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(12) United States Patent (10) Patent No.: US 6,489,291 B1 Suzuki Et Al

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(12) United States Patent (10) Patent No.: US 6,489,291 B1 Suzuki Et Al USOO648.9291B1 (12) United States Patent (10) Patent No.: US 6,489,291 B1 Suzuki et al. (45) Date of Patent: Dec. 3, 2002 (54) TOPICAL COMPOSITION FOR SKIN Patent Abstracts of Japan, vol. 1997, No. 04, Apr. 30, 1997 & JP 08 333230 A (KAO CORP), Dec. 17, 1996, Abstract. (75) Inventors: Yasuto Suzuki, Tochigi (JP); Mikako Database WPI, Section Ch, Week 200031, Derwent Publi Watanabe, Tochigi (JP); Naoko Tsuji, cations Ltd., London, GB; Class B05, AN 2000–359593 Tochigi (JP); Shigeru Moriwaki, XP002901566 & JP 2000 11914.4A (KAO CORP), Apr. 25, Tochigi (JP); Shinya Amano, Tochigi 2000, Abstract. (JP) * cited by examiner (73) Assignee: Kao Corporation, Tokyo (JP) Primary Examiner Dameron L. Jones ASSistant Examiner-Lauren O. Wells (*) Notice: Subject to any disclaimer, the term of this (74) Attorney, Agent, or Firm-Oblon, Spivak, McClelland, patent is extended or adjusted under 35 Maier & Neustadt, P.C. U.S.C. 154(b) by 0 days. (57) ABSTRACT (21) Appl. No.: 09/678,615 A topical skin composition containing a dipeptide com (22) Filed: Oct. 4, 2000 pound represented by, formula (1) or a Salt of the dipeptide: (30) Foreign Application Priority Data (1) Oct. 5, 1999 (JP) ........................................... 11-283794 R1 ti (51) Int. Cl." ........................ A01N 37/18: A01N 37/00; N- CH-CON-CH-(CH2) X AO1N 37/30; A61K 38/00; A61K 31/185; R2 k A61K 31/205; A61K 31/16; A61K 6/00; A61K 7/00; A61K 31/74 wherein R' represents a, hydrogen atom, an alkyl group, an (52) U.S. Cl. ........................ 514/2; 424/401; 424/78.03; alkanoyl group, or -CH(R)COOR7 (wherein R represents 514/554; 514/627 a hydrogen atom or a lower alkyl group, and R7 represents (58) Field of Search ................................. 514/562, 533, a hydrogen atom, a lower alkyl group, a lower alkenyl 514/547, 569, 570, 575, 524, 443, 2,553, group, or an aralkyl group); 554, 627; 424/401, 78.03 R represents a hydrogen atom or an alkyl group which may have a Substituent; (56) References Cited R represents a lower alkyl group or a phenyl group; U.S. PATENT DOCUMENTS R" represents a hydrogen atom or a lower alkyl group, and 4.513,009 A 4/1985 Roques et al. may form a heterocyclic ring together with R and an 6,075,052 A 6/2000 Suzuki et al. adjacent nitrogen atom; 6,171,595 B1 1/2001 Suzuki et al. R represents a hydrogen atom, an alkyl group which may have a Substituent, or an aralkyl group which may have FOREIGN PATENT DOCUMENTS a Substituent, and may form the heterocyclic ring EP O O54862 6/1982 together with R"; JP 2000-1191.44 4/2000 X represents -COOR (wherein R represents a hydro gen atom, a lower alkyl group, a lower alkenyl group, OTHER PUBLICATIONS or an aralkyl group) or -SO3H, and JP abstract 08333230. Dec. 17, 1996.* n is an integer of 0-4; and a pharmaceutically acceptable JPAbstract 40634.5797. Dec. 20, 1994.* carrier therefor. Chemical Abstracts, vol. 98, No. 3, Jan. 17, 1983, Abstract No. 11055W. 20 Claims, No Drawings US 6,489,291 B1 1 2 TOPCAL COMPOSITION FOR SKN R represents a hydrogen atom or an alkyl group which may have a Substituent; R represents a lower alkyl group or a phenyl group; BACKGROUND OF THE INVENTION R" represents a hydrogen atom or a lower alkyl group, and 1. Field of the Invention may form a heterocyclic ring together with R and an The present invention relates to a topical composition for adjacent nitrogen atom; the skin (hereinafter may be simply referred to as a topical R represents a hydrogen atom, an alkyl group which may skin composition) exhibiting effects of retarding aging of the have a Substituent, or an aralkyl group which may have skin or rejuvenating the Skin and of Suppressing hair growth. a Substituent, and may form the heterocyclic ring 1O together with R"; 2. Background Art X represents -COOR (wherein R represents a hydro Studies have revealed that aging of the skin is mainly gen atom, a lower alkyl group, a lower alkenyl group, caused by advancing age, drying, oxidation, or Sunlight (i.e., or an aralkyl group) or -SOH, and UV rays). Aging of the skin is recognized by a decrease in n is an integer of 0-4; and a pharmaceutically acceptable collagen or elastin in the dermis of the skin; a decrease in 15 carrier therefor. mucopolysaccharides, including hyaluronic acid; or the The present invention also provides, as a novel compound presence of cells which are damaged by UV rayS. which has not yet been described in any literature, For the prevention of wrinkle formation, however, Suffi N-(carboxymethyl)phenylalanyl-f-alanine, among dipep cient effects have not yet been attained, for example, by a tide