Solid forms comprising 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione and a coformer, compositions and methods of use thereof

Patent metadata

Field	Value
Publication number	US-11406629-B2
Application number	US-202017061456-A
Country	US
Kind code	B2
Filing date	Oct 1, 2020
Priority date	Mar 26, 2013
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

Abstract

Provided herein are solid forms comprising (a) 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione and (b) a coformer. Pharmaceutical compositions comprising the solid forms (e.g., cocrystals) and methods for treating, preventing and managing various disorders are also disclosed.

First claim

What is claimed is:

1. A method of treating relapsed and refractory multiple myeloma, the method comprising administering to a patient dexamethasone in combination with a solid form comprising (a) 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione (pomalidomide); and (b) a coformer; wherein:
the coformer is gallic acid and the solid form has an X-ray powder diffraction (XRPD) pattern comprising peaks at 15.52, 26.16, and 26.90 degrees 2θ±0.2 degrees 2θ;
the coformer is vanillin and the solid form has an XRPD pattern comprising peaks at 13.09, 12.25, and 25.61 degrees 2θ±0.2 degrees 2θ;
the coformer is cyclamic acid and the solid form has an XRPD pattern comprising peaks at 6.42, 7.88, and 18.54 degrees 2θ±0.2 degrees 2θ;
the coformer is D-glucose and the solid form has an XRPD pattern comprising peaks at 12.31, 20.68, and 25.52 degrees 2θ±0.2 degrees 2θ;
the coformer is propyl gallate and the solid form has an XRPD pattern comprising peaks at 7.78, 12.29, 25.23, and 25.61 degrees 2θ±0.2 degrees 2θ;
the coformer is saccharin and the solid form has an XRPD pattern comprising peaks at 15.98, 17.36, and 25.10 degrees 2θ±0.2 degrees 2θ;
the coformer is sodium lauryl sulfate and the solid form has an XRPD pattern comprising peaks at 2.66, 5.30, and 7.93 degrees 2θ±0.2 degrees 2θ;
the coformer is magnesium bromide and the solid form has an XRPD pattern comprising peaks at 17.16, 28.76, and 29.95 degrees 2θ±0.2 degrees 2θ;
the coformer is malonic acid and the solid form has an XRPD pattern comprising peaks at 13.99, 16.63, and 25.58 degrees 2θ±0.2 degrees 2θ;
the coformer is maltol and the solid form has an XRPD pattern comprising peaks at 11.87, 17.09, and 25.73 degrees 2θ±0.2 degrees 2θ;
the coformer is methyl paraben and the solid form has an XRPD pattern comprising peaks at 18.73, 21.98, and 26.70 degrees 2θ±0.2 degrees 2θ; or
the coformer is zinc chloride and the solid form has an XRPD pattern comprising peaks at 2.38, 3.22, and 25.71 degrees 2θ±0.2 degrees 2θ; and
wherein the patient has received at least two prior therapies.

2. The method of claim 1 , wherein the coformer is gallic acid and the solid form has an X-ray powder diffraction pattern comprising peaks at 15.52, 26.16, and 26.90 degrees 2θ±0.2 degrees 2θ.

3. The method of claim 2 , having an X-ray powder diffraction pattern further comprising peaks at 18.42 and 23.20 degrees 2θ±0.2 degrees 2θ.

4. The method of claim 1 , wherein the coformer is vanillin and the solid form has an X-ray powder diffraction pattern comprising peaks at 13.09, 12.25, and 25.61 degrees 2θ±0.2 degrees 2θ.

5. The method of claim 4 , having an X-ray powder diffraction pattern further comprising peaks at 16.91, and 28.01 degrees 2θ±0.2 degrees 2θ.

6. The method of claim 1 , wherein the coformer is cyclamic acid and the solid form has an X-ray powder diffraction pattern comprising peaks at 6.42, 7.88, and 18.54 degrees 2θ±0.2 degrees 2θ.

7. The method of claim 6 , having an X-ray powder diffraction pattern further comprising a peak at 19.25 degrees 2θ±0.2 degrees 2θ.

