Oxazolidinones as modulators of MGLUR5

Abstract

The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands, agonists and partial agonists for the mGluR5 receptor and may be useful for the treatment of various disorders of the central nervous system.

We claim: 
     
       1. A compound of formula I 
       
         
           
           
               
               
           
         
       
       where;
 R 1  is hydrogen or alkyl; 
 R 2  is hydrogen or alkyl; 
 R 3  is 
 
       
         
           
           
               
               
           
         
         Ar 1  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, or pyridazinyl, and is substituted with 1 R 3  substituent and with 0-3 substituents selected from halo, alkyl, haloalkyl, alkoxy, and haloalkoxy; 
         Ar 2  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, furanyl, thienyl, pyrazolyl, isoxazolyl, isothiazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, or benzimidazolyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, and phenyl; and 
         Ar 3  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, imidazolyl, oxazolyl, thiazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, or pyrrolopyridinyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, amino, alkylamino, and dialkylamino; 
         or a pharmaceutically acceptable salt thereof. 
       
     
     
       2. A compound of  claim 1  where R 1  is hydrogen or alkyl; R 2  is hydrogen or alkyl; R 3  is 
       
         
           
           
               
               
           
         
       
       Ar 1  is phenyl, pyridinyl, or pyrimidinyl and is substituted with 1 R 3  substituent and with 0-1 halo or alkoxy substituents; Ar 2  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, pyrazolyl, oxazolyl, oxadiazolyl, or tetrazolyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, hydroxy, alkoxy, and phenyl; and Ar 3  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, imidazolyl, thiazolyl, isoquinolinyl, quinolinyl, quinoxalinyl, or pyrrolopyridinyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, amino, alkylamino, and dialkylamino; or a pharmaceutically acceptable salt thereof. 
     
     
       3. A compound of  claim 2  where R 1  is hydrogen or alkyl; R 2  is hydrogen or alkyl; R 3  is 
       
         
           
           
               
               
           
         
       
       Ar 1  is phenyl, pyridinyl, halopyridinyl, alkoxypyridinyl, or pyrimidinyl; Ar 2  is phenyl, cyanophenyl, halophenyl, dihalophenyl, (haloalkyl)phenyl, alkylphenyl, dealkylphenyl, hydroxyphenyl, alkoxyphenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, (alkyl)pyrazolyl, oxazolyl, (alkyl)oxadiazolyl, (phenyl)oxadiazolyl, or tetrazolyl; and Ar 3  is phenyl, cyanophenyl, halophenyl, dihalophenyl, alkylphenyl, (haloalkyl)phenyl, alkoxyphenyl, (haloalkoxy)phenyl, (alkylthio)phenyl, (amino)phenyl, alkylaminophenyl, dialkylaminophenyl, alkoxycarbonylphenyl, alkylcarbonylphenyl, pyridinyl, cyanopyridinyl, halopyridinyl, alkylpyridinyl, cycloalkylpyridinyl, alkoxypyridinyl, pyrazinyl, pyrimidinyl, alkoxypyrimidinyl, aminopyrimidinyl, alkylaminopyrimidinyl, dialkylaminopyrimidinyl, pyridazinyl, isoquinolinyl, quinoxalinyl, imidazolyl, thiazolyl, or alkylthiazolyl or a pharmaceutically acceptable salt thereof. 
     
     
       4. A compound of  claim 3  where R 1  is hydrogen or methyl; R 2  is hydrogen or methyl; R 3  is 
       
         
           
           
               
               
           
         
       
       Ar 1  is phenyl, pyridinyl, fluoropyridinyl, methoxypyridinyl, or pyrimidinyl and is substituted with 1 R 3  substituent; Ar 2  is phenyl, cyanophenyl, chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl, trifluoromethylphenyl, methylphenyl, dimethylphenyl, hydroxyphenyl, methoxyphenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, (methyl)pyrazolyl, oxazolyl, (methyl)oxadiazolyl, (phenyl)oxadiazolyl, or tetrazolyl; and Ar 3  is phenyl, cyanophenyl, chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl, methylphenyl, t-butylphenyl, trifluoromethylphenyl, methoxyphenyl, trifluoromethoxyphenyl, methylthiophenyl, (amino)phenyl, dimethylaminophenyl, methoxycarbonylphenyl, methylcarbonylphenyl, pyridinyl, cyanopyridinyl, chloropyridinyl, fluoropyridinyl, methylpyridinyl, cyclopropylpyridinyl, methoxypyridinyl, pyrazinyl, pyrimidinyl, ethoxypyrimidinyl, methylaminopyrimidinyl, pyridazinyl, isoquinolinyl, quinoxalinyl, imidazolyl, thiazolyl, or methylthiazolyl; or a pharmaceutically acceptable salt thereof. 
     
     
       5. A compound of  claim 4  where R 1  is hydrogen; R 2  is hydrogen; Ar 1  is phenyl, pyridinyl, halopyridinyl, alkoxypyridinyl, or pyrimidinyl substituted in the meta position with R 3 . 
     
