	US 11,713,309 B2
	Solid forms of Cerdulatinib
Anjali Pandey, Fremont, CA (US); Julian Scott Northen, Sunderland (GB); Philippe Fernandes, Turnhout (BE); Ying Chen, Thousand Oaks, CA (US); Yuelie Lu, San Diego, CA (US); Sami Karaborni, Cupertino, CA (US); and Gus Kodersha, Warren, NJ (US)
Assigned to Alexion Pharmaceuticals, Inc., Boston, MA (US)
Filed by Alexion Pharmaceuticals, Inc., Boston, MA (US)
Filed on Nov. 16, 2020, as Appl. No. 17/98,852.
Application 17/098,852 is a continuation of application No. 16/402,684, filed on May 3, 2019, granted, now 10,865,198.
Claims priority of provisional application 62/667,226, filed on May 4, 2018.
Prior Publication US 2021/0130330 A1, May 6, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 403/12 (2006.01)

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

32 Claims

1. A crystalline salt of Compound I:

(a) wherein the salt is esylate, characterized by an X-ray powder diffractogram comprising peaks at 7.5, 18.1, and 14.9 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I esylate Type A);

(b) wherein the salt is mesylate, characterized by an X-ray powder diffractogram comprising peaks at 16.0, 16.4, and 16.7 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I mesylate Type A);

(c) wherein the salt is isethionate, characterized by an X-ray powder diffractogram comprising peaks at 15.8, 17.9, and 20.1 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I isethionate Type A);

(d) wherein the salt is naphthalenesulfonate, characterized by an X-ray powder diffractogram comprising peaks at 14.4, 20.2, and 7.5 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I naphthalenesulfonate Type A);

(e) wherein the salt is naphthalenesulfonate, characterized by an X-ray powder diffractogram comprising peaks at 9.0, 15.6, and 19.7 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I naphthalenesulfonate Type B);

(f) wherein the salt is naphthalenesulfonate, characterized by an X-ray powder diffractogram comprising peaks at 6.9, 13.6, and 13.3 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I naphthalenesulfonate Type C)

(g) wherein the salt is besylate, characterized by an X-ray powder diffractogram comprising peaks at 7.4, 14.9, and 15.3 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I besylate Type A);

(h) wherein the salt is besylate, characterized by an X-ray powder diffractogram comprising peaks at 6.0, 11.9, and 6.9 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I besylate Type B)

(i) wherein the salt is edisylate, characterized by an X-ray powder diffractogram comprising peaks at 14.7, 24.5, and 19.1 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I edisylate Type D);

(j) wherein the salt is camphorsulfonate, characterized by an X-ray powder diffractogram comprising peaks at 5.9, 14.3, and 17.8 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I camphorsulfonate Type A);

(k) wherein the salt is camphorsulfonate, characterized by an X-ray powder diffractogram comprising peaks at 4.7, 14.0, and 17.2 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I camphorsulfonate Type B);

(l) wherein the salt is camphorsulfonate, characterized by an X-ray powder diffractogram comprising peaks at 13.5, 16.8, and 9.5 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I camphorsulfonate Type C);

(m) wherein the salt is chlorobenzenesulfate, characterized by an X-ray powder diffractogram comprising peaks at 8.8, 18.5, and 9.5 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I chlorobenzenesulfate Type B);

(n) wherein the salt is tosylate, characterized by an X-ray powder diffractogram comprising peaks at 7.5, 15.0, and 8.9 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I tosylate Type C); or

(o) wherein the salt is tosylate, characterized by an X-ray powder diffractogram comprising peaks at 9.2, 19.2, and 6.3 °2θ, each ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I tosylate Type D).