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Synthesis of specifically deuterated adenosine A 1 antagonist: BG9928
Author(s) -
Conlon Patrick R.,
Kiesman William F.
Publication year - 2007
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1237
Subject(s) - chemistry , bicyclic molecule , antagonist , in vivo , pyrimidine , octane , adenosine , stereochemistry , deuterium , biochemistry , organic chemistry , receptor , physics , microbiology and biotechnology , quantum mechanics , biology
BG9928, a high affinity adenosine A 1 antagonist, is currently in Phase II clinical trials for the treatment of congestive heart failure. A deuterium‐labeled version of the molecule was synthesized and used as a standard for in vivo pharmacokinetic and in vitro metabolism studies. The labeled form of 3‐[4‐(2,6‐dioxo‐1,3‐dipropyl‐2,3,6,7‐tetrahydro‐1 H ‐purin‐8‐yl)‐bicyclo[2.2.2]oct‐1‐yl]‐propionic acid (BG9928) was obtained in a convergent manner by joining two major building blocks: the specifically labeled heterocycle 5,6‐diamino‐1,3‐dipropyl‐1 H ‐pyrimidine‐2,4‐dione ( 4 ) and the hemiester 4‐(2‐methoxycarbonyl‐ethyl)‐bicyclo[2.2.2]octane‐1‐carboxylic acid ( 10 ). Copyright © 2007 John Wiley & Sons, Ltd.