Use of certain crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide in treating epilepsy

Abstract

The invention relates to the novel modification A or A′ of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide of the formula its use and pharmaceutical preparations comprising this crystal modification.

1 . Modification A of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide of the formula  
       
         
           
           
               
               
           
         
       
       characterized by characteristic lines at interplanar spacings (d values) of 10.5 Å, 5.14 Å, 4.84 Å, 4.55 Å, 4.34 Å, 4.07 Å, 3.51 Å, 3.48 Å, 3.25 Å, 3.19 Å, 3.15 Å, 3.07 Å, 2.81 Å, determined by means of an X-ray powder pattern.  
     
     
         2 . Modification according to  claim 1 , characterized by an X-ray powder pattern having the following characteristic lines at interplanar spacings (d values) of 10.9 Å (weak), 10.5 Å (medium), 6.6 Å (weak), 5.63 Å (weak), 5.25 Å (weak), 5.14 Å (medium), 4.94 Å (weak), 4.84 Å (very strong), 4.55 Å (strong), 4.42 Å (very weak), 4.34 Å (medium), 4.23 Å (very weak), 4.16 Å (weak), 4.07 Å (medium), 4.01 Å (weak), 3.68 Å (very weak), 3.64 Å (very weak), 3.60 Å (weak), 3.56 Å (weak), 3.51 Å (medium), 3.48 Å (medium), 3.38 Å (very weak), 3.25 Å (strong), 3.19 Å (medium), 3.15 Å (medium), 3.11 Å (weak), 3.07 Å (medium), 2.93 Å (very weak), 2.87 Å (very weak), 2.81 Å (medium), 2.76 Å (weak), 2.73 Å (very weak), 2.68 Å (weak), 2.62 Å (very weak), 2.53 Å (weak), 2.43 Å (weak), 2.40 Å (very weak).  
     
     
         3 . Modification according to  claim 1  or  2 , characterized by the following absorptions in the FT-IR spectrum (KBr pellet—transmission method) 3092 cm −1  and 3412 cm −1 .  
     
     
         4 . Modification according to  claim 3 , characterized by the following absorptions in the FT-IR spectrum (KBr pellet—transmission method): 3412, 3189, 3092, 1634, 1560, 1473, 1397, 1325, 1300, 1284, 1235, 1125, 1053, 1036, 1014, 885, 840, 799, 781, 723, 688 and 640 cm − .  
     
     
         5 . Modification according to any one of claims  1 - 4 , characterized by the following absorptions in the FT-Raman spectrum (powder—reflection method 180°): 3093, 2972, 1628, 1614, 1558, 1465, 1446, 1393, 1279, 1245, 1147, 1080, 1061, 1036, 1014, 840, 724, 691, 667, 550, 499, 437 and 368 cm −1 .  
     
     
         6 . Modification A according to any one of claims  1 - 5 , characterized by an endothermic peak in the range from 230° C. to 260° C., the peak temperature being 239-245° C. and the endothermic signal being 209 J/g+/−10 J/g.  
     
     
         7 . Modification A′ of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide, characterized in that it is identical to the modification A according to any one of claims  1 - 6  but has defects in the crystal lattice.  
     
     
         8 . Modification A′ according to  claim 7 , characterized by line spacings, smaller compared to modification A according to any one of claims  1 - 6 , between the pairs of lines at interplanar spacings 3.68 Å and 3.64 Å, 3.51 Å and 3.48 Å, and 3.19 Å and 3.15 Å.  
     
     
         9 . Modification A or A′ according to any one of claims  1 - 8  in essentially pure form.  
     
     
         10 . Pharmaceutical preparations comprising the modification A or A′ of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide according to any one of claims  1 - 9  and pharmaceutically usable excipients and additives.  
     
     
         11 . Use of the modification A or A′ of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide according to any one of claims  1 - 9  as a pharmaceutical preparation.  
     
     
         12 . Use of the modification A or A′ of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide according to any one of claims  1 - 9  for the preparation of pharmaceutical preparations for the treatment of epilepsy and subindications thereof.  
     
     
         13 . A modification of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide characterized by bands at 3412 cm −1  and 3092 cm −1  in the FT-IR spectrum.  
     
     
         14 . A modification of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide characterized by a band at 1080 cm −1  in the FT-Raman spectrum.  
     
     
         15 . A pharmaceutical preparation comprising a modification according to  claim 13  or  14  and pharmaceutically usable excipients and additives.