Nitroalkenyl aryloxycarboxylic acids

摘要

Novel compounds of general formula and salts, amides and esters thereof wherein R is H, alkyl or aralkyl, each X is halogen or alkyl or 2 X radicals on adjacent atoms may be joined to form a hydrocarbon chain containing 3 or 4 carbon atoms, m is 2, 3 or 4 and n is 1, 2 or 3 are prepared by reaction of a compound of formula wherein R2 is H or alkyl with a primary amine followed without isolation of the Schiffs base by reaction with the nitro compound R.CH2. NO2 and optionally followed by conversion of a compound wherein R2 is H into its salt, amide or ester or hydrolysis of a compound wherein R2 is alkyl to the free acid. The intermediate of the second formula above may be prepared by a variety of methods such as formylation of the appropriate aryloxyalkanoic acid or ester or etherification of an appropriate formyl phenol or naphthol by reaction with propiololactone optionally substituted or by reaction with a haloalkanoic acid ester. 4-Formyl-2,3-dichlorophenol is prepared by introduction of the formyl group. Ethyl - (2,3 - dimethylphenoxy) - acetate is prepared by reaction of 2,3-dimethylphenol and ethyl bromoacetate. Pharmaceutical compositions in conventional forms for oral or parenteral administration and having diuretic and saluretic activity comprise an above novel compound or salt ester or amide in an inert diluent, carrier or coating.