[(1-alkenylsulfonyl)-phenoxy] alkanoic acids and derivatives thereof

摘要

1,138,873. [(1 - Alkenylsulphonyl) - phenoxy] - alkanoic acids. MERCK & CO. Inc. 22 April, 1966 [29 April, 1965], No. 17763/66. Heading C2C. Novel [(1 - alkenylsulphonyl) - phenoxy] - alkanoic acids of the general formula wherein R1, R2 and R3 are each hydrogen or alkyl; each X is a halogen, alkyl or alkoxy, with the possibility that when substituted on adjacent carbon atoms of the benzene nucleus two X radicals may be combined to form a hydrocarbylene chain containing four carbon atoms between its points of attachment; m is 0 or an integer of from 1 to 4 and n is an integer of from 1 to 4; and their non-toxic, pharmacologically acceptable esters, amides, metal salts and salts with organic bases; other than those compounds described and claimed in Specification 1,040,555, are prepared by oxidation of a mercaptan of the general formula wherein R is alkyl, or by treating an ester of the general formula wherein R5 is alkyl and X1 is a halogen, with a dehydrohalogenating agent and, if desired, hydrolysing the product so formed. Pharmaceutical compositions having diuretic and saluretic activity comprise as active ingredient a [(1-alkenylsulphonyl)-phenoxy]-alkanoic acid of the first general formula above or a non-toxic pharmacologically acceptable ester, amide or metal salt thereof or salt thereof with an organic base (other than a compound described and claimed in U.K. Specification 1,040,555) and a pharmaceutical carrier. Mercaptans of the second general formula above are prepared by treatment of an isomeric mercaptan of the general formula wherein R4 is hydrogen or a hydrocarbyl radical, with a base, followed by an acid. Methyl (3 - chloro - 4 - allylmercaptophenoxy)- acetate is prepared by reaction of methyl (3- chloro-4-mercaptophenoxy)-acetate with allyl bromide. Methyl [3 - chloro - 4 - (2 - chlorobutylmercapto)-phenoxy]-acetate is prepared by reaction of methyl (3-chloro-4-mercaptophenoxy)- acetate with 2-bromobutanol and thionyl chloride. Methyl (3-chloro-4-methallylmercaptophenoxy)-acetate is prepared by reaction of methyl (3-chloro-4-mercaptophenoxy)-acetate with methallyl chloride.