Back to results
US 2026/0209228 A1Published application
Bicyclic derivatives
AssigneeElanco Tiergesundheit AG
InventorsChouaib TAHTAOUI, Denise RAGEOT, Francois PAUTRAT, Pierre DUCRAY
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds of formula (I): which are useful in the control of endoparasites, for example heartworms, in warm-blooded animals.
Claims20
A compound of formula (I):
- wherein
- n is 0 or 1;
- X1 is selected from the group consisting of N and CR1;
- X2 is selected from the group consisting of N and CR2;
- X3 is selected from the group consisting of N and CR3;
- X4 is selected from the group consisting of N and CR4;
- X5 is selected from the group consisting of N and CR5;
- X6 is selected from the group consisting of N and CR6;
- wherein at least one of X1, X2, X3, and X5 is N or wherein none of X1, X2, X3, X4, X5, and X6 are N;
- G is the group
- Y1 is selected from the group consisting of CR8R9, O, S, and NR10;
- Y2 is selected from the group consisting of CR8R9, O, S, and NR10;
- wherein at least one of the groups Y1 or Y2 is CR8R9;
- Z1 is selected from the group consisting of N, O, S, and CR11;
- Z2 is selected from the group consisting of nil, N, and CR11;
- Z3 is selected from the group consisting of nil, N and CR11;
- Z4 is selected from the group consisting of N, O, S, and CR11;
- wherein no more than 2 of Z1, Z2, Z3, and Z4 are N and wherein only one of Z1 and Z4 is O or S, Z2 is nil only when Z1 is O or S, and Z3 is nil only when Z4 is O or S;
- R1 is selected from the group consisting of hydrogen, halogen, hydroxyl, —SH, —SC1-C4 alkyl, —S(O)(C1-C4 alkyl, —S(O)2(C1-C4 alkyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, —B(OR12)(OR13) wherein R12 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R13 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R12 and R13 together with the oxygen atoms to which they are attached form a 5- to 7-membered ring which is optionally substituted with 1 to 4 C1-C4 alkyl;
- —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R2 is selected from the group consisting of hydrogen, halogen, hydroxyl, —SH, —SC1-C4 alkyl, —S(O)(C1-C4 alkyl, —S(O)2(C1-C4 alkyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, —B(OR12)(OR13) wherein R12 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R13 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R12 and R13 together with the oxygen atoms to which they are attached form a 5- to 7-membered ring which is optionally substituted with 1 to 4 C1-C4 alkyl;
- —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R3 is selected from the group consisting of hydrogen, halogen, hydroxyl, —SH, —SC1-C4 alkyl, —S(O)(C1-C4 alkyl, —S(O)2(C1-C4 alkyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, —B(OR12)(OR13) wherein R12 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R13 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R12 and R13 together with the oxygen atoms to which they are attached form a 5- to 7-membered ring which is optionally substituted with 1 to 4 C1-C4 alkyl;
- —NH2, —NH(C1-C4 alkyl), and —N(C1-C4alkyl)2;
- R4 is selected from the group consisting of halogen, cyano, —CHO, hydroxyl, C1-C4alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy substituted-C1-C4 alkyl, benzyl optionally substituted with 1 to 5 halogen atoms, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —NH(C3-C6cycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —NH(4- to 7-membered heterocycloalkyl), —N(C1-C4 alkyl)(4- to 7-membered heterocycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —N(C1-C4 alkyl)(C1-C4 alkoxy), —C(O)NH(C1-C4 alkyl), —C(O)N(C1-C4 alkyl)2, —NHSO2(C1-C4 alkyl), —SC1-C4 alkyl, —S(O)C1-C4 alkyl, —SO2C1-C4 alkyl, —B(OR12)(OR13) wherein R12 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R13 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6cycloalkyl, or R12 and R13 together with the oxygen atoms to which they are attached form a 5- to 7-membered ring which is optionally substituted with 1 to 4 C1-C4 alkyl;
- 6- or 10 membered aryl;
- and a monocyclic heterocycle selected from the group of 4- to 7-membered heterocycloalkyl, 5-membered heteroaryl having at least one nitrogen atom via which the 5-membered heteroaryl ring is connected to the rest of the molecule;
- 6-membered heteroaryl having at least one nitrogen atom;
- each of the aryl, heterocycloalkyl, and heteroaryl ring in R4 is optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —NH(C3-C6 cycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —NHSO2(C1-C4 alkyl), —SC1-C4 alkyl, —S(O)C1-C4 alkyl, —SO2C1-C4 alkyl, —S(O)C1-C4-halogenoalkyl and —SO2C1-C4 halogenoalkyl;
- and wherein each 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 halogen, hydroxyl, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, cyano, carboxyl, carbamoyl, C1-C4 alkoxycarbonyl, —C(O)NH(C1-C4 alkyl), —C(O)N(C1-C4 alkyl)2, and C1-C4 alkoxy;
