New quaternary ammonium compounds

摘要

Novel compounds of the general formula wherein R1 represents an alkyl, alkenyl or alkynyl radical having not more than 4 carbon atoms, R2 represents an alkyl radical having from 1 to 4 carbon atoms, the benzyl or phenethyl radical or a benzyl or phenethyl radical mono- or poly-substituted by halogen atoms, by alkoxy or alkylthio groups having from 1 to 4 carbon atoms or by methyl, hydroxy, nitro or cyano groups, or R1 and R2 together with the adjacent nitrogen atom represent the pyrrolidino, piperidino, morpholino or thiamorpholino radical or a methylated pyrrolidino, piperidino, morpholino or thia-morpholino radical, R3 represents an alkyl radical having from 1 to 4 carbon atoms and, in the case where R2 is an alkyl radical, R3 may also represent the benzyl or phenethyl radical or a benzyl or phenethyl radical mono- or poly-substituted by halogen atoms, by alkoxy or alkylthio groups having from 1 to 4 carbon atoms or by methyl, hydroxy, nitro or cyano groups, R5 represents hydrogen or an alkyl radical, having from 1 to 3 carbon atoms, R6 represents an alkyl radical having from 1 to 3 carbon atoms, X represents an anion of an inorganic or organic acid non-toxic to the animal organism, are prepared either by reaction of a compound of general formula with a quaternizing reagent of the Formula R3X1, where R3 has the above meaning and X1/h represents a halogen atom, an alkylsulphate or arylsulphonate group, and optionally exchanging the anion of the quaternary salts so obtained by reaction with other inorganic or organic acids, or by reaction of the compound of general formula with a compound of general formula wherein the symbols have the above meaning and Hal represents a chlorine or bromine atom. Also compounds wherein R5 is H may be prepared by hydrolysis of the corresponding compounds wherein R5 is acyl. N - [b - (4 - N - methyl - N - acetylamino-benzoyl) - ethyl] - trimethyl ammonium chloride is prepared by reaction of trimethylamine and 41 - (N - methyl - N - acetylamino) - 3 - chloro-propiophenone.