GB880278A - Novel hydrazine derivatives and a process for the manufacture thereof - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0880278/IV (b)/1> and acid addition salts thereof, wherein each R1 is a C1-6 alkyl radical, R2 is an alkylene (C1-6 radical and R3 is a hydrogen atom or a 5-(C1-6 alkyl)-isoxazolyl-(3)-carbonyl radical and the preparation thereof by condensing a carbonyl compound of the general formula <FORM:0880278/IV (b)/2> wherein R4 represents a C1-6 alkylidene radical with a hydrazine H2N.NHR5 wherein R5 represents a hydrogen atom, a 5-(C1-6 alkyl)-isoxazoyl-(3)-carbonyl radical or an easily removable acyl radical, reducing the hydrazone thus obtained, removing from same the easily removable acyl radical wherein R5 represents such a group or, where R5 represent a hydrogen atom, acylating same by treatment with a compound of the general formula <FORM:0880278/IV (b)/3> wherein R6 represents a C1-6 alkyl radical and R7 represents a hydroxyl radical, a halogen atom or an alkoxy, acyloxy or an amino radical if desired and if desired transforming the product into an acid addition salt. 1-(p-Dimethylaminophenyl)-propanone-(2) is prepared by reacting diethyl malonate with magnesium and p-nitrophenyl-acetyl chloride to give diethyl-p-nitrophenacylmalonate, hydrolysing this to 1-p-nitrophenyl-propanone-(2) and reacting this with formalin in the presence of Raney-nickel and hydrogen under pressure. [5 - Methyl - isoxazolyl- (3) - carbonyl] - hydrazine is prepared by reacting acetonyl-acetone with nitric acid to form 3-carboxy-5-methyl-isoxazole, esterifying this to form the ethyl ester and reacting the ester with hydrazine.ALSO:Pharmaceutical compositions comprise compounds of the general formula <FORM:0880278/VI/1> and acid addition salts thereof with organic and inorganic acids wherein each R1 is an alkyl radical containing up to six carbon atoms, R2 an alkylene radical containing up to six carbon atoms and R3 is a hydrogen atom or a 5-alkyl-isoxazolyl-(3)-carbonyl radical containing up to six carbon atoms in its alkyl substituent, together with a carrier. The preparations may be in conventional liquid or solid dosage forms for parenteral or oral administration.