Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate.
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-trimethylbicyclo[2.2.1]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.
Ladányi
L
L
Egis Pharmaceuticals Ltd., Budapest, Hungary.
Sztruhár
I
I
Budai
Z
Z
Lukács
G
G
Mezei
T
T
Argay
G
G
Kálmán
A
A
Simig
G
G
D014151:Anti-Anxiety Agents / Q000737:chemistry* / Q000302:isolation & purification; D001892:Camphanes / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D014151:Anti-Anxiety Agents; D001892:Camphanes; C060555:deramciclane