US 11,891,386 B2
Indole compounds and their use
Peter Colabuono, Half Moon Bay, CA (US); Graham Johnson, Sanbornton, NH (US); David Douglas Manning, Orchard Park, NY (US); and Mark Allan Wolf, Williamsville, NY (US)
Assigned to ARIAGEN, INC., Manlo Park (CA)
Filed by ARIAGEN, INC., Menlo Park, CA (US)
Filed on Aug. 15, 2022, as Appl. No. 17/888,142.
Application 17/888,142 is a division of application No. 16/765,315, granted, now 11,459,322, previously published as PCT/US2018/061758, filed on Nov. 19, 2018.
Claims priority of provisional application 62/717,387, filed on Aug. 10, 2018.
Claims priority of provisional application 62/588,751, filed on Nov. 20, 2017.
Prior Publication US 2023/0145074 A1, May 11, 2023
Int. Cl. C07D 417/14 (2006.01); A61P 35/00 (2006.01); C07D 209/12 (2006.01); C07D 209/26 (2006.01); C07D 401/06 (2006.01); C07D 403/06 (2006.01); C07D 413/14 (2006.01); C07D 417/06 (2006.01)
CPC C07D 417/14 (2013.01) [A61P 35/00 (2018.01); C07D 209/12 (2013.01); C07D 209/26 (2013.01); C07D 401/06 (2013.01); C07D 403/06 (2013.01); C07D 413/14 (2013.01); C07D 417/06 (2013.01)] 19 Claims
 
1. A method of stimulating the immune system in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a compound of Structural Formula 8, or an enantiomer, diastereomer, or pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein R2 is a C1-C6 alkyl substituted with one or more hydroxyl, alkoxy, nitro, or cyano, and the compound is enantiomerically pure; or
wherein R2 is heteroaryl or

OG Complex Work Unit Chemistry
and R2a is H, C1-C6 alkyl, hydroxy, thioalkoxy (—S-alkyl), cyano (—CN), or amino; and
R4, R5, R6, and R7, are each, independently, hydrogen or halo.