GB976225A - Carbocycloxyalkyl cephalosporins - Google Patents

Abstract

Relates to antibiotic substances of the class represented by the formula <FORM:0976225/C1/1> wherein R1, taken alone, is -OH, C1-C8 acyloxy, or tertiary-amino; R2 is -OH when R1 is -OH; R2 is -OH when R1 is C1-C8 acyloxy; R2 is -O- when R1 is tertiary-amino; R1 and R2, when taken together, are -O-; R3 is C1-C4 alkylene; and R4 is benzyl, naphthyl, naphthyl-methyl, C4-C6 cycloalkyl or C4-C6 cycloalkylmethyl or a substitution product thereof containing at least one substituent consisting of halogen, nitro, trifluoromethyl, C1-C4 alkyl, or C1-C2 alkoxy; and the pharmaceutically acceptable salts, esters and amides thereof. The antibiotics may be prepared by acylation of the appropriate 7-amino compound with the appropriate acylating agent or by acylating 7-aminocephalosporanic acid with the appropriate acylating agent and then (a) heating the product with acidified water to form the corresponding acyl derivative of the nuclei of cephalosporin Cc compounds, (b) treating the product with citrus acetyl esterase to form the corresponding acyl derivative of the nuclei of desacetylcephalosporin C compounds or (c) refluxing the product in solution to form the corresponding acyl derivative of the nuclei of cephalosporin Ca compounds. The Specification includes many examples of compounds of the above formula and specific examples describe the production of the potassium salts of 7-benzyloxy- and 7-b -naphthoxy-acetamidocephalosporanic acid. Non-toxic derivatives of compounds of the above formula may be prepared by combining them with pharmaceutically acceptable cations, anions, alcohols, ammonia or amines. Specification 810,196 is referred to.