7'-Trifluoromethyl-spiro[imidazolidine-4,3'-indoline]-2,2',5-triones as aldose reductase inhibitors
AssigneeImperial Chemical Industries PLC
InventorsDavid R. Brittain, David Brown, Robin Wood
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Abstract
The invention concerns novel trifluoromethyl derivatives of 1'-halogenobenzyl-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (I), their pharmaceutically acceptable salts, and non-toxic, biodegradable precursors thereof. The derivatives are potent inhibitors of the enzyme aldose reductase and are useful in treating or preventing certain complications of diabetes. The invention also provides pharmaceutical compositions and processes for the manufacture of the derivatives.
Claims9
A compound selected from the group consisting of trifluoromethyl spiro[imidazolidine-4,3'-indoline]-2,2',5-trione of the formula I
- wherein the trifluoromethyl substituent in benzene ring A is located at the 7' position;
- and benzene ring B is dihalogenophenyl wherein Ra is fluoro or chloro, Rb is hydrogen and Rc is chloro, bromo or iodo;
- or Ra is hydrogen and Rb and Rc are independently chloro or bromo;
- and a salt with a base affording a pharmaceutically acceptable cation.
A compound selected from the group consisting of trifluoromethyl spiro[imidazolidine-4,3'-indoline]-2,2',5-trione of the formula III ##STR2## wherein benzene ring B is selected from 4-bromo-2-chloro-, 4-bromo-2-fluoro- and 2-fluoro-4-iodo-phenyl;
- Re is trifluoromethyl and Rd is hydrogen;
- and a salt with a base affording a pharmaceutically acceptable cation.
A compound selected from 1'-(4-bromo-2-fluorobenzyl)-7'-trifluoromethyl-spiro[imidazolidine-4,3'-in doline]-2,2',5-trione and a salt thereof with a base affording a pharmaceutically acceptable cation.
A compound selected from the group consisting of (d)-1'-(4-bromo-2-fluorobenzyl)-7'-trifluoromethyl-spiro[imidazolidine-4,3 '-indoline]-2,2',5-trione and a salt thereof with a base affording a pharmaceutically acceptable cation.
Dependencies are inferred from the claim text.