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US 8,507,474 B2Granted
Anthelmintic agents and their use
AssigneeIntervet International B.V.
InventorsChristophe Pierre Alain Chassaing, Thorsten Meyer
Life of this patent
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Abstract
This invention is directed to compounds of the formula (I) and salts therefore that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds of this invention, pharmaceutical compositions and kits comprising the compounds of this invention, uses of the compounds of this invention to make medicaments, and treatments comprising the administration of the compounds of this invention to animals in need of the treatments.
Claims10
A compound or salt thereof, wherein:
- the compound corresponds in structure to Formula (I):
- X1 is selected from the group consisting of —O—, —S—, and —NH—, the —NH— is optionally substituted with a substituent selected from the group consisting of alkyl and alkoxyalkyl, any such substituent is optionally substituted with one or more independently selected halogen;
- X2 is selected from the group consisting of straight-chain C3-C5-alkyl, and C4-C6-carbocyclyl the straight-chain C3-C5-alkyl, and C4-C6-carbocyclyl are optionally substituted with one or more independently selected alkyl;
- X3 is selected from the group consisting of —CH2—, —O—, —C(O)—, and —NH—, the —CH2— is optionally substituted with up to two substituents independently selected from the group consisting of alkyl and carbocyclyl, the —NH— is optionally substituted with a substituent selected from the group consisting of alkyl and alkoxyalkyl, any such substituent of —NH— is optionally substituted with one or more independently selected halogen;
- X4 is selected from the group consisting of —CH2, the —CH2— is optionally substituted with up to two substituents independently selected from the group consisting of alkyl, haloalkyl and alkenyl;
- X5 is selected from the group consisting of —C(S)— and —C(O)—;
- X6 is a linker selected from the group consisting of
- any such group is optionally substituted with one or more substituents independently selected from the group consisting of halogen, C1-C6-alkyl, hydroxy, C1-C6-alkoxy, oxo, and thiocarbonyl;
- X7 is selected from the group consisting of a bond, —O—, —NH—, —S—, —CH2—, the —NH— is optionally substituted with alkyl, the —CH2— is optionally substituted with one or more independently selected alkyl;
- Y is a 5-membered or 6-membered heteroaryl group, selected from the group consisting of furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiodiazolyl, oxadiazolyl, pyrrolyl, pyrazolyl, imidazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, and pyridazinyl, any such heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, alkyl, alkoxy, nitro, aminosulfonyl, alkoxycarbonyl, alkylsulfanyl, aryl, aryloxy, arylalkoxy, arylsulfanyl, heteroaryl, heteroaryloxy, and heteroarylsulfanyl, the alkyl, alkoxy, aminosulfonyl, alkoxycarbonyl, alkylsulfanyl, aryl, aryloxy, arylalkoxy, arylsulfanyl, heteroaryl, heteroaryloxy, and heteroarylsulfanyl are optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, alkyl, alkoxy, haloalkyl, and haloalkoxy;
- Z1 is selected from the group consisting of N and CH, the CH is optionally substituted with a substituent selected from the group consisting of halogen, nitro, cyano, aminosulfonyl, alkyl, alkoxy, alkoxycarbonyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroaryl, heteroarylsulfanyl, heteroarylsulfinyl, and heteroarylsulfonyl, the alkyl, alkoxy, alkoxycarbonyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanyl, aryl, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroaryl, heteroarylsulfanyl, heteroarylsulfinyl, and heteroarylsulfonyl are optionally substituted with one or more substituents independently selected from the group consisting of halogen and alkyl;
- and the aminosulfonyl is optionally substituted with up to two independently selected alkyl;
- Z2 is selected from the group consisting of N and CH, the CH is optionally substituted with a substituent selected from the group consisting of cyano, halogen, nitro, alkyl, alkoxy, haloalkyl, and haloalkylsulfanyl;
- Each of Z3, Z4, and Z5 is independently selected from the group consisting of N and CH, the CH is optionally substituted with a substituent selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, alkylsulfanyl, haloalkyl, haloalkoxy, and haloalkylsulfanyl.
