US 11,926,644 B2
Syntheses, activities, and methods of use of dihydronicotinamide riboside derivatives
Anthony Sauve, New Rochelle, NY (US); Farheen Sultana Mohammed, Jackson Heights, NY (US); and Yue Yang, New York, NY (US)
Assigned to Cornell University, Ithaca, NY (US)
Filed by Cornell University, Ithaca, NY (US)
Filed on Jul. 27, 2021, as Appl. No. 17/386,244.
Application 17/386,244 is a continuation of application No. 16/551,401, filed on Aug. 26, 2019, granted, now 11,098,076.
Application 16/551,401 is a continuation of application No. 15/744,602, granted, now 10,392,414, issued on Aug. 27, 2019, previously published as PCT/US2016/042600, filed on Jul. 15, 2016.
Claims priority of provisional application 62/192,917, filed on Jul. 15, 2015.
Prior Publication US 2021/0355152 A1, Nov. 18, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07H 19/048 (2006.01); A23L 33/10 (2016.01); A61K 31/706 (2006.01); C07H 1/00 (2006.01); C07H 1/06 (2006.01); C07H 19/04 (2006.01)
CPC C07H 19/048 (2013.01) [A23L 33/10 (2016.08); A61K 31/706 (2013.01); C07H 1/00 (2013.01); C07H 1/06 (2013.01); C07H 19/04 (2013.01); A23V 2002/00 (2013.01)] 20 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
wherein R1, R2, and R3 are independently selected from hydrogen, formyl, optionally substituted C1-C12 alkylcarbonyl, and optionally substituted C6-C10 arylcarbonyl,
X is OR6, and
R6 is hydrogen, optionally substituted C1-C12 alkyl, or optionally substituted C6-C10 aryl,
wherein the alkyl or aryl portion of R6 is optionally substituted with one or more substituents selected from halo, amino, alkyl, alkoxy, aryloxy, hydroxyalkyl, and any combination thereof,
wherein the compound of formula (I) has an octanol-water partition coefficient (cLogP) of at least 0.11,
with the provisos that, when R6 is hydrogen, R1, R2,and R3 are not all hydrogen or all acetyl,
when R6 is hydrogen, R1 is not benzoyl and R2 and R3 are not hydrogen, and
when R6 is methyl, ethyl, or propyl, R1, R2, and R3 are not all acetyl, or a salt thereof.