GSK1360707F

Source: Wikipedia, the free encyclopedia.
GSK1360707F
Identifiers
  • (1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane
JSmol)
SMILES
  • COC[C@@]12C[C@@]1(CCNC2)c3ccc(c(c3)Cl)Cl
  • InChI=1S/C14H17Cl2NO/c1-18-9-13-7-14(13,4-5-17-8-13)10-2-3-11(15)12(16)6-10/h2-3,6,17H,4-5,7-9H2,1H3/t13-,14-/m0/s1
  • Key:ICXJGCSEMJXNQF-KBPBESRZSA-N
  (verify)

GSK1360707F is a potent and selective

triple reuptake inhibitor.[1] It is chemically related to amitifadine and NS-2359 (GSK-372,475). Until recently,[when?] it was under development for the treatment of major depressive disorder; its development was put on hold for strategic reasons.[citation needed
]

Synthesis

Synthesis of GSK1360707F[2]
  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

Papio anubis) & humans for transporter occupancy using PET.[3]

See also

References

  1. PMID 20527970
    .
  2. Glaxo Group Ltd.
     
  3. S2CID 2964324
    .
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