PROCESS FOR PREPARING (S)-3-AMINO-1-SUBSTITUTED PYRROLIDINE, INTERMEDIATE PRODUCTS FOR SYNTHESIS THEREOF AND INTERMEDIATE PRODUCTS FOR SYNTHESIS OF ANTIBACTERIAL AGENTS BASED ON QUINOLONE

摘要

FIELD: medicine. SUBSTANCE: claimed invention describes process for preparing (S)-3- amino-1-substituted pyrrolidine derivatives which comprises protecting amino group of L-asparaginic acid, treating N-protected L-asparaginic acid using primary amine for preparation of (S)-3-amino-1-substituted pyrolidine, removing the protecting group used and recovering the desired product, and the amino group of L- asparaginic acid is protected by reacting with alkylsulfonyl-or arylsulfonyl halogen and the N-protected L-asparaginic acid is treated by reducing the latter or its lower dialkyl ester with reducing hydride the resulting N-protected 1,4-butanediol is reacted with about two equivalents of thionyl halogen or alkylsulfonyloxy or arylsulfonyloxy halogen in the presence of about three equivalents of base, and the resulting compound of formula: wherein Z is alkylsulfonyl or arylsulfonyl and L is halogen, alkylsulfonyloxy or arylsulfonyloxy is reacted with primary amine of formula: NH₂ wherein R is benzyl, unsubstituted or substituted with lower alkyl or lower alkoxy, or benzhydryl in the presence of tertiary amine to obtain 1-R-3 (protected amino) pyrrolidine in which R is as defined above, and the protecting group is removed by hydrolysis or reduction. The claimed invention also describes (S) azeridine derivatives of formula: wherein L is halogen or alkylsulfonyloxy or arylsulfonyloxy, and Z is alkylsulfonyl or arylsulfonyl which are intermediate products for synthesis of the above-identified (S)-3-amino-1-substituted pyrolidine derivatives. The claimed invention describes 1-benzyl-3- L[(tert-butoxycarbonylamino) propionylamino] pyrrolidine which is intermediate product for synthesis of antibacterial agents based on quinolone derivatives. EFFECT: improved properties of the title compounds.