Patent GB-1397621-A (GB)
Title: Derivatives or homologues of cysteine
IPC: A61Q5/02
Filed: 1972-04-21
Abstract: 1397621 Thio-aminoacid derivatives; pantothenic acid derivatives L'OREAL 21 April 1972 [23 April 1971] 18606/72 Headings C2C and C2V The invention comprises the compounds 3-(2- ethyl-hexylthio)-alanine, 3-hexadecylthio-alanine, 3-octadecylthio-alanine, 3-(octadec-9- enylthio)-alanine, 1,4-bis-(3-alaninylthio)but-2- ene, 3-(2,3-dihydroxy-propylthio)-alanine, 3- (2,2-dimethoxy-ethylthio)-alanine, 3-(3,3-diethoxy-propylthio)-alanine, 3-(1,2-propylenedioxy-ethylthio)-alanine, 3-(2,2-ethylenedioxypropylthio)-alanine, 3-#-ureido-ethylthio-alanine, 3-#-phenylacetamidoethylthio-alanine, 3-#-nicotinamidoethylthio-alanine, 3-[2-(2,4- dihydroxy - 3,3 - dimethyl - butyramido)- ethylthio]-alanine, 3-[9,11-dihydroxy-10,10- dimethyl - 4,8 - dioxo - 3,7 - diaza - undecylthio]- alanine, (this being a pantothenic acid derivative), 2,3-dihydroxy-1,4-bis-(3-alaninylthio)- butane, 3-(2-thenylthio) alanine, 2-acetamido-3- (2,4-dichloro-benzylthio)-propionic acid, 2- amino-4-(#-amino-ethylthio)-butyric acid, 3-(2- p - toluenesulphonamido - ethylthio) - alanine, 3-furfurylthio-alanine, 3-tetrahydrofurfurylthio-alanine, 3-(2-pyridyl-methylthio)-alanine, 3-(2-pyridyl-thio)-alanine, 3-[2-(2-pyridyl)- ethylthio]-alanine, 3-o-methoxybenzylthio-alanine, 3-p-butoxybenzylthio-alanine, 3-mfluorobenzylthio-alanine, 3-p-fluorobenzylthioalanine, 3-o-fluorobenzylthio-alanine, 3-(4- isopropyl-benzylthio)-aniline, 2-methanesulphonamido-3-dodecylthio-propionic acid, 5- ureido-3-thia-hexanedioic acid, 3-benzylthio-2- (9-octadecene-amido)-propionic acid, 2-propionamido-3-benzylthio-propionhydroxamic acid, 2,2<SP>1</SP>-bis-(3-alaninylthio)-diethylsulphone and its N,N<SP>1</SP>-diacetyl derivative, 3-(#-piperidinocarbonyl-ethylthio)-alanine, 2-acetamido-3- (pyrrolidinocarbonyl.methylthio)-propionic acid, 5-dodecanamido-3-thia-hexanedioic acid, 3-(1- naphthyl-methylthio)-alanine, methyl 2-amino- 4-o-chlorobenzylthio-butyrate hydrochloride, 2-propionamido-4-tetradecylthio-butyric acid, 1,4 - bis - [3 - (1 - amino - 1 - carboxypropyl)- thio]-but-2-ene, methyl 2-amino-3-o-chlorobenzylthio-propionate, N-(1-carboxyl-2-o-chlorobenzylthio-ethyl)-succinamic acid, 2-acetamido. 3-o-chlorobenzylthio-propionic acid, 2-acetamido - 3 - (2,6 - dichloro - benzylthio) - propionic acid, 2-acetamido-3-(3,4-dichloro-benzylthio)-propionic acid, 3-octylthio-2-propionamido-propionic acid, and propyl 2-amino-3- benzylthio-propionate; and also compositions suitable for application to the hair or the skin which comprises at least one compound as above and a suitable vehicle, with the proviso that (i) the composition does not contain a perfume and (ii) the composition is not orally ingestible. General methods for preparing these compounds are given, with at least one method indicated for each compound. Intermediates.-2 - Amino - 3 - (2,4 - dichlorobenzylthio)-propionic acid is prepared from cysteine hydrochloride and 2,4-dichlorobenzyl chloride in the presence of sodium ethoxide. The 3-(o-chlorobenzylthio) compound is obtained similarly. Triethylamine pantothenate is prepared from calcium pantothenate, oxalic acid and triethylamine. Reference has been directed by the Comptroller to Specification 1,191,042.