IP Library Granted Patent US 11,629,153
Granted Patent B2
US 11,629,153 · App. 17/136,464 · Granted Apr 18, 2023

Forms and compositions of a MK2 inhibitor

Inventors: Jianxin Han (Green Brook, NJ); Lianfeng Huang (Basking Ridge, NJ); Uday Jain (Plainsboro, NJ); Ying Li (Millburn, NJ); John Malona (Brookline, MA); Kevin Molter (Summit, NJ); Chittari Pabba (Slingerlands, NY); Alexander L. Ruchelman (Cream Ridge, NJ); Jean Xu (Warren, NJ); Daozhong Zou (Raritan, NJ)
Assignee: Celgene CAR LLC
C07D495/14A61K38/005
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Quick Facts
Patent No.
US 11,629,153
App. No.
17/136,464
Granted
Apr 18, 2023
Kind
B2
Abstract

The present invention provides solid forms of an MK2 inhibitor, compositions thereof, and methods of using the same.

Claims (48)

1. A crystalline form of Compound 1:

wherein Compound 1 is unsolvated; and

the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at:

i) about 6.19, about 9.33, about 9.64, about 12.39, about 12.49, about 12.59, about 13.11, about 13.25, about 16.31, about 18.70, about 18.84, about 19.09, about 20.92, about 21.35, about 23.17, about 24.02, about 24.94, about 26.44, about 29.14, and about 30.04 degrees 2-theta; or

ii) about 6.19, about 7.04, about 9.30, about 9.58, about 9.64, about 12.54, about 18.69, about 19.33, about 21.34, about 27.52, and about 29.18 degrees 2-theta; or

iii) about 4.89, about 6.01, about 6.10, about 9.83, about 12.06, about 20.55, about 20.98, about 25.75, and about 26.42 degrees 2-theta.

2. A crystalline form of Compound 1:

wherein the crystalline form is a hydrate; and

the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at:

i) about 7.03, about 13.54, about 13.91, about 14.13, about 21.25, about 21.51, about 24.73, and about 25.77 degrees 2-theta; or

ii) about 6.80, about 7.13, about 9.95, about 15.48, about 15.64, and about 21.44 degrees 2-theta.

3. A crystalline form of Compound 1:

wherein the crystalline form is a solvate; and

the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at:

i) about 7.11, about 8.92, about 10.41, about 10.68, about 11.00, about 13.70, about 22.11, and about 23.73 degrees 2-theta; or

ii) about 6.36, about 9.56, about 9.94, about 10.41, about 10.77, about 12.71, about 12.89, about 17.56, about 18.12, about 19.09, about 19.35, about 19.74, about 20.83, about 23.49, and about 24.08 degrees 2-theta; or

iii) about 10.37, about 12.81, about 19.31, about 19.75, and about 24.06 degrees 2-theta; or

iv) about 6.73, about 8.44, about 13.45, about 15.27, about 17.53, about 20.54, about 23.95, and about 24.49 degrees 2-theta.

4. The crystalline form of claim 1 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 6.19, about 7.04, about 9.30, about 9.58, about 9.64, about 12.54, about 18.69, about 19.33, about 21.34, about 27.52, and about 29.18 degrees 2-theta.

5. The crystalline form according to claim 4 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 7.04, about 12.54, and about 21.34 degrees 2-theta.

6. The crystalline form of claim 1 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 4.89, about 6.01, about 6.10, about 9.83, about 12.06, about 20.55, about 20.98, about 25.75, and about 26.42 degrees 2-theta.

7. The crystalline form according to claim 6 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 4.89, about 6.01, and about 9.83 degrees 2-theta.

8. The crystalline form of claim 2 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 7.03, about 13.54, about 13.91, about 14.13, about 21.25, about 21.51, about 24.73, and about 25.77 degrees 2-theta.

9. The crystalline form according to claim 8 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 7.03, about 13.54, about 13.91, and about 14.13 degrees 2-theta.

10. The crystalline form of claim 2 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 6.80, about 7.13, about 9.95, about 15.48, about 15.64, and about 21.44 degrees 2-theta.

