Claims for Patent: 9,156,795

Summary for Patent: 9,156,795

Title:	Hydrogen sulfate salt
Abstract:	The present invention relates to Compound 1 hydrogen sulfate salt and solvates, crystalline forms and amorphous forms thereof, and to processes for their preparation. ##STR00001##
Inventor(s):	DeMattei; John (San Diego, CA), Chuang; Tsung-Hsun (Longmont, CO), Squire; Christopher John (Macclesfield, GB), Roberts; Ronald John (Macclesfield, GB), Sharma-Singh; Gorkhn (Macclesfield, GB), Pervez; Mohammed (Macclesfield, GB), Ford; James Gair (Macclesfield, GB), Storey; Richard Anthony (Macclesfield, GB), Dickinson; Paul Alfred (Macclesfield, GB)
Assignee:	Array BioPharma, Inc. (Boulder, CO) Astrazeneca AB (Sodertalje, SE)
Application Number:	13/463,499
Patent Claims:	1. A crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide, wherein said hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5- -carboxylic acid (2-hydroxy-ethoxy)-amide has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59.degree., 20.97.degree., 27.65.degree., 12.24.degree., and 17.02.degree.. 2. The crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide according to claim 1, wherein said hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59.degree., 20.97.degree., 23.99.degree., 27.65.degree., 12.24.degree., 23.49.degree., 24.30.degree., 17.02.degree., 25.91.degree. and 22.50.degree.. 3. The crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide according to claim 1, which has a powder X-ray diffraction pattern substantially the same as the X-ray powder diffraction pattern shown in FIG. 1. 4. The crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide according to claim 1, wherein said hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59.degree., 20.97.degree., 27.65.degree., 12.24.degree., 23.49.degree., 23.99.degree., 17.02.degree. and 25.91.degree.. 5. A pharmaceutical composition comprising a crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidaz- ole-5-carboxylic acid (2-hydroxy-ethoxy)-amide, wherein said hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59.degree., 20.97.degree., 27.65.degree., 12.24.degree. and 17.02.degree., and a pharmaceutically acceptable excipient. 6. The pharmaceutical composition of claim 5, in a form for oral administration. 7. The pharmaceutical composition of claim 6, formulated as a tablet, lozenge, hard or soft capsule, emulsion, dispersible powder or granule, syrup, elixir, oily suspension or aqueous suspension. 8. The pharmaceutical composition of claim 7, formulated as a tablet or hard or soft capsule. 9. A pharmaceutical composition comprising a crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidaz- ole-5-carboxylic acid (2-hydroxy-ethoxy)-amide, wherein said hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59.degree., 20.97.degree., 23.99.degree., 27.65.degree., 12.24.degree., 23.49.degree., 24.30.degree., 17.02.degree., 25.91.degree. and 22.50.degree., and a pharmaceutically acceptable excipient. 10. The pharmaceutical composition of claim 9, in a form for oral administration. 11. The pharmaceutical composition of claim 10, formulated as a tablet, lozenge, hard or soft capsule, emulsion, dispersible powder or granule, syrup, elixir, oily suspension or aqueous suspension. 12. The pharmaceutical composition of claim 11, formulated as a tablet or hard or soft capsule. 13. A pharmaceutical composition, comprising a crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide which has a powder X-ray diffraction pattern substantially the same as the X-ray powder diffraction pattern shown in FIG. 1, and a pharmaceutically acceptable excipient. 14. The pharmaceutical composition of claim 13, in a form for oral administration. 15. The pharmaceutical composition of claim 14, formulated as a tablet, lozenge, hard or soft capsule, emulsion, dispersible powder or granule, syrup, elixir, oily suspension or aqueous suspension. 16. The pharmaceutical composition of claim 15, formulated as a tablet or hard or soft capsule. 17. A pharmaceutical composition comprising a crystalline hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-ca- rboxylic acid (2-hydroxy-ethoxy)-amide, wherein said hydrogen sulfate salt of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5- -carboxylic acid (2-hydroxy-ethoxy)-amide has an X-ray powder diffraction pattern with specific peaks at about 2-theta equal to 24.59.degree., 20.97.degree., 27.65.degree., 12.24.degree., 23.49.degree., 23.99.degree., 17.02.degree. and 25.91.degree., and a pharmaceutically acceptable excipient. 18. The pharmaceutical composition of claim 17, in a form for oral administration. 19. The pharmaceutical composition of claim 18, formulated as a tablet, lozenge, hard or soft capsule, emulsion, dispersible powder or granule, syrup, elixir, oily suspension or aqueous suspension. 20. The pharmaceutical composition of claim 19, formulated as a tablet or hard or soft capsule.