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Last Updated: September 21, 2021

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Claims for Patent: 8,735,392

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Summary for Patent: 8,735,392
Title:Crystalline (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt
Abstract: Provided herein are (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt forms, including crystalline forms, and methods of their preparation. Pharmaceutical compositions comprising a (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt are also provided, as are methods of using (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt to treat a disease or condition, such as a cancer.
Inventor(s): Wang; Bing (San Jose, CA), Chu; Daniel (Santa Clara, CA), Liu; Yongbo (Shanghai, CN), Peng; Shichun (Shanghai, CN)
Assignee: BioMarin Pharmaceutical Inc. (Novato, CA)
Application Number:13/277,607
Patent Claims: 1. A crystalline form of (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt, where the crystalline form exhibits at least one of: a solid state .sup.13C NMR spectrum with peaks at 143.2, 136.0, 131.8, 123.9, 112.2, 105.2, and 100.3 ppm.+-.0.2 ppm; a differential scanning calorimetry thermogram having an endotherm with a maximum at between about 320.degree. C. and about 335.degree. C.; a thermogravimetric analysis thermogram indicative of an unsolvated material; a dynamic vapor sorption isotherm plot which does not exhibit a significant weight change from 0 to 95% relative humidity; an X-ray powder diffraction pattern comprising characteristic peaks expressed in d-values (.ANG.) of about 11.9, 5.9, 4.9, 4.4, 4.3, 3.9, and 3.7; and an X-ray powder diffraction pattern comprising peaks at 2.theta. angle degrees.+-.0.2 2.theta. angle degrees of 7.4, 15.1, 18.1, 20.1, 20.4, 22.6, and 24.0.

2. The crystalline form of the (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt of claim 1, where the crystalline form has a purity of at least about 99.5%.

3. The crystalline form of the tosylate salt of claim 1, where the crystalline form is substantially free of an amorphous form of (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,- 9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one or a salt or solvate thereof.

4. A pharmaceutical composition comprising the crystalline form of the tosylate salt according to claim 1 and a pharmaceutically acceptable excipient.

5. The pharmaceutical composition according to claim 4, where the composition is formulated for oral administration to a subject.

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