Details for Patent: 9,365,538
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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. (Bridgewater, NJ) |
Assignee: | Celgene Corporation (Summit, NJ) |
Filing Date: | Jan 14, 2009 |
Application Number: | 12/353,383 |
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 an unsolvated crystalline 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.. 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 corresponds to the representative differential scanning calorimetry thermogram provided in FIG. 4. 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 corresponds to the representative thermal gravimetric analysis curve provided in FIG. 4. 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 corresponds to the representative infrared spectrum provided in FIG. 2. 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 corresponds to the representative Raman spectrum provided in FIG. 3. 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 does not exhibit a significant weight gain from 5% to 95% relative humidity. 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 corresponds to the representative moisture sorption/desorption isotherm provided in FIG. 5. 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 corresponds to the solubility curve provided in FIG. 51. 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 corresponds to Form A intrinsic dissolution curves provided in FIGS. 53 and 54. 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 corresponds to the representative X-ray powder diffraction pattern provided in FIG. 1. 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 has a differential scanning calorimetry thermogram having an endotherm at approximately 270.degree. C. 12. The polymorphic mixture of claim 1, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione has a thermogravimetric analysis curve indicative of an unsolvated material. |