Azabiphenylaminobenzoic acid derivatives as dhodh inhibitors

The compound according to claim 26, chosen from:

• 5-cyclopropyl-2-(2-phenylpyrimidin-5-ylamino)benzoic acid,
• 2-(6-Cyclopropyl-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 5-(2-Carboxy-4-cyclopropylphenylamino)-3-methyl-2-phenylpyridine 1-oxide,
• 5-Methyl-2-(6-(3-(trifluoromethyl)phenyl)pyridin-3-ylamino)benzoic acid,
• 5-cyclopropyl-2-(6-hydroxy-5-phenylpyridin-3-ylamino)benzoic acid,
• 5-cyclopropyl-2-(2-(2,6-difluoro-4-hydroxyphenyl)pyrimidin-5-ylamino)benzoic acid,
• 5-Cyclopropyl-2-(6-methoxy-5-phenylpyridin-3-ylamino)benzoic acid,
• 2-(5-Fluoro-6-phenylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(Ethyl(methyl)amino)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 5-Cyclopropyl-2-(3′-fluoro-2,4′-bipyridin-5-ylamino)benzoic acid,
• 2-(6-(Diethylamino)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-((2-Methoxyethyl)(methyl)amino)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(5-Chloro-6-phenylpyridin-3-ylamino)-5-methylbenzoic acid,
• 5-Cyclopropyl-2-(2-(2-cyclopropylphenyl)pyrimidin-5-ylamino)benzoic acid,
• 5-cyclopropyl-2-(5-phenylpyridin-3-ylamino)benzoic acid,
• 5-methyl-2-(quinolin-3-ylamine)benzoic acid,
• 5-methyl-2-(5,6,7,8-tetrahydroquinolin-3-ylamino)benzoic acid,
• 2-(5-Chloro-2-phenylpyridin-3-ylamino)-5-methylbenzoic acid,
• 5-Cyclopropyl-2-(5,6diphenylpyridin-3-ylamino)benzoic acid,
• 5-cyclopropyl-2-(2-(2,6-difluorophenyl)pyrimidin-5-ylamino)benzoic acid,
• 5-Cyclopropyl-2-(5-methylpyridin-3-ylamino)benzoic acid,
• 2-(2-(3-Cyclopropoxyphenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 5-Methyl-2-(6-morpholinopyridin-3-ylamino)benzoic acid,
• 5-Methyl-2-(5-methyl-6-morpholinopyridin-3-ylamino)benzoic acid,
• 5-cyclopropyl-2-(6cyclopropyl)-5-phenylpyridin-3-ylamino)benzoic acid,
• 2-(6-(2cyclopropylphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(2-Cyanophenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(2-(3-Chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 5-Methyl-2-(6-phenyl-5-(trifluoromethyl)pyridin-3-ylamino)benzoic acid,
• 5-Methyl-2-(5-methyl-6-(piperidin-1-yl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(Azepan-1-yl)-5-methylpyridin-3-ylamino)-5methylbenzoic acid,
• 2-(6-(3-Methoxyphenyl)-5-phenylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(2,3′-bipyridin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(3′-chloro-2,4′-bipyridin-5-ylamino)-5-methylbenzoic acid,
• 5-Methyl-2-(3-methyl-2,2′-bipyridin-5-ylamino)benzoic acid,
• 2-(5,6-Difluoropyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(3-Ethoxyphenyl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(3-Ethoxyphenyl)pyridin-3-ylamino)-5-fluorobenzoic acid,
• 2-(6-(3-Ethoxyphenyl)-5-methylpyridin-3-ylamino)benzoic acid,
• 2-(6-(3-Ethoxyphenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-Ethoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-Ethoxy-2-fluorophenyl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(3-Ethoxyphenyl)-4-methylpyridin-3-ylamino)-5-ethylbenzoic acid,
• 2-(6-(3-Ethoxyphenyl)-4-methylpyridin-3-ylamino)benzoic acid,
• 5-Bromo-2-(6-(3-ethoxyphenyl)pyridin-3-ylamino)benzoic acid,
• 5-Chloro-2-(6-(3-ethoxyphenyl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(5-Ethoxy-2-fluorophenyl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(3-Ethoxyphenyl)-5-methylpyridin-3-ylamino)-5-(trifluoromethyl)benzoic acid,
• 2-(6-(3-Methoxyphenyl)-5-methylpyridin-3-ylamino)-5-(trifluoromethyl)benzoic acid,
• 2-(6-(3-Methoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-Methoxyphenyl)-5-methylpyridin-3-ylamino)-6-methylbenzoic acid,
