SUBSTITUTED COMPOUNDS OF THIOPHEN AND FURAN-CONDENSED AZOLOPYRIMIDIN-5-(6H)-OH Russian patent published in 2018 - IPC C07D491/147 C07D495/14 C07D491/22 C07D495/22 C07D487/22 A61K31/519 A61P25/28 A61P9/00 A61P1/00 A61P7/00 

FIELD: medicine.

SUBSTANCE: invention relates to a novel compound of formula I or a pharmaceutically acceptable salt thereof having a selective impact on PDE1. In formula I

X represents -CH- or -N-; Y - O- or -S-; M is 0-3; each of R¹ is independently selected from the group consisting of: H, halogen, -C_1-6alkyl, -C_1-6haloalkyl, -C_1-6alkoxy, -C_1-6haloalkoxy, and phenyl; each of R³ and R⁴ is independently selected from the group consisting of: -H; halogen; -C_1-6alkyl; -C_1-6haloalkyl; -CH₂OH; -C_1-6alkoxy; -C_1-6haloalkoxy; optionally substituted 5- or 7-membered heteroaryl having 1-3 heteroatoms selected from: N, O, or S, in which the substituents are independently selected from C₁-C₆alkyl, HOCH₂, halogen, -CH₂N(C₁-C₄alkyl)-C(=O)-, N(C₁-C₄alkyl)₂, -CH₂N(C₁-C₄alkyl)₂, benzyl, -CH₂-5-7-membered monoheterocycloalkyl having 1 to 2 heteroatoms selected from N, O, optionally substituted C₁-C₄alkyl, oxo, C₁-C₄alkylsulfonyl, or -CH₂-5-6-membered monoheterocycloalkyl having a nitrogen atom in the ring condensed with a benzene ring, or -CH₂-7-9-membered bicyclic heterocycloalkyl having 1 to 2 heteroatoms selected from N or O; -(C₁-C₆alkyl)phenyl; -(C₁-C₆alkyl)-5-6-membered heteroaryl having 1 to 2 heteroatoms selected from N and O, and -(CR¹⁰R¹¹)_1-3NR¹²R¹³; or R³ and R⁴, taken together with the carbon atoms to which they are attached, form a saturated or unsaturated monocyclic ring system having the following structure: where D is a bond, or -O-, or -N(R⁹)-, where R⁹ represents -H, -C_1-6alkyl, -halogen-C_1-6alkyl, -C_1-6alkylthiomethyl, -C_1-6alkyl-SO₂methyl, -C_1-6alkoxyC_1-6alkyl, -halogen_1-6alkoxyalkyl, -C_1-6alkylphenyl, -C_1-6alkyl (C_3-6cycloalkyl), -C_1-6alkyl (4-6-membered saturated heterocycloalkyl with 1-2 heteroatoms, selected from N and O), -C_1-6alkyl(phenyl, optionally condensed with 5-6 membered saturated heterocycloalkyl with 1-2 heteroatoms, selected from O), C_1-6alkyl (5-6 membered heteroaryl with 1 to 3 heteroatoms selected from N, S or -SO₂) or 4-6 membered heterocycloalkyl with heteroatoms selected from O, S, wherein each of said substituents is optionally substituted with -Cl, -F or -CH₃; each of m and n is independently 0-3 upon condition that the sum of m and n is 1-3, when D is -O-, -N(R⁹) -, or is 2-3 when D represents a bond; and with the proviso that when D is a bond, R¹ does not represent -Cl in the para position; each of R⁵, R⁶, R⁷, R⁸ is independently selected from the group consisting of: -H, -C_1-6alkyl, -C_1-6haloalkyl, -OH, -C_1-6alkoxy, -C_1-6haloalkoxy; each of R¹⁰ and R¹¹ is independently selected from the group consisting of: -H, -C_1-6alkyl, -hydroxyC_1-6alkyl, -C_1-6alkoxyC_1-6alkyl, CH₂OH, -OH, -COCH₃, and -SO₂CH₃; each of R¹² and R¹³ is independently selected from the group consisting of: -H, -C_1-6alkyl, -C_3-6cycloalkyl, -C_1-6alkyl(phenyl), -C_1-6alkyl (5-6 membered heteroaryl with 1-2 heteroatoms selected from N and O), and -CH₂CON (C_1-6alkyl)₂; or R¹² and R¹³, taken together with the nitrogen atom to which they are attached form a 5-7 membered mono- or 7-9 membered bicyclic heterocycloalkyl ring with 1-2 heteroatoms selected from N and O, optionally substituted with one or two R¹⁴, where each R¹⁴ is independently selected from the group consisting of -H and -C_1-6alkyl.

EFFECT: compounds can be used in the treatment of a disease or disorder selected from the group comprising a variety of diseases and disorders, including cognitive deficits associated with diseases and disorders of the central nervous system, neurological disorders, cardiovascular disorders, renal disorders, hematologic disorders, disorders of the gastrointestinal tract and liver, cancerous disorders and neurodegenerative disorders.

56 cl, 1 tbl, 224 ex