BICYCLIC HETEROCYCLES AND USE THEREOF AS HIV INTEGRASE INHIBITORS Russian patent published in 2010 - IPC C07D498/04 A61K31/519 A61P31/18 

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula I with anti-HIV activity , where R¹ represents C_1-6(Ar¹)alkyl or C_1-6(Ar¹)oxyalkyl; R² represents hydrogen or OR¹⁴; R³ represents hydrogen, halogen, hydroxyl, cyano, C_1-6alkyl, C_5-7cycloalkenyl, C_1-6halogenalkyl, C_1-6alkoxy, C_1-6alkylthio, N(R⁸)(R⁹), NHAr², N(R⁶)COR⁷, OCON(R⁸)(R⁹), OCH₂CON(R⁹)(R⁹), CO₂R⁶, CON(R⁸)(R⁹), SOR⁷, S(=N)R⁷, SO₂R⁷, SO₂N(R⁶)(R⁶), PO(OR⁶)2, C_2-4(R¹²)alkynyl, R¹³, Ar² or Ar³; R⁴ represents hydrogen, halogen, C_1-6alkyl or C_1-6alkoxy; R⁵ represents hydrogen, halogen, C_1-6alkyl or C_1-6alkoxy; R⁶ represents hydrogen or C_1-6alkyl; R⁷ represents C_1-7alkyl; R⁸ represents hydrogen or C_1-6alkyl; R⁹ represents hydrogen, C_1-6alkyl, C_1-6hydroxyalkyl or C_1-6(C_1-6dialkylamino)alkyl; or N(R⁸)(R⁹) taken together represent azetidinyl, pyrrolydinyl, (R¹⁰)-piperidinyl, N-(R¹¹)-piperazinyl, morpholinyl or dioxothiazinyl; R¹⁰ represents hydrogen; R¹¹ represents hydrogen, C_1-6alkyl, COR⁶ or CO₂R⁶ ; R¹² represents hydrogen, hydroxyl, N(R⁶)(R⁶), OSO₂R⁷ or dioxothiazinyl; R¹³ represents dioxothiazinyl; R⁴ represents hydrogen or C_1-6alkyl; Ar¹ represents ,,, ,,,,,; or Ar² represents tetrazolyl, triazolyl, thiadiazolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, furanyl, thienyl, pyrrolyl, pyrimidinyl, pyrazinyl, pyridinyl, quinolinyl or indolyl, and is substituted with 0-2 substitutes selected from a group consisting of halogen, benzyl, C_1-6alkyl, C_1-6alkoxy, N((R⁸)(R⁹), CON(R⁸)(R⁹) and CO₂R⁸; Ar³ represents phenyl substituted with 0-2 substitutes selected from a group consisting of halogen, cyano, hydroxy, C_1-6alkyl, C_1-6alkoxy, (C_1-6alkoxy)methyl, C_1-6halogenalkoxy, N(R⁸)(R⁹), CON(R⁶)(R⁶) and CH₂N(R⁸)(R⁹), or represents dioxolanylphenyl; and X-Y-Z represents C(R¹⁴)₂OC(R¹⁴)₂C(R¹⁴)₂, C(R¹⁴)₂OC(R¹⁴)₂C(R¹⁴)₂C(R¹⁴)₂; or pharmaceutically acceptable salt thereof. The invention also relates to a pharmaceutical composition.

EFFECT: bicyclic heterocycles are disclosed, as well as their use HIV integrase inhibitors.

21 cl, 38 dwg, 8 tbl, 282 ex