11. The crystalline form according to claim 10 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.80 and about 7.13 degrees 2-theta.

12. The crystalline form of claim 3 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 7.11, about 8.92, about 10.41, about 10.68, about 11.00, about 13.70, about 22.11, and about 23.73 degrees 2-theta.

13. The crystalline form according to claim 12 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 7.11, about 8.92 and about 11.00 degrees 2-theta.

14. The crystalline form of claim 3 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 6.36, about 9.56, about 9.94, about 10.41, about 10.77, about 12.71, about 12.89, about 17.56, about 18.12, about 19.09, about 19.35, about 19.74, about 20.83, about 23.49, and about 24.08 degrees 2-theta.

15. The crystalline form according to claim 14 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.36, about 12.71, and about 12.89 degrees 2-theta.

16. The crystalline form of claim 3 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at about 10.37, about 12.81, about 19.31, about 19.75, and about 24.06 degrees 2-theta.

17. The crystalline form according to claim 16 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 12.81, about 19.31, and about 24.06 degrees 2-theta.

18. A pharmaceutical composition comprising a crystalline form according to claim 1 and a pharmaceutically acceptable carrier.

19. A pharmaceutical composition comprising a crystalline form according to claim 2 and a pharmaceutically acceptable carrier.

20. A pharmaceutical composition comprising a crystalline form according to claim 3 and a pharmaceutically acceptable carrier.

21. The crystalline form according to claim 1 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.19, about 7.04, about 9.30, about 9.58, about 9.64, about 12.54, about 18.69, about 19.33, about 21.34, about 27.52, and about 29.18 degrees 2-theta.

22. The crystalline form according to claim 1 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 4.89, about 6.01, about 6.10, about 9.83, about 12.06, about 20.55, about 20.98, about 25.75, and about 26.42 degrees 2-theta.

23. The crystalline form according to claim 2 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 7.03, about 13.54, about 13.91, about 14.13, about 21.25, about 21.51, about 24.73, and about 25.77 degrees 2-theta.

24. The crystalline form according to claim 2 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.80, about 7.13, about 9.95, about 15.48, about 15.64, and about 21.44 degrees 2-theta.

25. The crystalline form according to claim 3 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 7.11, about 8.92, about 10.41, about 10.68, about 11.00, about 13.70, about 22.11, and about 23.73 degrees 2-theta.

26. The crystalline form according to claim 3 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.36, about 9.56, about 9.94, about 10.41, about 10.77, about 12.71, about 12.89, about 17.56, about 18.12, about 19.09, about 19.35, about 19.74, about 20.83, about 23.49, and about 24.08 degrees 2-theta.

27. The crystalline form according to embodiment 14, wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 10.37, about 12.81, about 19.31, about 19.75, and about 24.06 degrees 2-theta.

28. The composition according to claim 18 , wherein the composition is substantially free of amorphous Compound 1.

29. The composition according to claim 18 , wherein the composition comprises at least about 90% by weight of crystalline Compound 1.

30. The composition according to claim 19 , wherein the composition is substantially free of amorphous Compound 1.

31. The composition according to claim 19 , wherein the composition comprises at least about 90% by weight of crystalline Compound 1.

32. The composition according to claim 20 , wherein the composition is substantially free of amorphous Compound 1.

33. The composition according to claim 20 , wherein the composition comprises at least about 90% by weight of crystalline Compound 1.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded May 3, 2023
From: CELGENE CAR LLC
To: BRISTOL-MYERS SQUIBB COMPANY
Reel/Frame 063526/0959 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2021
From: HAN, JIANXIN; HUANG, LIANFENG; JAIN, UDAY; LI, YING; MALONA, JOHN; MOLTER, KEVIN; PABBA, CHITTARI; RUCHELMAN, ALEXANDER L.; XU, JEAN; ZOU, DAOZHONG
To: CELGENE CAR LLC
Reel/Frame 055912/0669 →
Continuity (3)
Division 16494725
Provisional Application 62472015 · Mar 16, 2017
Related Publication 20210198276A1 · Jul 1, 2021