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general/serotonin-norepinephrine-dopamine-reuptake-inhibitors

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GSK1360707F

Chemical compound

GSK1360707F

Chemical compound

GSK1360707F is a potent and selective triple reuptake inhibitor. It is chemically related to amitifadine and NS-2359 (GSK-372,475). Until recently, it was under development for the treatment of major depressive disorder; its development was put on hold for strategic reasons.

Synthesis

number=2008031772

|inventor1-last=Bertani|inventor1-first=Barbara |inventor2-last=Di Fabio|inventor2-first=Romano |inventor3-last=Micheli|inventor3-first=Fabrizio |inventor4-last=Giovanna Tedesco;Silvia Terreni

  1. BOC Protecting group.
  2. Enolization and trapping with triflate group (cf Comins' reagent).
  3. Suzuki reaction
  4. Reduction (only 1 mol eq. LAH because N-BOC can be reduced to N-Me)
  5. Trifluoroacetic acid (TFA) removal of protecting group.
  6. Simmons–Smith reaction cyclopropanation.
  7. Williamson ether synthesis (c.f. NS patents & paxil).

Advanced Synthesis

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Transporter occupancy

GSK1360707F has recently (2013) been tested on baboons (Papio anubis) & humans for transporter occupancy using PET.

References

References

  1. (July 2010). "6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: a new potent and selective triple reuptake inhibitor". Journal of Medicinal Chemistry.
  2. (2010). "Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (−)-GSK1360707". Organic Process Research & Development.
  3. (2011). "Effects of nitrogen and alkene substitution on the PtCl2 catalyzed cycloisomerization of N-tethered 1,6-enyne precursors to the triple reuptake inhibitor GSK1360707". Tetrahedron Letters.
  4. (January 2011). "An enyne cycloisomerization approach to the triple reuptake inhibitor GSK1360707F". J. Org. Chem..
  5. (August 2013). "Monoamine transporter occupancy of a novel triple reuptake inhibitor in baboons and humans using positron emission tomography". The Journal of Pharmacology and Experimental Therapeutics.
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serotonin–norepinephrine–dopamine-reuptake-inhibitors
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