US 12,150,948 B2
Toll-like receptor ligands
Helene Bazin-Lee, Stevensville, MT (US); George Ettenger, Missoula, MT (US); Juhienah Khalaf, Hamilton, MT (US); and Kendal T. Ryter, Hamilton, MT (US)
Assigned to National Institutes of Health (NIH), U.S. Dept. of Health and Human Services (DHHS), U.S. Government, Bethesda, MD (US)
Filed by INIMMUNE CORPORATION, Missoula, MT (US)
Filed on Aug. 29, 2022, as Appl. No. 17/898,165.
Application 17/898,165 is a division of application No. 16/968,835, granted, now 11,458,151, previously published as PCT/US2019/017669, filed on Feb. 12, 2019.
Claims priority of provisional application 62/629,513, filed on Feb. 12, 2018.
Prior Publication US 2023/0055805 A1, Feb. 23, 2023
Int. Cl. A61P 31/04 (2006.01); A61K 31/7008 (2006.01); A61K 39/00 (2006.01); A61K 39/35 (2006.01); A61K 39/39 (2006.01); A61K 45/06 (2006.01); A61P 9/10 (2006.01); A61P 11/02 (2006.01); A61P 17/04 (2006.01); A61P 35/00 (2006.01); A61P 37/00 (2006.01); C07H 15/12 (2006.01); C07H 15/26 (2006.01)
CPC A61K 31/7008 (2013.01) [A61K 39/35 (2013.01); A61K 39/39 (2013.01); A61P 9/10 (2018.01); A61P 11/02 (2018.01); A61P 17/04 (2018.01); A61P 31/04 (2018.01); A61P 35/00 (2018.01); A61P 37/00 (2018.01); C07H 15/12 (2013.01); C07H 15/26 (2013.01); A61K 2039/57 (2013.01); A61K 45/06 (2013.01)] 30 Claims
 
1. A method of eliciting or enhancing, or modifying an immune response in a subject comprising administering to a subject in need thereof a therapeutically effective amount of the compound of formula (I-a), or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein,
R2a, R2b, and R2c are each independently-CH(R10)(R11);
R3a is-OP(O)(OH)2, —OSO3H, or —OCH2P(O)(OH)2;
R3b is hydrogen or COOH, or an ester thereof;
R10, at each occurrence, is independently C8-14alkyl;
R11, at each occurrence, is independently —O—C(═O)C1-15alkyl, —O—C(═O)C1-15alkylene-Z2, —O—C2-16alkylene-Z2, or —O—C2-16alkyl; and
Z2, at each occurrence, is independently phenyl or a 5- to 6-membered heteroaryl, wherein Z2 is optionally substituted with 1-5 substituents independently selected from C1-4alkyl, C1-4haloalkyl, —OC1-4alkyl, —OC1-4 haloalkyl, cyano, and halogen.