RU2021121071A - BICYCLIC DERIVATIVES - Google Patents

Claims (199)

1. Compound of formula (I),

where n is 0 or 1; X ₁ is selected from the group consisting of N and CR ₁ ; X ₂ is selected from the group consisting of N and CR ₂ ; X ₃ is selected from the group consisting of N and CR ₃ ; X ₄ is selected from the group consisting of N and CR ₄ ; X ₅ is selected from the group consisting of N and CR ₅ ; X ₆ is selected from the group consisting of N and CR ₆ ; where at least one of X ₁ , X ₂ , X ₃ and X ₅ is N, or where none of X ₁ , X ₂ , X ₃ , X ₄ , X ₅ ; and X ₆ is not N; G is a group

; Y ₁ is selected from the group consisting of CR ₈ R ₉ , O, S and NR ₁₀ ; Y ₂ is selected from the group consisting of CR ₈ R ₉ , O, S and NR ₁₀ ; where at least one of the groups Y ₁ or Y ₂ represents CR ₈ R ₉ ; Z ₁ is selected from the group consisting of N, O, S and CR ₁₁ ; Z ₂ is absent or selected from the group consisting of N and CR ₁₁ ; Z ₃ is absent or selected from the group consisting of N and CR ₁₁ ; Z ₄ is selected from the group consisting of N, O, S and CR ₁₁ ; where at most 2 of Z ₁ , Z ₂ , Z ₃ and Z ₄ are N, and where only one of Z ₁ and Z ₄ is O or S, Z ₂ is absent only if Z ₁ is O or S, and Z ₃ is absent only if Z ₄ is O or S; R ₁ is selected from the group consisting of hydrogen, halogen, hydroxyl, -SH, -SC ₁ -C ₄ alkyl, -S(O)(C ₁ -C ₄ alkyl, -S(O) ₂ (C ₁ -C ₄ alkyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkoxy, -B(OR ₁₂ )(OR ₁₃ ), where R ₁₂ in each individual case is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, R ₁₃ in each case selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, or R ₁₂ and R ₁₃ together with the oxygen atoms to which they are attached form a 5-7 membered ring, which is optionally substituted with 1-4 C ₁ -C ₄ alkyls, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ ; R ₂ is selected from the group consisting of hydrogen, halogen, hydroxyl, -SH, -SC ₁ -C ₄ alkyl, -S(O)(C ₁ -C ₄ alkyl, -S(O) ₂ (C ₁ -C ₄ alkyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkoxy, -B(OR ₁₂ )(OR ₁₃ ), where R ₁₂ in each individual case is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, R ₁₃ in each case selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, or R ₁₂ and R ₁₃ together with the oxygen atoms to which they are attached form a 5-7 membered ring, which is optionally substituted with 1-4 C ₁ -C ₄ alkyls, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ ; R ₃ is selected from the group consisting of hydrogen, halogen, hydroxyl, -SH, -SC ₁ -C ₄ alkyl, -S(O)(C ₁ -C ₄ alkyl, -S(O) ₂ (C ₁ -C ₄ alkyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkoxy, -B(OR ₁₂ )(OR ₁₃ ), where R ₁₂ in each individual case is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, R ₁₃ in each case selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, or R ₁₂ and R ₁₃ together with the oxygen atoms to which they are attached form a 5-7 membered ring, which is optionally substituted with 1-4 C ₁ -C ₄ alkyls, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ ; R ₄ is selected from the group consisting of halogen, cyano, -CHO, hydroxyl, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-substituted C ₁ -C ₄ alkyl, benzyl optionally substituted with 1-5 halogen atoms, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl), - N(C ₁ -C ₄ alkyl) ₂ , -NH(C ₃ -C ₆ cycloalkyl), -N(C ₁ -C ₄ alkyl)(C ₃ -C ₆ cycloalkyl), -NH(4-7 membered heterocycloalkyl ), -N(C ₁ -C ₄ alkyl)(4-7-membered heterocycloalkyl), -N(C ₁ -C ₄ alkyl)(C ₃ -C ₆ cycloalkyl), -N(C ₁ -C ₄ alkyl) (C ₁ -C ₄ alkoxy), -C (O) NH (C ₁ -C ₄ alkyl), -C (O) N (C ₁ -C ₄ alkyl) ₂ , -NHSO ₂ (C ₁ -C ₄ alkyl ), -SC ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ alkyl, -SO ₂ C ₁ -C ₄ alkyl, -B(OR ₁₂ )(OR ₁₃ ), where R ₁₂ in each individual case is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, R ₁₃ is in each case selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, or R ₁₂ and R ₁₃ together with the oxygen atoms to