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Last Updated: April 3, 2025

Claims for Patent: 6,740,669

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Summary for Patent: 6,740,669

Title:	Crystal modification of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and its use as antiepileptic
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 ##STR1## its use and pharmaceutical preparations comprising this crystal modification.
Inventor(s):	Portmann; Robert (Pratteln, CH), Hofmeier; Urs Christoph (St. Pantaleon, CH), Burkhard; Andreas (Basel, CH), Scherrer; Walter (Rheinfelden, CH), Szelagiewicz; Martin (Munchenstein, CH)
Assignee:	Novartis AG (Basel, CH)
Application Number:	09/125,329
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 6,740,669
Patent Claims:	1. Crystal modification A of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide of the formula ##STR3## characterized by characteristic lines at interplanar spacings (d values) of 10.5 .ANG., 5.14 .ANG., 4.84 .ANG., 4.55 .ANG., 4.34 .ANG., 4.07 .ANG., 3.51 .ANG., 3.48 .ANG., 3.25 .ANG., 3.19 .ANG., 3.15 .ANG., 3.07 .ANG., 2.81 .ANG., determined by means of an X-ray powder pattern. 2. The crystal 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 .ANG. (weak), 10.5 .ANG. (medium), 6.6 .ANG. (weak), 5.63 .ANG. (weak), 5.25 .ANG. (weak), 5.14 .ANG. (medium), 4.94 .ANG. (weak), 4.84 .ANG. (very strong), 4.55 .ANG. (strong), 4.42 .ANG. (very weak), 4.34 .ANG. (medium), 4.23 .ANG. (very weak), 4.16 .ANG. (weak), 4.07 .ANG. (medium), 4.01 .ANG. (weak), 3.68 .ANG. (very weak), 3.64 .ANG. (very weak), 3.60 .ANG. (weak), 3.56 .ANG. (weak), 3.51 .ANG. (medium), 3.48 .ANG. (medium), 3.38 .ANG. (very weak), 3.25 .ANG. (strong), 3.19 .ANG. (medium), 3.15 .ANG. (medium), 3.11 .ANG. (weak), 3.07 .ANG. (medium), 2.93 .ANG. (very weak), 2.87 .ANG. (very weak), 2.81 .ANG. (medium), 2.76 .ANG. (weak), 2.73 .ANG. (very weak), 2.68 .ANG. (weak), 2.62 .ANG. (very weak), 2.53 .ANG. (weak), 2.43 .ANG. (weak), 2.40 .ANG. (very weak). 3. The crystal modification according to claim 1, characterized by the following absorptions in the FT-IR spectrum (KBr pellet--transmission method) 3092 cm.sup.-1 and 3412 cm.sup.-1. 4. The crystal 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.sup.-1. 5. The crystal modification according to claim 1, characterized by the following absorptions in the FT-Raman spectrum (powder--reflection method 180.degree.): 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.sup.-1. 6. The crystal modification A according to claim 1, characterized by an endothermic peak in the range from 230.degree. C. to 260.degree. C., the peak temperature being 239-245.degree. C., and the endothermic signal being 209 J/g+/-10 J/g. 7. The crystal 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 claim 1 but has defects in the crystal lattice. 8. The crystal modification A' according to claim 7, characterized by line spacings, smaller compared to modification A, between the pairs of lines at interplanar spacings 3.68 .ANG. and 3.64 .ANG., 3.51 .ANG. and 3.48 .ANG. and 3.19 .ANG. and 3.15 .ANG.. 9. Modification A according to claim 1 in essentially pure form. 10. Crystal modification A of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide characterized by bands at 3412 cm.sup.-1 and 3092 cm.sup.-1 in the FT-IR spectrum. 11. Crystal modification A of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide characterized by bands at 1080 cm.sup.-1 in the FT-IR spectrum. 12. The crystal 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 claim 2 but has defects in the crystal lattice. 13. The crystal 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 claim 3 but has defects in the crystal lattice. 14. The crystal 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 claim 4 but has defects in the crystal lattice. 15. The crystal 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 claim 5 but has defects in the crystal lattice. 16. The crystal 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 claim 6 but has defects in the crystal lattice. 17. The crystal A' according to claim 7 in essentially pure form. 18. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of crystal modification A of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide according to claim 1. 19. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of crystal modification A' of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide according to claim 7. 20. The crystal 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 claim 10 but has defects in the crystal lattice. 21. The crystal 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 claim 11 but has defects in the crystal lattice.

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