Basische Phenoxy-acetamide und Verfahren zu ihrer Herstellung

摘要

1,197,597. Para-(phenoxyacetamido)-benzoic acid esters of dialkylamino alkanols. ETABS. CLIN BYLA. 6 Dec., 1967 [7 Dec., 1966], No. 55574/67. Heading C2C. Novel p - (phenoxyacetamido) - benzoic acid esters of dialkylaminoalkanols of the formula wherein R1 is hydrogen, halogen, C 1-6 alkyl, C 2-6 alkenyl, phenyl, phenylalkyl, hydroxyl, alkoxy, alkenoxy, cycloalkoxy, phenylalkoxy, acyl, nitro, amino or sulphamyl, R2 is hydrogen, halogen, C 1-6 alkyl, phenyl, phenylalkyl, alkoxy or C 1-5 acyl, R3 is hydrogen, C 1-6 alkyl, trifluoromethyl, or alkoxy, R4 is H or alkyl, X is a methylene group which may be substituted by one or two alkyl groups or by a phenyl group, and Y is a group having the formula in which n is 2 or 3 and each of R5 and R6 is C 1-6 alkyl or R5 and R6 together with the N atom to which they are attached form a heterocyclic ring which may contain a nuclear oxygen atom, provided that when R1 is a halogen atom and R2 is hydrogen the group X has not more than one substituent, and the acid addition salts thereof, are prepared by reacting the corresponding p-aminobenzoic acid ester with the appropriate phenoxyacyl halide or when R1 is amino by reducing the corresponding nitro compound. 2,4 - Dichloro - phenoxyacetic acid, 4 - (npentyloxy)-phenoxy aceticacid, 4-(n-hexyloxy)- phenoxyacetic acid and α-[4-(n-pentyloxy)-phenoxy]-n-butyric acid are prepared by the hydrolysis of the corresponding ethyl esters resulting from the condensation of the appropriate phenol with ethyl α-bromo-phenylacetate, ethyl bromo-acetate and ethyl α-bromo-nbutyrate respectively. 4 - n - Isopropoxy [or 4 - (n - butoxy), 4 - (npentyloxy), 4-(n-hezylozy), 4-cyclopentyloxy and 4-benzyloxy] - phenoxy - isobutyric acids are obtained by condensing the appropriate phenol with acetone and chloroform in the presence of powdered sodium carbonate. 4 - (n - Butoxy) - phenoxy - isobutyric acid chloride is made by reacting 4-(n-butoxy)- phenoxy-isobutyric acid with thionyl chloride. Therapeutic compositions, in the form of tablets, suppositories, preparations for local application and ampoules for drinking and injection, contain the above novel esters or acid addition salts thereof as the active ingredient. The compositions are suitable for the treatment of pathological states relating to lipid metabolism.