which they are attached form a 5-7 membered a ring which is optionally substituted with 1-4 C ₁ -C ₄ alkyls; 6- or 10-membered aryl; and a monocyclic heterocycle selected from the group consisting of 4-7 membered heterocycloalkyl, 5-membered heteroaryl containing at least one nitrogen atom, through which the 5-membered heteroaryl ring is attached to the rest of the molecule; 6-membered heteroaryl containing at least one nitrogen atom; each of the aryl, heterocycloalkyl and heteroaryl rings in R ₄ is optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, cyano, nitro, hydroxyl, oxo, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH (C ₁ -C ₄ alkyl), -N (C ₁ -C ₄ alkyl) ₂ , -NH(C ₃ -C ₆ cycloalkyl), -N(C ₁ -C ₄ alkyl)(C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ alkyl, -SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl; and where each of C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl and C ₁ -C ₄ alkoxy in R ₄ may be optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, hydroxyl, -NH ₂ , -NH (C ₁ -C ₄ alkyl), -N (C ₁ -C ₄ alkyl) ₂ , cyano, carboxyl, carbamoyl, C ₁ -C ₄ alkoxycarbonyl, -C (O) NH (C ₁ - C ₄ alkyl), -C(O)N(C ₁ -C ₄ alkyl) ₂ and C ₁ -C ₄ alkoxy; R ₅ is selected from the group consisting of hydrogen, halogen, hydroxyl, -SH, -SC ₁ -C ₄ alkyl, -S(O)(C ₁ -C ₄ alkyl, -S(O) ₂ (C ₁ -C ₄ alkyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkoxy, -B(OR ₁₂ )(OR ₁₃ ), where R ₁₂ in each individual case is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, R ₁₃ in each case selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, or R ₁₂ and R ₁₃ together with the oxygen atoms to which they are attached form a 5-7 membered ring, which is optionally substituted with 1-4 C ₁ -C ₄ alkyls, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ ; R ₆ is selected from the group consisting of hydrogen, halogen, hydroxyl, -SH, -SC ₁ -C ₄ alkyl, -S(O)(C ₁ -C ₄ alkyl, -S(O) ₂ (C ₁ -C ₄ alkyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkoxy, -B(OR ₁₂ )(OR ₁₃ ), where R ₁₂ in each individual case is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, R ₁₃ in each case selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl, or R ₁₂ and R ₁₃ together with the oxygen atoms to which they are attached form a 5-7 membered ring, which is optionally substituted with 1-4 C ₁ -C ₄ alkyls, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ ; R ₇ is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl optionally substituted with 1-5 halogen atoms, -C(H)O, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ alkoxy; R ₈ at each occurrence is independently selected from the group consisting of hydrogen, fluorine and C ₁ -C ₄ alkyl; R ₉ at each occurrence is independently selected from the group consisting of hydrogen, fluorine and C ₁ -C ₄ alkyl; R ₁₀ is selected from the group consisting of hydrogen and C ₁ -C ₄ alkyl; R ₁₁ is at each occurrence independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ ; 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, cyano, nitro, hydroxyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, -NH ₂ , -NH(C ₁ -C ₄ alkyl), -N(C ₁ -C ₄ alkyl) ₂ , -NH(C ₃ -C ₆ cycloalkyl), -N(C ₁ -C ₄ alkyl)(C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ alkyl, -SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl, where a 6- or 10-membered aryl is optionally fused to a 4-7-membered heterocycloalkyl containing 1 or 2 heteroatoms selected from the group, consisting of O, S and N, and where the carbon atoms of the heterocycloalkyl are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ , and any N in heterocycloalkyl, if valence permits, substituted with a substituent selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; A 5-10 membered heteroaryl containing 1 or 2 heteroatoms selected from the group consisting of O, S and N, and where 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 from halogen, cyano, nitro, hydroxyl, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl ) and -N(C ₁ -C ₄ alkyl) ₂ , and any N in heteroaryl, if valency permits, is optionally substituted with a substituent selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; 4-7 membered heterocycloalkyl containing 1 or 2 heteroatoms selected from the group consisting of O, S, N, where heterocycloalkyl is optionally benzo-fused, where carbon atoms of 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 halogen, cyano, nitro, hydroxyl, oxo, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ , and any N in heterocycloalkyl is optionally substituted with a substituent selected from the group consisting of from hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; 6- or 10-membered aryloxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, cyano, nitro, hydroxyl, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH (C ₁ -C ₄ alkyl), -N (C ₁ -C ₄ alkyl) ₂ , -NH (C ₃ -C ₆ cycloalkyl), -N ( C ₁ -C ₄ alkyl) (C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S (O)C ₁ -C ₄ alkyl, -SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl; 6- or 10-membered arylthiooxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, cyano, nitro, hydroxyl, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH (C ₁ -C ₄ alkyl), -N (C ₁ -C ₄ alkyl) ₂ , -NH (C ₃ -C ₆ cycloalkyl), -N ( C ₁ -C ₄ alkyl) (C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S (O)C ₁ -C ₄ alkyl, -SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl; and 5-10 membered heteroaryloxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl), -N(C ₁ -C ₄ alkyl) ₂ , -NH(C ₃ -C ₆ cycloalkyl), -N(C ₁ -C ₄ alkyl) (C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ alkyl , -SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl; excluding connections N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; 4-chloro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-1,6-naphthyridine-3-carboxamide; 8-bromo-N-[(4S)-chroman-4-yl]-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxamide; 4-chloro-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-1,6-naphthyridine-3-carboxamide; 4-chloro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(morpholin-4-yl)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(morpholin-4-yl)-1,6-naphthyridine-3-carboxamide; 4-chloro-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-1,5-naphthyridine-3-carboxamide; 4-chloro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-1,5-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; 8-chloro-4-(3,5-dichlorophenyl)-N-[(4S)-chroman-4-yl]pyrido[3,2-d]pyrimidine-7-carboxamide; 4-(3,5-dichlorophenyl)-N-[(4S)-chroman-4-yl]-8-(dimethylamino)-pyrido[3,2-d]pyrimidine-7-carboxamide; 4-(3,5-dichlorophenyl)-N-[(4S)-chroman-4-yl]-8-(morpholin-4-yl)-pyrido[3,2-d]pyrimidine-7-carboxamide; 8-bromo-4-chloro-4-N-[(4S)-chroman-4-yl]cinnoline-3-carboxamide; 8-bromo-4-N-[(4S)-chroman-4-yl]-4-(dimethylamino)cinnoline-3-carboxamide; 8-bromo-4-N-[(4S)-chroman-4-yl]-4-methoxycinnoline-3-carboxamide; 8-(3,5-dichlorophenyl)-4-N-[(4S)-chroman-4-yl]-4-(dimethylamino)cinnoline-3-carboxamide; 8-(3-chlorophenyl)-4-N-[(4S)-chroman-4-yl]-4-(dimethylamino)cinnoline-3-carboxamide; 8-(2,3-dichlorophenyl)-4-N-[(4S)-chroman-4-yl]-4-(dimethylamino)cinnoline-3-carboxamide; 8-(3,4-difluorophenyl)-4-N-[(4S)-chroman-4-yl]-4-(dimethylamino)cinnoline-3-carboxamide; 8-(3,5-dichlorophenyl)-4-N-[(4S)-chroman-4-yl]-4-methoxycinnoline-3-carboxamide; 8-(3-chlorophenyl)-4-N-[(4S)-chroman-4-yl]-4-methoxycinnoline-3-carboxamide; 8-(2,3-dichlorophenyl)-4-N-[(4S)-chroman-4-yl]-4-methoxycinnoline-3-carboxamide; 8-(3,4-fluorophenyl)-4-N-[(4S)-chroman-4-yl]-4-methoxycinnoline-3-carboxamide; 8-chloro-4-(2,3-dichlorophenyl)-N-[(4S)-chroman-4-yl]pyrido[3,2-d]pyridazine-7-carboxamide; 4-(2,3-dichlorophenyl)-N-[(4S)-chroman-4-yl]-8-(dimethylamino)-pyrido[3,2-d]pyridazine-7-carboxamide; 4-(2,3-dichlorophenyl)-N-[(4S)-chroman-4-yl]-8-(morpholin-4-yl)-pyrido[3,2-d]pyridazine-7-carboxamide; 