US 10,376,502 B2
Alkylated imino sugars exhibiting glucosidase inhibition and their method of use
Yanming Du, Cheshire, CT (US); Xiaodong Xu, Doylestown, PA (US); Hong Ye, Lansdale, PA (US); Jinhong Chang, Chalfont, PA (US); and Timothy M. Block, Doylestown, PA (US)
Assigned to Institute for Hepatitis and Virus Research
Filed by Baruch S. Blumberg Institute, Doylestown, PA (US); and Drexel University, Philadelphia, PA (US)
Filed on Jul. 30, 2015, as Appl. No. 14/813,931.
Application 14/813,931 is a division of application No. 14/388,175, granted, now 9,126,937, previously published as PCT/US2013/034033, filed on Mar. 27, 2013.
Claims priority of provisional application 61/616,753, filed on Mar. 28, 2012.
Prior Publication US 2015/0335630 A1, Nov. 26, 2015
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/45 (2006.01); A61K 31/4015 (2006.01); C07F 9/59 (2006.01); C07D 207/12 (2006.01); C07D 211/44 (2006.01); C07D 211/46 (2006.01); C07D 413/06 (2006.01)
CPC A61K 31/45 (2013.01) [A61K 31/4015 (2013.01); C07D 207/12 (2013.01); C07D 211/44 (2013.01); C07D 211/46 (2013.01); C07D 413/06 (2013.01); C07F 9/59 (2013.01)] 5 Claims
 
1. A method of treating a flavivirus infection said method comprising administering to a subject an effective amount of at least one compound having formula (III):

OG Complex Work Unit Drawing
including hydrates, solvates, pharmaceutically acceptable salts, and complexes thereof, wherein:
R1 at each occurrence is independently selected from the group consisting of hydrogen and COR4;
R5 is selected from a group consisting of optionally substituted C1-6 alkyl, optionally substituted branched C1-6 alkyl, optionally substituted cyclic C3-8 alkyl, optionally substituted C5-C10 bicylcoalkyl, optionally substituted aryl which may be substituted by 0-5 moieties, OR5, and NHR6;
R3 is selected from a group consisting of optionally substituted C1-6 alkyl, optionally substituted branched C1-6 alkyl, optionally substituted cyclic C3-8 alkyl, 1-adamantyl, 2-adamantyl, optionally substituted C5-C10 bicylcoalkyl, and optionally substituted aryl which may be substituted by 0-5 moieties;
R3 and R5 are taken together with the atom to which they are bound to form an optionally substituted ring having 5 ring atoms;
R3 and R5 are taken together with the atom to which they are bound to form an optibonally substituted ring having 5 ring atoms;
R3and R5 are taken together with the atom to which they are bound to form

OG Complex Work Unit Drawing
R3 and R5 are taken together with the atom to which they are bound to form

OG Complex Work Unit Drawing
R4 at each occurrence is independently selected from the group consisting of optionally substituted C1-6 alkyl and optionally substituted branched C1-6 alkyl;
R5 is selected from a group consisting of an optionally substituted C1-6 alkyl, optionally substituted branched C1-6 alkyl, optionally substituted cyclic C3-8 alkyl, optionally substituted C5 -C10bicyicoalkyl, optionally substituted aryl which may be substituted by 0-5 moieties;
R6is selected from a group consisting of hydrogen, an optionally substituted C1-6 alkyl, optionally substituted branched C1-6 alkyl, optionally substituted cyclic C3-8alkyl, optionally substituted C5-10 bicylcoalkyl, optionally substituted aryl which may be substituted by 0-5 moieties; and
R7a, R7b,R7c and R7d are each selected from a group consisting of hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted branched C1-6 alkyl, and optionally substituted C1-6 alkoxy.