SYNTHESIS OF CARBAMOYL PYRIDONE INHIBITORS OF HIV INTEGRASE AND INTERMEDIATE COMPOUNDS Russian patent published in 2014 - IPC C07D491/147 C07D471/22 A61K31/4355 A61K31/436 A61K31/437 A61P31/18 

FIELD: chemistry.

SUBSTANCE: invention relates to improved method of obtaining pyridine compounds (AA),(BB) and (CC) of respective formulas:

,

,

.

said compounds possess inhibiting action with respect to HIV-integrase. method consists in carrying out the following stages: P-1) bromination of compound of formula (I-I) with obtaining bromine-compound of formula (II-II)

,

where value R represents -CHO, -CH(OH)₂, -CH(OH)(OR⁴), -CH(OH)-CH₂OH or -CH(OR⁵)(OR⁶); P¹ represents benzyl; P³ represents H or protective group of carboxyl; R⁴ represents lower alkyl; R⁵ and R⁶ independently represent lower alkyl or R⁵ and R⁶ can represent alkyl and be connected with formation of 5-, 6- or 7-member ring, P-2) formation of side chain of 2,4-di-fluorophenyl-CH₂-NH-C(O)- with application of reagents 2,4-di-fluorophenyl-CH₂-NH₂ and carbon monoxide, stage of formation of Q ring by means of respective amine, selected from 3-amino-butan-1-ol, 2-amino-propan-1-ol and 2-pyrrolidinyl methylamine, and stage of debenzylation with obtaining compound of formula (AA), (BB) or (CC), where said stage P-2 is carried out after formation of Q ring.

EFFECT: method makes it possible to simplify obtaining target compounds due to carrying out regioselective bromination at the first stage.

6 cl, 3 ex, 7 dwg