11 more elements
A compound or salt thereof, wherein:
- the compound corresponds in structure to Formula (I):
- wherein,
- X1 is selected from the group consisting of —O—, —S—, and —NH—;
- X2 is selected from the group consisting of C4-C6-carbocyclyl, the C4-C6-carbocyclyl is optionally substituted with one or more independently selected alkyl;
- X3 is selected from the group consisting of —CH2—, and —O—, the —CH2— is optionally substituted with up to two substituents independently selected from the group consisting of alkyl and carbocyclyl;
- X4 is selected from the group consisting of —CH2—, the —CH2— is optionally substituted with up to two methyl-substituents;
- X5 is selected from the group consisting of —C(S)— and —C(O)—;
- X6 is a linker selected from the group consisting of
- any such group is optionally substituted with one or more substituents independently selected from the group consisting of halogen, C1-C6-alkyl, hydroxy, C1-C6-alkoxy, oxo, and thiocarbonyl;
- X7 is selected from the group consisting of a bond, —O—, —NH—, —S—, —CH2—, the —NH— is optionally substituted with alkyl, the —CH2— is optionally substituted with one or more independently selected alkyl;
- Y is a nitrogen-containing 5-membered or 6-membered heteroaryl group containing one, two, three or four nitrogen ring atoms, any such heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, alkyl, alkoxy, nitro, aminosulfonyl, alkylsulfanyl, the alkyl, alkoxy, aminosulfonyl, alkoxycarbonyl, alkylsulfanyl, are optionally substituted with one or more substituents independently selected from the group consisting of fluorine, bromine and chlorine;
- Z1 is CH which is substituted with a substituent selected from the group consisting of halogen, nitro, cyano, aminosulfonyl, alkyl, alkoxy, alkoxycarbonyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroaryl, heteroarylsulfanyl, heteroarylsulfinyl, and heteroarylsulfonyl, the alkyl, alkoxy, alkoxycarbonyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanyl, aryl, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroaryl, heteroarylsulfanyl, heteroarylsulfinyl, and heteroarylsulfonyl are optionally substituted with one or more substituents independently selected from the group consisting of halogen and alkyl;
- and the aminosulfonyl is optionally substituted with up to two independently selected alkyl;
- Z2 is CH which is substituted with a substituent selected from the group consisting of cyano, halogen, nitro, alkyl, alkoxy, haloalkyl, and haloalkylsulfanyl;
- Each of Z3, Z4, and Z5 is CH, the CH is optionally substituted with a substituent selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, alkylsulfanyl, haloalkyl, haloalkoxy, and haloalkylsulfanyl.
12 more elements
A compound or salt thereof, wherein:
- the compound corresponds in structure to Formula (I):
- wherein,
- X1 is —O— or —NH—;
- X2 is cyclohexyl;
- X3 is —O—;
- X4 is —CH2—;
- X5 is —C(S)— or —C(O)—;
- X6 is a linker selected from the group consisting of
- X7 is a bond or —NH—;
- Y is thiadiazolyl, pyridinyl or, pyrimidinyl, the thiadiazolyl, pyridinyl and pyrimidinyl are optionally substituted with one or more substituents independently selected from the group consisting of chloro, cyano, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, and hydroxy;
- Z1 is C-cyano or C-nitro;
- Z2 is C-difluoromethyl or C-trifluoromethyl;
- Z3, Z4, and Z5 are CH.
10 more elements
A compound or salt thereof, wherein:
- the compound corresponds in structure to Formula (I):
- wherein,
- X1 is —O— or —NH—;
- X2 is cyclohexyl;
- X3 is —O—;
- X4 is —CH2—;
- X5 is —C(S)— or —C(O)—;
- X6 is a linker selected from the group consisting of
- X7 is a bond or —NH—;
- Y is thiadiazolyl or pyridinyl, the thiadiazolyl and pyridinyl are optionally substituted with one or more substituents R independently selected from the group consisting of chloro, cyano, trifluoromethyl, difluoromethyl, methoxy, and trifluoromethoxy;
- Z1 is C-cyano or C-nitro;
- Z2 is C-difluoromethyl or C-trifluoromethyl;
- Z3, Z4, and Z5 are CH.
10 more elements
A compound or salt thereof, wherein:
- the compound corresponds in structure to:
Dependencies are inferred from the claim text.