	US 12,227,491 B2
	EGFR inhibitors
Xing Dai, Shanghai (CN); and Yueheng Jiang, Shanghai (CN)
Assigned to INVENTISBIO CO., LTD., Shanghai (CN)
Filed by INVENTISBIO CO., LTD., Shanghai (CN)
Filed on Mar. 21, 2023, as Appl. No. 18/187,430.
Application 18/187,430 is a continuation of application No. 17/046,621, granted, now 11,639,344, previously published as PCT/CN2019/086748, filed on May 14, 2019.
Claims priority of provisional application 62/678,634, filed on May 31, 2018.
Claims priority of application No. PCT/CN2018/086829 (WO), filed on May 15, 2018.
Prior Publication US 2023/0331703 A1, Oct. 19, 2023
Int. Cl. C07D 403/04 (2006.01); A61K 9/20 (2006.01); A61K 9/48 (2006.01); A61K 31/506 (2006.01)

CPC C07D 403/04 (2013.01) [A61K 9/20 (2013.01); A61K 9/48 (2013.01); C07B 2200/13 (2013.01)]

20 Claims

1. Crystals of crystalline form I of N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-(1-(2,2,2-trifluoroethyl)-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl) acrylamide monomesylate, wherein the crystalline form I is characterized by an XRPD pattern having four or more of the following peaks: 7.8, 10.2, 10.8, 11.2, 13.6, 13.9, 15.0, 16.4, 17.7, 18.4, 18.7, 18.9, 19.2, 19.8, 20.6, 20.8, 21.1, 22.6, 23.7, 23.9, 24.9, 25.9, and 27.8 degrees 2 theta, +0.2°, and the crystals are characterized by a particle size distribution of:

1) D90: about 150 μm to about 250 um; D50: about 90 μm to about 140 μm; and D10 of about 40 μm to about 75 um;

2) D90: about 100 μm to about 150 um; D50: about 20 μm to about 60 μm; and D10 of about 5 μm to about 15 um;

3) D90: about 120 μm to about 200 um; D50: about 50 μm to about 100 μm; and D10 of about 10 μm to about 20 um;

4) D90: about 140 μm to about 180 um; D50: about 90 μm to about 130 μm; and D10 of about 55 μm to about 85 um;

5) D90: about 50 μm to about 100 um; D50: about 20 μm to about 30 μm; and D10 of about 3.5 um to about 9 um;

6) D90: about 70 μm to about 95 um; D50: about 25 μm to about 40 μm; and D10 of about 5 μm to about 15 um;

7) D90: about 120 μm to about 160 um; D50: about 55 μm to about 85 μm; and D10 of about 5 μm to about 15 μm; or

8) D90: about 90 μm to about 130 um; D50: about 35 μm to about 60 μm; and D10 of about 10 μm to about 15 um.