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Semipreparative chiral supercritical fluid chromatography in the fractionation of lansoprazole and two related antiulcer drugs enantiomers
Author(s) -
Toribio Laura,
del Nozal María J.,
Bernal Yagüe L.,
Alonso Cristina,
Jiménez Juan J.
Publication year - 2008
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200700457
Subject(s) - lansoprazole , chemistry , enantiomer , rabeprazole , chromatography , supercritical fluid chromatography , elution , supercritical fluid , resolution (logic) , pantoprazole , high performance liquid chromatography , organic chemistry , proton pump inhibitor , pharmacology , omeprazole , medicine , biochemistry , artificial intelligence , computer science
The semipreparative chiral separation of lansoprazole and two related compounds (pantoprazole and rabeprazole) using supercritical fluid chromatography (SFC) is presented in this work. Different loads were evaluated in order to obtain high enantiomeric purities and production rates. The volumes injected were 1, 2 and 4 mL. The concentrations of the racemic mixtures were 3 and 6 g/L for lansoprazole and 1.5 g/L for pantoprazole and rabeprazole. In all the cases, the recoveries, for a purity higher than 99.9%, were better for the second eluted enantiomer than for the first one. This fact conditioned the production rate of the first eluted enantiomer that, considering a fixed purity, was always lower than that obtained for the other one. In the case of lansoprazole it was possible to obtain 0.025 and 0.090 mg/min of the first and second eluted enantiomer, respectively, with an enantiomeric purity of 99.9%. For rabeprazole enantiomers 0.037 and 0.062 mg/min, and in the case of pantoprazole the results were better (0.062 and 0.122 mg/min) due to the higher resolution.