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Effective resolution of racemic pirlindole at the preparative scale

✍ Scribed by Pascal De Tullio; Attilio Ceccato; Jean-François Liégeois; Bernard Pirotte; Apostolos Felikidis; Monique Stachow; Philippe Hubert; Jacques Crommen; Joseph Géczy; Jacques Delarge

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
122 KB
Volume
11
Category
Article
ISSN
0899-0042

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✦ Synopsis

Pirlindole, a racemic antidepressant drug, was recently resolved using the derivatization method coupled with preparative HPLC. In order to improve this technique, the use of amino acid derivatives as chiral derivatizing agents (CDA) was investigated. Among different residues, the (L)-phenylalanine methyl ester was found to be very effective to separate pirlindole enantiomers using a medium pressure liquid chromatographic (MPLC) method. This procedure is better adapted to preparative application than HPLC. Thus, several grams of the pirlindole antipodes were isolated and characterized. These two enantiomers permitted the study of the stereochemical influence at the pharmacological level.

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