Back to results
US 2022/0064159 A1Published application
Bicyclic derivatives
OwnerChouaib Tahtaoui, Denise Rageot +2inventors
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.
Claims21
A compound of compounds 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;
- 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(OR16)(OR17) wherein R16 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R17 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R16 and R17 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(OR16)(OR17) wherein R16 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R17 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R16 and R17 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(OR16)(OR17) wherein R16 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, Ru is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R16 and Ru 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;
- R4 is selected from the group consisting of halogen, cyano, —CHO, hydroxyl, C1-C4 alkyl, 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-C6 cycloalkyl), —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(OR16)(OR17) wherein R16 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R17 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R16 and Ru 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, alkyl, —S(O)(C1-C4 alkyl, —S(O)2(C1-C4 alkyl, cyano, C1-C4 alkyl, C1-C4 halogenoalkyl, C1-C4-alkoxy, —B(OR16)(OR17) wherein R16 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R17 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R16 and R17 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(OR16)(OR17) wherein R16 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, R17 is, each time taken, selected from the group consisting or hydrogen, C1-C4 alkyl, and C3-C6 cycloalkyl, or R16 and R17 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;
- M is selected from the group consisting of N—R13, O, and S;
- R13 is selected from the group consisting of hydroxy, C1-C4 alkoxy, and —NH2;
- V1 is selected from the group consisting of NR14, O, and S;
- R14 is hydrogen and C1-C4 alkyl;
- V2 and V3 are, independently, selected from the group consisting of CR15 and N;
- R15 is selected from the group consisting of hydrogen, halogen, hydroxy, C1-C4 alkyl, C1-C4 halogenoalkyl, and C1-C4 alkoxy;
- or a salt thereof.
49 more elements
Dependencies are inferred from the claim text.