Substituted imidazoles
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.
1. A compound of formula (I):
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 are each independently selected from the group consisting of hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, and C 1-4 haloalkyl;
R 6 is hydrogen;
R 8 and R 9 are each independently selected from the group consisting of hydrogen and C 1-4 alkyl, but with the proviso that R 8 and R 9 are not both hydrogen;
R 11 and R 12 are each independently selected from the group consisting of hydrogen, C 1-2 alkyl, and C 1-2 alkoxy;
or a pharmaceutically, veterinary, or agriculturally acceptable salt thereof, with the proviso that the compound of Formula (I) is not 2-[(1S)-1-(2,3-dimethyl-phenyl)ethyl]-1H-imidazole.
2. A compound as claimed in claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 are each independently hydrogen and C 1-4 alkyl.
3. A compound as claimed in claim 1 wherein R 11 and R 12 are both hydrogen.
4. A compound as claimed in claim 1 selected from the group consisting of:
2-[1-(2-chloro-3-methyl-phenyl)ethyl]-1H-imidazole;
2-[1-(2,4-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(4-chloro-3-methyl-phenyl)ethyl]-1H-imidazole;
2-[1-(2,3-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(3,4-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chlorophenyl)-ethyl]-1H-imidazole;
2-[1-(2-chloro-4-methoxy-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-2-methoxy-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-4-methoxy-phenyl)ethyl]-1H-imidazole;
2-[1(2,5-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-4-methyl-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-2-methyl-phenyl)ethyl]-1H-imidazole;
2-[1-(2-chloro-5-methoxy-phenyl)ethyl]-1H-imidazole; and
2-[1-(2-chloro-5-methyl-phenyl)ethyl]-1H-imidazole
or a pharmaceutically, veterinarily, or agriculturally acceptable salt thereof.
5. A method of treating a parasitic infection in plants or animals by administering an effective amount of a compound of formula (I)
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 are each independently selected from the group consisting of hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, and C 1-4 haloalkyl;
R 6 is hydrogen;
R 8 and R 9 are each independently selected from the group consisting of hydrogen and C 1-4 alkyl, but with the proviso that R 8 and R 9 are not both hydrogen;
R 11 and R 12 are each independently selected from the group consisting of hydrogen, C 1-2 alkyl, and C 1-2 alkoxy;
or a pharmaceutically, veterinary, or agriculturally acceptable salt thereof, and when treating animals, the compound is not 2-[(1S)-1-(2,3-dimethyl-phenyl)ethyl]-1H-imidazole.
6. The method of claim 5 for treating a parasitic infection in plants or animals by administering an effective amount of a compound of Formula (I) selected from the group consisting of:
2-[1-(2-chloro-3-methylphenyl)ethyl]-1H-imidazole;
2-[1-(2,4-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(4-chloro-3-methyl-phenyl)ethyl]-1H-imidazole;
2-[1-(2,3-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(3,4-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chlorophenyl)-ethyl]-1H-imidazole;
2-[1-(2-chloro-4-methoxyphenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-2-methoxyphenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-4-methoxyphenyl)ethyl]-1H-imidazole;
2-[1-(2,5-dichloro-phenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-4-methylphenyl)ethyl]-1H-imidazole;
2-[1-(3-chloro-2-methylphenyl)ethyl]-1H-imidazole;
2-[1-(2-chloro-5-methoxyphenyl)ethyl]-1H-imidazole; and
2-[1-(2-chloro-5-methyl-phenyl)ethyl]-1H-imidazole
or a pharmaceutically, veterinarily, or agriculturally acceptable salt thereof.
7. A composition comprising a compound of Formula (I)
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 are each independently selected from the group consisting of hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, and C 1-4 haloalkyl;
R 6 is hydrogen;
R 8 and R 9 are each independently selected from the group consisting of hydrogen and C 1-4 alkyl, but with the proviso that R 8 and R 9 are not both hydrogen;
R 11 and R 12 are each independently selected from the group consisting of hydrogen, C 1-2 alkyl, and C 1-2 alkoxy;
or a pharmaceutically, veterinary, or agriculturally acceptable salt thereof, with the proviso that the compound of Formula (I) is not 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole, and a pharmaceutically, veterinary, or agriculturally acceptable carrier or vehicle.