• 5-Fluoro-2-(6-(3-methoxyphenyl)-5-methylpyridin-3-ylamino)benzoic acid,
• 2-(6-(5-Ethoxy-2-fluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(2-Fluoro-5-methoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(2-fluoro-5-methoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(2-Fluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-Methoxyphenyl)-5-phenylpyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(3-methoxyphenyl)-5-phenylpyridin-3-ylamino)-5-methylbenzoate,
• 5-Methyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoic acid,
• Ethyl 5-methyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoate,
• 5-Methyl-2-(5-methyl-6-(3-(trifluoromethoxy)phenyl)pyridin-3-ylamino)benzoic acid,
• Ethyl 5-methyl-2-(5-methyl-6-(3-(trifluoromethoxy)phenyl)pyridin-3-ylamino)benzoate,
• 2-(5-Cyclopropyl-6-(3-methoxyphenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(5-cyclopropyl-6-(3-methoxyphenyl)pyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(2-Fluoro-5-isopropoxyphenyl)pyridin-3-ylamino)-5-ethylbenzoic acid,
• 2-(6-(3-Isopropoxyphenyl)-5-methylpyridin-3-ylamino)-5-ethylbenzoic acid,
• Ethyl 2-(6-(3-isopropoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(3-Cyclopropoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid, tert-Butyl 2-(6-(3-cyclopropoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(2-Chlorophenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid, tert-Butyl 2-(6-(2-chlorophenyl)-5-methylpyridin-3-ylamino)-5-ethylbenzoate,
• 2-(6-(3-Carbamoylphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(3-carbamoylphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(2-Fluoro-5-methoxyphenyl)-4-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(2-fluoro-5-methoxyphenyl)-4-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(3-Methoxyphenyl)-5-(trifluoromethyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(3-methoxyphenyl)-5-(trifluoromethyl)pyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(3-(Dimethylcarbamoyl)phenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(3-(dimethylcarbamoyl)phenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(3-Isopropoxyphenyl)-5-methylpyridin-3-ylamino)-3-methylbenzoic acid, tert-Butyl 2-(6-(3-isopropoxyphenyl)-5-methylpyridin-3-ylamino)-3-methylbenzoate,
• 3-Methyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoic acid,
• tert-Butyl 3-methyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoate,
• 2-(6-(2-Chlorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid, tert-Butyl 2-(6-(2-chlorophenyl)pyridin-3-ylamino)-5-methylbenzoate,
• 3-Fluoro-2-(6-(3-methoxyphenyl)-5-methylpyridin-3-ylamino)benzoic acid, tert-Butyl 3-fluoro-2-(6-(3-methoxyphenyl)-5-methylpyridin-3-ylamino)benzoate,
• 5-Cyclopropyl-2-(5-methyl-6-(3-(trifluoromethoxy)phenyl)pyridin-3-ylamino)benzoic acid,
• Ethyl 5-cyclopropyl-2-(5-methyl-6-(3-(trifluoromethoxy)phenyl)pyridin-3-ylamino)benzoate,
• 5-Cyclopropyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoic acid,
• Ethyl 5-cyclopropyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoate,
• 5-Methyl-2-(5-methyl-6-(2-(trifluoromethyl)phenyl)pyridin-3-ylamino)benzoic acid,
• tert-Butyl 5-methyl-2-(5-methyl-6-(2-(trifluoromethyl)phenyl)pyridin-3-ylamino)benzoate,
• 2-(6-(3-Chlorophenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid, tert-Butyl 2-(6-(3-chlorophenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 2-(6-(2-Fluorophenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid, tert-Butyl 2-(6-(2-fluorophenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoate,
• 5-Methyl-2-(5-methyl-6-(quinolin-5-yl)pyridin-3-ylamino)benzoic acid,