4-(3,5-dichlorophenyl)-N-[(4S)-chroman-4-yl]-8-(dimethylamino)-pyrido[3,2-d]pyridazine-7-carboxamide; 4-(3,5-dichlorophenyl)-N-[(4S)-chroman-4-yl]-8-(morpholin-4-yl)-pyrido[3,2-d]pyridazine-7-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3,5-trichlorophenyl)-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-5-fluoro-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-5-fluoro-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-5-methoxy-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-5-fluoro-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-5-methoxy-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-5-fluoro-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-5-methoxy-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-5-methoxy-4-(morpholin-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-5-methoxy-4-(dimethylamino)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-7-methoxy-4-(morpholin-4-yl)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-7-methoxy-4-(dimethylamino)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-7-methoxy-4-(dimethylamino)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-7-methoxy-4-(morpholin-4-yl)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-5-methoxy-4-(morpholin-4-yl)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-5-methoxy-4-(morpholin-4-yl)-1,6-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-5-methoxy-4-(dimethylamino)-1,6-naphthyridine-3-carboxamide; 7-chloro-N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-chloro-N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; 7-chloro-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-chloro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-chloro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; 7-methoxy-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-fluoro-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-methoxy-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-methoxy-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; 7-methoxy-N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-methoxy-N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; 7-fluoro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide; 7-fluoro-N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; 7-fluoro-N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(dimethylamino)-1,5-naphthyridine-3-carboxamide and 7-fluoro-N-[(4S)-chroman-4-yl]-8-(2,3,5-trifluorophenyl)-4-(morpholin-4-yl)-1,5-naphthyridine-3-carboxamide; or its salt. 2. Connection under item 1, where X ₁ represents CR ₁ ; X ₂ is CR ₂ ; X ₃ is CR ₃ ; X ₄ is CR ₄ ; X ₅ is CR ₅ ; and X ₆ is CR ₆ ; or its salt. 3. Connection under item 1, where X ₁ represents N; X ₂ is CR ₂ ; X ₃ is CR ₃ ; X ₄ is CR ₄ ; X ₅ is CR ₅ ; and X ₆ is N; or its salt. 4. Connection under item 1, where X ₁ represents CR ₁ ; X ₂ is CR ₂ ; X ₃ is CR ₃ ; X ₄ is CR ₄ ; X ₅ is N; and X ₆ is N; or its salt. 5. Connection under item 1, where X ₁ represents CR ₁ ; X ₂ is CR ₂ ; X ₃ is CR ₃ ; X ₄ is CR ₄ ; X ₅ is N; and X ₆ is CR ₆ ; or its salt. 6. Connection according to claim 1, where Q is a 6- or 10-membered aryl optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, cyano, nitro, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, -NH ₂ , -NH (C ₁ -C ₄ alkyl), -N (C ₁ -C ₄ alkyl) ₂ , -NH (C ₃ -C ₆ cycloalkyl) , -N (C ₁ -C ₄ alkyl) (C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S (O)C ₁ -C ₄ alkyl, -SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl; or its salt. 7. Connection according to claim 1, where Q is a 6-membered aryl optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, cyano, nitro, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, -NH ₂ , -NH(C ₁ -C ₄ alkyl), -N(C ₁ -C ₄ alkyl) ₂ , -NH(C ₃ -C ₆ cycloalkyl), -N (C ₁ -C ₄ alkyl) (C ₃ -C ₆ cycloalkyl), -NHSO ₂ (C ₁ -C ₄ alkyl), -SC ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ alkyl, - SO ₂ C ₁ -C ₄ alkyl, -S(O)C ₁ -C ₄ haloalkyl and -SO ₂ C ₁ -C ₄ haloalkyl, where a 