GB766325A - Penicillin salts of esters of 4-aminosalicylic acids - Google Patents

Abstract

The invention relates to penicillin salts of (a) an ester having the general formula <FORM:0766325/IV(b)/1> in which X is a bivalent saturated aliphatic hydrocarbon radical containing from 3-12C atoms, and (1) R1, R2, R3 and R4 are hydrogen, 1 to 10C alkyl, or aryl of up to 10C atoms, or (2) R3 and R4 are as in (1) and -N(R1)(R2 is a heterocyclic ring; (b) an ester of general formula <FORM:0766325/IV(b)/2> in which (1) R1 and R2 are hydrogen, an alkyl group containing 1 or 3 to 10C atoms, or aryl of up to 10C atoms and R3 and R4 are hydrogen, 1 to 10C alkyl or aryl of up to 10C atoms; or (2) R1 is ethyl, R2 is hydrogen, an aryl of up to 10C atoms, or an alkyl containing 1 or from 3 to 10C atoms and R3 and R4 are hydrogen, 1 to 10C alkyl or aryl of up to 10C atoms; or (3) the radical -N(R1)(R2) is heterocyclic ring other than the piperidino ring, and R3 and R4 are hydrogen, 1 to 10C alkyl or aryl of up to 10C atoms; or (4) the radical -N(R1)(R2) is the piperidino ring and R3 and R4 are 1 to 10C alkyl or aryl of up to 10C atom, or R3 is hydrogen and R4 is an aryl group containing not more than 10C atoms or an alkyl group containing from 5 to 10C atoms; or (5) R1 and R2 are both ethyl groups and R3 and R4 are 1 to 10C alkyl or aryl of up to 10C atoms. The salts are prepared by reacting penicillin with the appropriate ester in the presence of a solvent. The penicillin is the free acid, or a salt such as sodium or potassium penicillin and may be any penicillin, especially G, F, dihydro F or K. The ester is the free base, or a salt with an organic or inorganic acid, e.g. hydrochloric acid, or the N-oxide or N-hydrated oxide. Mixtures of esters and/or penicillins may be reacted. Specified solvents are water, hydrocarbons, e.g. hexane and benzene, halogenated hydrocarbons, e.g. chloroform and secondary butyl chloride; alcohols, e.g. ethanol and isopropanol; esters, e.g. ethyl acetate and butyl acetate; ethers such as diethyl ether and diisopropyl ether; ketones, e.g. acetone and methyl ethyl ketone and mixtures thereof. The salts may be used in the purification of penicillin from, e.g. organic solvent extract of fermentation broths. Specifications 766,326 and 766,327 are referred to.