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Details for Patent: 9,371,309

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Details for Patent: 9,371,309

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 Sante Fe, CA)
Assignee: Celgene Corporation (Summit, NJ)
Filing Date:Sep 22, 2011
Application Number:13/240,976
Claims:1. A polymorphic mixture comprising less than 20% by weight amorphous 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione and greater than 80% by weight of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate.

2. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has an X-ray powder diffraction pattern comprising peaks at approximately 16, 22, and 27 degrees 2.theta..

3. The polymorphic mixture of claim 2, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has an X-ray powder diffraction pattern further comprising a peak at approximately 18 degrees 2.theta..

4. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has an X-ray powder diffraction pattern comprising peaks at 15.8, 22.2, and 26.7 degrees 2.theta..

5. The polymorphic mixture of claim 4, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has an X-ray powder diffraction pattern further comprising a peak at 18.2 degrees 2.theta..

6. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate corresponds to the representative X-ray powder diffraction patterns provided in FIG. 6, FIG. 32, FIG. 33, and FIG. 34.

7. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has a differential scanning calorimetry thermogram comprising an endotherm with a maximum at about 268.degree. C.

8. The polymorphic mixture of claim 7, wherein the thermogram further comprises an endotherm corresponding to dehydration.

9. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has a differential scanning calorimetry thermogram corresponding to the representative differential scanning calorimetry thermograms provided in FIG. 9, FIG. 42, FIG. 43, and FIG. 44.

10. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has between approximately 0.46 and approximately 0.59 moles of water per mole of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.

11. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hemihydrate has a thermal gravimetric analysis curve comprising a weight loss of between about 3.1% and about 4.0% when heated from about 30.degree. C. to about 175.degree. C.
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