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US 7,547,718 B2Granted
Substituted imidazoles
AssigneePfizer Inc.
InventorsNathan Anthony Logan Chubb, Mark Roger Cox, Jerome Sebastien Dauvergne, Richard Andrew Ewin, Christelle Lauret
Life of this patent
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Abstract
This invention relates to a range of alpha substituted 2-benzyl substituted imidazole compounds and pharmaceutically acceptable salts and solvates thereof, to compositions comprising such compounds, processes for their synthesis and their use as parasiticides.
Claims19
A method of treating a parasite infestation in a mammal comprising treating the host animal with an effective amount of a compound of formula (I)
- wherein:
- R1, R2, R3, R4, R5 are independently selected from the group consisting of hydrogen, cyano, nitro, halo, hydroxy, C1-4 alkyl optionally substituted by one or more hydroxy groups, or C3-6 cycloalkyl which is further optionally substituted by one or more C1-4 alkyl or halo groups, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, phenyl, amino, NRxRy, or S(O)nR10;
- R6 is selected from the group consisting of hydrogen, —C0-2alkyleneR7, —C1-2alkyleneOR7, —C0-2alkyleneC(O)R7, —C1-2alkyleneOC(O)R7, —C1-2alkyleneOC(O)OR7, —C0-2alkyleneC(O)OR7, —C1-2alkyleneN(H)C(O)R7, —C1-2alkyleneN(R7)C(O)R7, —C0-2alkyleneC(O)NHR7, —C0-2alkyleneC(O)NR15R16, —C1-2alkyleneNHC(O)NR15R16, —C1-2alkyleneNR7C(O)NR15R16, —C1-2alkyleneOC(O)NHR7, —C1-2alkyleneOC(O)NR15R16, —C0-2alkyleneCH═N(R7), —C1-2alkyleneP(═O)(NR15R16)(NR15R16), —C0-2alkyleneSi(R7)3, and —C0-2alkyleneS(O)R10;
- where the C0-2alkylene or C1-2alkylene of R6 may, where chemically possible, optionally be substituted by one or more substituents selected from the group consisting of C1-6 alkyl, C3-6 cycloalkyl, C1-4alkylene(C3-6cycloalkyl), C0-6alkylenephenyl, which C0- 2alkylene or C1-2alkylene substituent may in turn be optionally further substituted, where chemically possible, by one or more substituents selected from the group consisting of hydrogen, cyano, nitro, halo, formyl, oxo, hydroxy, C(O)OH, C1-4alkyl, C1-4alkyleneC3-6cycloalkyl, C1-4alkoxy, C1-4alkyleneC1-4alkyoxy, —C(O)OC1-4alkyl, C1-4haloalkyl, C1-4haloalkoxy, amino, C1-4alkylamino, C1-4dialkylamino, and S(O)nR10;
- where each R7, R15 and R16, where chemically possible, is independently selected from the group consisting of hydrogen, C1-8alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C1-4alkylene(C3-6cycloalkyl), C1-4alkyleneC1-4alkoxy, C1-6haloalkyl, C0-6alkylenephenyl, C0-6alkylenenaphthyl, C0-6alkylene(tetrahydronaphthyl), and C0-2alkylene(Het), where Het is selected from oxetanyl, tetrahydropyranyl, piperidinyl, morpholinyl, furyl, pyridyl, benzofuranyl, benzothiazolyl, indolyl, 2,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, indolyl and 1,5-naphthyridinyl;
- or R15 and R16 together with the nitrogen to which they are attached may form a three to seven-membered saturated or unsaturated heterocyclic ring optionally containing one or more further N, O or S atoms or SO2 groups;
- where each of the above R7, R15 or R16 groups may independently include one or more optional substituents where chemically possible selected from hydrogen, cyano, nitro, halo, formyl, oxo, hydroxy, C(O)OH, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C3-6cycloalkyl, C1-4alkyleneC3-6cycloalkyl, C1-4alkoxy, C1-4alkyleneC1-4alkyoxy, C1-4alkoxyC1-4 alkoxy, C1-4alkanoyl, —C(O)OC1-4alkyl, C1-4haloalkyl, C3-6halocycloalkyl, C1-4haloalkoxy, C1-4haloalkanoyl, —C(O)OC1-4haloalkyl, phenyl, 4-halophenyl, 4-alkoxyphenyl, 2-cyanophenyl, phenoxy, 4-halophenoxy, benzyloxy, 4-halobenzyloxy, benzoyl, pyrazolyl, triazolyl, 2-halo-4-pyrimidinyl, 2-phenylethyl, amino, C1-4alkylamino, C1-4 dialkylamino, C(O)N(C1-4alkyl)2, N(C1-4alkylene)C(O)(C1-4alkyl) and S(O)nR10;
- R8 and R9 are independently selected from the group consisting of hydrogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy and C0-4 alkylenephenyl but with the proviso that R8 and R9 are not both hydrogen;
- where each of R8 and R9 may independently include one or more optional substituents where chemically possible selected from hydrogen, cyano, halo, hydroxy, C1-4 alkyl, C3-6 cycloalkyl, C1-4 alkoxy, —C(O)OC1-4 alkyl, C1-4 haloalkyl, C1-4haloalkoxy, and S(O)nR10;
- or R8 and R9 together with the carbon to which they are attached may form a three to six membered carbocyclic, saturated ring, which ring is optionally substituted with one or more substituents selected from the group consisting of halo, C1-2 alkyl, C1-2 alkoxy, C1-2 haloalkyl, C1-2 haloalkoxy;
- R11 and R12 are independently selected from the group consisting of hydrogen, halo, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, and C1-4 haloalkoxy;
- where Rx and Ry are independently selected from hydrogen, C1-4 alkyl, C1-4 haloalkyl, and S(O)nR10;
- each n is independently 0, 1 or 2;
- and each R10 is independently hydrogen, hydroxy, C1-4 alkyl, C1-4 haloalkyl, 4-halophenyl, amino, C1-6 alkyl amino and di C1-6 alkyl amino;
- or a pharmaceutically acceptable salt thereof.
12 more elements
Dependencies are inferred from the claim text.