8. The method of claim 1 , wherein the coformer is D-glucose and the solid form has an X-ray powder diffraction pattern comprising peaks at 12.31, 20.68, and 25.52 degrees 2θ±0.2 degrees 2θ.

9. The method of claim 8 , having an X-ray powder diffraction pattern further comprising peaks at 14.08, and 17.35 degrees 2θ±0.2 degrees 2θ.

10. The method of claim 1 , wherein the coformer is propyl gallate and the solid form has an X-ray powder diffraction pattern comprising peaks at 7.78, 12.29, 25.23, and 25.61 degrees 2θ±0.2 degrees 2θ.

11. The method of claim 10 , having an X-ray powder diffraction pattern further comprising peaks at 14.08, 17.35, and 24.29 degrees 2θ±0.2 degrees 2θ.

12. The method of claim 1 , wherein the coformer is saccharin and the solid form has an X-ray powder diffraction pattern comprising peaks at 15.98, 17.36, and 25.10 degrees 2θ±0.2 degrees 2θ.

13. The method of claim 12 , having an X-ray powder diffraction pattern further comprising peaks at 20.07 and 25.73 degrees 2θ±0.2 degrees 2θ.

14. The method of claim 1 , wherein the coformer is sodium lauryl sulfate and the solid form has an X-ray powder diffraction pattern comprising peaks at 2.66, 5.30, and 7.93 degrees 2θ±0.2 degrees 2θ.

15. The method of claim 14 , having an X-ray powder diffraction pattern further comprising peaks at 12.20, 17.27, and 25.53 degrees 2θ±0.2 degrees 2θ.

16. The method of claim 1 , wherein the coformer is magnesium bromide and the solid form has an X-ray powder diffraction pattern comprising peaks at 17.16, 28.76, and 29.95 degrees 2θ±0.2 degrees 2θ.

17. The method of claim 16 , having an X-ray powder diffraction pattern further comprising peaks at 25.72 and 29.87 degrees 2θ±0.2 degrees 2θ.

18. The method of claim 1 , wherein the coformer is malonic acid and the solid form has an X-ray powder diffraction pattern comprising peaks at 13.99, 16.63, and 25.58 degrees 2θ±0.2 degrees 2θ.

19. The method of claim 18 , having an X-ray powder diffraction pattern further comprising peaks at 17.27 and 24.29 degrees 2θ±0.2 degrees 2θ.

20. The method of claim 1 , wherein the coformer is maltol and the solid form has an X-ray powder diffraction pattern comprising peaks at 11.87, 17.09, and 25.73 degrees 2θ±0.2 degrees 2θ.

21. The method of claim 20 , having an X-ray powder diffraction pattern further comprising peaks at 13.93, 14.54, and 24.25 degrees 2θ±0.2 degrees 2θ.

22. The method of claim 1 , wherein the coformer is methyl paraben and the solid form has an X-ray powder diffraction pattern comprising peaks at 18.73, 21.98, and 26.70 degrees 2θ±0.2 degrees 2θ.

23. The method of claim 22 , having an X-ray powder diffraction pattern further comprising peaks at 17.10, 24.38, and 29.01 degrees 2θ±0.2 degrees 2θ.

24. The method of claim 1 , wherein the coformer is zinc chloride and the solid form has an X-ray powder diffraction pattern comprising peaks at 2.38, 3.22, and 25.71 degrees 2θ±0.2 degrees 2θ.

25. The method of claim 24 , having an X-ray powder diffraction pattern further comprising peaks at 11.95 and 16.61 degrees 2θ±0.2 degrees 2θ.

26. The method of claim 1 , wherein the molar ratio of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione to the coformer is about 1:1.

27. The method of claim 1 , wherein the prior therapies include lenalidomide and bortezomib.

Assignees

• Celgene Corp

Inventors

• Stahly G Patrick
• Jonaitis David
• Hui Ho-Wah
• Klopfer Kevin J

Classifications

• C07D275/06

  with hetero atoms directly attached to the ring sulfur atom · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07C307/02

  Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids · CPC title

• C07D419/14

  containing three or more hetero rings · CPC title

• C07C55/08

  Malonic acid · CPC title