Solid forms of an eIF4E inhibitor
The present invention relates to solid forms of 7-(5-chloro-2-(3-(5-cyano-6-((1-(3,3-difluorocyclobutyl)piperidin-4-yl)(methyl)amino)-2-methyl-4-oxopyrido[3,4-d]pyrimidin-3(4H)-yl)prop-1-yn-1-yl)phenyl)-N-(methylsulfonyl)thieno[3,2-b]pyridine-3-carboxamide, to pharmaceutical compositions comprising such solid forms, and to methods of using such solid forms and pharmaceutical compositions for the treatment of cancer.
1 . A crystalline form of 7-(5-chloro-2-(3-(5-cyano-6-((1-(3,3-difluorocyclobutyl)piperidin-4-yl)(methyl)amino)-2-methyl-4-oxopyrido[3,4-d]pyrimidin-3(4H)-yl) prop-1-yn-1-yl)phenyl)-N-(methylsulfonyl) thieno[3,2-b]pyridine-3-carboxamide hydrate, having a powder X-ray diffraction (PXRD) pattern comprising peaks at 2θ values of: 7.8, 6.4, and 5.2° 2θ±0.2° 2θ.
2 . The crystalline form of claim 1 , having a PXRD pattern further comprising a peak at a 2θ value of: 17.2° 2θ±0.2° 2θ.
3 . The crystalline form of claim 1 , having a Raman spectrum comprising wavenumber (cm −1 ) values of: 1694 and 1680 cm −1 ±2 cm −1 .
4 . The crystalline form of claim 1 , having a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 47.3, 125.4, and 153.6 ppm±0.2 ppm.
5 . The crystalline form of claim 1 , having a 1° F. solid state NMR spectrum comprising resonance (ppm) values of: −93.2 and −80.4 ppm±0.2 ppm.
6 . The crystalline form of claim 2 , wherein said crystalline form is further characterized as having a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 47.3, 125.4, and 153.6 ppm±0.2 ppm.
7 . The crystalline form of claim 2 , wherein said crystalline form is further characterized as having a 19 F solid state NMR spectrum comprising resonance (ppm) values of: −93.2 and −80.4 ppm±0.2 ppm.
8 . A pharmaceutical composition comprising the crystalline form of claim 1 , and a pharmaceutically acceptable carrier or excipient.
9 . A method of treating breast cancer in a subject, the method comprising administering to the subject in need thereof, a therapeutically effective amount of the crystalline form of claim 1 .