GSK1360707F

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

 * 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).

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