US 12,187,700 B2
Polymorphs and cocrystals of a cardiac troponin activator
Stephanie Azali, Thousand Oaks, CA (US); Mary Chaves, Thousand Oaks, CA (US); Ron C. Kelly, Thousand Oaks, CA (US); Steven M. Mennen, Thousand Oaks, CA (US); Darren L Reid, Thousand Oaks, CA (US); Osama Suleiman, Thousand Oaks, CA (US); Ashraf Wilsily, Thousand Oaks, CA (US); and Mark Wright, Thousand Oaks, CA (US)
Assigned to Amgen Inc., Thousand Oaks, CA (US); and Cytokinetics, Inc., South San Francisco, CA (US)
Appl. No. 17/593,110
Filed by Amgen Inc., Thousand Oaks, CA (US); and Cytokinetics, Inc., South San Francisco, CA (US)
PCT Filed Mar. 12, 2020, PCT No. PCT/US2020/022219
§ 371(c)(1), (2) Date Sep. 9, 2021,
PCT Pub. No. WO2020/185982, PCT Pub. Date Sep. 17, 2020.
Claims priority of provisional application 62/817,165, filed on Mar. 12, 2019.
Prior Publication US 2022/0185790 A1, Jun. 16, 2022
Int. Cl. C07D 401/06 (2006.01)
CPC C07D 401/06 (2013.01) [C07B 2200/13 (2013.01)] 39 Claims
 
1. A free base crystalline form of Compound A, selected from the following forms:
(i) a free base anhydrous crystalline Form I of Compound A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.78, 12.45, 15.70, 16.46, and 16.94±0.2° 2θ using Cu Kα radiation;
(ii) a free base anhydrous crystalline Form II of Compound A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.67, 11.54, 18.27, and 23.28±0.2° 2θ using Cu Kα radiation; and
(iii) a free base monohydrate crystalline Form III of Compound A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.31, 10.77, and 13.96±0.2° 2θ using Cu Kα radiation,
wherein Compound A is:

OG Complex Work Unit Chemistry
 
8. A free base anhydrous crystalline form of Compound A (“Form IV”), characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.06, 11.29, and 14.97±0.2° 2θ using Cu Kα radiation,
wherein Compound A is:

OG Complex Work Unit Chemistry
 
16. A crystalline form of Compound A hydrochloride salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.45, 16.93, 23.74, 24.59, and 26.57±0.2° 2θ using Cu Kα radiation,
wherein Compound A is:

OG Complex Work Unit Chemistry
 
18. A crystalline form of Compound A and dichloromethane, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 11.46, 16.91, 23.10, and 24.58±0.2° 2θ using Cu Kα radiation,
wherein Compound A is:

OG Complex Work Unit Chemistry
 
20. A crystalline form of Compound A and nitromethane, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.94, 15.86, 17.12, 19.51, 19.83, and 24.41±0.2° 2θ using Cu Kα radiation,
wherein Compound A is:

OG Complex Work Unit Chemistry