SUBSTITUTED PYRROLO[2,3-B]PYRIDINE AND PYRAZOLO[3,4-B]PYRIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS Russian patent published in 2024 - IPC C07D471/04 A61K31/437 A61P35/00 

FIELD: chemistry; pharmaceutics.

SUBSTANCE: invention relates to compounds which can inhibit Bruton’s tyrosine kinase (BTK) activity, specifically to a compound of formula (II) or a pharmaceutically acceptable salt thereof. In formula (II): ring Q is selected from , and , which are each unsubstituted or substituted with at least one substitute independently selected from R^X; L represents O; X¹, X², X³ and X⁴ independently selected from CR^X’ and N, where not more than 1 of X¹, X², X³ and X⁴ can represent N; R¹ is C_1-10alkyl, where alkyl is unsubstituted or substituted with at least one substituent independently selected from R^X1; R² is selected from hydrogen, halogen, CN, -OR^A2, -C(O)NR^A2R^B2 and C_1-10alkyl, where alkyl is unsubstituted or substituted with at least one substituent independently selected from R^X2; R³ is hydrogen; R⁴ is hydrogen; R⁵ is selected from phenyl and heteroaryl, where phenyl and heteroaryl are each unsubstituted or substituted with at least one substituent independently selected from R^X5; each R^A2 is independently selected from hydrogen, C_1-10alkyl and C_3-10cycloalkyl, where alkyl and cycloalkyl are each unsubstituted or substituted with at least one substituent independently selected from R^X2; every R^B2 is hydrogen; each R^X' is independently selected from hydrogen, deuterium, C_1-10alkyl, C_3-10cycloalkyl, halogen, CN and -(CR^c1R^d1)_tOR^b1; each R^X is independently selected from hydrogen, C_1-10alkyl, -(CR^c1R^d1)_tOR^b1, (CR^c1R^d1)_tNR^a1C(O)R^bl, -(CR^clR^dl)tNR^a1C(O)OR^bl and -(CR^clR^d1)_tNR^alS(O)₂NR^alR^bl, where alkyl is unsubstituted or substituted with at least one substituent independently selected from R^Y; each R^X1 is independently selected from hydrogen, halogen, CN, -(CR^clR^dl)tOR^bl, -(CR^clR^dl)_tNR^a1C(O)R^bl, -(CR^clR^dl)_tNR^alC(O)OR^bl, -(CR^clR^dl)_tNR^alC(O)NR^alR^bl, -(CR^clR^dl)_tN=S(O)R^alR^bl, -(CR^clR^dl)_tNR^alS(O)_rR^bl and -(CR^clR^dl)_tNR^alS(O)₂NR^alR^bl; R^X2 is deuterium; each R^X5 is independently selected from hydrogen, halogen, CN, NO₂ and -(CR^clR^dl)_tOR^b1; each R^al and each R^bl is independently selected from hydrogen, C_1-10alkyl and C_3-10cycloalkyl; each R^cl and each R^dl is hydrogen; each R^Y is independently selected from -OR^a2, -(CR^c2R^d2)_tOR^b2, -(CR^c2R^d2)_tNR^a2C(O)R^b2, -(CR^c2R^d2)_tNR^a2CO₂R^b2, -(CR^c2R^d2)_tNR^a2SO₂NR^a2R^b2, -NR^a2C(O)R^b2, -NR^a2C(O)^ORb2, -CHF₂, -CF₃, -OCHF₂ and -OCF₃; each R^a2 and each R^b2 is independently selected from hydrogen and C_1-10alkyl; each R^c2 and each R^d2 is hydrogen; each r is selected from 0, 1 and 2; each t is selected from 0, 1, 2, 3 and 4; heteroaryl is 5–8-membered monocyclic aromatic ring containing one heteroatom selected from N. Also disclosed is a pharmaceutical composition and use of said compound.

EFFECT: disclosed compounds are capable of inhibiting BTK and can be used for treating, relieving or preventing a condition which is caused by BTK inhibition, and for treating cell proliferation disorders.

19 cl, 4 tbl, 198 ex