O-METHYL DERIVATIVES OF AZITHROMYCIN A SHOWING ANTIBACTERIAL ACTIVITY, AZITHROMYCINS AS INTERMEDIATE COMPOUNDS FOR SYNTHESIS OF O-METHYL DERIVATIVES OF AZITHROMYCIN A AND A METHOD OF SYNTHESIS OF O-METHYL DERIVATIVES OF AZITHROMYCIN A Russian patent published in 1995 - IPC

FIELD: organic chemistry. SUBSTANCE: products: azithromycin derivatives of the formula (I) at corresponding meanings of radicals or pharmaceutically acceptable salts with inorganic or organic acids. Method of synthesis involves benzylation of azithromycin, O-methylation of C-6, C-11, C-4 hydroxy-groups at 2′,, O, 3′-N-bis(benzylhydroxycarbonyl)-N-demethylerythromycin followed by separation by column chromatography on silica gel and some additional stages. Ia R¹=R²=CO₂CH₂C₆H₅, R³= CH₃, R⁴=R⁵=H Ib R¹=R²=CO₂CH₂C₆H₅, R³= R⁴=CH₃R⁵=H Ic R¹=R²=CO₂CH₂C₆H₅, R³= R⁵=H , R⁴=CH₃ Id R¹=R²=CO₂CH₂C₆H₅, R³= R⁴= R⁵= CH₃ Ie R¹=R²= R⁴= R⁵=H, R³=CH₃ If R¹=R²=R⁵=H, R³=R⁴= CH₃ Ig R¹=R²=R³= R⁵=H, R⁴=CH₃ Ih R¹=R²= H, R³= R⁴=R⁵=CH₃ Ii R¹=R⁴=R⁵=H, R²=R³= CH₃ Ij R¹=R⁵=H, R²=R³=R⁴=CH₃ Ik R¹=R³=H, R²= R⁴=CH₃ Ie R¹=H, R²= R³=R⁴=R⁵=CH₃. EFFECT: improved method of synthesis. 15 cl