US 11,926,640 B2
Prodrugs of glutamine analogs
Barbara Slusher, Kingsville, MD (US); Rana Rais, West Friendship, MD (US); Lukas Tenora, Prague (CZ); Pavel Majer, Sykesville, MD (US); and Andrej Jancarik, Koprivnice (CZ)
Assigned to The Johns Hopkins University, Baltimore, MD (US); and Ústav organické chemie a biochemie AV CR, v.v.i., Prague (CZ)
Filed by THE JOHNS HOPKINS UNIVERSITY, Baltimore, MD (US); and Ústav organické chemie a biochemie AV CR, v.v.i., Prague (CZ)
Filed on Mar. 19, 2021, as Appl. No. 17/207,388.
Application 17/207,388 is a division of application No. 16/454,853, filed on Jun. 27, 2019, granted, now 10,954,257.
Application 16/454,853 is a division of application No. 15/885,258, filed on Jan. 31, 2018, granted, now 10,336,778.
Application 15/885,258 is a continuation in part of application No. PCT/US2016/044767, filed on Jul. 29, 2016.
Claims priority of provisional application 62/199,566, filed on Jul. 31, 2015.
Prior Publication US 2021/0206787 A1, Jul. 8, 2021
Int. Cl. A61K 31/404 (2006.01); A61P 35/00 (2006.01); C07C 227/14 (2006.01); C07C 245/18 (2006.01); C07C 271/22 (2006.01); C07D 209/18 (2006.01); C07D 209/20 (2006.01); C07D 211/90 (2006.01); C07D 263/04 (2006.01); C07D 263/18 (2006.01); C07D 309/10 (2006.01); C07D 317/38 (2006.01); C07D 317/40 (2006.01); C07D 473/34 (2006.01); C07F 9/24 (2006.01); C07F 9/6561 (2006.01); C07H 15/203 (2006.01); C07H 19/207 (2006.01); C07K 5/062 (2006.01); C07K 5/078 (2006.01); C07K 5/083 (2006.01); A61K 38/00 (2006.01)
CPC C07F 9/2458 (2013.01) [A61K 31/404 (2013.01); A61P 35/00 (2018.01); C07C 227/14 (2013.01); C07C 245/18 (2013.01); C07C 271/22 (2013.01); C07D 209/18 (2013.01); C07D 209/20 (2013.01); C07D 211/90 (2013.01); C07D 263/04 (2013.01); C07D 263/18 (2013.01); C07D 309/10 (2013.01); C07D 317/38 (2013.01); C07D 317/40 (2013.01); C07D 473/34 (2013.01); C07F 9/65616 (2013.01); C07H 15/203 (2013.01); C07H 19/207 (2013.01); C07K 5/06026 (2013.01); C07K 5/06156 (2013.01); C07K 5/0808 (2013.01); A61K 38/00 (2013.01)] 16 Claims
 
1. A compound having formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
X is —(CH2)n—, wherein n is 1;
R1 is selected from the group consisting of H, C1-6 alkyl, and substituted C1-6 alkyl;
R2 is —C(═O)—O—(CR3R4)m—O—C(═O)—R10;
R2′ is selected from the group consisting of H, C1-C6 alkyl, and substituted C1-C6 alkyl;
each R3 and R4 are independently H, C1-C6 alkyl, substituted C1-C6 alkyl, aryl,

OG Complex Work Unit Chemistry
substituted aryl or
m is 1; and
R10 is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, monosaccharide, acylated monosaccharide, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.