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Generated: July 26, 2017

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Title:Polymorphic forms of 3-(4-amino-1-oxo-1, 3 dihydro-isoindo1-2-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. (Bridgewater, NJ)
Assignee: Celgene Corporation (Summit, NJ)
Filing Date:Jul 23, 2008
Application Number:12/220,336
Claims:1. The unsolvated crystalline Form A of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione, which has a differential scanning calorimetry thermogram having an endotherm at approximately 270.degree. C.

2. Unsolvated crystalline Form A of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione corresponding to the representative X-ray powder diffraction pattern provided in FIG. 1.

3. An unsolvated crystalline Form A of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 1, which has an X-ray powder diffraction pattern comprising peaks at approximately 8, 14.5, and 16 degrees 2.theta..

4. An unsolvated crystalline Form A of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3, wherein the X-ray powder diffraction pattern further comprises peaks at approximately 17.5, 20.5, 24 and 26 degrees 2.theta..

5. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3 corresponding to the representative differential scanning calorimetry thermogram provided in FIG. 4.

6. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3, which has a thermogravimetric analysis curve indicative of an unsolvated material.

7. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3 corresponding to the representative thermal gravimetric analysis curve provided in FIG. 4.

8. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3 corresponding to the representative infrared spectrum provided in FIG. 2.

9. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3 corresponding to the representative Raman spectrum provided in FIG. 3.

10. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3, which does not exhibit a significant weight gain from 5% to 95% relative humidity.

11. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3 corresponding to the representative moisture sorption/desorption isotherm provided in FIG. 5.

12. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3, corresponding to the solubility curve provided in FIG. 51.

13. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3, corresponding to the Form A intrinsic dissolution curves provided in FIGS. 53 and 54.

14. The unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3 or 4, wherein the recited peaks have an intensity at least equal to the median intensity of the other peaks in the pattern.

15. A pharmaceutical composition comprising a therapeutically effective amount of an unsolvated crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione of claim 3, 4, 2, or 1, and a pharmaceutically acceptable excipient, diluent, or carrier.

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. The pharmaceutical composition of claim 16, which is a single unit dosage form.
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