HETEROCYCLIC COMPOUND Russian patent published in 2021 - IPC C07D213/42 C07D213/65 C07D213/68 C07D213/73 C07D213/75 C07D239/20 C07D253/06 C07D401/12 A61K31/437 A61K31/4375 A61K31/44 A61K31/4406 A61K31/444 A61K31/4965 A61K31/495 A61K31/497 A61K31/505 A61K31/53 A61P35/00 

FIELD: pharmaceutical industry.

SUBSTANCE: invention relates to a compound of formula (I)

where (1) ring A is represented by the formula

where the combination of X¹, X² and X³ (X¹, X², X³) is (carbon atom, carbon atom, carbon atom) or (carbon atom, carbon atom, nitrogen atom); R¹ represents (1) a fluorine atom, a chlorine atom, a bromine atom, (2) methyl, trifluoromethyl, or (3) a hydroxy group substituted with methyl or trifluoromethyl; R² is (1) a halogen atom, (2) a cyano group, (3) a C_1-6 alkyl group optionally substituted with 1-3 substituents selected from a halogen atom and a hydroxy group, (4) a C_1-6 alkoxy group optionally substituted with 1-3 halogen atoms , or (5) a mono- or di-C_1-6 alkylamino group; and Ring B is optionally further substituted with 1-3 substituents selected from (1) a halogen atom, (2) a C_1-6 alkyl group optionally substituted with 1-3 hydroxy groups, and (3) a C_1-6 alkoxy group, or (2) Ring A is represented by the formula

where the combination of X⁴ and X⁵ (X⁴, X⁵) is (carbon atom, carbon atom); ring C is optionally further substituted with 1 to 3 halogen atoms; ring D is a 5-7-membered aromatic heterocycle containing, as ring-forming atoms, in addition to carbon atoms, from 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom, or a 5-7-membered non-aromatic heterocycle, containing, as ring-forming atoms, in addition to carbon atoms, from 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom; ring D is optionally further substituted with 1-3 substituents selected from (1) a halogen atom and (2) a hydroxy group; X⁶ represents a hydrogen atom, a fluorine atom or a chlorine atom; X⁷ represents a fluorine atom or a chlorine atom; the combination of X⁸ and X⁹ (X⁸, X⁹) is (carbon atom, nitrogen atom), (nitrogen atom, carbon atom) or (nitrogen atom, nitrogen atom); ring E is optionally further substituted with 1-3 substituents selected from (1) a C_1-6 alkyl group and (2) an amino group; and X¹⁰ is an amino group optionally substituted with 1-2 substituents selected from (1) a C_1-6 alkyl group optionally substituted with 1-3 substituents selected from a hydroxy group and a 3-14-membered non-aromatic heterocyclic group containing as ring-forming atoms, in addition to carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom, (2) a C_3-10 cycloalkyl group optionally substituted with 1-3 hydroxy groups, (3) a 3-14-membered non-aromatic heterocyclic group containing as ring-forming atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom, and (4) a 5-14 membered aromatic heterocyclic group containing as ring-forming atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom, optionally substituted by 1-3 C_1-6 alkyl groups; or X⁹ and X¹⁰ are connected to each other to form a 5-14-membered aromatic heterocycle containing, as ring-forming atoms, in addition to carbon atoms, from 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom, or 3-14-membered non-aromatic heterocycle containing, as ring-forming atoms, in addition to carbon atoms, from 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom, each of which is optionally substituted with an oxo group, or pharmacologically acceptable salts thereof.

EFFECT: present compounds have an inhibitory effect on GCN2 and are useful for the prevention or treatment of GCN2-associated diseases including cancer.

16 cl, 8 tbl, 193 ex