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Details for Patent: 9,353,080

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Details for Patent: 9,353,080

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:Sep 22, 2011
Application Number:13/241,022
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 crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione dihydrate.

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 dihydrate has an X-ray powder diffraction pattern comprising peaks at approximately 20, 24.5, and 29 degrees 2.theta..

3. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione dihydrate has an X-ray powder diffraction pattern comprising peaks at 20.0, 24.7, and 28.6 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 dihydrate corresponds to the representative X-ray powder diffraction patterns provided in FIGS. 23 and 35.

5. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione dihydrate has a differential scanning calorimetry thermogram comprising an endotherm with a maximum at about 269.degree. C.

6. The polymorphic mixture of claim 5, wherein the thermogram further comprises an endotherm at about 99.degree. C.

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 dihydrate has a differential scanning calorimetry thermogram corresponding to the representative differential scanning calorimetry thermograms provided in FIGS. 24 and 45.

8. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione dihydrate has a thermal gravimetric analysis curve comprising a weight loss of about 12% up to about 175.degree. C.
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