Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Conjugate or complex
Reexamination Certificate
2000-01-11
2001-01-09
Jarvis, William R. A. (Department: 1614)
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Conjugate or complex
Reexamination Certificate
active
06171595
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a skin external preparation having effects for preventing or alleviating skin aging or for inhibiting hair growth.
2. Description of the Related Art
As a result of researches on the aging of the skin, influences of aging, drying, oxidation, sun light (ultraviolet ray) and the like are mentioned as the causes for the aging of the skin. The aging of the skin is recognized by a decrease of collagen or elastin in the dermis of the skin, a decrease in mucopolysaccharides including hyaluronic acid, cellular damage by ultraviolet rays or the like.
For the prevention of wrinkle formation, however, sufficient effects have not yet been attained, for example, by a collagen-containing cosmetic composition. In addition, various researches have been made on the aging of the skin caused by exposure to ultraviolet rays in consideration of the relation with ultraviolet rays, however, a cosmetic composition superseding an ultraviolet absorber or ultraviolet protector has not yet been developed.
There is an increasing tendency to have a liking for a hairless body, particularly, hairless arms or legs, from the viewpoint of aesthetic appearance. In order to remove the body hair, various methods have been made use of, for example, a mechanical removing method by using a shaver, a pair of hair-tweezers or the like, a method of removing the hair even from the hair bulb by using a depilatory agent and a method of removing the body hair by the chemical action of a depilatory agent.
The above-described hair removing methods however give physical or chemical stimulation to the skin and in addition, are limited in maintaining the removed state. There is accordingly a demand for the development of a method which facilitates the body hair removal.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a skin external preparation having effects for preventing or alleviating the aging of the skin such as formation of wrinkles or for inhibiting hair growth.
The present invention relates to a skin external preparation comprising a compound represented by any one of the following formulas (1), (2), (3) and (4):
wherein X represents
Z represents —CON(R
8
)R
9
or —COOR
10
,
R
1
represents a hydrogen atom or a substituted or unsubstituted alkyl, alkenyl, aralkyl or alkoxy group, or with R
2
, may form a heterocyclic ring together with the adjacent nitrogen atom,
R
2
represents a hydrogen atom or a C
1-6
alkyl or alkenyl group, or with R
1
, may form said heterocyclic ring,
R
3
, R
8
, R
9
and R
10
individually represent a hydrogen atom, an alkyl group or an alkenyl group,
R
4
, R
5
and R
6
individually represents a hydrogen atom, an alkyl group, an alkenyl group or an aralkyl group, and
R
7
represents an aralkyl group;
wherein R
11
represents a hydrogen atom or a C
1-12
alkyl or alkenyl group,
R
12
and R
14
individually represent a hydrogen atom or a C
1-8
alkyl group,
R
13
represents a hydrogen atom or a substituted or unsubstituted alkyl, alkenyl or aralkyl group, or with R
15
, may form a heterocyclic ring together with the adjacent nitrogen atom, and
R
15
represents a hydrogen atom or with R
13
, may form said heterocyclic ring;
wherein R
16
and R
17
individually represent a hydrogen atom or an alkyl or alkenyl group, and
R
18
and R
19
individually represent a hydrogen atom, an aralkyl group or a substituted or unsubstituted alkyl or alkenyl group;
wherein R
20
represents a hydrogen atom, a C
1-8
alkyl or alkenyl group or an aralkyl group,
R
21
represents a hydrogen atom or a substituted or unsubstituted alkyl, alkenyl or aralkyl group,
R
22
represents a hydrogen atom or a C
1-6
alkyl or alkenyl group, or with R
23
, may form a heterocyclic ring with the adjacent nitrogen atom,
R
23
represents a hydrogen atom or a substituted or unsubstituted alkyl, alkenyl or aralkyl group, or with R
22
, may form said heterocyclic ring,
R
24
represents a hydrogen atom or a C
1-8
alkyl or alkenyl group, and
n stands for an integer of 0 to 5.
