IP Library Granted Patent US 11,970,500
Granted Patent B1
US 11,970,500 · App. 18/526,535 · Granted Apr 30, 2024

Crystalline form of (s)-7-(1-acryloylpiperidin-4-yl)- 2-(4-phenoxyphenyl)-4,5,6,7-tetra- hydropyrazolo[1,5-a]pyrimidine-3-carboxamide, preparation, and uses thereof

Inventors: Zhiwei Wang (Beijing, CN); Yunhang Guo (Beijing, CN); Gongyin Shi (Beijing, CN); Lai Wang (Beijing, CN)
Assignee: BeiGene Switzerland GmbH
C07D487/04A61P35/02A61P35/04C07B2200/13
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Quick Facts
Patent No.
US 11,970,500
App. No.
18/526,535
Granted
Apr 30, 2024
Kind
B1
Abstract

The present invention relates to a crystalline form of (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetr a-hydropyrazolo[1,5-a]pyrimi dine-3-carboxamide for inhibiting Btk, methods of preparation thereof and pharmaceutical compositions, and use of the crystalline form above in the treatment of a disease, or in the manufacturing of a medicament for the treatment of a disease.

Claims (30)

1. A method for treating a B-cell proliferative disease in a subject, comprising administering to the subject in need thereof Compound 1,

wherein the B-cell proliferative disease is selected from a group consisting of chronic lymphocytic leukemia, small lymphocytic lymphoma, mantle cell lymphoma, Waldenstrom's macroglobulinemia, marginal zone lymphoma, and follicular lymphoma; and

Compound 1 is administrated at a dose of 320 mg once a day (QD).

2. The method of claim 1 , wherein Compound 1 has a purity of at least 99.3%.

3. The method of claim 1 , wherein Compound 1 has a purity of at least 99.5%.

4. The method of claim 3 , wherein the B-cell proliferative disease is mantle cell lymphoma.

5. The method of claim 4 , wherein the subject has received at least one prior therapy.

6. The method of claim 3 , wherein the B-cell proliferative disease is Waldenström's macroglobulinemia.

7. The method of claim 3 , wherein the B-cell proliferative disease is marginal zone lymphoma.

8. The method of claim 7 , wherein the subject has received at least one prior therapy.

9. The method of claim 8 , wherein the marginal zone lymphoma is relapsed or refractory marginal zone lymphoma.

10. The method of claim 3 , wherein the B-cell proliferative disease is chronic lymphocytic leukemia.

11. The method of claim 3 , wherein the B-cell proliferative disease is small lymphocytic lymphoma.

12. The method of claim 3 , wherein the B-cell proliferative disease is follicular lymphoma.

13. The method of claim 3 , wherein an amorphous form or a crystalline form of Compound 1 is administered.

14. The method of claim 13 , wherein a crystalline form of Compound 1 is administered.

15. The method of claim 14 , wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising diffraction peaks having 20 angle values at 14.8±0.2°, 16.4±0.2° and 21.4±0.2°.

16. The method of claim 15 , wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising diffraction peaks having 20 angle values at 14.8±0.2°, 15.6±0.2°, 16.4±0.2° and 21.4±0.2°.

17. The method of claim 16 , wherein the B-cell proliferative disease is mantle cell lymphoma, wherein the subject has received at least one prior therapy.

18. The method of claim 16 , wherein the B-cell proliferative disease is Waldenström's macroglobulinemia.

19. The method of claim 16 , wherein the B-cell proliferative disease is relapsed or refractory marginal zone lymphoma, wherein the subject has received at least one prior therapy.

20. The method of claim 16 , wherein the B-cell proliferative disease is chronic lymphocytic leukemia or small lymphocytic lymphoma.

21. The method of claim 13 , wherein an amorphous form of Compound 1 is administered.

22. The method of claim 21 , wherein the amorphous form of Compound 1 has a mid-point temperature of a glass transition temperature at 79.7° C.

23. The method of claim 22 , wherein the amorphous form has an enantiomeric excess value of at least 97%.

24. The method of claim 23 , wherein the B-cell proliferative disease is mantle cell lymphoma, wherein the subject has received at least one prior therapy.

25. The method of claim 23 , wherein the B-cell proliferative disease is Waldenström's macroglobulinemia.

26. The method of claim 23 , wherein the B-cell proliferative disease is relapsed or refractory marginal zone lymphoma, wherein the subject has received at least one prior therapy.

27. The method of claim 23 , wherein the B-cell proliferative disease is chronic lymphocytic leukemia or small lymphocytic lymphoma.

28. The method of claim 3 , wherein Compound 1 is administered orally.

Assignments (4)
CHANGE OF NAME Recorded Jun 27, 2025
From: BEIGENE SWITZERLAND GMBH
To: BEONE MEDICINES I GMBH
Reel/Frame 071544/0358 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2024
From: WANG, ZHIWEI; GUO, YUNHANG; SHI, GONGYIN
To: BEIGENE, LTD.
Reel/Frame 066287/0080 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2024
From: BEIGENE, LTD.
To: BEIGENE SWITZERLAND GMBH
Reel/Frame 066287/0092 →
CHANGE OF ASSIGNEE ADDRESS Recorded Jan 30, 2024
From: BEIGENE SWITZERLAND GMBH
To: BEIGENE SWITZERLAND GMBH
Reel/Frame 066378/0879 →
Priority Claims (1)
WO PCT/CN2016/09510 · Aug 16, 2016 · international
Continuity (3)
Continuation 17858826 · Jul 6, 2022
Continuation 17146855 · Jan 12, 2021
Continuation 16325447