group which may have a substituent, or an aralkyl group which may have a substituent, and may form the heterocyclic ring together with R
4
;
X represents —COOR
8
(wherein R
8
represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, or an aralkyl group) or —SO
3
H; and
n is an integer of 0-4; and a pharmaceutically acceptable carrier therefor.
The present invention also provides, as a novel compound which has not yet been described in any literature, N-(carboxymethyl)phenylalanyl-&bgr;-alanine, among dipeptide compounds represented by formula (1), or a salt thereof.
Various other objects, features and many of the attendant advantages of the present invention will be readily appreciated as the same becomes better understood by reference to the following detailed description of the preferred embodiments.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
In formula (1), an alkyl group represented by R
1
is preferably a C1-C6 alkyl group, may be a linear or branched alkyl group, and is more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, or a t-butyl group.
An alkanoyl group represented by R
1
is preferably a C1-C6 alkanoyl group, may,be a linear or branched alkanoyl group, and is more preferably an acetyl group, a propionyl group, or a butyryl group.
A lower alkyl group represented by R
3
, R
4
, R
6
, R
7
, or R
8
is preferably a C1-C6 alkyl group, may be a linear or branched alkyl group, and is more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, or a t-butyl group.
A lower alkenyl group represented by R
7
or R
8
is preferably a C2-C6 alkenyl group, more preferably a vinyl group or a propenyl group.
An aralkyl group represented by R
7
or R
8
is a C7-C18 aralkyl group. Specific examples include a phenyl C1-C6 alkyl group, a biphenyl C1-C6 alkyl group, and a naphthyl C1-C6 alkyl group. Of these, a phenyl C1-C6 alkyl group is preferable, and a benzyl group is more preferable.
An alkyl group which may have a substituent, represented by R
2
, may be a C1-C6 alkyl group, a carboxy C1-C6 alkyl group, or a C1-C6 alkoxycarbonyl C1-C6 alkyl group. Of these, a C1-C6 alkyl group is preferable. R
2
is more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, or a t-butyl group.
An alkyl group which may have a substituent, represented by R
5
, may be a C1-C6 alkyl group, a carboxy C1-C6 alkyl group, or a C1-C6 alkoxycarbonyl C1-C6 alkyl group. Of these, a C1-C6 alkyl group and a carboxy C1-C6 alkyl group are preferable. R
5
is more preferably a methyl group, an isopropyl group, an isobutyl group, a t-butyl group, a carboxymethyl group, or a carboxyethyl group.
A heterocyclic ring which is formed by R
4
and R
5
may be pyrrolidine or piperidine.
An integer n is preferably 0, 1, or 2.
In formula (1), R
1
is more preferably a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkanoyl group, or —CH(R
6
)COOR
7
(wherein R
6
represents a hydrogen atom or a C1-C6 alkyl group, and R
7
represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, or a phenyl C1-C6 alkyl group). R
2
is more preferably a hydrogen atom or a C1-C6 alkyl group. R
3
is more preferably a C1-C6 alkyl group or a phenyl group. R
4
is more preferably a hydrogen atom or a C1-C6 alkyl group. R
5
is more preferably a hydrogen atom, a C1-C6 alkyl group, a phenyl C1-C6 alkyl group, or a carboxy C1-C6 alkyl group. X is more preferably —COOR
8
(wherein R
8
represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, or a phenyl C1-C6 alkyl group) or —SO
3
H. An integer n is more preferably 0, 1, or 2.
Examples of salts of a dipeptide compound (1) include alkali metal salts, alkaline earth metal salts, amine salts, amino acid salts, and acid addition salts. Of these, alkali metal salts and amino acid salts are preferable. A dipeptide compound (1) may have optical activity, and its steric configuration may be any of R, S, and a racemic mixture. The compound may also be in the form of a hydrate.
Among dipeptide compounds of formula (1), the more preferred compounds are as follows:
Phe-Gly (compound 11); Phe-&bgr;-Ala (compound 12); Phe-Phe (compound 13); Phe-Leu (compound 14); Phe-Ala (compound 15); and Phe-Asp (compound 16): Phe-Tau (compound 17).
Of these, compound 1 and compound 12 are more preferable.
A compound of formula (1) in which R
1
is a hydrogen atom may be synthesized through a process described in “K. Ienalga, K. Higashihara, and H. Kimura, Chem. Pharm. Bull., 35, 1249-1254 (1987).” A compound of formula (1) in which R
1
is not a hydrogen atom but is any of the aforementioned groups may be synthesized through, for example, the following process:
(wherein Y represents a halogen atom, a p-toluenesulfonyl group, or a methanesulfonyloxy group; R
1
represents any of the afore
Amano Shin-ya
Moriwaki Shigeru
Suzuki Yasuto
Tsuji Naoko
Watanabe Mikako
Jones Dameron L.
Kao Corporation
Wells Lauren Q.
LandOfFree
Topical composition for skin does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Topical composition for skin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Topical composition for skin will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2935968