GB971164A - Therapeutic compositions comprising ª‡-aminoxy-alkanoic acids and derivatives thereof - Google Patents

Abstract

Compounds of the general formula <FORM:0971164/C1/1> wherein R1 is a hydrogen atom or a C1-5 alkyl radical, R2 is a hydrogen atom or a C1-6 alkyl radical or an alkaline earth, alkali metal or ammonium cation and R3 is a hydrogen atom or a C2-5 acyl radical may be prepared by reacting the appropriate a -bromo-aliphatic acid with acetoxime to form the corresponding a -isopropylideneaminooxy aliphatic acid (racemic) which may be resolved by fractional crystallization of the ephedrine salt. The optical isomers may be converted to the corresponding a -aminooxy aliphatic acids by steam distillation with concentrated HCl and these acids may be converted to the hydrobromides by steam distillation with 20% HBr. The acids (in hemihydrochloride form) may be converted to the alkyl esters by reaction with the appropriate alkanol in the presence of HCl gas and to the corresponding a -acylminooxy aliphatic acids by reaction with the appropriate acid anhydride. Alkali metal and alkaline-earth metal salts of the aminooxy aliphatic acids may be prepared by reacting the acid with the appropriate alkali metal hydroxide or an alkaline-earth metal salt sodium hydroxide.ALSO:Pharmaceutical and veterinary compositions useful in the treatment of stress and mental diseases including epilepsy comprise a carrier and a compound of general formula <FORM:0971164/A5-A6/1> wherein R1 is a hydrogen atom or a C1-5 alkyl radical, R2 is a hydrogen atom, an alkaline earth or alkali metal cation (including substituted and unsubstituted ammonium) a a C1-5 alkyl radical and R3 is a C2-5 acyl radical, or a pharmacologically acceptable acid addition salt thereof. The preferred compound is amino-oxyacetic acid hemihydrochloride and in compounds wherein stereoisomeresin occurs the laevo form is preferred to the racemic mixture. The compositions may be in conventional unit dosage forms for oral or parenteral administration, e.g. tablets, pills, elixirs, solutions, suspensions and premixes with animal feeds. As optional active ingredients which may be included in the compositions there are mentioned numerous reductions, e.g. barbiturates; ataractics, e.g. reserpine, ectylurea, chlorpromazine, meprobamate, prochlorperazine, promazine, azacyclonol and phenaglycodol; analgesics, e.g. aspirin, phenacetin, salicylamide, and N-acetyl-p-aminophenol; anticonvulsants, e.g. diphenylhydantoin, paramethadione, phenylacetylurea, phensuxamide, primadone and trimethadone, vitamins and chlline chloride.