Journal
TETRAHEDRON
Volume 72, Issue 41, Pages 6334-6339Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.08.013
Keywords
Metabolite; Isolation; Structure determination; Synthesis; Selective alpha 1D adrenoceptor antagonist; 2-Amino-4-oxo-1,4-dihydropyridine-3-carboxamide
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5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride (TAK-259) is a novel, selective, and orally active alpha(1D) adrenoceptor antagonist with anti-urinary frequency effect. A metabolite (2) of TAK-259 was identified from monkey urine samples. To elucidate the structure of 2, extraction and purification of the metabolite from TAIL 259-treated monkey urine was conducted. Structural analysis of the purified compounds using NMR indicated the compound to be 2-amino-5-chloro-1-[5-chloro-2(methylsulfonyl)benzyl]-4-oxo-1,4-dihydropyridine-3-carboxamide (2a). An authentic sample of compound 2a was synthesized via regioselective alkylation of 4-methoxypyridin-2-amine. The biological activity of metabolite 2a was also evaluated, and the compound found not to possess affinity toward any known alpha(1) adrenoceptor subtype. (C) 2016 Elsevier Ltd. All rights reserved.
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