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US 9,309,208 B2Granted
Methods of making and using thioxothiazolidine and rhodanine derivatives as HIV-1 and JSP-1 inhibitors
AssigneesSouthern Methodist University, The Johns Hopkins University
InventorsEdward R. Biehl, Sukanta Kamila, Ted M. Dawson
Life of this patent
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Abstract
The present invention provides methods of making and using 5-(2-(indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one derivatives having HIV-1 or JSP-1 inhibitory activity.
Claims2
A thioxothiazolidin compound of formula (I):
- wherein R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halo, alkyl, aryl, hydroxyl, alkoxyl, aryloxyl, aralkoxyl, cyano, nitro, alkylcarbamido, arylcarbamido, dialkylcarbamido, diarylcarbamido, alkylarylcarbamido, alkylthiocarbamido, arylthiocarbamido, dialkylthiocarbamido, diarylthiocarbamido, alkylarylthiocarbamidb, amino, alkylamino, arylamino, dialkylamino, diarylamino, arylalkylamino, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, arylalkylamino-carbonyl, alkylcarbonyloxy, arylcarbonyloxy, carboxyl, alkoxycarbonyl, aryloxycarbonyl, sulfo, alkylsulfonylamido, arylsulfonylamido, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, arylsulfinyl and heteroaryl.
A thioxothiazolidin compound is selected from (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-2-thioxo-3-p-tolylthiazolidin-4-one;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-(3,4-dimethylphenyl)-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(5-methoxy-1H-indol-3-yl)-2-oxoethylidene)-2-thioxo-3-p-tolylthiazolidin-4-one;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-(4-methoxyphenyl)-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(5-methoxy-1H-indol-3-yl)-2-oxoethylidene)-3-(4-methoxyphenyl)-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(5-methoxy-1H-indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one;
- (Z)-4-(5-(2-(5-methoxy-1H-indol-3-yl)-2-oxoethylidene)-4-oxo-2-thioxothiazolidin-3-yl)benzonitrile;
- (Z)-4-(5-(2-(1H-indol-3-yl)-2-oxoethylidene)-4-oxo-2-thioxothiazolidin-3-yl)benzonitrile;
- (Z)-5-(2-(5-chloro-1H-indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-(benzo[d]thiazol-6-yl)-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-(benzo[d]thiazol-6-yl)-2-thioxothiazolidin-4-one;
- (Z)-3-(2-(3-(benzo[d]thiazol-6-yl)-4-oxo-2-thioxothiazolidin-5-ylidene)acetyl)-1H-indole-5-carbonitrile;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-(3,5-dibromo-4-hydroxyphenyl)-2-thioxothiazolidin-4-one;
- (Z)-5-(2-(1H-indol-3-yl)-2-oxoethylidene)-3-(3,5-dichloro-4-hydroxyphenyl)-2-thioxothiazolidin-4-one;
- (Z)-3-(3,5-dibromo-4-hydroxyphenyl)-5-(2-(5-methoxy-1H-indol-3-yl)-2-oxoethylidene)-2-thioxothiazolidin-4-one;
- or (Z)-3-(3,5-dichloro-4-hydroxyphenyl)-5-(2-(5-methoxy-1H-indol-3-yl)-2-oxoethylidene)-2-thioxothiazolidin-4-one.
13 more elements
Dependencies are inferred from the claim text.