Crystalline forms of linezolid intermediate

Abstract

The present invention relates to novel crystalline forms of the linezolid intermediate S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine referred to herein as Form A, Form B, and Form C.

1 . A crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 13.2±0.2, 14.8±0.2, 15.1±0.2, and 25.0±0.2 degrees 2 theta.  
   
   
       2 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 1  further characterized by PXRD peaks at 3.0±0.2, 16.1±0.2, 17.9±0.2, 19.3±0.2, and 23.0±0.2 degrees 2 theta.  
   
   
       3 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 1  which contains less than 5% by weight of other crystalline forms of S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II).  
   
   
       4 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 1 , characterized by a powder X-ray diffraction (PXRD) pattern substantially as indicated in  FIG. 1 .  
   
   
       5 . A crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II), characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 15.6±0.2, 19.2±0.2, 22.5±0.2, and 24.3±0.2 degrees 2 theta.  
   
   
       6 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 5  further characterized by PXRD peaks at 7.2±0.2, 14.6±0.2, 16.5±0.2, 20.1±0.2, and 23.0±0.2 degrees 2 theta.  
   
   
       7 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 5  which contains less than 5% by weight of other crystalline forms of S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II).  
   
   
       8 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 5 , characterized by a powder X-ray diffraction (PXRD) pattern substantially as indicated in  FIG. 2 .  
   
   
       9 . A crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II), characterized by a powder X-ray diffraction (PXRD) pattern with peaks at 5.8±0.2, 11.5±0.2, 19.6±0.2, and 26.3±0.2 degrees 2 theta.  
   
   
       10 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 9  further characterized by PXRD peaks at 13.2±0.2, 20.4±0.2, 21.6±0.2, 22.3±0.2, 23.0±0.2, and 23.8±0.2 degrees 2 theta.  
   
   
       11 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 9  which contains less than 5% by weight of other crystalline forms of S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II).  
   
   
       12 . The crystalline S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) of  claim 9 , characterized by a powder X-ray diffraction (PXRD) pattern substantially as indicated in  FIG. 3 .