GSK1360707F

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GSK1360707F
GSK1360707F.svg
Systematic (IUPAC) name
(1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane
Identifiers
PubChem CID: 24802841
Chemical data
Formula C14H17Cl2NO
Molecular mass 286.196 g/mol
  • COCC13CC1(CCNC3)c(cc2Cl)ccc2Cl
  (verify)

GSK1360707F is a new and potent selective triple reuptake inhibitor.[1] structurally related to amitifadine and NS-2359 (GSK-372,475).

Synthesis

Synthesis of GSK1360707F: WO 2008031772 
  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).


PET

GSK1360707F has recently (2013) been tested on baboons (Papio anubis) & humans for transporter occupancy.[2]

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until recently was under development for the treatment of major depressive disorder; its development was put on hold for strategic reasons.

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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