Premium
Synthesis of 3 H‐ and 14 C‐cisapride
Author(s) -
Janssen C. C. M.,
Lenoir H. H. C.,
Thijssen J. J. A.,
Knaeps A. A.,
Heykants J. J. P.
Publication year - 1987
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.2580241212
Subject(s) - cisapride , chemistry , benzamide , moiety , piperidine , stereochemistry , reductive amination , chemical synthesis , carboxamide , pharmacology , organic chemistry , biochemistry , in vitro , medicine , catalysis
Cisapride, (±)‐ cis ‐4‐amino‐5‐chloro‐ N [1‐[3(4‐fluorophenoxy)propyl]‐3‐methoxy‐4‐piperidinyl]‐2‐methoxybenzamide, is a new gastrokinetic drug with a potent stimulating effect on the gastrointestinal motor activity. Metabolic studies required the synthesis of cisapride labelled at one of the three major moieties. Hence, cisapride was tritiated either in the fluorophenyl moiety by means of reductive dehalogenation, or via reductive amination in the piperidine ring. 14 C‐Cisapride was labelled in the benzamide function. The title compounds were obtained at a specific activity of 17.0 Ci/mmol, 59.8 mCi/mmol and 7.8 mCi/mmol, respectively and with HPLC purities of > 98 %.