• tert-Butyl 5-methyl-2-(5-methyl-6-(quinolin-5-yl)pyridin-3-ylamino)benzoate,
• 2-(3′-Fluoro-3-methyl-2,4′-bipyridin-5-ylamino)-5-methylbenzoic acid,
• tert-Butyl 2-(3′-fluoro-3-methyl-2,4′-bipyridin-5-ylamino)-5-methylbenzoate,
• 5-Methyl-2-(5-methyl-6-(pyrazin-2-yl)pyridin-3-ylamino)benzoic acid,
• tert-Butyl 5-methyl-2-(5-methyl-6-(pyrazin-2-yl)pyridin-3-ylamino)benzoate,
• 5-Cyclopropyl-2-(6-phenyl-5-(trifluoromethyl)pyridin-3-ylamino)benzoic acid,
• Ethyl 5-cyclopropyl-2-(6-phenyl-5-(trifluoromethyl)pyridin-3-ylamino)benzoate,
• 5-Cyclopropyl-2-(6-(3-methoxyphenyl)-5-(trifluoromethyl)pyridin-3-ylamino)benzoic acid,
• Ethyl 5-cyclopropyl-2-(6-(3-methoxyphenyl)-5-(trifluoromethyl)pyridin-3-ylamino)benzoate,
• 5-Chloro-2-(6-(2-fluorophenyl)pyridin-3-ylamino)benzoic acid,
• 5-Chloro-2-(6-(2-chlorophenyl)pyridin-3-ylamino)benzoic acid,
• 5-Chloro-2-(6-(quinolin-5-yl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(2-Chlorophenyl)pyridin-3-ylamino)-5-cyclopropylbenzoic acid,
• Ethyl 2-(6-(2-chlorophenyl)pyridin-3-ylamino)-5-cyclopropylbenzoate,
• 5-Chloro-2-(6-(2-(trifluoromethyl)phenyl)pyridin-3-ylamino)benzoic acid,
• 5-Fluoro-2-(6-(2-(trifluoromethyl)phenyl)pyridin-3-ylamino)benzoic acid,
• 2-(3′-Fluoro-2,4′-bipyridin-5-ylamino)-5-methylbenzoic acid,
• 2-(2-(2-Fluorophenyl)pyrimidin-5-ylamino)-5-methylbenzoic acid, tert-Butyl 2-(2-(2-fluorophenyl)pyrimidin-5-ylamino)-5-methylbenzoate,
• 2-(6-(2,6-Difluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• Ethyl 2-(6-(2,6-difluorophenyl)pyridin-3-ylamino)-5-methylbenzoate,
• 2-(2-(2-Chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• Methyl 2-(2-(2-chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoate,
• 2-(2-(2-Chlorophenyl)pyrimidin-5-ylamino)-5-methylbenzoic acid,
• tert-Butyl 2-(2-(2-chlorophenyl)pyrimidin-5-ylamino)-5-methylbenzoate,
• 5-Methyl-2-(5-methyl-6-(3-(pyrrolidine-1-carbonyl)phenyl)pyridin-3-ylamino)benzoic acid,
• 2-(6-(3-(Cyclopropylcarbamoyl)phenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 5-Cyclopropyl-2-(2-(2-fluorophenyl)pyrimidin-5-ylamino)benzoic acid,
• 2-(2-(2-trifluoromethylphenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(2-o-tolylpyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(2-(2-cyclopropoxyphenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(2-(2,5-difluorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(2-(2,3-difluorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(2-(2-fluoro-5-chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(2-(2-trifluoromethylphenyl)pyrimidin-5-ylamino)-5-methylbenzoic acid,
• 2-(2-(2-fluoro-5-trifluoromethoxyphenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid,
• 2-(6-(2-trifluoromethylphenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-phenylpyridin-3-ylamino)-5-cyclopropylbenzoic acid,
• 2-(6-(2-fluorophenyl)pyridin-3-ylamino)-5-cyclopropylbenzoic acid,
• 2-(6-(3,5-difluoropyridin-4-yl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-cyclopropylcarbamoylphenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(2,4-difluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(2,5-difluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(2-fluorophenyl)pyridin-3-ylamino)-5-cyclopropyl-3-fluorobenzoic acid,
• 2-(6-(2,3,6-trifluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(5-methyl-6-(pyrimidin-5-yl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(2,3-difluorophenyl)pyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(5-fluoro-2-methoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• 2-(6-(4-carbamoylphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid,
• or a pharmaceutically acceptable salt or N-oxide thereof.

