2-THIOSUBSTITUTED CARBAPENEMS, INTERMEDIATE COMPOUNDS FOR SYNTHESIS, METHODS OF SYNTHESIS (VARIANTS), PHARMACEUTICAL COMPOSITION Russian patent published in 1999 - IPC

FIELD: organic chemistry, antibiotics, pharmacy. SUBSTANCE: invention relates to new antibiotics of carbapenem group and their nontoxic pharmaceutically acceptable salts exhibiting antibacterial activity. They can be used both separately and in combination with other antibiotics for treatment of human and animals with bacterial infections. Compounds of the formula (I) where moiety -S- means 5-membered heterocyclic substituted ring where: (A) Z means oxygen, sulfur atom; (B) R₀ means -CH(OR₄)CH₃ where R₄ means hydrogen atom; (C) R₁ means (C₁-C₃)-alkyl. Substituents of a group -S- are taken from (CH₂)_nR₂ where: (D) n is a whole number from 0 to 4; (E) R₂ means: (1) methyl-group, bromine, chlorine, iodine atom, -OSO₂CH₃, azido-group; (II) a group of the formula -S(O)_n″R^a where n'' is a whole number from 0 to 2; R^a means a group bound by carbon atom and taken from substituted or nonsubstituted (C₁-C₆)-alkyl, substituted or nonsubstituted phenyl, substituted or nonsubstituted phenyl-(C₁-C₆)-alkyl being chlorine, bromine atoms and hydroxy-group can be substituents; (III) R₂ is taken from hydroxy-group, OR^a, OC(O)NR^aR^a where R^a means independently values indicated above or where R₁₃ means and B^- is a physiologically acceptable anion; (IV) or R₂ means a residue bound by nitrogen atom and means: formula (a) where R^p means oxygen atom; R^L and R^J mean independently hydrogen atom, alkyl, substituted or nonsubstituted amine, heterocycle where heterocycle means 5- or 6-membered ring containing two atoms N or O; or R^L and R^J with the bound nitrogen atom form nonsubstituted monocyclic ring containing two heteroatoms taken independently form O or N being substituents are hydroxyl, oxo-group; (b) acyclic quaternary ammonium group of the formula: where R₇, R₈, R₉ mean alkyl; B^- is a physiologically acceptable anion; (V) or R₂ means a group bound by carbon atom and has a formula: where R₂ and R₃ are indicated above, and pharmaceutical acceptable salts of the compound described. Invention relates to also a method of synthesis of antibiotics of carbapenem group and some intermediate compounds. Invention proposes methods of treatment of human and animals with infectious diseases that involve administration of the above indicated compounds to human or animals and pharmaceutical preparations containing these compounds. EFFECT: improved method of synthesis and treatment. 6 cl, 14 dwg, 409 ex