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US 10,647,654 B2Granted
Glucose transport inhibitors and methods of using same
AssigneeOhio University
InventorsStephen Bergmeier, Xiaozhuo Chen
Life of this patent
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Abstract
Compounds that inhibit or reduce glucose transport and methods of using the compounds to treat cancer are provided herein.
Claims19
A compound according to formula (I), an enantiomer thereof, or a salt thereof:
- wherein X is selected from the group consisting of:
- halogen;
- hydrogen;
- —O-alkyl;
- hydroxyl (—OH);
- azido (—N3);
- cyano (—CN);
- nitro (—NO2);
- and methoxycarbonyl (—CO2Me);
- wherein R1 and R2 are independently selected from the group consisting of:
- and hydrogen;
- wherein R3 and R4 are independently selected from the group consisting of:
- hydrogen;
- halogen;
- alkyl;
- —O-alkyl;
- hydroxyl (—OH);
- cyano (—CN);
- and methoxycarbonyl (—CO2Me);
- wherein one of R1 and R2 is hydrogen;
- wherein R6 is selected from the group consisting of:
- hydrogen;
- alkyl;
- and aryl;
- wherein R5 is selected from the group consisting of:
- hydroxyl (—OH);
- —O-alkyl;
- —NH-alkyl;
- and —N-(alkyl)2;
- wherein R7 is selected from the group consisting of:
- alkyl;
- aryl;
- and heteroaryl and
- wherein R8 is selected from the group consisting of:
- alkyl;
- aryl;
- and heteroaryl.
34 more elements
A compound according to formula (II), an enantiomer thereof, or a salt thereof:
- wherein X is selected from the group consisting of:
- hydrogen;
- halogen;
- —O-alkyl;
- hydroxyl (—OH);
- cyano (—CN);
- azido (—N3);
- nitro (—NO2);
- and methoxycarbonyl (—CO2Me);
- wherein R1 and R2 are independently selected from the group consisting of:
- hydrogen;
- hydroxymethyl (—CH2OH);
- and methoxycarbonyl (—CO2Me);
- wherein one of R1 and R2 is hydrogen;
- wherein when R1 is hydrogen, R3 is hydroxyl (—OH) and R4 is —O-alkyl;
- and
- wherein when R2 is hydrogen, R3 is —O-alkyl and R4 is hydroxyl (—OH).
14 more elements
A method of treating lung cancer in a subject comprising:
- administering to a subject in need of such treatment a therapeutically effective amount of a compound according to formula (I), an enantiomer thereof, or a salt thereof:
- wherein X is selected from the group consisting of:
- halogen;
- hydrogen;
- —O-alkyl;
- hydroxyl (—OH);
- azido (—N3);
- cyano (—CN);
- nitro (—NO2);
- and methoxycarbonyl (—CO2Me);
- wherein R1 and R2 are independently selected from the group consisting of:
- and hydrogen;
- wherein R3 and R4 are independently selected from the group consisting of:
- hydrogen;
- halogen;
- alkyl;
- —O-alkyl;
- hydroxyl (—OH);
- cyano (—CN);
- and methoxycarbonyl (—CO2Me);
- wherein one of R1 and R2 is hydrogen;
- wherein R6 is selected from the group consisting of:
- hydrogen;
- alkyl;
- and aryl;
- wherein R5 is selected from the group consisting of:
- hydroxyl (—OH);
- —O-alkyl;
- —NH-alkyl;
- and —N-(alkyl)2;
- wherein R7 is selected from the group consisting of:
- alkyl;
- aryl;
- and heteroaryl and
- wherein R8 is selected from the group consisting of:
- alkyl;
- aryl;
- and heteroaryl.
35 more elements
A method of treating lung cancer in a subject comprising:
- administering to a subject in need of such treatment a therapeutically effective amount of a compound according to formula (II), an enantiomer thereof, or a salt thereof:
- wherein X is selected from the group consisting of:
- hydrogen;
- halogen;
- —O-alkyl;
- hydroxyl (—OH);
- cyano (—CN);
- azido (—N3);
- nitro (—NO2);
- and methoxycarbonyl (—CO2Me);
- wherein R1 and R2 are independently selected from the group consisting of:
- hydrogen;
- hydroxymethyl (—CH2OH);
- and methoxycarbonyl (—CO2Me);
- wherein one of R1 and R2 is hydrogen;
- wherein when R1 is hydrogen, R3 is hydroxyl (—OH) and R4 is —O-alkyl;
- and
- wherein when R2 is hydrogen, R3 is —O-alkyl and R4 is hydroxyl (—OH).
15 more elements
Dependencies are inferred from the claim text.