SI9011744B - New esters of carboxylic acid with amino-alcohols, their quaternary products and the preparation and application of these compounds - Google Patents

Abstract

The new compounds of formula (I) (where A, R1, Ra and R2 are defined in the description) can be manufactured by processes known per se and used as the active ingredients of drugs.

Claims (6)

Claims 1 Compounds R (I), R -, - Č-CO-OA K in which A stands for group < CH2 > m-CH -CH Q ' (cH2) n-CH (II) in which m and n independently of one another Q 1 represent one of the double bonds -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -, -CH = CH-, and JI Q 'represents a group = NR or a group = NRR', wherein R is H or optionally a halogen or hydroxy substituted C1-C4 alkyl radical, and R 'is a C1-C4 alkyl radical and R and R' may together form also a C4-C6-alkylene residue and wherein in the case of quaternary compounds there is an anion equivalent (X®) opposite the positive charge of the N-atom, R 1 is a thienyl, phenyl, furyl, cyclopentyl or cyclohexyl residue, these residues may also be substituted by methyl, thienyl and phenyl as well as fluorine or chlorine, R 1 represents hydrogen, OH, C 1 -C 4 -alkoxy or C 1 -C 4 -alkyl, Ra represents H, F, C 1 or CH 2. Compounds according to claim 1, wherein Rx is 2-thienyl. Compounds according to claim 1 or 2, wherein R 2 stands for OH. Compounds according to claim 1, 2 or 3, wherein A stands for RNR · ® z wherein R and X ° have the upper meaning and R 'has the upper meaning with the exception of hydrogen. Compounds according to claims 1-4, wherein Ra represents 2-thienyl and A stands for a residue or to form '3a, wherein X® is the equivalent of an anion, preferably Br® or CH 2 SO 2 Process for the preparation of compounds according to Claims 1 to 5 or 7, characterized in that the ester of the formula R a S (IV), R 1 -C-CO-OR R 3 2 in which R 1 stands for C 1 -C 4 -alkyl the residue, and Rr R2 and Ra have the above meaning, are esterified with an amino alcohol of formula (V) HO-CH (CH2) n-CH in which m, n and Q have the above meaning and Q ”stands for = NR or for = NH, in an inert organic solvent or in a melt in the presence of a transesterification catalyst and the resulting compound optionally a) if Q 'is = NR (wherein R is other than hydrogen), quaterified with a mono derivative of Z - C 1 -C 10 alkyl) of the corresponding alkane reactive (Z = leaving group), or b) if Q 'is = NH, is substituted and quaternary with the terminal alkane Z- (C4-C6-alkylene) -Z, without intermediate isolation. k in the form of 3a as their metobromides or metomethanesulfonates. For: BOERINGERINGELHEIM KG PATENTNA PISARNA, d.o.o. LAI PIJANA. ČOPOVA 14 ΡΛ b