US 11,911,369 B2
Prodrugs of riluzole and their method of use
Jay Edward Wrobel, Lawrenceville, NJ (US); Allen B. Reitz, Lansdale, PA (US); Jeffery Claude Pelletier, Lafayette Hill, PA (US); Garry Robert Smith, Royersford, PA (US); and Haiyan Bian, Princeton, NJ (US)
Assigned to Biohaven Therapeutics Ltd., Tortola (VG)
Filed by Biohaven Therapeutics Ltd., New Haven, CT (US)
Filed on May 4, 2020, as Appl. No. 16/865,498.
Prior Publication US 2022/0396555 A1, Dec. 15, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 277/82 (2006.01); A61K 31/428 (2006.01); A61P 25/00 (2006.01); A61P 25/28 (2006.01); A61K 38/06 (2006.01); C07K 5/083 (2006.01); C07K 5/087 (2006.01); A61K 31/454 (2006.01); A61K 31/496 (2006.01); A61K 31/5377 (2006.01); A61K 38/05 (2006.01); A61K 45/06 (2006.01); C07D 417/12 (2006.01); C07K 5/062 (2006.01); A61K 9/00 (2006.01); A61K 9/16 (2006.01); A61K 9/20 (2006.01); A61K 9/48 (2006.01)
CPC A61K 31/428 (2013.01) [A61K 9/006 (2013.01); A61K 9/1617 (2013.01); A61K 9/2004 (2013.01); A61K 31/454 (2013.01); A61K 31/496 (2013.01); A61K 31/5377 (2013.01); A61K 38/05 (2013.01); A61K 38/06 (2013.01); A61K 45/06 (2013.01); A61P 25/00 (2018.01); A61P 25/28 (2018.01); C07D 277/82 (2013.01); C07D 417/12 (2013.01); C07K 5/06026 (2013.01); C07K 5/0806 (2013.01); C07K 5/0808 (2013.01); C07K 5/0812 (2013.01); A61K 9/0056 (2013.01); A61K 9/2018 (2013.01); A61K 9/2063 (2013.01); A61K 9/485 (2013.01); A61K 9/4858 (2013.01); A61K 9/4866 (2013.01); A61K 2300/00 (2013.01)] 9 Claims
 
1. A pharmaceutical composition comprising:
(i) compound having formula (I):

OG Complex Work Unit Chemistry
including enantiomers, diastereomers, hydrates, solvates, pharmaceutically acceptable salts, and complexes thereof, wherein:
R1 is CR10aR10bNR11R12,
R10a and R10b are hydrogen,
R11 is hydrogen,
R12 is COCR13aR13bNR15aR15b,
R13a and R13b are hydrogen,
R15a is hydrogen, and
R15b is C1-C6 alkyl; and
(ii) a pharmaceutically acceptable carrier.