Imidazolylketone derivatives
The invention provides novel compounds having the general formula (I) wherein R 1 , R 2 , R 3 and R 4 n are as described herein, compositions including the compounds and methods of using the compounds.
1. A Compound of formula (I)
wherein
R 1 is methyl, ethyl, isopropyl, pentan-3-yl or cyanophenyl;
R 2 is H, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxy, halocycloalkoxy or hydroxyalkyl;
R 3 is H, chloro, fluoro, cyano, or methoxy;
R 4 is H, halogen, cyano, nitro, substituted amino, alkyl, cycloalkyl, halocycloalkyl, cycloalkyl alkyl, halocycloalkylalkyl, alkynyl, alkoxy, haloalkoxy, alkylsulfanyl, cycloalkylsulfanyl, haloalkylsulfanyl, alkylsulfonyl, cycloalkylsulfonyl, haloalkylsulfonyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxy, halocycloalkoxy or hydroxyalkyl, wherein substituted amino is substituted with R 8 and R 9 ;
or R 3 and R 4 together form —CH 2 —CH 2 —C(O)—N(CH 3 )— or —CH═CH—S—
R 5 , R 6 and R 7 are independently selected from H, halogen, cyano, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkyl alkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxy, halocycloalkoxy and hydroxyalkyl;
R 8 is alkyl, cycloalkyl, formyl, alkylcarbonyl or alkoxycarbonyl;
R 9 is H, alkyl or cycloalkyl;
or a pharmaceutically acceptable salt thereof;
with the proviso that at least one of R 2 , R 3 and R 4 is different from H and that (4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)-methanone, 2-fluoro-4-[(1-methyl-1H-imidazol-5-yl)carbonyl]-benzonitrile, 4-[(1-methyl-1H-imidazol-5-yl)carbonyl]-benzonitrile, 2-bromo-4-[(1-methyl-1H-imidazol-5-yl)carbonyl]-benzonitrile, (4-chlorophenyl)[1-(1-methyl ethyl)-1H-imidazol-5-yl]-methanone, [4-(1-methyl ethyl)phenyl](1-methyl-1H-imidazol-5-yl)-methanone, (4-ethylphenyl)(1-methyl-1H-imidazol-5-yl)-methanone, (1-methyl-1H-imidazol-5-yl)(4-methylphenyl)-methanone, (4-chlorophenyl)(1-ethyl-1H-imidazol-5-yl)-methanone, (4-chloro-3-methylphenyl)(1-methyl-1H-imidazol-5-yl)methanone, (1-methyl-1H-imidazol-5-yl)[3-(trifluoromethyl)phenyl]-methanone, (4-chloro-2-fluoro-5-methoxyphenyl)(1-methyl-1H-imidazol-5-yl)-methanone, (2-fluorophenyl)(1-methyl-1H-imidazol-5-yl)-methanone, and (3-bromophenyl)(1-methyl-1H-imidazol-5-yl)-methanone are excluded.
2. A compound according to claim 1 , wherein R 2 is H or halogen.
3. A compound according to claim 1 , wherein R 2 is H, chloro or fluoro.
4. A compound according to claim 1 , wherein R 2 is H.
5. A compound according to claim 1 , wherein R 3 is H, chloro or methoxy.
6. A compound according to claim 1 , wherein R 4 is H, halogen, cyano, substituted amino, alkyl, alkynyl, alkoxy, alkylsulfanyl, haloalkylsulfanyl or alkylsulfonyl, wherein substituted amino is substituted with R 8 and R 9 .
7. A compound according to claim 1 , wherein R 4 is halogen, cyano, substituted amino or alkylsulfanyl, wherein substituted amino is substituted with with R 8 and R 9 .
8. A compound according to claim 1 , wherein R 4 is halogen, cyano, substituted amino or alkylsulfanyl, wherein substituted amino is substituted with formyl and alkyl.
9. A compound according to claim 1 , wherein R 3 and R 4 together form —CH 2 —CH 2 —C(O)—N(CH 3 )— or —CH═CH—S—.
10. A compound according to claim 1 , wherein R 3 and R 4 together form —CH 2 —CH 2 —C(O)—N(CH 3 )—.
11. A compound according to claim 1 , wherein R 5 , R 6 and R 7 are independently selected from H, halogen or cyano.
12. A compound according to claim 1 , wherein R 8 is alkyl, formyl, alkylcarbonyl or alkoxycarbonyl.
13. A compound according to claim 1 , wherein R 8 is formyl.
14. A compound according to claim 1 , wherein R 9 is H or alkyl.
15. A compound according to claim 1 , wherein R 9 is alkyl.
16. A compound according to claim 1 , wherein R 9 is methyl.
17. A compound of claim 1 selected from
(3,4-dichlorophenyl)(1-methyl-1H-imidazol-5-yl)methanone;
4-(1-ethyl-1H-imidazole-5-carbonyl)benzonitrile;
1-methyl-6-(1-methyl-1H-imidazole-5-carbonyl)-3,4-dihydroquinolin-2(1H)-one;
6-(1-ethyl-1H-imidazole-5-carbonyl)-1-methyl-3,4-dihydroquinolin-2(1H)-one;
(1-methyl-1H-imidazol-5-yl)(4-(methylthio)phenyl)methanone;
2-chloro-4-(isopropyl-1H-imidazole-5-carbonyl)benzonitrile;
(3-methoxy-4-(trifluoromethylthio)phenyl)(1-methyl-1H-imidazol-5-yl)methanone;
4-(1-(pentan-3-yl)-1H-imidazole-5-carbonyl)benzonitrile;
N-(4-(1-ethyl-1H-imidazole-5-carbonyl)phenyl)-N-methylformamide; and
4-(5-(4-chlorobenzoyl)-1H-imidazol-1-yl)benzonitrile;
and pharmaceutically acceptable salts thereof.