Chemical and Pharmaceutical Bulletin p. 1799 - 1807 (1992)
Update date:2022-08-04
Topics:
Satoh
Okumura
Shiokawa
Nilvadipine (I), isopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridi ne-5-carboxylate, has a unique 1,4-dihydropyridine structure in that the substituents at all five positions of the nucleus differ from one another. It is an exellent calcium antagonist drug in terms of its potency, its duration of action and its selectivity in the blood vascular system. During the development of I, some metabolites were isolated from the urine and bile of both rats and dogs after oral administration. With data obtained from the metabolism of known 1,4-dihydropyridines at hand, we proposed the synthesis of a series of compounds (1-11) for comparison with the metabolites isolated from I as a method for structure determination. Indeed, of the compounds synthesized five of them (3-7) were found to coincide with the metabolites from both rat and dog urine and bile isolates.
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