US 12,433,868 B2
Polymorphic forms of ST-246 and methods of preparation
Shanthakumar R. Tyavanagimatt, Sammamish, WA (US); Melialani A. C. L. S. Anderson, Corvallis, OR (US); William C. Weimers, Corvallis, OR (US); Dylan Nelson, Corvallis, OR (US); Tove′ C. Bolken, Keizer, OR (US); Dennis E. Hruby, Albany, OR (US); Michael H. O'Neill, Painesville, OH (US); Gary Sweetapple, Madison, OH (US); and Kelley A. McCloughan, South Haven, MI (US)
Assigned to Siga Technologies, Inc., Corvallis, OR (US)
Filed by Siga Technologies, Inc., Corvallis, OR (US)
Filed on Dec. 19, 2023, as Appl. No. 18/545,961.
Application 18/545,961 is a division of application No. 17/136,674, filed on Dec. 29, 2020, granted, now 11,890,270.
Application 17/136,674 is a division of application No. 16/520,897, filed on Jul. 24, 2019, granted, now 10,933,050.
Application 16/520,897 is a division of application No. 16/025,057, filed on Jul. 2, 2018, granted, now 10,406,137, issued on Sep. 10, 2019.
Application 16/025,057 is a division of application No. 15/661,194, filed on Jul. 27, 2017, granted, now 10,045,964, issued on Aug. 14, 2018.
Application 15/661,194 is a division of application No. 14/959,180, filed on Dec. 4, 2015, granted, now 9,744,154, issued on Aug. 29, 2017.
Application 14/959,180 is a division of application No. 13/069,813, filed on Mar. 23, 2011, granted, now 9,339,466, issued on May 17, 2016.
Claims priority of provisional application 61/316,747, filed on Mar. 23, 2010.
Claims priority of provisional application 61/373,031, filed on Aug. 12, 2010.
Prior Publication US 2024/0156782 A1, May 16, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/404 (2006.01); A61K 9/16 (2006.01); A61K 9/48 (2006.01); A61K 39/275 (2006.01); C07D 209/70 (2006.01); C07D 209/76 (2006.01)
CPC A61K 31/404 (2013.01) [A61K 9/1652 (2013.01); A61K 9/4866 (2013.01); A61K 39/275 (2013.01); C07D 209/70 (2013.01); C07D 209/76 (2013.01)] 8 Claims
OG exemplary drawing
 
1. A unit dosage form comprising a pharmaceutical composition formulated for oral administration, wherein:
(a) said pharmaceutical composition comprises a polymorph Form I of 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop [f] isoindol-2 (1H)-benzamide which shows an X-ray powder diffraction pattern having characteristic peaks at a reflection angle 2θ of about
7.63, 10.04, 11.47, 14.73, 15.21, 15.47, 16.06, 16.67, 16.98, 18.93, 19.96, 20.52, 20.79, 22.80, 25.16, 26.53, 27.20, 27.60, 29.60, 30.23, 30.49, 30.68, 31.14, 33.65, 34.33, 35.29, 35.56, 36.30, 37.36, 38.42, 38.66
degrees and further comprises one or more pharmaceutically acceptable ingredients selected from the group consisting of carriers, excipients, diluents, additives, fillers, lubricants and binders; and
(b) said polymorph Form I has a D90% particle size diameter of up to about 300 microns.