Patent RU-2322444-C2 (RU)
Inventor: NATESAN SEL VAKUMAR
IPC: C07D263/20
Filed: 2001-12-26
Granted: 2008-04-20
Abstract: FIELD: organic chemistry, medicine. 
     SUBSTANCE: invention relates to compound of the formula (I):   wherein R 1  represents azido, -OR 4 , -NHR 4  wherein R 4  represents hydrogen atom or unsubstituted groups chosen from acyl, thioacyl, (C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 6 )-cycloalkoxythiocarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-alkenylcarbonyl, (C 1 -C 6 )-alkoxythiocarbonyl, (C 2 -C 6 )-alkenyloxythiocarbonyl, -C(=O)-C(=O)-(C 1 -C 6 )-alkoxy, -C(C=S)-S-(C 1 -C 6 )-alkyl, -(C=S)-NH 2 , -(C=S)-NH-(C 1 -C 6 )-alkyl, -C(=S)-N-((C 1 -C 6 )-alkyl) 2 , -C(=S)-NH-(C 2 -C 6 )-alkenyl, -C(C=S)-(C=O)-(C 1 -C 6 )-alkoxy, thiomorpholinylthiocarbonyl; R 2  and R 3  can be similar or different and represent independently hydrogen atom, halogen atom, (C 1 -C 6 )-alkyl group, halogen-(C 1 -C 6 )-alkyl; heterocyclic moiety represents 5-membered heterocycle wherein Z represents sulfur (S), oxygen (O) atom or -NR b  wherein R b  represents hydrogen atom or unsubstituted (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, aryl or aryl-(C 1 -C 6 )-alkyl; Y 1  represents group =O or =S ; Y 2  and Y 3  represent independently hydrogen atom, and if Y 2  and Y 3  present in common on adjacent carbon atoms then they form 6-membered aromatic cyclic structure substituted if necessary with (C 1 -C 6 )-alkyl, or to its pharmaceutically acceptable salt. Also invention relates to a pharmaceutical composition possessing antibacterial activity and containing as an active compound the compound of the formula (I) taken in the effective dose and a pharmaceutically acceptable carrier, diluting agent, excipient. Also, invention relates to method for synthesis of compound of the formula (I). Method for synthesis of compound of the formula (I) wherein R 1  represents group -NHR 4  wherein R 4  means acyl, (C 1 -C 6 )-alkoxycarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-alkenylcarbonyl, -C(=O)-C(=O)-(C 1 -C 6 )-alkoxy and -(C=S)-S-(C 1 -C 6 )-alkyl involves acetylation of compound of the formula (I) wherein R 1  represents -NHR 4  group wherein R 4  represents hydrogen atom and all symbols are given above and using halide. Method for synthesis of compound of the formula (I) wherein R 1  represents -NHR 4  group wherein R 4  means thioacyl, (C 3 -C 6 )-cycloalkoxythiocarbonyl, (C 1 -C 6 )-alkoxythiocarbonyl, (C 2 -C 6 )-alkenyloxythiocarbonyl involves the following steps: (i) conversion of compound of the formula (I) wherein R 1  represents -NHR 4  wherein R 4  represents hydrogen atom, and all symbols are given above to compound of the formula (I) wherein R 1  represents isothiocyanate group by reaction with thiophosgene, and (ii) conversion of compound of the formula (I) wherein R 1  represents isothiocyanate group to compound of the formula (I) wherein R 1  represents -NHR 4  wherein R 4  represents -C(=S)-OR 4d  wherein R 4d  represents (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, and all symbols are given above, in reaction with alcohol. Compounds of the formula (I) are used in treatment of bacterial infection that involves administration of compound of the formula (I) in a patient needing in this treatment. Invention provides synthesis of oxazolidinone compounds possessing antibacterial activity. 
     EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved method of synthesis. 
     7 cl, 1 tbl, 144 ex