PHOSPHOINOSITIDE-3-KINASE INHIBITORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAID INHIBITORS Russian patent published in 2011 - IPC C07D495/04 C07D491/48 C07D519/00 A61K31/519 A61K31/5377 A61P35/00 

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formulae and including their stereoisomers, as well as pharmaceutically acceptable salt, where X denotes O or S; R¹ is selected from H, F, CI, Br, I, CN, -CR¹⁴R¹⁵-NR¹⁶R¹⁷, -CR¹⁴R¹⁵-NHR¹⁰, -(CR¹⁴R¹⁵)NR¹⁰R¹¹, -(CR¹⁴R¹⁵)_nNR¹²C(=Y)R¹⁰, -(CR¹⁴R¹⁵)_nNR¹²S(O)₂R¹⁰, -(CR¹⁴R¹⁵)_mOR¹⁰, -(CR¹⁴R¹⁵)_nS(O)₂R¹⁰, -C(OR¹⁰)R¹¹R¹⁴, -C(R¹⁴)=CR¹⁸R¹⁹, -C(=Y)OR¹⁰, -C(=Y)NR¹⁰R¹¹, -C(=Y)NR¹²OR¹⁰, -C(=O)NR¹²S(O)₂R¹⁰, -C(=O)NR¹²(CR¹⁴R¹⁵)_mNR¹⁰R¹¹, -NHR¹², -NR¹²C(=Y)R¹⁰, -S(O)₂R¹⁰, -S(O)₂NR¹⁰R¹¹, C₂-C₁₂ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₄ carbocyclyl, piperidinyl, thiopyranyl, phenyl or C₅-C₆ heteroaryl; R² is selected from H, C₂-C₁₂ alkyl and thiazolyl; R³ denotes a condensed bicyclic heteroaryl selected from indazole, indole, benzoimidazole, pyrrolopyridine, imidazopyridine and quinoline; R¹⁰, R¹¹ and R¹² independently denote H, C₂-C₁₂ alkyl, C₃ carbocyclyl, heterocyclyl selected from pyrrolidine, morpholine and piperazine, phenyl or heteroaryl selected from pyrazole, pyridine, benzothiophene; or R¹⁰ and R¹¹ together with a nitrogen atom with which they are bonded possibly form a saturated C₃-C₆ heterocyclic ring, possibly containing one additional ring atom selected from N or O, where said heterocyclic ring is possibly substituted with one or more groups independently selected from oxo, (CH₂)_mOR¹⁰, NR¹⁰R¹¹, SO₂R¹⁰, C(=O)R¹⁰, NR¹²S(O)R¹¹, C(=Y)NR¹⁰R¹¹, C₁-C₁₂ alkyl and heterocyclyl selected from pyrrolidine; R¹⁴ and R¹⁵ are independently selected from H or C₁-C₁₂ alkyl; R¹⁶ and R¹⁷ independently denote H or phenyl; R¹⁸ and R¹⁹ together with a carbon atom with which they are bonded form a C₃-C₂₀ heterocyclic ring, where said alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, phenyl, heteroaryl, piperidinyl and condensed bicyclic heteroaryl possibly substituted with one or more groups independently selected from F, CI, Br, I, CF₃, -C(=Y)R¹⁰, -C(=Y)OR¹⁰, oxo, R¹⁰, -C(=Y)NR¹⁰R¹¹, -(CR¹⁴R¹⁵)_nNR¹⁰R¹¹, -NR¹⁰R¹¹, -NR¹²C(=Y)R¹⁰, -NR¹²C(=Y)NR¹⁰R¹¹, -NR¹²SO₂R¹⁰, OR¹⁰, SR¹⁰, -S(O)₂R¹⁰, -S(O)₂NR¹⁰R¹¹, possibly substituted with carbocyclyl, selected from cyclopropyl, possibly substituted heterocyclyl selected from piperazine, possibly substituted with alkyl and alkylsulphonyl, pyrrolidine, morpholine, piperdine, possibly substituted CH₃, phenyl and possibly substituted heteroaryl selected from imidazole and triazole; Y denotes O; m equals 0, 1 or 2; n equals 1 and t equals 2. The invention also relates to a pharmaceutical composition which modulates lipid kinase activity, based on said compounds.

EFFECT: obtaining novel compounds and a composition based on said compounds, which can be used to treat lipid kinase-mediated diseases, for example, cancer.

48 cl, 2 tbl, 372 ex