6-membered aryl is fused to a 4-7-membered heterocycloalkyl containing 1 or 2 heteroatoms selected from the group consisting of O, S and N, and where the carbon atoms of the heterocycloalkyl are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, oxo, C ₁ -C ₄ alkyl , C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ , and any N in heterocycloalkyl s substituted with a substituent selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; or its salt. 8. Connection according to claim 1, where Q is a 5-10 membered heteroaryl containing 1 or 2 heteroatoms selected from the group consisting of O, S and N, and where the carbon atoms of the heteroaryl are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen , cyano, nitro, -OH, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH (C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ , and any N in heteroaryl is optionally substituted with a substituent selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; or its salt. 9. Connection according to claim 1, where Q is a 4-7 membered heterocycloalkyl containing 1 or 2 heteroatoms selected from the group consisting of O, S, N, where the heterocycloalkyl is optionally benzo-fused, where the carbon atoms of the heterocycloalkyl or the optionally benzo-fused heterocycloalkyl are optionally substituted with 1, 2, 3 or 4 substituents independently selected from the group consisting of halo, cyano, nitro, hydroxy, oxo, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, -NH ₂ , -NH(C ₁ -C ₄ alkyl) and -N(C ₁ -C ₄ alkyl) ₂ , and any N in heterocycloalkyl is optionally substituted with a substituent selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; or its salt. 10. Connection according to claim 1, where n is 1; or its salt. 11. Connection under item 1, where Y ₁ represents CR ₈ R ₉ and Y ₂ represents O; or its salt. 12. Connection according to any one of paragraphs. 1-11, where R ₄ is selected from the group consisting of C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, -N(C ₁ -C ₄ alkyl) ₂ and 4-7-membered heterocycloalkyl; or its salt. 13. The compound according to claim 1, selected from the group consisting of N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-[(1R)-tetralin-1-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-[(1S)-tetralin-1-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-[(1R or S)-tetralin-1-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(1,2-dihydronaphthalen-1-yl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; trans-8-(2,3,3a,4,5,6,7,7a-octahydroindol-1-yl)-N-[(4S)-chroman-4-yl]-4-(dimethylamino)-1, 7-naphthyridine-3-carboxamide; cis-8-(2,3,3a,4,5,6,7,7a-octahydroindol-1-yl)-N-[(4S)-chroman-4-yl]-4-(dimethylamino)-1, 7-naphthyridine-3-carboxamide; 8-(5-chloroindolin-1-yl)-N-[(4S)-chroman-4-yl]-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-(5-chloroindol-1-yl)-N-[(4S)-chroman-4-yl]-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-morpholino-8-phenylsulfanyl-1,7-naphthyridine-3-carboxamide; 8-(benzenesulfonyl)-N-[(4S)-chroman-4-yl]-4-morpholino-1,7-naphthyridine-3-carboxamide; 4-amino-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-isopropoxy-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(4-methylpiperazin-1-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,6-difluorophenyl)-4-(4-methylpiperazin-1-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-pyrrolidin-1-yl-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[(4S)-7-fluorochroman-4-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-(1H-indol-4-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-phenyl-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-cyclopropyl-8-(3,5-dichlorophenyl)-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[(1S)-indan-1-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-6-cyanochroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-((4S)-7-chlorochroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-((4R)-7-chlorochroman-4-yl)-8-(3,5-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,6-difluoro-3-methoxy-phenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; 