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US5236950.Pdf |||||||||||||||| USOO.5236950A United States Patent (19) 11 Patent Number: 5,236,950 Aoyama et al. 45 Date of Patent: Aug. 17, 1993 (54) PROCESS FOR HAIR GROWTH 2652256 6/1977 Fed. Rep. of Germany . 2812978 10/1979 Fed. Rep. of Germany . 75) Inventors: Hajime Aoyama; Satoshi Ono; Osamu 3738405 5/1989 Fed. Rep. of Germany . Oohashi; Hirokazu Narita; Shuntaro 119.0002 10/1959 France, Takano, all of Toyama, Japan 60-004113 10/1985 Japan. 61-207321 9/1986 Japan . 73) Assignee: Toyama Chemical Co., Ltd., Tokyo, 8302390 7/1983 PCT Int'l Appl. Japan 780801 8/1957 United Kingdom . 923400 4/1963 United Kingdom . 21 Appl. No.: 311,945 944834 12/1963 United Kingdom. (22 Filed: Feb. 17, 1989 83/02390 7/1983 World int. Prop. O. (30) Foreign Application Priority Data OTHER PUBLICATIONS Feb. 18, 1988 JP Japan .................................. 63-33968 Derwent Abstract WPI Acc No. 75-62757W/38 Jun. 3, 1988 JP Japan ................................ 63.36824 (Takasago). 51) Int. Cl................................................. A61K 7/06 Derwent Abstract WPI Acc No. JP49069845 52 U.S. Cl. .................................... 514/478; 514/354; (Takasago). 514/356; 514/532; 514/556; 514/715; 514/738; Derwent-Ref: 60454Y/34 Nov. 1, 1976. 514/739 Derwent-Ref: 85-077293/13 Jul. 25, 1983. 58) Field of Search ................. 514/70,478, 556, 354, Derwent-Ref: 85-077294/13 Jul. 28, 1983. 514/356, 532, 715, 738 Derwent-Ref: 86-141951/22 Sep. 27, 1984. Derwent-Ref: 62505B/34 Dec. 27, 1977. (56) References Cited Chemical Abstracts, vol. 83, p. 435, 1975, No. 65330r, U.S. PATENT DOCUMENTS Yoshigi Hideki, et al., "Cosmetics With Improved 4,139,619 2/1979 Chidsey, III et al. ... ... 424/45 Moisture Retentivity'. 4,192,953 3/1980 Mishima et al. .......... ... 568/673 4,260,551 4/1981 Mishima et al. ...... ... 260/410.6 Primary Examiner-Nicholas S. Rizzo 4,346,109 8/1982 Yamatsu et al. .................... 424/318 Attorney, Agent, or Firm-Oblon, Spivak, McClelland, 4,491,592 1/1985 Katoh et al. .......... ... 424/38 Maier & Neustadt 4,596,812 6/1986 Chidsey, III et al............... 514/256 4,738,801 4/1988 Tahara et al. ......... 260/410.9 R 57 ABSTRACT 4,939, 17 7/1990 Moeller et al. ..................... 514/530 This invention relates to a hair-restorer comprising, as an active ingredient, (a) an acyclic branched higher FOREIGN PATENT DOCUMENTS aliphatic hydrocarbon of 20 carbon atoms which may 0129778 1/1985 European Pat. Off. be substituted with hydroxyl group or acyloxy group, 0204586 12/1986 European Pat. Off. 315913 11/1987 European Pat. Off. or (b) an acyclic branched carboxylic acid of 20 carbon 0287876 10/1988 European Pat. Off. atoms or its derivative and to a process for hair growth. 1467925 1/1969 Fed. Rep. of Germany . 1467955 2/1969 Fed. Rep. of Germany. 38 Claims, No Drawings 5,236,950 1 2 hydrocarbon group of 20 carbon atoms includes, for PROCESS FOR HAIR GROWTH example, phytyl group (3,7,11,15-tetramethyl-2-hexa decen-1-yl group), isophytyl group (3,7,11,15-tet This invention relates to a novel hair-restorer and a ramethyl-1-hexadecen-3-yl group), geranyllinallyl group process for hair growth. More particularly, this inven (3,7,11,15-tetramethylhexadecane-1,6,10,14-tetraen-3-yl tion relates to a hair-restorer comprising, as an active group) and the like; the acyclic branched higher ali ingredient, a compound represented by the general phatic hydrocarbon group of 20 carbon atoms substi formula II: tuted with hydroxyl group includes, for example, 7 hydroxymethyl-3,11,15-trimethylhexadecane-2,6,10,14 R-R2 (I) 10 tetraen-1-yl, 2,3-dihydroxy-3,7,11,15-tetramethylhex adecanyl group and the like; the acyclic branched wherein R is an acyclic branched higher aliphatic hy higher aliphatic hydrocarbon group of 20 carbon atoms drocarbon group of 20 carbon atoms which may be substituted with acyloxy group includes the above acy substituted with hydroxyl or acyloxy group, or an acy clic branched higher aliphatic hydrocarbon groups clic branched acyl group of 20 carbon atoms, and R2 is 15 a hydroxyl group or a substituted or unsubstituted alk substituted with the same acyloxy group as in the defini oxy, alkylthio, alkylsulfinyl, alkylsulfonyl, car tion of R2 to be described hereinafter, for example, bamoyloxy or acyloxy group when R is the former 2,3-diacetoxy-3,7,11,15-tetramethylhexadecanyl group group, and is a hydroxyl group or a substituted or un and the like; and the acyclic branched acyl group of 20 substituted alkoxy group when R is the latter group, or carbon atoms includes, for example, 3,7,11,15-tet a pharmaceutically acceptable salt thereof and to a 20 ramethyl-2-hexadecenoyl group and the like. process for hair growth. With respect to R2, the alkoxy group includes, for Hair-restorers conventionally comprise various effec example, Ci-galkoxy groups such as methoxy, ethoxy, tive ingredients. Known hair-restorers comprise, for n-propoxy, isopropoxy, butoxy and the like, the alkyl example, amino acids such as serine, methionine and the thio group includes C1-8alkylthio groups such as