Study of local anesthetics. XLIX. Basic esters of N-alkyl substituted alkoxycarbanilic acids with spasmolytic and local anesthetic effects
Benes, L.; Borovanský, A.; Cizmárik, J.; Svec, P.; Bezáková, Z.; Koubalík, B.; Sládová, L.
Ceskoslovenska Farmacie 24(2): 53-58
1975
ISSN/ISBN: 0009-0530 PMID: 1157099 Document Number: 87818
A series of 43 compounds 2-diethylaminoethyl-, 2-piperidinoethyl-, 1-methyl-2-diethylaminoethyl- and 1-methyl-2-piperidinoethylesters of 2-, 3-, 4-alkoxycarbanilic acids and their N-alkylderivates was prepared. N-alkylation was performed by alkylation of p- to -luenesulfonamides with dimethylsulfate (N-methylderivatives) or reduction of acylanilines with LiAl hydride. A toluene solution of phosgene was used to prepare the respective isocyanates from alkoxyanilines and chlorides of carbanilic acids from N-alkylalkoxyanilines. The bases, later changed to hydrochlorides, were prepared by the acid chlorides and isocyanates reacting respectively with alcohols and alcoholates respectively. In 1 instance the quaternary compound (2-)3-pentyloxyphenylkarbamoyloxyethyl-N-ethyl piperidinium bromide was prepared. All of the synthetized compounds were submitted to pharmacological screening.