IP Library Granted Patent US 11,254,657
Granted Patent B2
US 11,254,657 · App. 16/780,780 · Granted Feb 22, 2022

Plinabulin compositions

Inventors: Lan Huang (Bronx, NY); Aniruddh Singh (Carteret, NJ)
Assignee: BeyondSpring Pharmaceuticals, Inc.
C07D403/06B01D9/0045B01D9/0054B01D9/0063B01D2009/0086C07B2200/13
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Quick Facts
Patent No.
US 11,254,657
App. No.
16/780,780
Granted
Feb 22, 2022
Kind
B2
Abstract

Disclosed herein are plinabulin polymorphs, compositions, their use and preparation as therapeutic agents. In particular, some embodiments relate to plinabulin monohydrate in a crystalline form.

Claims (16)

1. A plinabulin composition, comprising plinabulin and no more than about 2% by weight of impurities, other than solvent molecules, based on the total weight of non-solvent molecules in the composition, wherein the plinabulin composition comprises less than 1% methanol.

2. The plinabulin composition of claim 1 , wherein the plinabulin comprises no more than 1.9% by weight impurities, other than solvent molecules, based on the total weight of non-solvent molecules in the composition.

3. The plinabulin composition of claim 1 , wherein the impurities includes one or more impurities introduced during the synthesis of plinabulin.

4. The plinabulin composition of claim 1 , wherein the plinabulin composition comprises plinabulin and no more than about 1% by weight of impurities other than solvent molecules, based on the total weight of non-solvent molecules in the composition.

5. The plinabulin composition of claim 1 , wherein the plinabulin is plinabulin monohydrate in crystalline form.

6. The plinabulin composition of claim 5 , wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least three characteristic peaks selected from the group consisting of peaks at approximately 8.1°, 13.1°, 16.3°, 23.9°, 24.2°, 24.5°, and 26.6° 2θ.

7. The plinabulin composition of claim 5 , wherein the crystalline form has a melting point of about 267° C.

8. The plinabulin composition of claim 1 , where the weight of impurities is based on a HPLC analysis.

9. The plinabulin composition of claim 1 , comprising as solvents polyoxyl 15 hydroxystearate and propylene glycol.

10. The plinabulin composition of claim 9 , wherein the solvent comprises 40% by weight polyoxyl 15 hydroxystearate and 60% by weight propylene glycol.

11. The plinabulin composition of claim 1 , wherein the plinabulin comprises no more than 0.9% by weight impurities, other than solvent molecules, based on the total weight of non-solvent molecules in the composition.

12. The plinabulin composition of claim 6 , exhibiting an X-ray powder diffraction pattern comprising at least peaks at approximately 8.1°, 13.1°, 16.3°, 23.9°, 24.2°, 24.5°, and 26.6° 2θ.

13. The plinabulin composition of claim 1 , wherein the plinabulin composition comprises less than 0.9% methanol.

14. The plinabulin composition of claim 1 , wherein the plinabulin composition comprises less than 1% ethanol.

15. The plinabulin composition of claim 1 , wherein the plinabulin composition comprises less than 1% ethyl acetate.

16. The plinabulin composition of claim 1 , wherein the plinabulin composition comprises less than 1% acetic acid.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2020
From: HUANG, LAN
To: BEYONDSPRING PHARMACEUTICALS, INC.
Reel/Frame 052735/0691 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2020
From: SINGH, ANIRUDDH
To: JOHNSON MATTHEY PHARMA SERVICES
Reel/Frame 052736/0335 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2020
From: JOHNSON MATTHEY PHARMA SERVICES
To: BEYONDSPRING PHARMACEUTICALS, INC.
Reel/Frame 052737/0015 →
Continuity (4)
Continuation 16212386 · Dec 6, 2018
Continuation 15741635
Provisional Application 62191990 · Jul 13, 2015
Related Publication 20200277280A1 · Sep 3, 2020
Cited By (4)
US 12,377,094 US 12,433,886 US 12,458,638 US 12,458,639