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Synthesis of [ 14 C]‐labelled repinotan hydrochloride and its major metabolite M‐6
Author(s) -
Seidel D.,
Conrad M.,
Schoof Y.,
SchoheLoop R.
Publication year - 2002
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.629
Subject(s) - chemistry , moiety , acetophenone , hydrochloride , metabolite , phenol , yield (engineering) , stereochemistry , ring (chemistry) , carbon 14 , chemical synthesis , medicinal chemistry , organic chemistry , catalysis , in vitro , biochemistry , materials science , physics , quantum mechanics , metallurgy
For studies of pharmacokinetics and drug metabolism of the new 5‐HT 1A agonist repinotan, the 14 C‐labelled version was synthesized. Starting from [U‐ 14 C]phenol, a 10‐step synthesis led to 457 mg (1.58 GBq) of [U‐ 14 C]repinotan hydrochloride, labelled uniformly in the aromatic ring of the chromane moiety. For a study in man, a mono‐carbon‐14 labelled substance was required. Therefore a 7‐step synthesis was performed starting from [carbonyl‐ 14 C]2‐hydroxy‐acetophenone. The yield was 106 mg (0.396 GBq) of [4‐chromane‐ 14 C]repinotan hydrochloride. The carbon‐14 labelled major metabolite, hydroxylated in the 6‐position of the chromane moiety, was synthesised as reference compound. Copyright © 2002 John Wiley & Sons, Ltd.