A compound of formula (I):

• wherein:
• R1 is chosen from a hydrogen atom, halogen atoms, C1-4 alkyl, C3-4 cycloalkyl, —CF3 and —OCF3,
• R2 is chosen from a hydrogen atom, halogen atoms and C1-4 alkyl groups,
• R3 is chosen from —COOR5, —CONHR5, tetrazolyl, —SO2NHR5 and —CONHSO2R5 groups, wherein R5 is chosen from a hydrogen atom and linear or branched C1-4 alkyl groups,
• R4 is chosen from a hydrogen atom and C1-4 alkyl groups,
• R9 is chosen from a hydrogen atom and phenyl groups,
• G1 represents a group chosen from N and CR6, wherein R6 is chosen from a hydrogen atom, halogen atoms, C1-4 alkyl groups, C3-4 cycloalkyl groups, C1-4 alkoxy groups, —CF3, —OCF3, monocyclic N-containing C5-7 heteroaryl groups, monocyclic N-containing C3-7 heterocyclyl groups and C6-10 aryl groups which are optionally substituted with at least one substituent chosen from halogen atoms and C1-4 alkyl groups,
• G2 represents a group chosen from:
• a hydrogen atom, hydroxy groups, halogen atoms, C3-4 cycloalkyl groups, C1-4 alkoxy groups and —NRaRb, wherein
• Ra is chosen from C1-4 alkyl groups, and Rb is chosen from C1-4 alkyl groups and C1-4 alkoxy-C1-4 alkyl groups, or
• Ra and Rb together with the nitrogen atom to which they are attached form a saturated 6 to 8 membered heterocyclic ring optionally containing one oxygen atom as an additional heteroatom,
• a monocyclic or bicyclic 5 to 10 membered heteroaromatic ring containing one or more nitrogen atoms, which is optionally substituted by at least one substituent chosen from halogen atoms, C1-4 alkyl groups, C1-4 alkoxy groups, C3-4 cycloalkyl groups, C3-4 cycloalkoxy groups, —CF3, —OCF3, and —CONR7R8, wherein R7 and R8 are independently chosen from a hydrogen atom, linear or branched C1-4 alkyl groups, C3-7 cycloalkyl groups, or R7 and R8 together with the nitrogen atom to which they are attached form a group of formula
• wherein n is an integer from 0 to 3, and
• a phenyl group, which is optionally substituted by at least one substituent chosen from halogen atoms, C1-4 alkyl groups, hydroxyl, C1-4 alkoxy groups, C3-4 cycloalkyl groups, C3-4 cycloalkoxy groups, cyano groups, —CF3, —OCF3, —CONR7R8, oxadiazolyl groups, triazolyl groups, pyrazolyl groups and imidazolyl groups, wherein the oxadiazolyl, triazolyl, pyrazolyl and imidazolyl groups are optionally substituted by C1-4 alkyl group or C3-7 cycloalkyl groups and wherein R7 and R8 are independently chosen from a hydrogen atom, linear or branched C1-4 alkyl groups, and C3-7 cycloalkyl groups, or R7 and R8 together with the nitrogen atom to which they are attached form a group of formula
• wherein n is an integer from 0 to 3,
• or, G2 together with R6 forms a non-aromatic C5-10 carbocyclic group or a C6-10 aryl group,
• or a pharmaceutically acceptable salt or N-oxide thereof,
• with the proviso that when G2 is a hydrogen or chlorine atom, a methoxy or butoxy group or together with R6 forms a phenyl group, then R1 is not a hydrogen atom or a chlorine atom.