GSK1360707F: Difference between revisions

{{short description|Chemical compound}}

{{notability|reason=Article text originally stated "This research chemical is still relatively new so no details are available for it yet", an apparent violation of the general notability guideline (WP:GNG)|date=August 2014}}

{{Drugbox

| verifiedrevid = 451604166

| IUPAC_name = (1''R'',6''S'')-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane

| image = GSK1360707F.svg

| width = 200

| tradename =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1013098-04-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9DE44WJ46X

| DrugBank =

| ChemSpiderID = 32739425

| smiles = COC[C@@]12C[C@@]1(CCNC2)c3ccc(c(c3)Cl)Cl

| StdInChI = 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

| StdInChIKey = ICXJGCSEMJXNQF-KBPBESRZSA-N

'''GSK1360707F''' is a potent and selective [[SNDRI|triple reuptake inhibitor]].<ref>{{cite journal | vauthors = Micheli F, Cavanni P, Andreotti D, Arban R, Benedetti R, Bertani B, Bettati M, Bettelini L, Bonanomi G, Braggio S, Carletti R, Checchia A, Corsi M, Fazzolari E, Fontana S, Marchioro C, Merlo-Pich E, Negri M, Oliosi B, Ratti E, Read KD, Roscic M, Sartori I, Spada S, Tedesco G, Tarsi L, Terreni S, Visentini F, Zocchi A, Zonzini L, Di Fabio R | display-authors = 6 | title = 6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: a new potent and selective triple reuptake inhibitor | journal = Journal of Medicinal Chemistry | volume = 53 | issue = 13 | pages = 4989–5001 | date = July 2010 | pmid = 20527970 | doi = 10.1021/jm100481d }}</ref> It is chemically related to [[amitifadine]] and [[NS-2359]] (GSK-372,475). Until recently,{{when|date=June 2021}} it was under development for the treatment of [[major depressive disorder]]; its development was put on hold for strategic reasons.{{cn|date=June 2021}}

[[Image:GSK1360707Fsynthesis.svg|700px|thumb|center|Synthesis of GSK1360707F<ref>{{Cite patent|country=WO|number=2008031772

|title=Azabicyclic compounds as inhibitors of monoamines reuptake

|pubdate=2008-03-20

|assign=[[GlaxoSmithKline|Glaxo Group Ltd.]]

|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

}}</ref>]]

#[[Tert-butyloxycarbonyl protecting group|BOC]] [[Protecting group]].

#Enolization and trapping with [[triflate]] group (cf [[Comins' reagent]]).

#Reduction (only 1&nbsp;mol eq. LAH because N-BOC can be reduced to N-Me)

#[[Williamson ether synthesis]] (c.f. NS patents & paxil).

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==Advanced Synthesis==

<ref>{{cite journal|doi=10.1021/op100139f | volume=14 | title=Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (−)-GSK1360707 | year=2010 | journal=Organic Process Research & Development | pages=912–917 | vauthors=Elitzin VI, Harvey KA, Kim H, Salmons M, Sharp MJ, Tabet EA, Toczko MA}}</ref><ref>{{cite journal|doi=10.1016/j.tetlet.2011.05.005 | volume=52 | title=Effects of nitrogen and alkene substitution on the PtCl2 catalyzed cycloisomerization of N-tethered 1,6-enyne precursors to the triple reuptake inhibitor GSK1360707 | year=2011 | journal=Tetrahedron Letters | pages=3518–3520 | vauthors=Elitzin V}}</ref><ref>{{cite journal | pmid = 21174473 | doi=10.1021/jo102098y | volume=76 | title=An enyne cycloisomerization approach to the triple reuptake inhibitor GSK1360707F | date=January 2011 | journal=J. Org. Chem. | pages=712–5 | vauthors=Deschamps NM, Elitzin VI, Liu B, Mitchell MB, Sharp MJ, Tabet EA}}</ref>

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== Transporter occupancy ==

GSK1360707F has recently (2013) been tested on [[baboons]] (''[[Papio anubis]]'') & humans for transporter occupancy using [[Positron emission tomography|PET]].<ref>{{cite journal | vauthors = Comley RA, Salinas CA, Slifstein M, Petrone M, Marzano C, Bennacef I, Shotbolt P, Van der Aart J, Neve M, Iavarone L, Gomeni R, Laruelle M, Gray FA, Gunn RN, Rabiner EA | display-authors = 6 | title = Monoamine transporter occupancy of a novel triple reuptake inhibitor in baboons and humans using positron emission tomography | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 346 | issue = 2 | pages = 311–7 | date = August 2013 | pmid = 23685546 | doi = 10.1124/jpet.112.202895 | s2cid = 2964324 }}</ref>

== See also ==

*[[NS-2359]]

== References ==

{{Serotonergics}}

[[Category:Serotonin–norepinephrine–dopamine reuptake inhibitors]]