compounds represented by formula (1), or a Salt thereof. collagen-containing cosmetic composition. In addition, a Various other objects, features and many of the attendant number of research projects have focused on Skin aging advantages of the present invention will be readily appre caused by exposure to UV rayS. However, cosmetic com ciated as the same becomes better understood by reference positions SuperSeding UV absorbing agents or UV protect to the following detailed description of the preferred ing agents have not yet been developed. embodiments. There is a trend towards a preference for hairleSS bodies, 25 DETAILED DESCRIPTION OF PREFERRED particularly, hairleSS arms or legs, for reasons of aesthetic EMBODIMENTS appearance. Various methods have been tried in the pursuit In formula (1), an alkyl group represented by R' is of body hair removal, for example, a mechanical hair preferably a C1-C6 alkyl group, may be a linear or branched removal method making use of a shaver or hair-tweezers, a alkyl group, and is more preferably a methyl group, an ethyl method for removing body hair from the hair root by use of group, an n-propyl group, an isopropyl group, an n-butyl a hair removing agent, and a method for removing body hair group, an isobutyl group, or a t-butyl group. through chemical action of a hair removing agent. An alkanoyl group represented by R' is preferably a However, the aforementioned hair removing methods C1-C6 alkanoyl group, maybe a linear or branched alkanoyl physically or chemically Stimulate the Skin, and are limited group, and is more preferably an acetyl group, a propionyl by the unsatisfactory duration of the hairless State. 35 group, or a butyryl group. Therefore, there is a need for the development of a method A lower alkyl group represented by R. R", R, R", or R which facilitates removal of body hair. is preferably a C1-C6 alkyl group, may be a linear or branched alkyl group, and is more preferably a methyl SUMMARY OF THE INVENTION group, an ethyl group, an n-propyl group, an isopropyl In View of the foregoing, an object of the present inven 40 group, an n-butyl group, an isobutyl group, or a t-butyl tion is to provide a topical composition for the skin exhib grOup. iting effects with respect to retarding aging of the skin, Such A lower alkenyl group represented by R7 or R is pref as wrinkle formation, or rejuvenating the Skin, and of erably a C2-C6 alkenyl group, more preferably a vinyl Suppressing hair growth. group or a propenyl group. The present inventors have found that a dipeptide com 45 An aralkyl group represented by R or R is a C7-C18 pound having a Specific structure or a Salt thereof exhibits aralkyl group. Specific examples include a phenyl C1-C6 excellent effects with respect to Suppressing wrinkle alkyl group, a biphenyl C1-C6 alkyl group, and a naphthyl formation, preventing a reduction in Skin elasticity, and C1-C6 alkyl group. Of these, a phenyl C1-C6 alkyl group Suppressing hair growth, and that the compound or the Salt 50 is preferable, and a benzyl group is more preferable. is effectively employed in a topical Skin composition for An alkyl group which may have a Substituent, represented retarding aging of the Skin or Suppressing hair growth. by R, may be a C1-C6 alkyl group, a carboxy C1-C6 alkyl Accordingly, the present invention provides a topical skin group, or a C1-C6 alkoxycarbonyl C1-C6 alkyl group. Of composition comprising a dipeptide compound represented these, a C1-C6 alkyl group is preferable. R is more by formula (1) or a salt of the dipeptide: preferably a methyl group, an ethyl group, an n-propyl 55 group, an isopropyl group, an isobutyl group, or a t-butyl (1) grOup. R1 An alkyl group which may have a Substituent, represented ti-R by R, may be a C1-C6 alkyl group, a carboxy C1-C6 alkyl N-CH-CON-ti- (CH2) X 60 group, or a C1-C6 alkoxycarbonyl C1-C6 alkyl group. Of R2 k these, a C1-C6 alkyl group and a carboxy C1-C6 alkyl group are preferable. R is more preferably a methyl group, wherein R' represents a hydrogen atom, an alkyl group, an an isopropyl group, an isobutyl group, a t-butyl group, a alkanoyl group, or -CH(R)COOR7 (wherein R represents carboxymethyl group, or a carboxyethyl group. a hydrogen atom or a lower alkyl group, and R7 represents 65 A heterocyclic ring which is formed by Rand R may be a hydrogen atom, a lower alkyl group, a lower alkenyl pyrrolidine or piperidine. group, or an aralkyl group); An integer n is preferably 0, 1, or 2. US 6,489,291 B1 3 4 In formula (1), R is more preferably a hydrogen atom, a -continued C1-C6 alkyl group, a C1-C6 alkanoyl group, or -CH(R) (compound 5) COOR7 (wherein R represents a hydrogen atom or a C1-C6 alkyl group, and R7 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, or a phenyl C1-C6 alkyl group).
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