	US 12,213,965 B2
	Riluzole prodrugs and their 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 Jul. 5, 2021, as Appl. No. 17/367,484.
Application 17/367,484 is a continuation of application No. 16/689,150, filed on Nov. 20, 2019, granted, now 11,052,070, issued on Jul. 6, 2021.
Application 16/689,150 is a continuation of application No. 16/449,948, filed on Jun. 24, 2019, granted, now 10,905,681, issued on Feb. 2, 2021.
Application 16/449,948 is a continuation of application No. 15/549,154, granted, now 10,485,791, issued on Nov. 26, 2019, previously published as PCT/US2016/019787, filed on Feb. 26, 2016.
Claims priority of provisional application 62/127,684, filed on Mar. 3, 2015.
Prior Publication US 2023/0017637 A1, Jan. 19, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/428 (2006.01); A61K 9/00 (2006.01); A61K 9/16 (2006.01); A61K 9/20 (2006.01); A61K 31/454 (2006.01); A61K 31/496 (2006.01); A61K 31/506 (2006.01); A61K 31/5377 (2006.01); A61K 31/541 (2006.01); A61K 38/05 (2006.01); A61K 38/06 (2006.01); A61K 39/00 (2006.01); A61K 45/06 (2006.01); A61P 25/00 (2006.01); A61P 25/28 (2006.01); A61P 35/00 (2006.01); C07D 277/82 (2006.01); C07D 417/12 (2006.01); C07K 5/062 (2006.01); C07K 5/083 (2006.01); C07K 5/087 (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 31/506 (2013.01); A61K 31/5377 (2013.01); A61K 31/541 (2013.01); A61K 38/05 (2013.01); A61K 38/06 (2013.01); A61K 39/4636 (2023.05); A61K 45/06 (2013.01); A61P 25/00 (2018.01); A61P 25/28 (2018.01); A61P 35/00 (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)]

5 Claims

1. A method of attenuating presynaptic glutamate release, the method comprising administering to a subject an effective amount of at least one compound having formula:

wherein R²³is selected from the group consisting of H, CH₃, CH₂CH₃, CH₂CH₂CH₃, CH₂CCH, CH(CH₃)₂, CH₂CH(CH₃)₂, CH(CH₃) CH₂CH₃, CH₂OH, CH₂OCH₂Ph, CH₂CH₂OCH₂Ph, CH(OH) CH₃, CH₂Ph, CH₂(cyclohexyl), CH₂(4-OH-Ph), (CH₂)₄NH₂, (CH₂)₃NHC(NH₂) NH, CH₂(3-indole), CH₂(5-imidazole), CH₂CO₂H, CH₂CH₂CO₂H, CH₂CONH₂, and CH₂CH₂CONH₂;

or an enantiomer, diastereomer, hydrate, solvate, pharmaceutically acceptable salt, or complex thereof.