Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate. |
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Authors: | L Ladányi I Sztruhár Z Budai G Lukács T Mezei G Argay A Kálmán G Simig |
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Institution: | Egis Pharmaceuticals Ltd., Budapest, Hungary. |
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Abstract: | The synthesis, stereostructure, and enantiomeric separation by chromatography of a new, chiral anxiolytic agent, deramciclane fumarate (2, (-)-1R,2S,4R]-2-(2-dimethylaminoethoxy)-2-phenyl-1,7, 7-trimethylbicyclo2.2.1]heptane fumarate, EGIS-3886), is described. The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X-ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 x 4.6 mm; 10 microm) and hexane-ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99. 9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed. |
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