     
       6. A compound of  claim 5  where; Ar 2  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, (uranyl, thienyl, pyrazolyl, isoxazolyl, isothiazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, or benzimidazolyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, and phenyl; Ar 3  is phenyl or pyridinyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, amino, alkylamino, and dialkylamino; or a pharmaceutically acceptable salt thereof. 
     
     
       7. A compound of  claim 6  where Ar 2  is phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, pyrazolyl, oxazolyl, oxadiazolyl, or tetrazolyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, hydroxy, alkoxy, and phenyl; Ar 3  is phenyl or pyridinyl, and is substituted with 0-3 substituents selected from halo, cyano, alkyl, haloalkyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, amino, alkylamino, and dialkylamino; or a pharmaceutically acceptable salt thereof. 
     
     
       8. A compound of  claim 7  where; A 2  is phenyl, cyanophenyl, halophenyl, dihalophenyl, (haloalkyl)phenyl, alkylphenyl, dialkylphenyl, hydroxyphenyl, alkoxyphenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, (alkyl)pyrazolyl, oxazolyl, (alkyl)oxadiazolyl, (phenyl)oxadiazolyl, or tetrazolyl; Ar 3  is phenyl, cyanophenyl, halophenyl, dihalophenyl, dihalophenyl, alkylphenyl, (haloalkyl)phenyl, alkoxyphenyl, (haloalkoxy)phenyl, (alkylthio)phenyl, (amino)phenyl, alkylaminophenyl, dialkylaminophenyl, alkoxycarbonylphenyl, alkylcarbonylphenyl, pyridinyl, cyanopyridinyl, halopyridinyl, alkylpyridinyl, cycloalkylpyridinyl, alkoxypyridinyl; or a pharmaceutically acceptable salt thereof. 
     
     
       9. A compound of  claim 8  where Ar 2  is phenyl, cyanophenyl, chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl, trifluoromethylphenyl, methylphenyl, dimethylphenyl, hydroxyphenyl, methoxyphenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, (methyl)pyrazolyl, oxazolyl, (methyl)oxadiazolyl, (phenyl)oxadiazolyl, or tetrazolyl; Ar 3  is phenyl, cyanophenyl, chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl, methylphenyl, t-butylphenyl, trifluoromethylphenyl, methoxyphenyl, trifluoromethoxyphenyl, methylthiophenyl, (amino)phenyl, dimethylaminophenyl, methoxycarbonylphenyl, methylcarbonylphenyl, pyridinyl, cyanopyridinyl, chloropyridinyl, fluoropyridinyl, methylpyridinyl, cyclopropylpyridinyl, methoxypyridinyl, thiazolyl, or methylthiazolyl; or a pharmaceutically acceptable salt thereof. 
     
     
       10. A compound of  claim 1  with the indicated stereochemistry 
       
         
           
           
               
               
           
         
       
     
     
