Synthesis of enantiopure antiobesity drug lorcaserin

Ivana Gazic Smilovic; Jerome Cluzeau; Frank Richter; Sven Nerdinger; Erwin Schreiner; Gerhard Laus; Herwig Schottenberger

doi:10.1016/j.bmc.2018.02.038

Synthesis of enantiopure antiobesity drug lorcaserin

Bioorg Med Chem. 2018 May 15;26(9):2686-2690. doi: 10.1016/j.bmc.2018.02.038. Epub 2018 Feb 21.

Authors

Ivana Gazic Smilovic¹, Jerome Cluzeau¹, Frank Richter², Sven Nerdinger³, Erwin Schreiner², Gerhard Laus⁴, Herwig Schottenberger⁴

Affiliations

¹ Lek Pharmaceuticals DD, Kolodvorska 27, 1234 Mengeš, Slovenia.
² Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria.
³ Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria. Electronic address: sven.nerdinger@sandoz.com.
⁴ Leopold-Franzens University, Innrain 80-82, 6020 Innsbruck, Austria.

PMID: 29496415
DOI: 10.1016/j.bmc.2018.02.038

Abstract

Acylation of enantiomerically pure (R)-2-(3-chlorophenyl)propan-1-amine using chloroacetyl chloride, followed by borane reduction and aluminum chloride catalyzed cyclization yielded enantiopure lorcaserin.

Keywords: 5-HT agonist; Enantiopure; Lorcaserin; Obesity.

MeSH terms

Anti-Obesity Agents / chemical synthesis*
Anti-Obesity Agents / chemistry
Benzazepines / chemical synthesis*
Benzazepines / chemistry
Chemistry Techniques, Synthetic / methods
Cyclization
Stereoisomerism

Substances

Anti-Obesity Agents
Benzazepines
lorcaserin