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US 7,678,796 B2Granted
MGluR5 modulators I
AssigneeAstraZeneca AB
InventorsAndreas Wallberg, Karolina Nilsson, Björn Holm, Mats Nagard, Kenneth Granberg, Abdelmalik Slassi, Louise Edwards, Methvin Isaac, Tao Xin, Tomislav Stefanac
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Abstract
The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.
Claims21
A compound of formula (I)
- wherein
- R1 is methyl, halogen or cyano;
- R2 is hydrogen or fluoro;
- R3 is hydrogen, fluoro or C1-C3 alkyl;
- R4 is C1-C3 alkyl or cyclopropyl;
- Y is a bond;
- X is
- and Z is
- wherein
- R5 is hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy;
- C1-C3 haloalkoxy;
- or halogen;
- R6 is hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy;
- C1-C3 haloalkoxy;
- or halogen;
- R7 is hydrogen, fluoro or C1-C3 alkyl;
- as well as pharmaceutically acceptable salts, tautomers and/or enantiomers thereof.
14 more elements
A compound selected from;
- 3-{3-[(R)-1-(4-Methyl-5-pyrimidin-5-yl-4H-[1,2,4]triazol-3-yl)-pyrrolidin-2-yl]-isoxazol-5-yl}-benzonitrile;
- 3-{5-[(R)-1-(4-Methyl-5-pyrazin-2-yl-4H-[1,2,4]triazol-3-yl)-pyrrolidin-2-yl]-tetrazol-2-yl}-benzonitrile;
- 3-{3-[(R)-1-(4-Methyl-5-pyrazin-2-yl-4H-[1,2,4]triazol-3-yl)-pyrrolidin-2-yl]-isoxazol-5-yl}-benzonitrile;
- 5-(5-{(R)-2-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyrimidine;
- 4-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1-methyl-1H-pyridin-2-one;
- 5-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1-methyl-1H-pyridin-2-one;
- 4-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridazine;
- (+/−)5-(5-{2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyrimidine;
- 2-(5-{(S)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyrazine;
- 4-(5-{(R)-2-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1-methyl-1H-pyridin-2-one;
- 4-(5-{(R)-2-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one;
- 4-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one;
- 6-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2-methyl-2H-pyridazin-3-one;
- 5-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2H-pyridazin-3-one;
- 5-(5-{(R)-2-[5-(3-Fluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2H-pyridazin-3-one;
- 6-(5-{(R)-2-[5-(3-Fluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2-methyl-2H-pyridazin-3-one;
- 1-Methyl-4-{4-methyl-5-[(R)-2-(5-m-tolylisoxazol-3-yl)pyrrolidin-1-yl]-4H-[1,2,4]triazol-3-yl}-1H-pyridin-2-one;
- 5-{4-Methyl-5-[(R)-2-(5-m-tolyl-isoxazol-3-yl)-pyrrolidin-1-yl]-4H-[1,2,4]triazol-3-yl}-2H-pyridazin-3-one;
- 4-(5-{(R)-2-[5-(3-Fluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one;
- 2-Methyl-5-{4-methyl-5-[(R)-2-(5-m-tolyl-isoxazol-3-yl)-pyrrolidin-1-yl]-4H-[1,2,4]triazol-3-yl}-2H-pyridazin-3-one;
- 4-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1,6-dimethyl-1H-pyridin-2-one;
- 4-{4-Methyl-5-[(R)-2-(5-m-tolyl-isoxazol-3-yl)-pyrrolidin-1-yl]-4H-[1,2,4]triazol-3-yl}-1H-pyridin-2-one;
- 6-{4-Methyl-5-[(R)-2-(5-m-tolyl-isoxazol-3-yl)-pyrrolidin-1-yl]-4H-[1,2,4]triazol-3-yl}-3H-pyrimidin-4-one;
- 4-(5-{(R)-2-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridazine;
- 5-(5-{(R)-2-[5-(3-Chlorophenyl)isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2-methyl-2H-pyridazin-3-one;
- 5-(5-{(R)-2-[5-(3-Fluorophenyl)isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2-methyl-2H-pyridazin-3-one;
- 6-(5-{(R)-2-[5-(3-Chlorophenyl)isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-3H-pyrimidin-4-one;
- 6-(5-{(R)-2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one
- 5-(5-{(R)-2-[5-(2,5-Difluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2H-pyridazin-3-one;
- 6-(5-{(R)-2-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-1,2,4-triazol-3-yl)-3H-pyrimidin-4-one;
- 4-(5-{(R)-2-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one;
- 5-(5-{(R)-2-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-2H-pyridazin-3-one;
- 4-(5-{(R)-2-[5-(2-Fluoro-5-methyl-phenyl)-isoxazol-3-yl]-pyrrolidin-1-yl}-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one;
- and
- as well as pharmaceutically acceptable salts, tautomers and/or enantiomers thereof.
32 more elements
Dependencies are inferred from the claim text.