SOLID FORMS COMPRISING (S)-7-(1-ACRYLOYLPIPERIDIN-4-YL)-2-(4-PHENOXYPHENYL)-4,5,6,7-TETRAHYDROPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXAMIDE, AND OXALIC ACID, COMPOSITIONS AND METHODS OF USE THEREOF
Provided herein are formulations, processes, solid forms and methods of use relating to (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide.
1 . A solid form comprising (a) (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide; and (b) oxalic acid.
2 . The solid form of claim 1 , which is substantially crystalline.
3 . The solid form of claim 2 , which is substantially a cocrystal.
4 . The solid form of claim 2 , which is substantially a salt.
5 . The solid form of claim 2 , which is a crystal form comprising Compound 1:
which has an X-ray powder diffraction pattern comprising peaks at approximately 8.2, 11.7, and 21.6°2θ.
6 . The crystal form of claim 5 which has an X-ray powder diffraction pattern further comprising peaks at approximately 8.6, 18.5, and 19.6°2θ.
7 . The crystal form of claim 5 which has a thermogravimetric analysis thermogram comprising a total mass loss of approximately 0.7% of the total mass of the crystal form when heated from about 17.6° C. to about 130° C.
8 . The crystal form of claim 5 which has a differential scanning calorimetry thermogram comprising an endothermic event with an onset temperature at approximately 159.1° C. when heated from about 50° C. to about 200° C.
9 . The crystal form of claim 5 which is an oxalic acid co-crystal form.
10 . The crystal form of claim 5 which is an oxalic acid salt.
11 . The crystal form of claim 5 , wherein the molar ratio of oxalic acid to Compound 1 is about 0.5.
12 . The crystal form of claim 5 which is substantially pure.
13 . A method for treating or preventing a B-cell proliferative disease, or a condition treatable or preventable by inhibition of a kinase pathway, comprising administering an effective amount of a solid form of claim 1 to a subject in need thereof.
14 . The method of claim 13 , wherein the kinase pathway is the BTK pathway.
15 . A method for achieving a Response Evaluation Criteria in Solid Tumors (RECIST 1.1) of complete response, partial response or stable disease in a subject comprising administering an effective amount of a solid form of claim 1 to a subject having a solid tumor.