In the above formula (2), the compound represented by the following formula (2a):
wherein R
12a
represents a hydrogen atom or a C
1-8
alkyl group, R
13a
represents a hydrogen atom or an alkyl or aralkyl group which may be substituted by a carbamoyl group, R
15a
represents a hydrogen atom or with R
13a
, may form a pyrrolidinyl or piperidinyl group together with the adjacent nitrogen atom; or a salt thereof is novel and the present invention also provides this compound or salt thereof.
The skin external preparation according to the present invention has excellent effects for preventing or alleviating the aging of the skin or for inhibiting hair growth and can be synthesized easily.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
A description will next be made of the compound of the formula (1).
In the formula (1), R
1
preferably represents a hydrogen atom, a C
1-12
alkyl or alkenyl group which may have a substituent, a C
7-16
aralkyl group or a C
1-12
alkoxy group. As the alkyl or alkenyl group which may have a substituent, a linear or branched C
1-12
alkyl or alkenyl group, and a C
1-6
alkyl or alkenyl group having a substituent such as carbamoyl, hydroxy or carboxyl group are more preferred, of which linear or branched C
3-5
alkyl or alkenyl groups and C
1-4
alkyl or alkenyl groups having the above-described substituent are still more preferred. Among them, preferred examples include n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, carbamoylmethyl, 2-carbamoylethyl and hydroxymethyl groups. Examples of the aralkyl group include phenylalkyl and naphthylalkyl groups, of which phenyl-C
1-6
alkyl groups are preferred, with benzyl and phenetyl groups being more preferred. As the alkoxy group, linear or branched C
1-8
alkoxy groups are preferred.
X represents —COOR
3
,
with the —COOR being preferred. As R
3
, a hydrogen atom and C
1-12
alkyl or alkenyl groups are preferred, with a hydrogen atom, and methyl, ethyl, n-propyl, n-butyl and isobutyl groups are particularly preferred. As each of R
4
, R
5
and R
6
, a hydrogen atom, C
1-6
alkyl or alkenyl groups and C
7-16
alkyl groups are preferred, with a hydrogen atom and methyl, ethyl and benzyl groups being particularly preferred. As R
7
, C
7-16
aralkyl groups are preferred, with benzyl and phenethyl groups being particularly preferred.
R
2
is preferred when it represents a hydrogen atom or a C
1-6
alkyl or alkenyl group, or it is coupled with R
1
to form a pyrrolidine ring. Z represents —CON(R
8
)R
9
or —COOR
10
, with the —CON(R
8
)R
9
being preferred. As each of R
8
, R
9
and R
10
, a hydrogen atom and C
1-6
alkyl or alkenyl groups are preferred, with a hydrogen atom being more preferred.
A description will next be made of the compound of the formula (2).
In the formula (2), as R
11
, a hydrogen atom and C
1-6
alkyl groups are preferred, with a hydrogen atom and methyl, ethyl, n-propyl, isopropyl, n-butyl and isobutyl groups being particularly preferred. As each of R
12
and R
14
, a hydrogen atom and C
1-6
alkyl groups are preferred, with a hydrogen atom and methyl group being particularly preferred. As R
14
, the hydrogen atom is particularly preferred. As R
13
, a hydrogen atom, C
1-6
alkyl or alkenyl groups each of which may be substituted with a carbamoyl group and C
7-16
aralkyl groups are preferred, with a hydrogen atom, C
1-4
alkyl or alkenyl groups each of which may be substituted with a carbamoyl group and phenyl-C
1-6
alkyl groups being more preferred and isopropyl, isobutyl, sec-butyl, benzyl and 2-(carbamoyl)ethyl groups being particularly preferred. R
15
is particularly preferred when it represents a hydrogen atom or with R
13
, forms a pyrrolidinyl or piperidinyl group together with the adjacent nitrogen atom.
A description will next be made of the compound of the formula (3).
In the formula (3), as each of R
16
and R
17
, a hydrogen atom and C
1-6
alkyl or alkenyl groups are preferred, with a hydrogen atom and methyl, n-propyl, isopropyl, n-but
Imokawa Genji
Kanazawa Satoshi
Moriwaki Shigeru
Nishizawa Yoshinori
Ohashi Yukihiro
Jarvis William R. A.
Kao Corporation
Kim Vickie
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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