US 10,376,503 B2
Solid forms comprising 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione and a coformer, compositions and methods of use thereof
G. Patrick Stahly, West Lafayette, IN (US); David Jonaitis, Brookston, IN (US); Ho-Wah Hui, Basking Ridge, NJ (US); and Kevin J. Klopfer, Flemington, NJ (US)
Assigned to Celgene Corporation, Summit, NJ (US)
Filed by Celgene Corporation, Summit, NJ (US)
Filed on Mar. 9, 2018, as Appl. No. 15/917,421.
Application 15/917,421 is a division of application No. 15/607,163, filed on May 26, 2017, granted, now 9,974,780.
Application 15/607,163 is a division of application No. 14/780,289, granted, now 9,695,146, issued on Jul. 4, 2017, previously published as PCT/US2014/031694, filed on Mar. 25, 2014.
Claims priority of provisional application 61/805,444, filed on Mar. 26, 2013.
Prior Publication US 2018/0200245 A1, Jul. 19, 2018
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/04 (2006.01); A61K 31/454 (2006.01); C07C 55/08 (2006.01); C07C 65/03 (2006.01); C07C 65/21 (2006.01); C07C 69/88 (2006.01); C07C 305/04 (2006.01); C07C 307/02 (2006.01); C07D 275/06 (2006.01); C07D 309/40 (2006.01); C07H 3/02 (2006.01); A61K 47/02 (2006.01); A61K 47/12 (2006.01); C07D 419/14 (2006.01); G01N 23/2005 (2018.01)
CPC A61K 31/454 (2013.01) [A61K 47/02 (2013.01); A61K 47/12 (2013.01); C07C 55/08 (2013.01); C07C 65/03 (2013.01); C07C 65/21 (2013.01); C07C 69/88 (2013.01); C07C 305/04 (2013.01); C07C 307/02 (2013.01); C07D 275/06 (2013.01); C07D 309/40 (2013.01); C07D 401/04 (2013.01); C07D 419/14 (2013.01); C07H 3/02 (2013.01); G01N 23/2005 (2013.01); C07B 2200/13 (2013.01); C07C 2601/14 (2017.05)] 38 Claims
 
1. A method of treating multiple myeloma, the method comprising administering to a patient dexamethasone in combination with a solid form comprising (a) 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione (pomalidomide); and (b) a coformer; wherein
the coformer is gallic acid and the solid form has an X-ray powder diffraction (XRPD) pattern comprising peaks at 22.98, 26.16, and 26.90 degrees 2θ±0.2 degrees 2θ;
the coformer is vanillin and the solid form has an XRPD pattern comprising peaks at 13.09, 17.30, and 25.61 degrees 2θ±0.2 degrees 2θ;
the coformer is cyclamic acid and the solid form has an XRPD pattern comprising peaks at 6.42, 7.88, and 15.73 degrees 2θ±0.2 degrees 2θ;
the coformer is D-glucose and the solid form has an XRPD pattern comprising peaks at 17.09, 20.68, and 25.52 degrees 2θ±0.2 degrees 2θ;
the coformer is propyl gallate and the solid form has an XRPD pattern comprising peaks at 7.78, 25.23, and 25.61 degrees 2θ±0.2 degrees 2θ;
the coformer is saccharin and the solid form has an XRPD pattern comprising peaks at 15.98, 19.09, and 25.10 degrees 2θ±0.2 degrees 2θ;
the coformer is sodium lauryl sulfate and the solid form has an XRPD pattern comprising peaks at 2.66, 5.30, and 7.93 degrees 2θ±0.2 degrees 2θ;
the coformer is magnesium bromide and the solid form has an XRPD pattern comprising peaks at 3.23, 28.76, and 29.95 degrees 2θ±0.2 degrees 2θ;
the coformer is malonic acid and the solid form has an XRPD pattern comprising peaks at 12.23, 16.63, and 25.58 degrees 2θ±0.2 degrees 2θ;
the coformer is maltol and the solid form has an XRPD pattern comprising peaks at 16.51, 17.09, and 25.73 degrees 2θ±0.2 degrees 2θ;
the coformer is methyl paraben and the solid form has an XRPD pattern comprising peaks at 18.73, 25.69, and 26.70 degrees 2θ±0.2 degrees 2θ; or
the coformer is zinc chloride and the solid form has an XRPD pattern comprising peaks at 2.38, 17.17, and 25.71 degrees 2θ±0.2 degrees 2θ.