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- W2053818269 abstract "Four acetoxyethoxycarbonyl derivatives of closely related primary and secondary amines were synthesized as model prodrugs. The degradation kinetics of these compounds were studied in aqueous solutions as a function of pH and temperature to determine their stability and to assess their suitability as potential prodrugs of amines. At pH </ 4, the model prodrugs of primary amines degraded by specific acid-catalysed ester hydrolysis. At pH ⩾ 5, the model prodrugs of primary amines degraded by parallel pathways involving hydroxide ion-catalyzed ester hydrolysis and intramolecular acyl transfer. The model prodrug derived from a secondary amine appeared to degrade by ester hydrolysis only, over the entire pH range studied (1 ⩽ pH ⩽ 9) and thus appeared to be a very promising prodrug form. The log rate constant vs pH profiles for all 4 compounds were very similar indicating that the hydrolytic rates were determined primarily by the nature of the common ester functional group. The amine substituents exhibited little influence on hydrolytic rates. Overall, the stability of these model prodrugs was adequate to allow them to be considered for pharmaceutical formulation either as solids or as solutions." @default.
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- W2053818269 date "1987-12-01" @default.
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- W2053818269 title "N-(Acyloxyalkoxycarbonyl) derivatives as potential prodrugs of amines. I. kinetics and mechanism of degradation in aqueous solutions" @default.
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- W2053818269 doi "https://doi.org/10.1016/0378-5173(87)90173-6" @default.
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