Alkylated imino sugars exhibiting glucosidase inhibition and their method of use

Patent metadata

Field	Value
Publication number	US-10376502-B2
Application number	US-201514813931-A
Country	US
Kind code	B2
Filing date	Jul 30, 2015
Priority date	Mar 28, 2012
Publication date	Aug 13, 2019
Grant date	Aug 13, 2019

Abstract

Pharmaceutical compositions of the invention comprise alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include Viral hemorrhagic fevers, and any other diseases involving glucosidase activity.

First claim

What is claimed is:

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):

including hydrates, solvates, pharmaceutically acceptable salts, and complexes thereof, wherein:
R 1 at each occurrence is independently selected from the group consisting of hydrogen and COR 4 ;
R 5 is selected from a group consisting of optionally substituted C 1-6 alkyl, optionally substituted branched C 1-6 alkyl, optionally substituted cyclic C 3-8 alkyl, optionally substituted C 5 -C 10 bicylcoalkyl, optionally substituted aryl which may be substituted by 0-5 moieties, OR 5 , and NHR 6 ;
R 3 is selected from a group consisting of optionally substituted C 1-6 alkyl, optionally substituted branched C 1-6 alkyl, optionally substituted cyclic C 3-8 alkyl, 1-adamantyl, 2-adamantyl, optionally substituted C 5 -C 10 bicylcoalkyl, and optionally substituted aryl which may be substituted by 0-5 moieties;
R 3 and R 5 are taken together with the atom to which they are bound to form an optionally substituted ring having 5 ring atoms;
R 3 and R 5 are taken together with the atom to which they are bound to form an optibonally substituted ring having 5 ring atoms;
R 3 and R 5 are taken together with the atom to which they are bound to form

R 3 and R 5 are taken together with the atom to which they are bound to form

R 4 at each occurrence is independently selected from the group consisting of optionally substituted C 1-6 alkyl and optionally substituted branched C 1-6 alkyl;
R 5 is selected from a group consisting of an optionally substituted C 1-6 alkyl, optionally substituted branched C 1-6 alkyl, optionally substituted cyclic C 3-8 alkyl, optionally substituted C 5 -C 10 bicyicoalkyl, optionally substituted aryl which may be substituted by 0-5 moieties;
R 6 is selected from a group consisting of hydrogen, an optionally substituted C 1-6 alkyl, optionally substituted branched C 1-6 alkyl, optionally substituted cyclic C 3-8 alkyl, optionally substituted C 5-10 bicylcoalkyl, optionally substituted aryl which may be substituted by 0-5 moieties; and
R 7a , R 7b ,R 7c and R 7d are each selected from a group consisting of hydrogen, halogen, optionally substituted C 1-6 alkyl, optionally substituted branched C 1-6 alkyl, and optionally substituted C 1-6 alkoxy.

2. The method of claim 1 , wherein the at least one compound is administered in a composition further comprising at least one excipient.

3. The method of claim 1 , wherein the flavivirus is bovine viral diarrhea virus (BVDV).

4. The method of claim 3 , wherein the flavivirus is dengue fever virus (DV).

5. The method of claim 1 , wherein the flavivirus is West Nile virus (WNV).

Assignees

• Baruch S Blumberg Inst
• Univ Drexel
• Institute For Hepatitis And Virus Res

Inventors

• Du Yanming
• Xu Xiaodong
• Ye Hong
• Chang Jinhong
• Block Timothy M

Classifications

• C07D207/12

  Oxygen or sulfur atoms · CPC title

• C07D211/44

  attached in position 4 · CPC title

• A61K31/4015

  having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide · CPC title

• C07D211/46

  having a hydrogen atom as the second substituent in position 4 · CPC title

• C07F9/59

  Hydrogenated pyridine rings · CPC title