Pyridinylimidazoles
OwnerLaramie Mary Gaster, Michael Stewart Hadley +5inventors
InventorsLaramie Mary Gaster, Michael Stewart Hadley, John David Harling, Frank Peter Harrington, Jag Paul Heer, Thomas Daniel Heightman, Andrew Hele Payne
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Abstract
Compounds of formula (I) and pharmaceutically acceptable salts thereof wherein R1, R2 and R3 represent various functional groups, and one of X1 and X2 is N and the other is NR10; and their use as pharmaceuticals.
Claims10
A compound of formula (I) or a pharmaceutically acceptable salt thereof:
- 85
- (I)
- wherein R1 is naphthyl, anthracenyl, or phenyl optionally substituted with one or more substituents selected from the group consisting of halo, C1-6alkoxy, C1-6alkylthio, C1-6alkyl, C1-6haloalkyl, O—(CH2)m—Ph, S—(CH2)m—Ph, cyano, phenyl, and CO2R, wherein R is hydrogen or C1-6alkyl and m is 0-3;
- or R1 is phenyl or pyridyl fused with an aromatic or non-aromatic cyclic ring of 5-7 members wherein said cyclic ring optionally contains up to three heteroatoms, independently selected from N, O and S, and is optionally substituted by ═O;
- R2 represents hydrogen, C1-6alkyl, C1-6alkoxy, phenyl, C1-6haloalkyl, halo, NH2, NH—C1-6alkyl or NH(CH2)n—Ph wherein n is 0-3;
- R3 represents C1-6alkyl, —(CH2)p—CN, —(CH2)p—COOH, —(CH2)p—CONHR4R5, —(CH2)pCOR4, —(CH2)q(OR6)2, —(CH2)pOR4, —(CH2)q—CH═CH—CN, —(CH2)q—CH═CH—CO2H, —(CH2)p—CH═CH—CONHR4R5, —(CH2)pNHCOR7 or —(CH2)pNR8R9,
- R4 and R5 are independently hydrogen or C1-6alkyl;
- R6 is C1-6alkyl;
- R7 is C1-7alkyl, or optionally substituted aryl, heteroaryl, arylC1-6alkyl or heteroarylC1-6alkyl;
- R8 and R9 are independently selected from hydrogen, C1-6alkyl, aryl and arylC1-6alkyl;
- p is 0-4;
- q is 1-4;
- one of X1 and X2 is N and the other is NR10;
- and
- R10 is hydrogen, C1-6alkyl, or C3-7cycloalkyl;
- provided that the compound is not:
- i) 2-[5-(2-methylphenyl)-2-propyl-1H-imidazol-4-yl]pyridine,
- ii) 2-[2-(1,1-dimethylethyl)-5-(4-methoxyphenyl)-1H-imidazol-4-yl]pyridine,
- iii) 2-[2-(1,1-dimethylethyl)-5-phenyl-1H-imidazol-4-yl]pyridine,
- iv) 2-[5-(3,5-dichlorophenyl)-2-methyl-1H-imidazol-4-yl]pyridine,
- v) 2-[5-(3,5-dimethylphenyl)-2-methyl-1H-imidazol-4-yl]pyridine,
- vi) 2-[5-(3,5-dimethylphenyl)-2-ethyl-1H-imidazol-4-yl]pyridine,
- vii) 2-[5-(3,5-dimethylphenyl)-2-amino-1H-imidazol-4-yl]pyridine,
- viii) 2-[5-(3,5-dimethylphenyl)-2-isopropyl-1H-imidazol-4-yl]pyridine,
- ix) 2-[5-(3,5-dimethylphenyl)-2-propyl-1H-imidazol-4-yl]pyridine,
- x) 2-[5-(3,5-dimethylphenyl)-2-carboxamide-1H-imidazol-4-yl]pyridine,
- xi) 2-[5-(3,5-dimethylphenyl)-2-cyano-1H-imidazol-4-yl]pyridine, or
- xii) 2-[5-(3,5-dimethylphenyl)-2-methoxymethyl-1H-imidazol-4-yl]pyridine.
A compound according to any one of the preceding claims wherein R3 is C1-6alkyl or (CH2)pNHCOR7 wherein R7 is C1-7alkyl, or optionally substituted aryl, heteroaryl, arylC1-6alkyl or heteroarylC1-6alkyl.
A compound according to any one of the preceding claims wherein R10 is hydrogen.
A pharmaceutical composition comprising a compound according to any one of the preceding claims, but without provisos iv) to xii), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.
Dependencies are inferred from the claim text.