| US 7,547,718 B2 | ||
| Substituted imidazoles | ||
| Nathan Anthony Logan Chubb, Sandwich (United Kingdom); Mark Roger Cox, Sandwich (United Kingdom); Jerome Sebastien Dauvergne, Sandwich (United Kingdom); Richard Andrew Ewin, Sandwich (United Kingdom); and Christelle Lauret, Sandwich (United Kingdom) | ||
| Assigned to Pfizer Limited, Sandwich, Kent (United Kingdom) | ||
| Filed on Nov. 26, 2007, as Appl. No. 11/945,064. | ||
| Application 11/945064 is a division of application No. 11/619735, filed on Jan. 04, 2007. | ||
| Claims priority of provisional application 60/760765, filed on Jan. 19, 2006. | ||
| Prior Publication US 2008/0125473 A1, May 29, 2008 | ||
| Int. Cl. A61K 31/41 (2006.01); A61K 31/415 (2006.01); A01N 43/50 (2006.01); A01K 29/00 (2006.01) | ||
| U.S. Cl. 514—396 [514/359; 514/385; 119/651] | 19 Claims |
1. 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)
![]() 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.
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