DERIVATIVES OF PENEM, THEIR SYNTHESIS AND A PHARMACEUTICAL COMPOSITION CONTAINING SAID AND SHOWING ANTIBACTERIAL ACTIVITY Russian patent published in 1999 - IPC

FIELD: pharmacy, antibiotics. SUBSTANCE: invention relates to new derivatives of penem of the general formula (I) where R₁ means (C₁-C₆)-hydroxyalkyl; R₃ means carboxyl-group or esterified carboxyl-group that can be easily activated in vivo or carboxylate anion; R₃ means hydrogen atom, (C₁-C₄)-alkyl optionally substituted with carboxamide-group; R₄ means hydrogen atom, (C₁-C₆)-alkyl optionally substituted with phenyl, (C₁-C₆)-aminoalkyl; or R₃ and R₄ bound together form pyrrolidine, piperidine or aziridine ring optionally substituted with hydroxyl-group, alkanoylhydroxy-group and carbamoylhydroxy-group; R₅ and R₆ mean hydrogen atom independently each of other, (C₁-C₆)-alkyl, (C₁-C₆)-alkylcarboxamide or bound together they form 4-methyl- -piperazine; n = 1, 2 or 3, and their pharmaceutically acceptable salts showing antibacterial properties. Compound of the general formula (I) is synthesized by interaction of hydroxy-substituted penem of the formula (II) with sulfonyl chloride derivative in an inert solvent. Synthesized derivative of sulfonyl of the formula (V) is subjected for interaction with compound of the formula (VI) at temperature from -20 to +20 C in an organic solvent followed by conversion of compound (VII) to compound of the formula (I) by hydrolysis, hydrogenolysis. Alternatively, compound of the formula (V) is subjected for interaction with halide of the formula (VIII) where Y - a group to be esterified and X - halide. Invention relates to also a pharmaceutical composition including a compound of the formula (I) taken at effective amount and pharmaceutically acceptable carrier. Compounds of the formulas (I)-(VIII) are given in description of an invention. EFFECT: improved method of synthesis, enhanced effectiveness of antibacterial composition. 8 cl, 2 tbl, 1 dwg, 9 ex