Edge Rewrite
restyle Source code View original
// HTMLRewriter · presentation

This page was redesigned at the edge.

Cloudflare fetched the original article and streamed it through HTMLRewriter to apply an entirely new visual system without rebuilding the source page.

Jump to content

Sunepitron

From Wikipedia, the free encyclopedia
Sunepitron
Clinical data
Other namesCP-93,393
Routes of
administration		Oral
ATC code
  • none
Identifiers
  • 1-{[2-(pyrimidin-2-yl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methyl}pyrrolidine-2,5-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC17H23N5O2
Molar mass329.404 g·mol−1
3D model (JSmol)
  • O=C1N(C(=O)CC1)CC4CCC3N(CCN(c2ncccn2)C3)C4

Sunepitron (developmental code name CP-93,393) is a combined 5-HT1A receptor agonist and α2-adrenergic receptor antagonist.[1][2] It was previously under development by Pfizer for the treatment of depression and anxiety.[3] It made it to phase III clinical trials before being discontinued.[2][3]

Chemistry

[edit]

Synthesis

[edit]
Sunepitron synthesis: G.N. Bright, K.A. Desai, U.S. patent 5,122,525 (1992).

The synthesis starts by conversion of the pyridine dicarboxylic acid (1) to its acid chloride; rxn with MeOH then affords the ester (2). Catalytic hydrogenation serves to reduce the pyridine ring to a piperidine of undefined stereochemistry (3). Alkylation of this intermediate with chloroacetonitrile affords (4). Treatment of that intermediate with Raney nickel reduces the cyano group to the corresponding primary amine; this product then undergoes an internal ester-amine interchange to yield the cyclized lactam (5). LAH serves to reduce the lactam to an amine; the ester on the other ring is reduced to a carbinol in the process, affording the aminoalcohol (7). The basic function is next alkylated with 2-chloropyrimidine (7). Rxn of the alcoholin (8) with MsCl leads to the mesylate; that group is next displaced by sodium azide (9); the azide group is next reduced to the primary amine. Resolution of this product as its mandelate salt then yields (10) as a single enantiomer. Rxn of that product with succinic anhydride converts the pendant amine to a succinimide, affording the anxiolytic agent sunepitron (1).

See also

[edit]

References

[edit]
  1. ↑ Goodnick PJ (July 1999). "Psychopharmacology of depression in the next millennium". CNS Spectrums. 4 (7): 21–35. doi:10.1017/s1092852900011998. PMID 18438295. S2CID 28460185.
  2. 1 2 Stahl SM (2000). Essential psychopharmacology: neuroscientific basis and practical application. Cambridge, UK: Cambridge University Press. p. 265. ISBN 0-521-64615-4.
  3. 1 2 Kaplan EP, Turkington C (2001). Making the antidepressant decision: how to choose the right treatment option for you and your loved ones. Chicago, Ill: Contemporary Books. ISBN 0-7373-0417-0.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Sunepitron&oldid=1365717241"