Synfacts 2008(3): 0222-0222  
DOI: 10.1055/s-2008-1042653
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Dual Serotonin Reuptake Inhibitor/Histamine H3 Antagonist

Contributor(s): Philip Kocienski
X. Deng*, J. T. Liang, J. Liu, H. McAllister, C. Schubert, N. S. Mani
Johnson & Johnson Pharmaceutical Research and Development, San Diego, USA
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21. Februar 2008 (online)


A common side effect to the use of serotonin reuptake inhibitors as antidepressants is the persistance of cognitive impairment and fatigue, even as mood improves. Histamine H3 inhibitors improve cognition and increase wakefulness. The target molecule inhibits both serotonin reuptake and histamine H3 thereby offering an imroved treatment for depression. A salient feature of the synthesis is the rare use of a Friedel-Crafts alkylation of a benzylic alcohol to generate the di­arylmethane motif.