	US 11,891,380 B2
	Solid state forms of Belumosudil and Belumosudil salts
Polina Lapido, Rishon le Zion (IL); Inbal Shumacher, Kadima (IL); and Ofir Shaul, Hod Hasharon (IL)
Assigned to TEVA PHARMACEUTICALS INTERNATIONAL GMBH, Jona (CH)
Filed by TEVA PHARMACEUTICALS INTERNATIONAL GMBH, Jona (CH)
Filed on Aug. 22, 2023, as Appl. No. 18/236,458.
Application 18/236,458 is a division of application No. 18/075,513, filed on Dec. 6, 2022, granted, now 11,773,083.
Application 18/075,513 is a continuation of application No. PCT/US2021/070924, filed on Jul. 22, 2021.
Claims priority of provisional application 63/137,212, filed on Jan. 14, 2021.
Claims priority of provisional application 63/104,329, filed on Oct. 22, 2020.
Claims priority of provisional application 63/075,368, filed on Sep. 8, 2020.
Claims priority of provisional application 63/054,918, filed on Jul. 22, 2020.
Prior Publication US 2023/0391755 A1, Dec. 7, 2023
Int. Cl. C07D 403/12 (2006.01)

CPC C07D 403/12 (2013.01) [C07B 2200/13 (2013.01)]

16 Claims

1. A crystalline form of Belumosudil Mesylate designated form M2, which is characterized by data selected from one or more of the following:

(a) an XRPD pattern having peaks at 6.3, 12.8, 15.8, 19.3 and 26.5 degrees 2-theta±0.2 degrees 2-theta;

(b) an XRPD pattern substantially as depicted in FIG. 7;

(c) an XRPD pattern having peaks at 6.3, 12.8, 15.8, 19.3 and 26.5 degrees 2-theta±0.2 degrees 2-theta, and also having any one, two, three, four or five additional peaks selected from 7.8, 20.4, 23.7, 25.1 and 27.4 degrees two theta±0.2 degrees two theta;

(d) an X-ray powder diffraction pattern having peaks at 6.3, 7.8, 12.8, 15.8, 19.3, 20.4, 23.7, 25.1, 26.5 and 27.4 degrees 2-theta±0.2 degrees 2-theta;

(e) a solid state ¹³C NMR spectrum with characteristic peaks at 156.1, 132.7, 135.5, 119.8 and 110.9 ppm±0.2 ppm;

(f) a solid state ¹³C NMR spectrum having the following chemical shift absolute differences from reference peak at 166.9 ppm±1 ppm: 10.8, 34.2, 36.4, 47.1 and 56.0 ppm±0.1 ppm;

(g) a solid state ¹³C NMR spectrum substantially as depicted in FIG. 19, 20 or 21; and

(h) combinations of these data.