N-(1-arylpyrazol-4l) sulfonamides and their use as parasiticides
AssigneesPfizer Inc., Pfizer Products Inc.
InventorsDouglas James Critcher, Nigel Derek Arthur Walshe, Christelle Lauret
Life of this patent
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Abstract
The invention relates to a sulfonamide compound of formula (I) or a pharmaceutically, veterinarily or agriculturally acceptable salt or solvate thereof, where the groups R1-R5 are described in the description, to compositions comprising such compounds, processes for their synthesis and their use as parasiticides.
Claims8
A compound of formula (I) or a pharmaceutically, veterinarily or agriculturally acceptable salt thereof,
- wherein:
- R1 is phenyl optionally substituted by one or more groups independently selected from the group consisting of halo, cyano, hydroxy, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkanoyl, C1-6 haloalkanoyl, —S(O)nC1-6alkyl, —S(O)nC1-6haloalkyl and pentafluorothio;
- R2 is cyano;
- R3 is C1-6 alkyl, C1-6 haloalkyl, or —(C0-3alkylene)-phenyl;
- R4 is hydrogen, C1-6 alkyl, C1-6haloalkyl, —(C0-3alkylene)-R7 or (C1-3alkylene)-R8;
- R5 is hydrogen;
- R6 is C1-6 alkyl or C1-6 haloalkyl;
- R7is C3-8cycloalkyl, —S(O)nR9, phenyl, het, —CO2R6 or C(O)N(Ra)Rb;
- R8 is hydroxy, C1-6 alkoxy, C1-6 haloalkoxy, cyano, —N(Ra)Rb or —O—C(O)R6;
- R9 is C1-6 alkyl, C1-6 haloalkyl, C3-8cycloalkyl, —N(Ra)Rb, phenyl or het;
- Ra and Rb independently represent hydrogen, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl or C2-6 haloalkenyl, or Ra additionally is —(C0-3alkylene)-C3-8 cycloalkyl, —(C0-3alkylene)-phenyl or —(C0-3alkylene)-het, or together Ra and Rb form a 4- to 7-membered ring, optionally substituted by one or more groups independently selected from the group consisting of halo, hydroxy, C1-6 alkyl, C1-6haloalkyl, C1-6 alkoxy and C1-6haloalkoxy;
- n is the integer 0, 1 or 2;
- where het represents a four- to seven-membered heterocyclic group, which is aromatic or non-aromatic and which contains one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and mixtures thereof,
- where both phenyl and het may be optionally substituted, where the valence allows, by one or more substituents independently selected from the group consisting of halo, hydroxy, cyano, nitro, C1-6 alkyl, C1-6haloalkyl, C1-6 alkenyl, C1-6haloalkenyl, C1-6alkoxy, C1-6haloalkoxy, C3-8 cycloalkyl, C1-6 alkanoyl, C1-6 haloalkanoyl, C1-6 alkylcarbonyloxy, C1-6 alkoxycarbonyl and NRaRb;
- where C3-8cycloalkyl may be optionally substituted by one or more groups independently selected from the group consisting of halo, C1-6alkyl, C1-6haloalkyl, C1-6alkenyl C1-6haloalkenyl, hydroxy, C1-6alkoxy and C1-6haloalkoxy;
- and
- where any alkylene group may be optionally substituted by one or more halo.
A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically, veterinarily or agriculturally acceptable salt thereof,
- wherein:
- R1 is phenyl, optionally substituted by one or more groups independently selected from the group consisting of halo, cyano, hydroxy, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkanoyl, C1-6 haloalkanoyl, —S(O)nC1-6alkyl, —S(O)nC1-6haloalkyl and pentafluorothio;
- R2 is cyano;
- R3 is C1-6 alkyl, C1-6 haloalkyl, or —(C0-3alkylene)-phenyl;
- R4 is hydrogen, C1-6 alkyl, C1-6haloalkyl, —(C0-3alkylene)-R7 or —(C1-3alkylene)-R8,
- R5 is hydrogen;
- R6 is C1-6 alkyl or C1-6 haloalkyl;
- R7 is C3-8 cycloalkyl, —S(O)nR9, phenyl, het, —CO2R6 or C(O)N(Ra)Rb;
- R8 is hydroxy, C1-6 alkoxy, C1-6 haloalkoxy, cyano, —N(Ra)Rb or —O—C(O)R6;
- R9 is C1-6 alkyl, C1-6 haloalkyl, C3-8cycloalkyl, —N(Ra)Rb, phenyl or het;
- Ra and Rb independently represent hydrogen, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl or C2-6 haloalkenyl or Ra additionally is —(C0-3alkylene)-C3-8 cycloalkyl, —(C0-3alkylene)-phenyl or —(C0-3alkylene)-het, or together Ra and Rb form a 4- to 7-membered ring, optionally substituted by one or more groups independently selected from the group consisting of halo, hydroxy, C1-6 alkyl, C1-6haloalkyl, C1-6 alkoxy and C1-6haloalkoxy;
- n is the integer 0, 1 or 2;
- where het represents a four- to seven-membered heterocyclic group, which is aromatic or non-aromatic and which contains one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and mixtures thereof;
- where both phenyl and het may be optionally substituted, where the valence allows, by one or more substituents independently selected from the group consisting of halo, hydroxy, cyano, nitro, C1-6 alkyl, C1-6haloalkyl, C1-6 alkenyl, C1-6haloalkenyl, C1-6alkoxy, C1-6haloalkoxy, C3-8 cycloalkyl, C1-6 alkanoyl, C1-6 haloalkanoyl, C1-6alkylcarbonyloxy, C1-6 alkoxycarbonyl and NRaRb;
- where C3-8cycloalkyl may be optionally substituted by one or more groups independently selected from the group consisting of halo, C1-6alkyl, C1-6haloalkyl, C1-6 alkenyl, C1-6haloalkenyl, hydroxy, C1-6alkoxy and C1-6haloalkoxy;
- and
- where any alkylene group may be optionally substituted by one or more halo.
Dependencies are inferred from the claim text.