meth like; vasodilators such as acetylcholine derivative and 25 ylthio, ethylthio, n-propylthio, isopropylthio, butylthio the like; anti-inflammatory agents such as salicylic acid, and the like; the alkylsulfinyl group includes C1-8alkyl lithospermi radix extract and the like; hormone prepara sulfinyl groups such as methylsulfinyl, ethylsulfinyl, tions such as estradiol and the like; vitamins such as n-propylsulfinyl, isopropylsulfinyl, butylsulfinyl and vitamin E and the like; keratolytics; wetting agents; the like; the alkylsulfonyl group includes C1-8alkylsulfo perfumes; dandruff-suppressing agents; refrigerants; 30 nyl groups such as methylsulfonyl, ethylsulfonyl, n crude drug extracts; and fatty acids. propylsulfonyl, isopropylsulfonyl, butylsulfonyl and the Japanese Patent Application Kokai (Laid-Open) No. like, and the acyloxy group includes, C2-20aliphatic 4113/1985 describes, as an active ingredient for hair-res acyloxy groups, for example, C2-20alkanoyloxy groups torer, an alcohol having an odd number of carbon atoms such as acetyloxy, propionyloxy, butyryloxy, or its derivative. Japanese Patent Application Kokai 35 isobutyryloxy, isovaleryloxy, pivaloyloxy, lauroyloxy, (Laid-Open) No. 207321/1986 describes, as an active palmitoyloxy, stearoyloxy and the like, C3-20alk ingredient for hair-restorer, a higher aliphatic alcohol of enoyloxy groups such as acryloyloxy and the like, C3 22-34 carbon atoms. 20alkynoyloxy groups such as propioloyloxy and the The conventional hair-restorers, however, do not like and C3-7cycloalkylcarbonyloxy groups such as cy have sufficient effect for hair restoration. 40 clopropylcarbonyloxy, cyclohexylcarbonyloxy and the In view of the above situation, the present inventors like; aroyloxy groups such as benzoyloxy, naph have made research on substances having an excellent thoyloxy and the like; and 5- or 6-membered heterocy hair-restoration effect for alopecia without exhibiting clic carbonyloxy groups such as nicotinoyloxy, any side effect. As a result, it has been found that the 45 isonicotinoyloxy, 1,4-dihydropyridylcarbonyloxy, compounds represented by the general formula I or prolyloxy, thenoyloxy, furoyloxy and the like; the car their pharmaceutically acceptable salts exhibit an excel bamoyloxy group includes, for example, carbamoyloxy lent hair growth effect. group; N-C1-8alkylcarbamoyloxy groups such as N An object of this invention is to provide a hair-res methylcarbamoyloxy, N-ethylcarbamoyloxy and the torer comprising, as an active ingredient, a substance of like; N,N-di-C1-8alkylcarbamoyloxy groups such as excellent hair-restoration effect. SO N,N-dimethylcarbamoyloxy, N,N-diethylcar Another object of this invention is to provide a topi cal composition for application to mammalian (e.g. bamoyloxy and the like; and N-arylcarbamoyloxy mice, sheep, rabbits, monkeys, minks, humans and the groups such as N-phenylcarbamoyloxy and the like. like) skin. The above groups may have at least one substitutent A further object of this invention is to provide a 55 selected from C-4alkyl groups such as methyl, ethyl, process for hair growth. n-propyl, isopropyl and the like; C3-7cycloalkyl groups Other objects and advantages of this invention will such as cyclopropyl, cyclobutyl, cyclohexyl and the become apparent from the following description. like; C1-4alkoxy groups such as methoxy, ethoxy, n According to this invention, there is provided a hair propoxy, isopropoxy and the like; C1-alkylthiogroups 60 such as methylthio, ethylthio, n-propylthio, isopro restorer comprising, as an active ingredient, a com pylthio and the like; C2-acyloxy groups such as acetyl pound represented by the general formula I): oxy, propionyloxy, butyryloxy and the like; C1-alky R-R2 I lenedioxy groups such as methylenedioxy, ethylene dioxy and the like; hydroxyl group; aryl groups such as wherein R and R2 have the same meanings as defined 65 phenyl, 3-nitrophenyl, naphthyl and the like; carboxyl above or a pharmaceutically acceptable salt thereof. group; C1-4alkoxycarbonyl groups such as methoxycar In the compound of the general formula I, with bonyl, ethoxycarbonyl and the like; amino group; C1. respect to R, the acyclic branched higher aliphatic 4alkylamino groups such as methylamino, ethylamino 5,236,950 3 4. and the like; di-(C1-4alkyl)amino groups such as dimeth like; and sulfoxides such as dimethyl sulfoxide and the ylamino, diethylamino, methylethylamino and the like; like. These solvents can be used alone or in admixture of and tri-(C1-4alkyl)ammonio groups such as trime tWO Or Ote. thylammonio, triethylammonio and the like. In the above reaction, the compound of the general Of these substituents, the hydroxyl group, the car formula II) or the reactive derivative in the carboxyl boxyl group, the amino group, the alkylamino groups, group thereof is used in an amount of at least 1 mole per etc. may be protected by, for example, the conventional mole of the compound of the general formula (Ib) or the protective groups described in, for example, Protective salt thereof.
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