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Hydroxymethylketones as Pro‐drugs

The hydroxymethylketone group (-CO-CH,OH) was investigated as an isostere or pro-drug replacement for the carboxyl radical (-COOH) in a series of well-known therapeutic acids. Conversion of the HMK group to the acid could occur by an oxidative decarboxylation analogous to some carbohydrate pathways. Advantages of such a pro-drug might accrue from the neutral character of the H M K group concerning oral absorption, transport mechanisms, and overall pharmacokinetics when compared to the parent acid. The HMKs shown in TABLE 1 were prepared by conventional synthetic routes from the parent acids. The resulting products are stable, crystalline solids that were characterized by the usual spectroscopic and elemental analyses. In some cases the