GB1503030A - Water soluble forms of triazolylthiomethyl cephem derivatives - Google Patents

Abstract

1503030 Triazolylthiomethyl cephem compounds BRISTOL-MYERS CO 31 Dec 1975 [2 Jan 1975] 53315/75 Heading C2C Novel compounds of the Formula (I) wherein R is an alkali metal, preferably Na or K, may be prepared (1) by treating an aqueous suspension of 7-[D-α-amino-α-(p-hydroxyphenyl)acetamido] - 3 - (1,2,3 - triazol - 5- ylthiomethyl) - 3 - cephem - 4 - carboxylic acid (II) or a solvate or hydrate thereof with acetaldehyde and sufficient water-soluble alkali metal base to raise the pH of the mixture to between 5À5 and 8 and to form a solution of the desired salt of (I), then recovering the salt from solution; or (2) forming a suspension of (II) or a solvate or hydrate thereof in an inert organic solvent, which is a solvent for the triethylamine salt of the acetaldehyde reaction product of (II) and a non-solvent for the alkali metal salt of (I), treating the suspension with acetaldehyde and sufficient triethylamine to form a salt of the acetaldehyde reaction product of (II), and precipitating the desired alkali metal salt of (I) by adding a solvent-soluble sodium or potassium base; or (3) forming a suspension of (II) or a solvate or hydrate thereof in an inert organic solvent, which is a non-solvent for the alkali metal salt (I), treating the suspension with acetaldehyde and a solvent soluble base in amount sufficient to raise pH to 5-5 to 8, and recovering the desired salt (I). Pharmaceutical compositions suitable on reconstitution with water for use as parenterally administrable antibiotic formulations comprise a compound of Formula I as defined above and a solid pharmaceutically acceptable water-soluble organic acid or glycine hydrochloride present in such amount that the pH of the reconstituted formulation is between 5 and 6.