CA2470519C — Heteroaryl substituted pyrrole modulators of metabotropic glutamate receptor-5

USPTO Abstract

Pyrrole compounds selected from the group consisting of 3-(1-pyridin-2-yl-1H-pyrrol-3-yl)benzonitrile; 2-[3-(3-chlorophenyl)-1H-pyrrol-1-yl]pyridine; 2-[3-(3-methoxyphenyl)-1H-pyrrol-1-yl]pyridine; 3-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile; 2-{1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}pyridine; 2-[1-(3,5-dichlorophenyl)-1H-pyrrol-3-yl]pyridine; 2-[1-(3-methylphenyl)-1H-pyrrol-3-yl]pyridine; 2-[1-(3-methoxyphenyl)-1H-pyrrol-3-yl]pyridine; 3-[3-(1,3-thiazol-2-yl)-1H-pyrrol-1-yl]benzonitrile; 3-fluoro-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile; 3-(3-bromo-4-pyridin-2-yl-1H-pyrrol-1-yl)-5-fluorobenzonitrile; 3-fluoro-5-(3-methyl-4-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile; 3-(3-chloro-4-pyridin-2-yl-1H-pyrrol-1-yl)-5-fluorobenzonitrile; 3-fluoro-5-[3-(1H-pyrazol-1-yl)-1H-pyrrol-1-yl]benzonitrile; 2-chloro-6-(3-pyridin-2-yl-1H-pyrrol-1-yl)pyridine; 2-(pyridin-3-yloxy)-6-(3-pyridin-2-yl-1H-pyrrol-1-yl)pyridine; 2-chloro-4-methyl-6-(3-pyridin-2-yl-1H-pyrrol-1-yl)pyridine; 3-chloro-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile; 2-{1-[3-fluoro-5-(pyridin-3-yloxy)phenyl]-1H-pyrrol-3-yl} pyridine; 3-bromo-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile; 3-methyl-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile; 3-fluoro-5-[3-(1,3-thiazol-2-yl)-1H-pyrrol-1-yl]benzonitrile; and pharmaceuticallyacceptable salts thereof, are characterized by being substituted directly with a heteroaryl moiety containing N adjacent to the point of connection of the heteroaryl, and are mGluR5 modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorder and panic, as well as in the treatment of pain, circadian rhythm disorders, and other diseases.