GSK1360707F

_Hello all readers, today we are going to talk about GSK1360707F. This is a very broad and relevant topic today, covering a wide variety of aspects ranging from _aspect1 to _aspect2. GSK1360707F is a very influential figure in the _tema1 field and his legacy has left its mark on _tema2. Throughout history, GSK1360707F has been the object of controversy and admiration, generating debates and reflections that have transcended time. Therefore, it is important to delve into its origins, impact and meaning, to better understand its importance in _tema3 and _tema4. In this article we will explore the different nuances of GSK1360707F and how it has marked a before and after in _tema5. Stay tuned for the following lines to discover more about this exciting topic._

Chemical compound

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Pharmaceutical compound

GSK1360707F

Identifiers
IUPAC name (1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicycloheptane
CAS Number	1013098-04-8 Y
PubChem CID	24802841
ChemSpider	32739425
UNII	9DE44WJ46X
CompTox Dashboard (EPA)	DTXSID601029661
Chemical and physical data
Formula	C14H17Cl2NO
Molar mass	286.20 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC12C1(CCNC2)c3ccc(c(c3)Cl)Cl
InChI 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
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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

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.^[3]

See also

• NS-2359

References

1. ^ Micheli F, Cavanni P, Andreotti D, Arban R, Benedetti R, Bertani B, et al. (July 2010). "6-(3,4-dichlorophenyl)-1--3-azabicycloheptane: a new potent and selective triple reuptake inhibitor". Journal of Medicinal Chemistry. 53 (13): 4989–5001. doi:10.1021/jm100481d. PMID 20527970.
2. ^ WO 2008031772, Bertani, Barbara; Di Fabio, Romano & Micheli, Fabrizio et al., "Azabicyclic compounds as inhibitors of monoamines reuptake", published 2008-03-20, assigned to Glaxo Group Ltd. 
3. ^ Comley RA, Salinas CA, Slifstein M, Petrone M, Marzano C, Bennacef I, et al. (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. 346 (2): 311–7. doi:10.1124/jpet.112.202895. PMID 23685546. S2CID 2964324.