BICYCLIC DERIVATIVES Russian patent published in 2023 - IPC C07D405/12 C07D311/68 C07D471/04 C07D519/00 A61K31/4375 A61K31/4709 A61K31/472 A61K31/353 A61K31/4725 A61P33/10 

FIELD: pharmaceuticals.

SUBSTANCE: invention relates to a compound of formula (I) or a veterinarily or pharmaceutically acceptable salt thereof or their use for the manufacture either as a drug for the treatment and/or control of D. immitis, H. contortus, T. colubriformis, A. viteae, or L. sigmodontis. In the general formula (I), n is 0 or 1; X1 is N; X2 is CR2; X3 is CR3; X4 is CR4; X5 is CR5; and X6 is N; X1 is CR1; X2 is CR2; X3 is CR3; X4 is CR4; X5 is N; and X6 is CR6; X1 is N; X2 is CR2; X3 is CR3; X4 is CR4; X5 is N; and X6 is CR6; X1 is N; X2 is CR2; X3 is CR3; X4 is CR4; X5 is CR5; and X6 is CR6; X1 is CR1; X2 is CR2; X3 is CR3; X4 is CR4; X5 is CR5; and X6 is CR6; X1 is CR1; X2 is CR2; X3 is N; X4 is CR4; X5 is CR5; and X6 is CR6; X1 is CR1; X2 is N; X3 is CR3; X4 is CR4; X5 is CR5; and X6 is CR6; G is a group Y1 is selected from the group consisting of CR8R9, O, and S; Y2 is selected from the group consisting of CR8R9, O, and S; where at least one of the Y1 or Y2 groups is CR8R9; Z1 is selected from the group consisting of N and CR11; Z2 is CR11; Z3 is absent or selected from the group consisting of N and CR11;

Z4 is selected from the group consisting of O, S and CR11; and Z3 is absent only if Z4 is O or S; R1, R2, R3 are hydrogen; R4 is selected from the group consisting of halo, cyano, hydroxyl, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, - NH(C3-C6 cycloalkyl), -N(C1-C4 alkyl)(C3-C6 cycloalkyl), -N(C1-C4 alkyl)(C1-C4 alkoxy), 6-membered aryl; and a monocyclic heterocycle selected from the group consisting of 4–7 membered heterocycloalkyl containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, a 5-membered heteroaryl containing one nitrogen atom, through which the 5-membered the heteroaryl ring is attached to the rest of the molecule; 6-membered heteroaryl containing one nitrogen atom; each of the aryl, heterocycloalkyl, and heteroaryl rings in R4 is optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, hydroxyl, oxo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy; and where each of C1-C4 alkyl, C3-C6 cycloalkyl and C1-C4 alkoxy in R4 may be optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, hydroxyl,

-NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, cyano and C1-C4 alkoxy; R5, R6, R7, R8, R9 are hydrogen; R11 is at each occurrence independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl; and Q is selected from the group consisting of 6- or 10-membered aryl optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, hydroxyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3- C6cycloalkyl,

-NH2, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NH(C3-C6 cycloalkyl), -N(C1-C4 alkyl)(C3-C6 cycloalkyl), where 6- or 10-membered aryl is optional fused to a 4-7 membered heterocycloalkyl containing 1 or 2 N heteroatoms, and wherein the carbon atoms of the heterocycloalkyl are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl , C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2, and any N in heterocycloalkyl, if valency permits, is substituted with a substituent selected from the group consisting of hydrogen, C1-C4 alkyl and C3-C6 cycloalkyl; 5-10 membered heteroaryl containing 1 or 2 N heteroatoms, and wherein the carbon atoms of the 5-10 membered heteroaryl are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2, and any N in heteroaryl, if valency permits, is optionally substituted with a substituent selected from the group consisting of hydrogen, C1-C4 alkyl and C3-C6 cycloalkyl; 4-7 membered heterocycloalkyl containing 1 or 2 N heteroatoms, wherein the heterocycloalkyl is optionally benzo-fused, wherein the carbon atoms of the 4-7 membered heterocycloalkyl or optionally benzo-fused 4-7 membered heterocycloalkyl are optionally substituted with 1, 2, 3 or 4 substituents independently selected from the group consisting of halo, cyano, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl) and -N(C1-C4 alkyl)2, and any N in heterocycloalkyl is optionally substituted with a substituent selected from the group consisting of hydrogen, C1-C4 alkyl and C3-C6 cycloalkyl; 6- or 10-membered aryloxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl ), -N(C1-C4 alkyl)2; 6- or 10-membered arylthiooxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, -NH2, -NH(C1-C4 alkyl ), -N(C1-C4alkyl)2.

EFFECT: development of compounds for treatment and/or control of endoparasites D. immitis, H. contortus, T. colubriformis, A. viteae, or L. sigmodontis.

8 cl, 1 tbl, 12 ex