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US 2012/0059034 A1Published application
Novel crystalline hydrate, amorphous and polymorphic forms of dihydro-benzoxazole-6-yl-acetamide derivative and processes for their preparation
OwnerÁdám Demeter, Zoltán Német +4inventors
InventorsÁdám Demeter, Zoltán Német, András Nemes, Ferenc Sebok, Gizella Bartáné Szalai, László Czibula
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Abstract
The invention relates to novel crystalline hydrate, amorphous and crystalline polymorphic forms of 2-[4-(4-Fluoro-benzyl)-piperidine-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazole-6-yl)-acetamide (I) (radiprodil). Processes for the preparation of these forms, compositions containing these forms, and methods of use thereof are also described.
Claims28
A crystalline or amorphous form selected from the group consisting of:
- a crystalline anhydrate form A of 2-[4-(4-fluorobenzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide having
- a) characteristic X-ray powder diffraction reflections at about 7.8, 22.0, 23.7, 27.0 and 27.6±0.2° 2θ,
- b) an X-ray powder diffraction pattern substantially in accordance with FIG. 1,
- c) characteristic FT Raman absorption bands at about 3106, 1680, 1641, 1470, 1274 and 507±4 cm−1, or
- d) an FT Raman spectrum substantially in accordance with FIG. 3;
- a crystalline anhydrate form B of 2-[4-(4-fluorobenzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide having
- a) characteristic X-ray powder diffraction reflections at about 5.4, 12.9, 16.9 and 21.0±0.2° 2θ,
- b) an X-ray powder diffraction pattern substantially in accordance with FIG. 6,
- c) characteristic FT Raman absorption bands at about 2877, 1684, 1642, 1545, 1476 and 887±4 cm−1, or
- d) an FT Raman spectrum substantially in accordance with FIG. 8;
- a crystalline hydrate form of 2-[4-(4-Fluorobenzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide *nH2O, where n is equal to 0.5, 1, 1.5 or 2;
- a crystalline dihydrate form of 2-[4-(4-fluorobenzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide having
- a) characteristic X-ray powder diffraction reflections at about 3.6, 14.7, 19.1, 25.2 and 28.3±0.2° 2θ,
- b) an X-ray powder diffraction pattern substantially in accordance with FIG. 11,
- c) characteristic FT Raman absorption bands at about 3068, 1772, 1669, 1641 and 1313±4 cm−1, or
- d) an FT Raman spectrum substantially in accordance with FIG. 13;
- a crystalline monohydrate form of 2-[4-(4-fluorobenzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide having
- a) characteristic X-ray powder diffraction reflections at about 4.9, 15.1, 18.1, 26.8 and 30.2±0.2° 2θ,
- b) an X-ray powder diffraction pattern substantially in accordance with FIG. 16,
- c) characteristic FT Raman absorption bands at about 2887, 1642, 1484, 1295 and 726, ±4 cm−1, or
- d) an FT Raman spectrum substantially in accordance with FIG. 18;
- and
- an amorphous form of 2-[4-(4-fluorobenzyl)-piperidin-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide having
- a) no X-ray powder diffraction reflections, only the typical ‘halo’ pattern,
- b) characteristic FT Raman absorption bands at about 3071, 1687, 1640, 1414, 1280 and 852±4 cm−1, or
- c) an FT Raman spectrum substantially in accordance with FIG. 23.
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Dependencies are inferred from the claim text.