IP Library Granted Patent US 10,882,867
Granted Patent B2
US 10,882,867 · App. 16/494,725 · Granted Jan 5, 2021

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 10,882,867
App. No.
16/494,725
Granted
Jan 5, 2021
Kind
B2
Abstract

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

Claims (25)

1. A crystalline form of Compound 1:

2. The crystalline form according to claim 1 , wherein Compound 1 is unsolvated.

3. The crystalline form according to 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 6.19, 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.

4. The crystalline form according to claim 3 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 9.33, about 9.64, and about 16.31 degrees 2-theta.

5. The crystalline form according to claim 3 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.19, about 9.33, about 9.64, and about 16.31 degrees 2-theta.

6. The crystalline form according to claim 3 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.19, about 9.33, about 9.64, about 16.31, and about 24.02 degrees 2-theta.

7. The crystalline form according to claim 3 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at 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.

8. The crystalline form according to claim 1 , wherein the crystalline form is a hydrate.

9. The crystalline form according to claim 1 , wherein the crystalline form is a solvate.

10. The crystalline form according to claim 9 , wherein the crystalline form is characterized by one or more peaks in its powder X-ray diffraction pattern selected from those at 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.

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 6.73, about 8.44, and about 23.95 degrees 2-theta.

12. The crystalline form according to claim 10 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.73, about 8.44, about 17.53, and about 23.95 degrees 2-theta.

13. The crystalline form according to claim 10 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.73, about 8.44, about 15.27, about 17.53, and about 23.95 degrees 2-theta.

14. The crystalline form according to claim 10 , wherein the crystalline form is characterized by a powder X-ray diffraction pattern having peaks at about 6.73, 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.

15. A complex comprising Compound 1:

and a co-former X,

wherein X is selected from the group consisting of t-aconitic acid, L-ascorbic acid, aspartic acid, benzoic acid, citric acid, gentisic acid, glutaric acid, 1-hydroxy-2-naphthoic acid, isethionic acid, ketoglutaric acid, L-lysine, maleic acid, malonic acid, methanesulfonic acid, naphthalene-1,5-disulphonic acid, oxalic acid, phosphoric acid, saccharin, thiocyanic acid, p-toluenesulfonic acid, and vanillin.

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

17. A pharmaceutical composition comprising the complex according to claim 15 and a pharmaceutically acceptable carrier.

18. The composition according to claim 16 , wherein the composition comprises at least about 90% by weight of crystalline Compound 1.

19. The composition according to claim 16 , wherein the composition comprises at least about 95% by weight of crystalline Compound 1.

20. The composition according to claim 16 , wherein the composition is substantially free of amorphous Compound 1.

21. The composition according to claim 17 , wherein the composition comprises at least about 90% by weight of crystalline complex.

22. The composition according to claim 17 , wherein the composition comprises at least about 95% by weight of crystalline complex.

23. The composition according to claim 17 , wherein the composition is substantially free of one or more of amorphous Compound 1 or co-former X.

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 Nov 26, 2019
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 051114/0971 →
Continuity (2)
Provisional Application 62472015 · Mar 16, 2017
Related Publication 20200148701A1 · May 14, 2020