GB788135A - Purification of n, n-bis-(dehydroabietyl) alkylene diamine penicillin - Google Patents

Abstract

Substantially pure penicillin salts of N,N1-bis-(dehydro-abietyl) alkylene diamines in which the alkylene has up to 8 carbon atoms in the molecule are prepared by subjecting a mixture containing a major proportion of a penicillin salt of an N,N1-bis-(dehydroabietyl) alkylene diamine and a minor proportion of a penicillin salt of a N,N1-bis-(dihydroabietyl) alkylene diamine and/or a N,N1-bis-(tetrahydroabietyl) alkylene diamine to intimate contact with a solvent comprising essentially n-butanol, allowing the said penicillin salts to remain in contact with the said solvent until precipitation of the desired penicillin N,N1-bis-(dehydroabietyl) alkylene diamine occurs. It is preferred to mix a solution of the mixed dehydro-, dihydro- and tetrahydro-abietyl alkylene diamines in n-butanol with a solution of a penicillin acid in n-butanol or chloroform, when the penicillin alkylene diamines form in situ, and allow to stand at e.g. 5 DEG C. in order that the N,N1-bis-(dehydroabietyl) alkylene diamine dipenicillin may crystallize, the dihydro- and tetrahydro-compounds remaining in solution. Alternatively, crude N,N1-bis-(dehydroabietyl) alkylene diaminedipenicillin may be purified by crystallizatio from n-butanol solution. The penicillin may be penicillin G, penicillin O, penicillin F, penicillin X, penicillin K or other penicillin including biosynthetic penicillins. In one example, there is described the preparation of N,N1 - bis - (dehydroabietyl) ethylene diamine di penicillin G. Pure N,N1-bis-(dehydroabietyl) ethylene diamine is obtained by treating N,N1-bis-(dehydroabietyl) ethylene diamine dibenzyl penicillin in chloroform water solution with sodium carbonate to pH 9.5. The dehydroabietyl ethylene diamine passes into the chloroform layer which is separated and the solvent removed. The dihydrochloride is obtained by treating the residue with methanol hydrochloric acid. Specification 753,739 is referred to.ALSO:Substantially pure penicillin salts of N,N1-bis-(dehydroabietyl)alkylene diamines in which the alkylene has up to 8 carbon atoms in the molecule (see Group IV (b)) are employed in pharmaceutical preparations. Penicillin may be penicillins G, O, F, X, K and biosynthetic penicillins. Specification 753,739 is referred to.