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filingDate 1974-04-17-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1975-11-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1412915-A
titleOfInvention Phenoxyalkyl-carboxylic acid derivatives
abstract 1412915 Phenoxyalkanoic acid derivatives BOEHRINGER MANNHEIM GmbH 17 April 1974 [21 April 1973] 16781/74 Heading C2C Novel phenoxyalkenoic acids of the formula wherein R 1 and R 2 each are H or CH 3 , n is 1 or 2, Z is OH or alkoxy and Y is a 5- or 6- membered monocyclic heterocyclic ring, containing 1 or 2 S, O or N atoms and optionally substituted by halogen atoms, C 1-6 alkyl, C 1-6 alkoxy or C 2-12 alkoxyalkoxy radicals, or optionally fused to a benzene ring, which may be substituted by halogen atoms, or alkoxy or alkylene radicals, are prepared by the phydroxy-benzylamine or p-(2-aminoethyl)-phenol with acids of the formula Y-COOH or reactive derivatives thereof, and with compounds of the formula XC(R 1 )R 2 .COZ, where X is an anion of a hydrohalic or sulphonic acid, and, if desired or necessary, hydrolysing, esterifying or salifying the resulting product. 4-[y-CONH-(CH 2 ) n ]phenols are obtained by hydrolysing the 4-[ Y-CONH-(CH 2 ) n ]- phenyl esters of acids of the formula YCOOH, resulting from the reaction between carbonyl chlorides of the formula YCOCl and p-hydroxybenzylamine or p- (2-aminoethyl)phenol. N- (4-hydroxybenzyl)acetamide and N-(4-hydroxyphenethyl)acetamide are obtained by hydrolysing the corresponding acetates, resulting from the acetylation of p-hydroxybenzylamine and p - (2 - aminoethyl)phenol. N-(4-hydroxyphenethyl)acetamide may also be obtained by acetylating p-(2-aminoethyl)phenol. Ethyl [(4-acetamidomethyl)phenoxy]acetate is prepared by reacting N-(4-hydroxybenzyl)- acetamide with ethyl bromoacetate. Ethyl 2-[(4- acetamidomethyl)phenoxy] - 2 - methylpropionate, ethyl [4 - (2 - acetamidoethyl)phenoxy]acetate and ethyl 2 - [4 - (2 - acetamidoethyl)phenoxy] - 2- methylpropionate are prepared in a similar manner. Ethyl [4 - (aminomethyl)phenoxy]acetate is prepared by esterifying [4-(aminomethyl)-phenoxy]acetic acid, obtained by hydrolysing ethyl [4-(acetamidomethyl)phenoxy]acetate. The following compounds were obtained using similar methods: [4 - (2 - aminoethyl)phenoxy]acetic acid, 2 - [4 - (aminomethyl)phenoxy]- 2 - methylpropionic acid and 2-[4-(2-aminoethyl)phenoxy]- 2-methylpropionic acid and the ethyl esters thereof. Pharmaceutical compositons, suitable for oral, parenteral or topical administration, contain the above novel compounds or salts thereof in admixture with solid or liquid pharmaceutical carriers or diluents. The compounds may be used in the treatment of atherosclerosis.
priorityDate 1973-04-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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