8-METHYL-1-PHENYLIMIDAZO[1,5-a]PYRAZINE COMPOUNDS Russian patent published in 2015 - IPC C07D487/04 C07D519/00 A61K31/4985 A61P29/00 A61P37/00 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to novel 8-methyl-1-phenylimidazo[1,5-a]pyrazine derivatives of formula

or pharmaceutically acceptable salts thereof, where R1 is 1-2 groups independently selected from hydrogen, hydroxy, (1-6C)alkoxy, halogen; R2 is H or (1-6C)alkyl; R3 is (R31)(R32)CH-O; or (1-6C)alkoxy; or heteroaryl, which is an indole, pyrrole, indazole, pyrrolopyridine, thienopyrrole, optionally substituted with 1-2 groups selected from R34, R35, R36, halogen, hydroxy; R31 is (1-5C)alkyl, optionally substituted with one hydroxy; R32 is (1-5C)alkyl; R34 is (1-6C)alkyl; R35 is (1-6C)alkoxy; R36 is hydrogen or (1-6C)alkyl; R4 is or or R4 is (1-4C)alkyl, independently substituted with 1 substitute selected from R8, hydroxy; where m, n, r equals 1 or 2; Y is CR5 or N; X is O, CHR6, C(R66)(R67), NR7, C=O; Z is O or Z forms with R9 a 5-member heterocyclyl substituted with R91; R5 is H or (1-6C)alkyl; R6 is R61, R62, R63, R65, H, hydroxy; R7 is R71, R72, R73, R74, H; R8 is imidazole; R9: H or (1-6C)alkyl, optionally substituted with one or more fluorine atoms; R61 is amino(1-4C)alkyl, [(1-6C)alkyl]amino(1-4C)alkyl, (di)[(1-6C)alkyl]amino(1-4C)alkyl, [(1-4C)alkylcarbonyl]amino(1-4C)alkyl, [(1-4C)alkoxycarbonyl]amino(1-4C)-alkyl; R62 is (1-4C)alkylcarbonyloxy, (3-6C)cycloalkylaminocarbonyloxy; R63 is amino, [(1-6C)alkyl]amino, (di)[(1-6C)alkyl]amino, [(1-6C)alkoxy(2-6C)alkyl]amino, [(1-6C)alkyl][(1-6C)alkoxy(2-6C)alkyl]amino, [(1-6C)-alkylcarbonyl][(1-6C)alkoxy(2-6C)alkyl]amino; all alkyl groups in R63 are optionally substituted with 2 fluorine atoms; R65 is an N-bonded heterocyclyl, which is pyrazine, azetidine, morpholine, optionally substituted with 1 oxo group, or 2 fluorine atoms or one R651 group; R66 is [(1-6C)alkyl]amino(1-4C)alkyl; R67 is hydroxy; R71 is (1-6C)alkyl; R72 is (1-4C)alkyl, substituted with 1 R725 group; R73 is R732carbonyl, R733carbonyl or R735carbonyl; R74 is a heterocyclyl which is tetrahydropyran or piperidine, optionally substituted with one R741 group; R91 is (1-6C)alkyl, substituted with 3 fluorine atoms; R651 is (1-4C)alkyl, (1-4C)alkylcarbonyl; R725 is (di)[(1-6C)alkyl]-aminocarbonyl; R732 is (1-4C)alkyl, amino(1-4C)alkyl, (di)[(1-6C)alkyl]-amino(1-4C)alkyl, hydroxy(1-4C)alkyl, (1-6C)alkoxy(1-4C)alkyl; R733 is (1-6C)alkoxy; R735 is amino; R741 is (1-4C)alkylcarbonyl. The invention also relates to use of the compound of formula I.

EFFECT: obtaining novel 8-methyl-1-phenylimidazo[1,5-a]pyrazine derivatives which are useful in treating an Lck-mediated condition.

14 cl, 1 t bl, 77 ex