US 12,435,085 B2
Crystalline forms and formulations of a VCP/p97 inhibitor
Han-Jie Zhou, Foster City, CA (US); and Bing Yao, Millbrae, CA (US)
Assigned to CASI Pharmaceuticals, Inc., Rockville, MD (US)
Appl. No. 17/998,333
Filed by CASI Pharmaceuticals, Inc., Rockville, MD (US)
PCT Filed May 10, 2021, PCT No. PCT/US2021/031621
§ 371(c)(1), (2) Date Nov. 9, 2022,
PCT Pub. No. WO2021/231322, PCT Pub. Date Nov. 18, 2021.
Claims priority of provisional application 63/023,123, filed on May 11, 2020.
Prior Publication US 2023/0174529 A1, Jun. 8, 2023
Int. Cl. C07D 471/04 (2006.01); A61K 9/48 (2006.01); A61K 45/06 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 9/485 (2013.01); A61K 9/4858 (2013.01); A61K 9/4866 (2013.01); A61K 45/06 (2013.01); C07B 2200/13 (2013.01)] 17 Claims
 
1. A crystalline form of 1-(4-(benzylamino)-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carboxamide tosylate having at least one of the following properties:
(a) an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 1;
(b) an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 7.5° 2-Theta, 10.8° 2-Theta, 12.5° 2-Theta, 17.4° 2-Theta, 18.8° 2-Theta, 20.3° 2-Theta, 20.5° 2-Theta, 22.4° 2-Theta, 22.5° 2-Theta, and 22.6° 2-Theta;
(c) a thermo-gravimetric analysis (TGA) substantially similar to the one set forth in FIG. 2;
(d) a DSC thermogram substantially similar to the one set forth in FIG. 3;
(e) a DSC thermogram with an endotherm at about 233° C.;
(f) combinations thereof.