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US 8,569,495 B2Granted
Anthelmintic agents and their use
AssigneeIntervet International B.V.
InventorsChristophe Pierre Alain Chassaing, Jörg Schröder, Thomas Simon Ilg, Manfred Uphoff, Thorsten Meyer
Life of this patent
Estimating the term…
Abstract
This invention is directed to compounds and salts 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 and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments.
Claims31
A compound or salt thereof, wherein:
- the compound corresponds in structure to:
- each of R1, R2, R3, R4, and R5 is independently selected from the group consisting of hydrogen, halogen, cyano, alkyl, and alkoxy, wherein:
- the alkyl, and alkoxy, are optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, alkyl, alkoxy, haloalkyl, haloalkoxy, alkylsulfanyl, and haloalkylsulfanyl;
- X1 is selected from the group consisting of —O—, and —NH—, wherein:
- the —NH— is optionally substituted with a substituent selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, carbocyclyl, and carbocyclylalkyl, wherein:
- 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, straight-chain C3-C5-alkenyl, straight-chain C3-C5-alkynyl, and C4-C6-carbocyclyl, wherein:
- the straight-chain C3-C5-alkyl, straight-chain C3-C5-alkenyl, straight-chain C3-C5-alkynyl, 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 —S—, wherein:
- the —CH2— is optionally substituted with up to two substituents independently selected from the group consisting of alkyl and carbocyclyl, and
- wherein:
- any such substituent is optionally substituted with one or more independently selected halogen;
- Z1 is CH, wherein:
- the CH is substituted with a substituent selected from the group consisting of halogen, nitro, cyano, aminosulfonyl, alkyl, alkoxycarbonyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, aryl, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroaryl, heteroarylsulfanyl, heteroarylsulfinyl, and heteroarylsulfonyl, wherein:
- the alkyl, 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, wherein:
- the CH is optionally substituted with a substituent selected from the group consisting of cyano, halogen, nitro, alkyl, haloalkyl, and haloalkylsulfanyl;
- and
- each of Z3, Z4, and Z5 is CH, wherein:
- the CH is optionally substituted with a substituent selected from the group consisting of halogen, cyano, nitro, alkyl, alkylsulfanyl, haloalkyl, haloalkoxy, and haloalkylsulfanyl;
- and
- A is O or S.
20 more elements
A compound or salt thereof, wherein:
- the compound corresponds in structure to:
- each of R1, R2, R3, R4, and R5 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, and C1-C6-alkoxy, wherein:
- the C1-C6-alkyl, and C1-C6-alkoxy, are optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, halo-C1-C6-alkyl, and halo-C1-C6-alkoxy;
- X1 is selected from the group consisting of —O—, and —NH—, wherein:
- the —NH— is optionally substituted with a substituent selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, carbocyclyl, and carbocyclylalkyl, wherein:
- any such substituent is optionally substituted with one or more independently selected halogen;
- X2 is C4-C6-carbocyclyl optionally substituted with one or more independently selected C1-C6-alkyl;
- and
- X3 is selected from the group consisting of —CH2—, —O—, —C(O)—, and —S—, wherein:
- the —CH2— is optionally substituted with up to two substituents independently selected from the group consisting of alkyl and carbocyclyl, and
- wherein:
- any such substituent is optionally substituted with one or more independently selected halogen;
- Z1 is CH, wherein:
- the CH is substituted with a substituent selected from the group consisting of halogen, nitro, cyano, aminosulfonyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, phenylsulfonyl, and heteroaryl, wherein:
- the C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfanyl, phenylsulfonyl, and heteroaryl are optionally substituted with one or more substituents independently selected from the group consisting of halogen and C1-C6-alkyl, and
- the aminosulfonyl is optionally substituted with up to two independently selected C1-C6-alkyl;,
- Z2 is CH, wherein:
- the CH is optionally substituted with a substituent selected from the group consisting of cyano, halogen, nitro, alkyl, alkoxy, haloalkyl, and haloalkylsulfanyl;
- and
- each of Z3, Z4, and Z5 is CH, wherein:
- the CH is optionally substituted with a substituent selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, alkylsulfanyl, haloalkyl, haloalkoxy, and haloalkylsulfanyl;
- and
- A is O or S.
20 more elements
A compound of the formula
Dependencies are inferred from the claim text.