Hydrocarbylpolythioalkanoyl-(phenylthio and phenoxy)-alkanoic acids and derivatives thereof

摘要

Novel compounds of the formula FORM:1117993/C2/1 (wherein A is -O- or -S-; R is H, alkyl, haloalkyl or cycloalkyl or substituted or unsubstituted aryl; R1 and R2 are H or C1- 5 alkyl; R3 is alkyl or substituted or unsubstituted aryl or aralkyl; y is 2 or 3; m is 0, 1, 2, 3 or 4; n is 1, 2, 3, 4 or 5; and X is halogen, CF3, alkyl or alkoxy, or two adjacent X radicals are joined in a hydrocarbon chain of chain length 4 carbon atoms) and salts thereof; and their alkyl esters and N-unsubstituted or N-mono- or di-alkyl-substituted amides; are prepared (1) by reaction of a corresponding compound containing the side-chain -CO.C(R) = CR1R2 with the appropriate R3(S)yH compound; or (2) by a process similar to (1), except that the starting material contains the side-chain -CO.CH(R)-CH2NR4R5 (wherein R4 and R5 are alkyl or NR4R5 is a heterocyclic residue) or an acid-addition salt or quaternary ammonium derivative thereof; and (3), for the salts, esters, and amides, by conventional procedures effected on the free acids. Starting materials are prepared by the following process: FORM:1117993/C2/2 FORM:1117993/C2/3 FORM:1117993/C2/4 FORM:1117993/C2/5 FORM:1117993/C2/6 FORM:1117993/C2/7 FORM:1117993/C2/8 FORM:1117993/C2/9 FORM:1117993/C2/10 FORM:1117993/C2/110 (wherein HA is a salt-forming acid; w is a positive integer; R3Y is a hydrocarbon halide; Z is a halogen; Z1 is a halogen; E is carboxy, alkoxycarbonyl, carbamoyl, N-alkyl-carbamoyl or cyano; R7 in COOR7 is a hydrocarbon radical and is otherwise H or -CHR1R2; and R6 is alkyl). Compounds IX and XII may also be prepared from the appropriate phenols and alkanoyl halides followed by heating of the thus-produced phenol esters with AlCl3. 31-Hydroxyalkanophenones may also be prepared by nitrating appropriate alkanophenones to give 31-nitro-alkanophenones, reducing these to 31-amino -alkanophenones and converting these to the required products. Examples illustrate many of the above processes and minor variants thereof. 2,3-Dichloro-anisole is prepared by methylation of 2,3-dichloro-phenol. 3-Chloroanisole is prepared similarly. The acids and derivatives thereof of the invention, which are stated to be diuretic and saluretic agents, may be made up into pharmaceutical compositions with suitable carriers.