       11. A compound of  claim 1  selected from the group consisting of
 (4R,5R)-5-phenyl-4-(6-(phenylethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-phenyl-4-(2-(phenylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-phenyl-4-(2-(3-pyridinylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-methoxyphenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(5-(3-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-methoxyphenyl)-4-(2-(phenylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-phenyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-(3-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-methoxyphenyl)-4-(3-(2-pyridinylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-methoxyphenyl)-4-(3-(4-pyridinylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-methoxy phenyl)-4-(3-((6-methoxy-2-pyridinyl)ethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-methoxyphenyl)-4-(3-(1,3-thiazol-4-ylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-((6-fluoro-3-pyridinyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-((2-fluoro-4-pyridinyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 5-((3-((4R,5R)-5-(3-methoxyphenyl)-2-oxo-1,3-oxazolidin-4-yl)phenyl)ethynyl)nicotinonitrile; 
 (4R,5R)-4-(3-((5-fluoro-3-pyridinyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-phenyl-4-(3-(phenylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3,4-dimethylphenyl)-4-(3-(phenylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5S)-4-(3-(phenylethynyl)phenyl)-5-(2-thienyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-methylphenyl)-4-(3-(phenylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2-fluorophenyl)-4-(3-(phenylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(3-(phenylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(3-(phenylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-(phenylethynyl)phenyl)-5-(3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-((2-fluorophenyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-((3-fluorophenyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(6-(phenylethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-methyl-5-phenyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(2-fluoro-5-(3-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(2-fluoro-5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-5-(3-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(2-fluoro-5-((2-fluoro-4-pyridinyl)ethynyl)-3-pyridinyl)-5-(3-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(2-fluoro-5-(3-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(2-fluoro-5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-5-(4-fluorophenyl)-1,3 oxazolidin-2-one; 
 (4R,5R)-4-(5-fluoro-2-((5-fluoro-3-pyridinyl)ethynyl)-4-pyridinyl)-5-(4-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-chlorophenyl)-4-(2-fluoro-5-(3-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(2-fluoro-5-((6-fluoro-2-pyridinyl)ethynyl)-3-pyridinyl)-5-(4-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3,5-difluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3,4-difluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3,4-difluorophenyl)-4-(5-(3-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3,4-difluorophenyl)-4-(5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 3-((5-((4R,5R)-5-(3,4-difluorophenyl)-2-oxo-1,3-oxazolidin-4-yl)-3-pyridinyl)ethynyl)benzonitrile; 
 (4R,5R)-5-(2,4-difluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,4-difluorophenyl)-4-(5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,4-difluorophenyl)-4-(5-pyridinylethynyl)-3-pyridinyl)-1-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-((4-fluoro-2-pyridinyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-((3-fluoro-2-pyridinyl)ethynyl)phenyl)-5-(3-methoxyphenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-(phenylethynyl)-3-pyridinyl)-5-(3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-5-methyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5S)-5-(4-fluorophenyl)-5-methyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-5-methyl-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-((3-fluoro-2-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-(2-pyrazinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-(4-pyridinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-((2-fluoro-4-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 3-((5-((4R,5R)-5-(4-fluorophenyl)-2-oxo-1,3-oxazolidin-4-yl)-3-pyridinyl)ethynyl)benzonitrile; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-((6-fluoro-2-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(6-(phenylethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-methyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-5-methyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5S)-4-methyl-5-phenyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-methyl-5-phenyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-((3-fluoro-2-pyridinyl)ethynyl)-3-pyridinyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one; 
 (4R,5S)-4-(3-(phenylethynyl)phenyl)-5-(2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-pyridinyl)-4-(3-(2-pyridinylethynyl)phenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(3-(phenylethynyl)phenyl)-5-(4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5S)-4-(3-(phenylethynyl)phenyl)-5-(4-pyrimidinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(5-((5-fluoro-3-pyridinyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(2-(3-pyridinylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(2-(phenylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(2-(phenylethynyl)-4-pyrimidinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,3-difluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(5-((4-fluorophenyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(5-((2-fluorophenyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,3-difluorophenyl)-4-(5((2-fluorophenyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,3-difluorophenyl)-4-(5-((4-fluorophenyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-(phenylethynyl)-3-pyridinyl)-5-(2,4,6-trifluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-(phenylethynyl)-3-pyridinyl)-5-(2,3,4-trifluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(4-(phenylethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(2-fluoro-5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(2-methoxy-5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(5-fluoro-2-(phenylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2-fluorophenyl)-4-(5-fluoro-2-(phenylethynyl)-4-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,4-difluorophenyl)-4-(6-(phenylethynyl)-2-pyridinyl-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,4-difluorophenyl)-4-(6-((3-fluorophenyl)ethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-(phenylethynyl)-3-pyridinyl)-5-(4-pyrimidinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,3-dichlorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4S,5R)-5-(1-methyl-1H-pyrazol-5-yl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(5-((3-fluoro-2-pyridinyl)ethynyl)-3-pyridinyl)-4-methyl-1,3-oxazolidin-2-one; 
 (4R,5S)-4-(5-(phenylethynyl)-3-pyridinyl)-5-(2-thienyl-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(4-((2-fluorophenyl)ethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(4-((3-fluorophenyl)ethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(4-((4-fluorophenyl)ethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-chlorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-chlorophenyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5S)-5-(2-chlorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 4-((4R,5R)-2-oxo-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-5-yl)benzonitrile; 
 (4R,5R)-5-(4-fluorophenyl)-4-(6-((3-fluoro-2-pyridinyl)ethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(4-fluorophenyl)-4-(6-((2-fluoro-4-pyridinyl)ethynyl)-2-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)-5-(2-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2,5-difluorophenyl)-4-(5-(2-pyrazinylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-((2-chlorophenyl)ethynyl)-3-pyridinyl)-5-(3-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(5-((3-fluorophenyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(3-fluorophenyl)-4-(5-((3-methylphenyl)ethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-4-(5-((3-chlorophenyl)ethynyl)-3-pyridinyl)-5-(3-fluorophenyl)-1,3-oxazolidin-2-one; 
 (4R,5R)-5-(2-fluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; and 
 5R)-5-(2,5-difluorophenyl)-4-methyl-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one; 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
       12. The compound of  claim 1  which is (4R,5R)-5-(2,5-difluorophenyl)-4-(5-(phenylethynyl)-3-pyridinyl)-1,3-oxazolidin-2-one 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically salt thereof. 
     
     
       13. A composition comprising a compound of  claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. 
     
     
       14. A method for the treatment of schizophrenia which comprises administering to a patient a therapeutically affective amount of a compound of  claim 1 . 
     
     
       15. The compound of claim 1 which is (4R,5R)-5-(2-chlorophenyl)-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one 
       
         
           
           
               
               
           
         
       
       . 
     
     
       16. A composition comprising the compound of claim 15, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.