Hydantoin derivatives

Details Hydantoin derivatives Hydantoin derivatives

C - Chemistry, Metallurgy

07

D

260/305.3

C07D 491/107 (2006.01) C07D 491/10 (2006.01)

Patent

CA 1226866

HYDANTOIN DERIVATIVES Abstract The 8-deutero, 8-tritio and 8-halo-substituted derivatives of d-6-fluoro-spiro-[chroman-4,4'-imidazolidine] -2',5'-dione (sorbinil) have been prepared. These compounds all have the 4S-configuration and are of value in the field of medicinal chemistry as aldose reductose inhibitors for the control of chronic diabetic complications. More specifically, the novel compounds of this invention are selected from the group consisting of the 4S-isomers of asymmetric spiro-hydantoins of the formula: Image (I) and the base salts thereof with pharmacologically acceptable cations, wherein X is deuterium, tritium of halogen (fluorine, chlorine, bromine or iodine). The labeled 8-deutero and 8-tritio derivatives are useful in metabolism pharmacokinetic studies and in binding studies with the drug in animals and man. The 8-halo derivatives are useful as intermediates for the labeled forms of the drug, in addition to being potent aldose reductose inhibitors per se. Methods for the preparation of these compounds are pro- vided in some detail.

452774

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