Small molecule inhibitors of SLC15A4 with anti-inflammatory activity

A compound of formula (I)

• or a pharmaceutically acceptable salt thereof, wherein:
• X is NR4 or S;
• R1 is H or —C(O)—C1-10alkyl;
• R2 is
• R3 is halogen;
• R4 is H, —C1-10alkyl, —C(O)—C1-10alkyl, —C(O)—C3-10cycloalkyl, —S(O)2—C1-10alkyl, or
• and
• n is 0, 1, 2, 3, or 4.

A compound, which compound is:

• 1-(2-(((1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• N-((1H-indol-5-yl)methyl)-N-(benzo[d]thiazol-2-yl)butyramide;
• N-((5-bromo-1H-indol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-(2-(((5-bromo-1H-indol-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-((isoquinolin-5-ylmethyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-((pyrazolo[1,5-a]pyridin-5-ylmethyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-((3,4-dimethoxybenzyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((1-benzyl-1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((1H-benzo[d]imidazol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• (2-(((1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)(cyclopropyl)methanone;
• N-((1H-indol-5-yl)methyl)-1-(propylsulfonyl)-1H-benzo[d]imidazol-2-amine;
• 1-(2-(((1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)-3,5,5-trimethylhexan-1-one;
• 1-(2-(((1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)-3-cyclopentylpropan-1-one;
• (2-(((1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)(cyclohexyl)methanone;
• 1-(2-(((1H-indol-5-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)-3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)propan-1-one;
• 1-(2-(((6-methoxypyridin-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((5-fluoro-1H-indol-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((5-fluoro-1H-indol-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• N-((1H-indol-5-yl)methyl)-N-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)butyramide;
• 1-(2-((dibenzo[b,d]furan-4-ylmethyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((5-(4-fluorophenyl)-1H-pyrazol-4-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(4-(((1-butyryl-1H-benzo[d]imidazol-2-yl)amino)methyl)-5-(4-fluorophenyl)-1H-pyrazol-1-yl)butan-1-one;
• N-((1H-indol-5-yl)methyl)-N-(2,3-dihydro-1H-inden-2-yl)butyramide;
• N-((1H-benzo[d]imidazol-2-yl)methyl)-N-((1H-indol-5-yl)methyl)butyramide;
• 1-(2-(((1H-indol-5-yl)methyl)amino)-5-fluoro-1H-benzo[d]imidazol-1-yl)butan-1-one;
• N-((9-ethyl-9H-carbazol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-(2-(((9-ethyl-9H-carbazol-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 1-(2-(((1-phenyl-1H-pyrazol-4-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• N-((5-bromo-1H-indol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((1H-indol-5-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-9H-carbazol-3-yl)methyl)-N-(1-methyl-1H-benzo[d]imidazol-2-yl)butyramide;
• 3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)-N-((9-ethyl-9H-carbazol-3-yl)methyl)-N-(1-methyl-1H-benzo[d]imidazol-2-yl)propenamide;
• N-((5-bromo-1H-indol-3-yl)methyl)-3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)-N-(1-methyl-1H-benzo[d]imidazol-2-yl)propenamide;
• 1-(2-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)ethyl)-N-((9-ethyl-9H-carbazol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• N-((1,6,7,8-tetrahydrocyclopenta[g]indol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-(2-(((1,6,7,8-tetrahydrocyclopenta[g]indol-3-yl)methyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• 3-(((1H-benzo[d]imidazol-2-yl)amino)methyl)-1H-indole-6-carbonitrile;
• N-((5-chloro-1H-indol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 9-ethyl-6-(((1-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)-9H-carbazole-3-carbonitrile;
• N-((9-ethyl-3,3-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-6-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-3,3-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-6-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-butyl-N-((9-ethyl-3,3-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-6-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-butyl-N-((9-ethyl-9H-carbazol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• N-((1H-indol-5-yl)methyl)-1-butyl-1H-benzo[d]imidazol-2-amine;
• 1-butyl-N-(dibenzo[b,d]furan-4-ylmethyl)-1H-benzo[d]imidazol-2-amine;
• 1-butyl-N-((6-methoxypyridin-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• N-(benzo[d][1,3]dioxol-5-ylmethyl)-1-butyl-1H-benzo[d]imidazol-2-amine;
• N-((5-bromo-1H-indol-3-yl)methyl)-1-butyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-3-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-6-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-3-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-6-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-butyl-N-((9-ethyl-3-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-6-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• (R)-1-(1H-benzo[d]imidazol-2-yl)-N-((9-ethyl-9H-carbazol-3-yl)methyl)ethan-1-amine;
• Methyl 3-(((1H-benzo[d]imidazol-2-yl)amino)methyl)-1H-indole-5-carboxylate;
• 3-(((1H-benzo[d]imidazol-2-yl)amino)methyl)-1H-indole-5-carboxylic acid;
• N-((1H-benzo[g]indol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• N-((1H-benzo[g]indol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-9H-carbazol-3-yl)methyl)quinolin-3-amine;
• 1-(2-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)ethyl)-N-(3,4-dimethoxybenzyl)-1H benzo[d]imidazol-2-amine;
• N-((7-ethyl-7H-benzo[c]carbazol-10-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• N-((7-ethyl-7H-benzo[c]carbazol-10-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-(4-(tert-butyl)phenyl)-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine
• N-((6-(3,5-dimethylisoxazol-4-yl)-9-ethyl-9H-carbazol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine
• N-((6-(3,5-dimethylisoxazol-4-yl)-9-ethyl-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine
• N-((6-bromo-9-ethyl-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((6-(benzo[d][,3]dioxol-5-yl)-9-ethyl-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• 3-(9-ethyl-6-(((i-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)-9H-carbazol-3-yl)phenol;
• N-((9-ethyl-6-methoxy-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((5-methoxy-1H-indol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine;
• N-((9-ethyl-6-(4-methylpentyl)-9H-carbazol-3-yl)methyl)-1-methyl-1H-benzo[d]imidazol-2-amine
• 1-(2-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)ethyl)-N-((1-phenyl-1H-pyrazol-4-yl)methyl)-1H-benzo[d]imidazol-2-amine;
• 1-(2-((benzo[d][,3]dioxol-5-ylmethyl)amino)-1H-benzo[d]imidazol-1-yl)butan-1-one;
• or a pharmaceutically acceptable salt thereof.