Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic

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Abstract
The synthesis of an analogue of amiloride in which the acylguanidine moiety has been replaced by a 1,2,4-oxadiazol-3-amine unit is described. This substance (3, CGS 4270) exhibited a diuretic profile similar to that of amiloride when evaluated in the rat and the dog. In the rat, combination with hydrochlorothiazide increased diuresis and saluresis and returned potassium levels to control values. A series of 5-aryl-1,2,4-oxadiazol-3-amines not directly related to amiloride was prepared, but these substances had no diuretic activity.

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