Details for Patent: 8,431,598
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Title: | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |
Abstract: | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione are disclosed. Compositions comprising the polymorphic forms, methods of making the polymorphic forms and methods of their use are also disclosed. |
Inventor(s): | Jaworsky; Markian S. (Hopewell, NJ), Chen; Roger Shen-Chu (Edison, NJ), Muller; George W. (Rancho Santa Fe, CA) |
Assignee: | Celgene Corporation (Summit, NJ) |
Filing Date: | May 26, 2011 |
Application Number: | 13/117,066 |
Claims: | 1. A solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione comprising an unsolvated crystalline Form A of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione having a differential scanning calorimetry thermogram endotherm at approximately 270.degree. C., wherein the crystalline form is present at greater than about 80% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 2. The solid form of claim 1, wherein the crystalline form is present at greater than about 90% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 3. The solid form of claim 1, wherein the crystalline form is present at greater than about 95% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 4. The solid form of claim 1, wherein the crystalline form is present at greater than about 97% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 5. A solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione comprising an unsolvated crystalline form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione having a differential scanning calorimetry thermogram endotherm at approximately 270.degree. C. and an X-ray powder diffraction pattern comprising peaks at approximately 8, 14.5, and 16 degrees 2.theta. and a thermogravimetric analysis curve indicative of an unsolvated material, wherein the crystalline form is present at greater than about 80% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 6. The solid form of claim 5, wherein the crystalline form is present at greater than about 90% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 7. The solid form of claim 5, wherein the crystalline form is present at greater than about 95% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 8. The solid form of claim 5, wherein the crystalline form is present at greater than about 97% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 9. The solid form of any one of claims 5, 6, 7, and 8, wherein the X-ray powder diffraction pattern further comprises peaks at approximately 17.5, 20.5, 24 and 26 degrees 2.theta.. 10. A solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione comprising an unsolvated crystalline form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione having an X-ray powder diffraction pattern comprising peaks at approximately 8, 14.5, 16, 17.5, 20.5, 24, and 26 degrees 2.theta., wherein the crystalline form is present at greater than about 80% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 11. The solid form of claim 10, wherein the crystalline form is present at greater than about 90% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 12. The solid fault of claim 10, wherein the crystalline form is present at greater than about 95% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 13. The solid form of claim 10, wherein the crystalline form is present at greater than about 97% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 14. A pharmaceutical composition comprising a therapeutically effective amount of the solid form of any one of claims 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, and 13, and a pharmaceutically acceptable excipient, diluent, or carrier. 15. The pharmaceutical composition of claim 14, which is a single unit dosage form. 16. The pharmaceutical composition of claim 15, wherein the therapeutically effective amount is about 5 mg, about 10 mg, about 25 mg, or about 50 mg. 17. A pharmaceutical composition comprising from about 5 mg to about 25 mg of a solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione comprising an unsolvated crystalline form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione having a differential scanning calorimetry thermogram endotherm at approximately 270.degree. C., and a pharmaceutically acceptable excipient, diluent, or carrier; wherein the crystalline form is present at greater than about 80% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 18. The pharmaceutical composition of claim 17, wherein the crystalline form is present at greater than about 90% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 19. The pharmaceutical composition of claim 17, wherein the crystalline form is present at greater than about 95% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 20. The pharmaceutical composition of claim 17, wherein the crystalline form is present at greater than about 97% by weight of the total weight of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 21. The pharmaceutical composition of any one of claims 17, 18, 19, and 20, comprising about 5 mg of the solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 22. The pharmaceutical composition of any one of claims 17, 18, 19, and 20, comprising about 10 mg of the solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. 23. The pharmaceutical composition of any one of claims 17, 18, 19, and 20, comprising about 25 mg of the solid form of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione. |