- R5 is selected from the group consisting of hydrogen, halogen, hydroxyl, —SH, —SC1-C4 alkyl, —S(O)(C1-C4 alkyl, —S(O)2(C1-C4 alkyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, —B(OR12)(OR13) wherein R12 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R13 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R12 and R13 together with the oxygen atoms to which they are attached form a 5- to 7-membered ring which is optionally substituted with 1 to 4 C1-C4 alkyl;
- —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R6 is selected from the group consisting of hydrogen, halogen, hydroxyl, —SH, —SC1-C4 alkyl, —S(O)(C1-C4 alkyl, —S(O)2(C1-C4 alkyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, —B(OR12)(OR13) wherein R12 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R13 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R12 and R13 together with the oxygen atoms to which they are attached form a 5- to 7-membered ring which is optionally substituted with 1 to 4 C1-C4 alkyl;
- —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2;
- R7 is selected from the group consisting of hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl optionally substituted with 1 to 5 halogen atoms, —C(H)O, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 halogenoalkyl, and C1-C4-alkoxy;
- R8 is, each time selected, independently selected from the group consisting of hydrogen, fluoro, and C1-C4 alkyl;
- R9 is, each time selected, independently selected from the group consisting of hydrogen, fluoro, and C1-C4 alkyl;
- R10 is selected from the group consisting of hydrogen and C1-C4 alkyl;
- R11 is, each time selected, independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, C3-C6 cycloalkyl, —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 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 halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl,
- —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —NH(C3-C6 cycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —NHSO2(C1-C4 alkyl), —SC1-C4 alkyl, —S(O)C1-C4 alkyl, —SO2C1-C4 alkyl,
- —S(O)C1-C4-halogenoalkyl and —SO2C1-C4 halogenoalkyl, wherein the 6- or 10 membered aryl is optionally fused with a 4- to 7-membered heterocycloalkyl having 1 or 2 heteroatoms selected from the group O, S, and N and wherein the carbons of the heterocycloalkyl are optionally substituted with 1, 2 or 3 substituents independently selected from the group halogen, cyano, nitro, hydroxyl, oxo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2 and any N in the heterocycloalkyl is, valency permitting, substituted with a substituent selected from the group consisting of hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl;
- 5- to 10-membered heteroaryl having 1 or 2 heteroatoms selected from the group O, S, and N and wherein the carbons of the 5- to 10-membered heteroaryl are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2 and any N in the heteroaryl, valency permitting, is optionally substituted with a substituent selected from the group consisting of hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl;
- a 4- to 7-membered heterocycloalkyl having 1 or 2 heteroatoms selected from the group O, S, N, wherein the heterocycloalkyl is optionally benzo-fused, wherein the carbons of the 4- to 7-membered heterocycloalkyl or optionally benzo-fused 4- to 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, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), and —N(C1-C4 alkyl)2 and any N in the 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 halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —NH(C3-C6 cycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —NHSO2(C1-C4 alkyl), —SC1-C4 alkyl, —S(O)C1-C4 alkyl, —SO2C1-C4 alkyl, —S(O)C1-C4-halogenoalkyl and —SO2C1-C4 halogenoalkyl;
- 6- or 10 membered arylthio-oxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —NH(C3-C6 cycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —NHSO2(C1-C4 alkyl), —SC1-C4 alkyl, —S(O)C1-C4 alkyl, —SO2C1-C4 alkyl, —S(O)C1-C4-halogenoalkyl and —SO2C1-C4 halogenoalkyl;
- and 5- to 10-membered heteroaryloxy optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, oxo, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 halogenoalkyl, C1-C4 alkoxy, —NH2, —NH(C1-C4 alkyl), —N(C1-C4 alkyl)2, —NH(C3-C6 cycloalkyl), —N(C1-C4 alkyl)(C3-C6-cycloalkyl), —NHSO2(C1-C4 alkyl), —SC1-C4 alkyl, —S(O)C1-C4 alkyl, —SO2C1-C4 alkyl, —S(O)C1-C4-halogenoalkyl and
- —SO2C1-C4 halogenoalkyl;
- excluding the compounds:
- 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 a salt thereof.
121 more elements
Dependencies are inferred from the claim text.