Imidazo[4,5-c]pyridin-4-one analogues as GABAA receptor ligands
AssigneeMerck Sharp & Dohme Corp.
InventorSimon Charles Goodacre
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Abstract
A compound of formula I, or a pharmaceutically acceptable salt thereof: wherein X1 represents hydrogen, halogen, C1-6 alkyl, trifluoromethyl or C1-6 alkoxy; X2 represents hydrogen or halogen; Y represents a chemical bond, an oxygen atom, or a —NH— linkage; Z represents an optionally substituted aryl or heteroaryl group; R1 represents hydrocarbon, a heterocyclic group, trifluoromethyl, —SO2Ra, —SO2NRaRb, —CORa, —CO2Ra or —CONRaRb; and Ra and Rb independently represent hydrogen, hydrocarbon or a heterocyclic group; pharmaceutical compositions including the compound and methods for treating anxiety, convulsions and cognitive disorders are disclosed.
Claims9
A compound of formula I:
- wherein:
- X1 represents hydrogen, halogen, C1-6 alkyl, trifluoromethyl or C1-6 alkoxy;
- X2 hydrogen or halogen;
- Y represents a chemical bond, an oxygen atom, or a —NH— linkage;
- Z represents a group selected from phenyl, naphthyl, pyridinyl, quinolinyl, isoquinolinyl, pyridazinyl, pyrimidinyl, pyrazinyl, furyl, benzofuryl, dibenzofuryl, thienyl, benzthienyl, pyrrolyl, indolyl, pyrazolyl, indazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazoly, benzimidazolyl, thiadiazolyl, triazolyl and tetrazolyl, which is unsubstituted or substituted with one or more groups selected from C1-6 alkyl, adamantyl, phenyl, halogen, C1-6 haloalkyl, C1-6 aminoalkyl, trifluoromethyl, hydroxy, C1-6 alkoxy, aryloxy, keto, C1-3 alkylenedioxy, nitro, cyano, carboxy, C2-6 alkoxycarbonyl, C2-6 alkoxycarbonyl(C1-6)alkyl, C2-6 alkylcarbonyloxy, arylcarbonyloxy, aminocarbonyloxy, C2-6 alkylcarbonyl, arylcarbonyl, C1-6 alkylthio, C1-6 alkylsulphinyl, C1-6 alkylsulphonyl, arylsulphonyl, —NRvRw,—NRvCORw, —NRvCO2Rw, —NRvSO2Rw, —CH2NRvSO2Rw, —NHCONRvRw, —CONRvRw, —SO2NRvRw and —CH2SO2NRvRw, in which Rv and Rw independently represent hydrogen, C1-6 alkyl, phenyl or phenyl(C1-6)alkyl;
- R1 represents C1-6 alkyl, phenyl, naphthyl, pyridinyl, quinolinyl, isoquinolinyl , pyridazinyl, pyrimidinyl, pyrazinyl, furyl, benzofuryl, dibenzofuryl, thienyl, benzthienyl, pyrrolyl indolyl, pyrazolyl, indazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, benzimidazolyl, thiadiazolyl, triazolyl, tetrazolyl, trifluoromethyl, —SO2Ra, —SO2NRaRb, —CORa, or —CONRaRb;
- and
- Ra and Rb independently represent hydrogen, C1-6 alkyl, phenyl, naphthyl, pyridinyl, quinolinyl, isoquinolinyl, pyridazinyl, pyrimidinyl, pyrazinyl, furyl, benzofuryl, dibenzofuryl, thienyl, benzthienyl, pyrrolyl, indolyl, pyrazolyl, indazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, benzimidazolyl, thiadiazolyl, triazolyl, tetrazolyl;
- or a pharmaceutically acceptable salt thereof.
A compound which is selected from the group consisting of:
- 3′-(5-methyl-4-oxo-4,5-dihydroimidazo[4,5-c]pyridin-1-yl)biphenyl-2-carbonitrile;
- 1-[4-fluoro-3-(5-fluoropyridin-3-yl)phenyl]-5-methyl-1,5-dihydroimidazo[4,5-c]pyridin-4-one;
- 5,2′-difluoro-5′-(5-methyl-4-oxo-4,5-dihydroimidazo[4,5-c]pyridin-1-yl)-biphenyl-2-carbonitrile;
- 1-[4-fluoro-3-(pyridin-3-yl)phenyl]-5-methyl-1,5-dihydroimidazo[4,5-c]pyridin-4-one;
- 5-methyl-1-(2,2′, 3′-trifluorobiphenyl-5-yl)-1,5-dihydroimidazo[4,5-c]pyridin-4-one;
- 4,2′-difluoro-5′-(5-methyl-4-oxo4,5-dihydroimidazo[4,5-c]pyridin-1-yl)biphenyl-2-carbonitrile;
- or a pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.