Spiro oxazolidinedione aldose reductase inhibitors

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Abstract
Spiro oxazolidinediones derived from 5- and 6-membered ring aralkyl ketones are potent aldose reductase inhibitors in vitro and in vivo [in rats]. Their novel and general synthesis was devised with .alpha.-hydroxyimidates and 4-alkoxy-2-oxo-3-oxazolines as key intermediates, since traditional synthetic routes through .alpha.-hydroxy amides usually led to .alpha.,.beta.-unsaturated amides. Resolution with cinchonidine afforded optically active spiro oxazolidinediones. Optimum biological activity resided in (4S)-6-chlorospiro[4H-2,3-dihydrobenzopyran-4,5''-oxazolidine]-2'',4''-dione and its 6,8-dichloro congener. [These drugs may be useful in preventing some of the complications of diabetes.].