Patent RU-2410377-C2 (RU)
Inventor: LANGE JOZEFUS KH M
IPC: A61P29/00
Filed: 2006-02-16
Granted: 2011-01-27
Abstract: FIELD: medicine, pharmaceutics. 
     SUBSTANCE: claimed invention relates to novel derivatives of 1H-imidazole of formula   I, in which R 1  represents hydrogen, halogen atom, C 1-3 -alkyl group, and said C 1-3 -alkyl groupcan include 1-3 fluorine atoms or R 1  represents cyclopropyl, piano, or methylsulfanyl group, R 2  represents phenyl group, which can be substituted with 1 substituent Y, selected from methoxy, chlorine, fluorine, trifluoromethyl and cyano, or R 2  represents pyridyl group, on condition that R 2  is not 6-methyl-2-pyridyl group, or R 2  represents fully saturated 6-7-member monocyclic, condensed bicyclic ring system or benzothiazolyl, benzodioxane or thiazole group, and said groups can be substituted by 1 fluorine atom, or R 2  represents group of general formula CH 2 -R 5 , in which R 5  represents phenyl group or fully saturated 7-member condensed bicyclic carbocyclic ring system, or R 5  represents piperidine or tetrahydrofuran ring system, which can be substituted by methyl, or R 2  represents methylsulfonylamino(C 3 )alkyl group, R 3  represents hydrogen, halogen atom, C 1-6 -alkylsulfonyl, cyanogroup, or R 3  represents C 1-8 -alkyl group, and said C 1-8 -alkyl group can be substituted by 1-3 fluorine atoms, or R 3  represents phenyl group, which is substituted by substituent Y, where Y has value, specified above, or R 3  represents furanyl group, R 4  represents one of subgroups   (i) or   (ii), where R 6  represents C 4-8 -branched or linear alkyl group or naphtyl group, R 7  represents hydrogen atom, linear C 1-6 -alkyl group, R 8  represents C 2-6 -alkyl group, substituted by 1-3 fluorine atoms, or R 8  represents C 3-8 -cycloalkyl group, piperidine group, C 3-8 -cycloalkyl- C 1-2 -alkyl group, tetrahydrofuranyl- C 1-2 -alkyl group, C 5-10 -bicycloalkyl group, C 5-10 -bicycloalkyl-C 1-2 -alkyl group, C 6-10 -tricycloalkyl group, C 6-10 -tricycloalkyl-C 1-2 -alkyl group, and said groups can be substituted by 1-3 substituents, selected from methyl or hydroxyl, or R 8  represents phenyl group, substituted by 1-2 substituents Y, specified above, or R 8  represents naphtyl, 1,2,3,4-tetrahydronaphtyl or indanyl group, and said groups can be substituted by 1 substituent Y, or R 8  represents phenyl- C 1-3 -alkyl group, diphenyl- C 1-3 -alkyl group, and said groups can be substituted ob their phenyl ring by 1 substituent Y, where Y has value specified above, or R 8  represents benzyl group, substituted by 2 substituents Y, or R 8  represents quinilinyl, pyridinyl, benzimidazole or naphtylmethyl group which can be substituted by substituent Y, where Y has value, specified above, or R 8  represents asabicyclo[3,3,0]octanyl group, on condition that R 8  is neither 6-methoxybenzothiazole-2-yl group, nor [3-chlor-5-(trifluoromethyl)pyrid-2-yl]methyl group, or R 7  and R 8  together with nitrogen atom, to which they are bound, form saturated, non-aromatic, monocyclic or bicyclic heterocyclic group, including only one nitrogen atom, having 7-10 ring atoms, which can be subslituted by 3 C 1-3 -alkyl groups, or R 7  and R 8  together with nitrogen atom, to which they are bound, form saturated, monocyclic heterocyclic group, optionally including another N atom, having 6 ring atoms, and said heterocyclic group is substituted by C 1-3 -alkyl groups, on condition that R 7  and R 8  together with nitrogen atom, to which they are bound, do not form trimethylsubstituted asabicyclo[3,3,0]octanyl group, as well as their stereoisomers and pharmacologically acceptable salts of said formula (I) compounds and their stereoisomers Invention also relates to intermediate compounds of formula XIV, pharmaceutical composition based on formula I compound, method of obtaining such pharmaceutical composition and application of formula T compound. 
     EFFECT: obtained are novel derivatives of IH-imidazole, which are modulators of cannabinoid CB 2 -receptors. 
     8 cl, 1 tbl, 3 ex