US 12,005,046 B2
Riluzole prodrugs and their use
Jay Edward Wrobel, Lawrenceville, NJ (US); Allen B. Reitz, Lansdale, PA (US); Jeffrey Claude Pelletier, Lafayette Hill, PA (US); Garry Robert Smith, Royersford, PA (US); and Haiyan Bian, Princeton, NJ (US)
Assigned to Biohaven Therapeutics Ltd., New Haven, CT (US)
Filed by Biohaven Therapeutics Ltd., New Haven, CT (US)
Filed on Feb. 1, 2021, as Appl. No. 17/164,654.
Application 17/164,654 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 2021/0236471 A1, Aug. 5, 2021
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)
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 2300/00 (2013.01)] 8 Claims
 
1. A method for treating cancer, said method comprising administering to a subject an effective amount of at least one compound having formula:

OG Complex Work Unit Chemistry
wherein R23 is selected from the group consisting 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.