8-((4S)-3,5-dichlorophenyl)-4-(dimethylamino)-N-(7-methoxychroman-4-yl)-1,7-naphthyridine-3-carboxamide; 8-((4R)-3,5-dichlorophenyl)-4-(dimethylamino)-N-(7-methoxychroman-4-yl)-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-((8S)-5,6,7,8-tetrahydroquinolin-5-yl)-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-((8R)-5,6,7,8-tetrahydroquinolin-5-yl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichloro-2-pyridyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; 4-chloro-N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-[methoxy(methyl)amino]-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[(1S)-tetralin-1-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-methoxy-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[(1R)-indan-1-yl]-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[(1R)-tetralin-1-yl]-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-N-((8S)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl)-4-(dimethylamino)-1,7-naphthyridine-3- carboxamide; 8-(3,5-dichlorophenyl)-N-((8R)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl)-4-(dimethylamino)-1,7-naphthyridine-3- carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(4-oxo-imidazolidin-1-yl)-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[rac-(3R,4S)-3-methylchroman-4-yl]-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-cyano-8-(3,5-dichlorophenyl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-isopropyl-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-[3-(dimethylamino)-2,6-difluorophenyl]-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-4-(dimethylamino)-N-[(4S)-7-methylchroman-4-yl]-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-N-[(7S)-6,7-dihydro-5H-thieno[3,2-b]pyran-7-yl]-4-(dimethylamino)-1,7- naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-N-[(7R)-6,7-dihydro-5H-thieno[3,2-b]pyran-7-yl]-4-(dimethylamino)-1,7- naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-difluorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2-fluorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-(2,3,5-trifluorophenyl)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-4-(dimethylamino)-8-(3,4,5-trifluorophenyl)-1,7-naphthyridine-3-carboxamide; 8-[3,5-bis(trifluoromethyl)phenyl]-N-[(4S)-chroman-4-yl]-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; 8-(3,5-dichlorophenyl)-N-[(4S)-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl]-4-(dimethylamino)-1,7- naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,4-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(2,3-dichlorophenyl)-4-(dimethylamino)-1,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)isoquinoline-3-carboxamide; N-[(4S)-chroman-4-yl]-8-(3,5-dichlorophenyl)-4-(dimethylamino)-2,7-naphthyridine-3-carboxamide; N-[(4S)-chroman-4-yl]-1-(3,5-dichlorophenyl)-5-(dimethylamino)isoquinoline-6-carboxamide; (4S)-chroman-4-yl]-5-(3,5-dichlorophenyl)-1-(dimethylamino)naphthalene-2-carboxamide; N-[(4S)-chroman-4-yl]-4-(3,5-dichlorophenyl)-8-(dimethylamino)quinoline-7-carboxamide; N-[(4S)-chroman-4-yl]-4-(3,5-dichlorophenyl)-8-(dimethylamino)isoquinoline-7-carboxamide or a salt of each of the above compounds. 14. Composition containing a compound according to any one of paragraphs. 1-13 or a salt thereof and at least one acceptable carrier. 15. The use of a compound according to any one of paragraphs. 1-13 or its salts as a drug. 16. The use of a compound according to any one of paragraphs. 1-13 or salts thereof in the manufacture of a medicament for the treatment of endoparasites. 17. The use of a compound according to any one of paragraphs. 1-13 or salts thereof in the manufacture of a medicament for the treatment of heartworm. 18. The use of a compound according to any one of paragraphs. 1-13 or salts thereof in the manufacture of a medicament for the control of heartworm.