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
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.
1. A crystalline tosylate salt 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 having an X-ray powder diffraction pattern comprising peaks at 2θ angle degrees ±0.2 of 7.5, 20.1, and 24.1.
2. The crystalline tosylate salt of claim 1 , having an X-ray powder diffraction pattern comprising peaks at 2θ angle degrees ±0.2 of 7.5, 15.1, 18.1, 20.1, 20.5, 22.6, and 24.1.
3. A crystalline tosylate salt 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 exhibiting a solid state 13 C NMR spectrum with peaks at 143.2, 136.0, 131.8, 123.9, 112.2, 105.2, and 100.3 ppm ±0.2 ppm.
4. A pharmaceutical composition comprising the crystalline tosylate salt of claim 1 and a pharmaceutically acceptable excipient.
5. A pharmaceutical composition comprising the crystalline tosylate salt of claim 3 and a pharmaceutically acceptable excipient.
6. A pharmaceutical composition comprising the crystalline tosylate salt of claim 2 and a pharmaceutically acceptable excipient.