Therapeutic monosaccharide-based inhibitors of hexokinase and glucokinase for parasitic diseases, along with methods of their formation and use

Patent metadata

Field	Value
Publication number	US-9956240-B2
Application number	US-201514880098-A
Country	US
Kind code	B2
Filing date	Oct 9, 2015
Priority date	Nov 21, 2014
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Methods for treating a mammal that is infected by a parasitic organism are provided, along with pharmaceutical compositions and compounds. The method includes administering to the mammal the pharmaceutical composition of FIG. 1 , where: R 1 , R 2 , R 3 , and R 4 comprises, independently, H, OH, NH 2 , SH, a halogen, or an organic group or a derivative thereof; X 1 is O, NH, CH 2 , or S; m is 0 or 1; X 2 comprises an organic linkage, such as CH 2 ; n is an integer from 0 to 10; and R 5 comprises an aromatic organic group.

First claim

What is claimed:

1. A method of treating a mammal that is infected by a parasitic organism, the method comprising:
administering to the mammal a pharmaceutical compound having the structure

where:
R 1 , R 2 , R 3 , and R 4 comprises, independently, H, OH, NH 2 , SH, or an organic group;
X 1 is O, NH, CH 2 , or S;
m is 1;
X 2 comprises an organic linkage;
n is an integer from 0 to 10; and
R 5 comprises an aromatic organic group.

2. The method as in claim 1 , wherein R 1 is a hydroxymethyl group.

3. The method as in claim 1 , wherein R 2 , R 3 , and R 4 are each a hydroxyl group.

4. The method as in claim 1 , wherein X 1 is O.

5. The method as in claim 1 , wherein X 2 is CH 2 .

6. The method as in claim 1 , wherein n is 0.

7. The method as claim 1 , wherein R 5 comprises a benzene group.

8. The method as in claim 1 , wherein R 5 comprises a phenol group.

9. The method as in claim 1 , wherein R 5 comprises a benzothiophene group.

10. The method as in claim 9 , wherein R 5 is a benzothiophene group with a sulfonyl group.

11. The method as in claim 1 , wherein the pharmaceutical compound has the structure

12. The method as in claim 1 , wherein the pharmaceutical compound has the structure

13. A method of treating a mammal that is infected by a parasitic organism, the method comprising administering to the mammal a pharmaceutical compound having the structure

14. A compound having the structure

15. A compound having the structure

Assignees

• Univ South Carolina

Inventors

• D'Antonio Edward L
• D'Antonio Jennifer

Classifications

• C07H5/06

  Aminosugars · CPC title

• C07H13/12

  by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid · CPC title

• C07H13/08

  having the esterifying carboxyl radicals directly attached to carbocyclic rings · CPC title

• A61K31/7008 Primary

  Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine · CPC title

• C07H13/04

  having the esterifying carboxyl radicals attached to acyclic carbon atoms · CPC title