US 11,866,434 B2
Process for making a PD-1/PD-L1 inhibitor and salts and crystalline forms thereof
Dengjin Wang, Wilmington, DE (US); Daniel Carper, Wilmington, DE (US); Zhongjiang Jia, Kennett Square, PA (US); Bo Shen, Garnet Valley, PA (US); Joseph A. Sclafani, Malvern, PA (US); Robert Wilson, Wilmington, DE (US); Jiacheng Zhou, Newark, DE (US); Osama Suleiman, Cambridge (GB); and Mark Wright, Cambridge (GB)
Assigned to Incyte Corporation, Wilmington, DE (US)
Filed by Incyte Corporation, Wilmington, DE (US)
Filed on Nov. 5, 2021, as Appl. No. 17/520,174.
Claims priority of provisional application 63/110,792, filed on Nov. 6, 2020.
Prior Publication US 2022/0144831 A1, May 12, 2022
Int. Cl. C07D 471/04 (2006.01)
CPC C07D 471/04 (2013.01) [C07B 2200/13 (2013.01)] 41 Claims
 
1. A crystalline form of the compound of formula 1, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
the compound of formula 1 is the free base sesquihydrate of the compound of formula 1 having Form I, which has at least one XRPD peak, in terms of 2-theta (±0.2 degrees), selected from 7.0, 8.5, 10.0, 10.6, 14.6, 15.2, 15.8, 17.2, 20.1, 21.1, 23.9, 24.8, 26.1, 28.1, 29.6, and 30.2 degrees;
the compound of formula 1 is the free base of the compound of formula 1 having Form II, which has at least one XRPD peaks, in terms of 2-theta (±0.2 degrees), selected from 8.5, 15.0, 15.7, 17.0, 18.6, 20.2, 20.5, 21.7, 25.5, and 26.7 degrees; or
the compound of formula 1 is a methanesulfonic acid salt having Form III, which has at least one XRPD peaks, in terms of 2-theta (±0.2 degrees), selected from 5.2, 7.5, 8.2, 8.8, 9.4, 11.6, 12.4, 13.0, 14.0, 14.8, 15.8, 16.6, 16.9, 17.3, 17.9, 19.2, 23.6, 24.5, 25.5, and 26.6 degrees.