Amine derivatives and skin preparations for external use...

Details Amine derivatives and skin preparations for external use... Amine derivatives and skin preparations for external use...

2001-03-14

2001-12-11

Gerstl, Robert (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C424S401000, C548S232000, C564S507000

Reexamination Certificate

active

06329409

ABSTRACT:

TECHNICAL FIELD
The present invention relates to an amine derivative which has excellent preventing effects (wrinkle preventing and improving effect, pigmentation preventing and improving effect, etc.) on aging of the skin, and improving effects (keratonosis improving effect, pimple preventing and improving effect, etc.) on cutaneous aberration caused by abnormal keratinization, and an external skin care composition containing such an amine derivative.
BACKGROUND ART
In the skin, balance between cell growth and keraninization is destroyed by external irritation such as ultraviolet rays, aging, etc., and so its healthy formation is prevented to induce pachymenia and keratonosis.
As a method for preventing and improving cutaneous aberration, it has heretofore been conducted to apply a moisturizer, blood circulation accelerator or pigmentation preventing agent to the skin. However, the homeostasis that a living body possesses has not been sufficiently improved.
Various compositions and methods have been proposed for preventing or removing wrinkles (Japanese Patent Application Laid-Open Nos. 185005/1987, WO 94/21595, etc.). However, it has been desired to develop compounds which exhibit far excellent effects.
It is accordingly an object of the present invention to provide a novel compound having excellent effects of preventing the occurrence of wrinkles and removing the wrinkles, preventing and improving pigmentation, improving keratinization, and preventing and improving pimple, and the like, and an external skin care composition containing such a compound.
DISCLOSURE OF THE INVENTION
According to the present invention, there is provided an amine derivative represented by the general formula (1):
wherein
R
1
is a hydrocarbon group having 1 to 30 carbon atoms, which may be interrupted by an ether linkage, with the proviso that phenyl and benzyl groups are excluded;
one of A and B is
 and the other of them is —OR
4
;
R
2
and R
3
are the same or different from each other and are individually a hydrogen atom, an amidino group, an alkanoyl group or a hydrocarbon group having 1 to 20 carbon atoms, which may have 1 to 3 substituent groups selected from hydroxyl, alkoxy and carboxyl groups, or R
2
and R
3
may form a 5- or 6-membered nitrogen-containing heterocycle together with the adjacent nitrogen atom, or R
3
and R
4
, or R
3
and R
5
may be bonded to each other through a carbonyl group to form an oxazolidone ring;
R
4
and R
5
are the same or different from each other and are individually a hydrogen atom or a phosphoryl group, or R
4
or R
5
may form the oxazolidone ring together with R
3
; and
n is a number of 0 or 1, or a quaternary ammonium salt or acid-addition salt thereof.
According to the present invention, there is also provided an external skin care composition comprising the amine derivative represented by the general formula (1), or a quaternary ammonium salt or acid-addition salt thereof.
The compound according to the present invention has a structural feature that the oxygen atom is present adjacently to R
1
in the general formula (1). When the external skin care composition comprising the compound (1) is used, aging of the skin is prevented (prevention and improvement of wrinkles, prevention and improvement of pigmentation, etc.), cutaneous troubles caused by abnormal keratinization are improvement (improvement of keratinization, prevention and improvement of pimple).


REFERENCES:
patent: 4609659 (1986-09-01), Hartman
patent: WO 91/14688 (1991-10-01), None
W. R. Roush, et al., J. Org. Chem., vol. 50, No. 20, pp. 3752-3757, “Directed Openings of 2,3-Epoxy Alcohols Via Reactions With Isocyanates: Synthesis of (+)-Erythro-Dihydrosphingosine”, 1985.
A. Bongini, et al., J. Chem. Soc. Perkin Trans. 1, No. 5, pp. 935-939, “A New Approach To (±)-2-Amino-2-Deoxytetritol Derivatives”, 1985.
S. W. McCombie, et al., Tetrahedron Letters, vol. 28, No. 45, pp. 5395-5398, “Cyclofunctionalisation Reactions of Epoxyalcohol Derivatives. 3. Cyclisation-Acyl Migration of N-Benzoylcarbamates to Stereodefined Oxazolidinones. A New, Diasterospecific Route to Thiamphenicol”, 1987.
G. Cardillo, et al., J. Org. Chem., vol. 51, No. 5, pp. 713-717, “Oxazolidin-2-Ones From Allylic Amines by Means of Iodine and Carbonate Anion on Polymeric Support. A Convenient Synthesis of (±)-Propranolol”, 1986.

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