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Manifaxine

Chemical compound

Manifaxine
Summary

Chemical compound

Manifaxine (developmental code name GW-320,659) is a norepinephrine–dopamine reuptake inhibitor developed by GlaxoSmithKline through structural modification of radafaxine, an isomer of hydroxybupropion and one of the active metabolites of bupropion. Manifaxine was researched for treatment of attention deficit hyperactivity disorder (ADHD) and obesity and was found to be safe, reasonably effective, and well-tolerated for both applications. However, no results were reported following these initial trials and development was discontinued.

Synthesis

pmid=8558500 }}</ref> Patent:<ref>James Leroy Kelley, et al. EP0426416 (1991 to Wellcome Foundation Ltd).</ref> See also:<ref>Frank Ivy Carroll, et al. US9562001 (2012 to Research Triangle Institute).</ref><ref>Frank Ivy Carroll, et al. US20180215701 (Research Triangle Institute).</ref>

The Grignard reaction between 3,5-difluorobenzonitrile (1) and ethylmagnesium bromide gives 3,5-difluoropropiophenone (2). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone (3). Intermolecular ring formation with DL-alaninol (2-aminopropanol) completes the synthesis of manifaxine (4).

References

References

  1. "Manifaxine - AdisInsight".
  2. (August 2002). "GW320659 for the treatment of attention-deficit/hyperactivity disorder in children". Journal of the American Academy of Child and Adolescent Psychiatry.
  3. (December 2005). "Pharmacogenetics and obesity: common gene variants influence weight loss response of the norepinephrine/dopamine transporter inhibitor GW320659 in obese subjects". Pharmacogenetics and Genomics.
  4. (1 January 1996). "(2 S ,3 S ,5 R )-2-(3,5-Difluorophenyl)-3,5- dimethyl-2-morpholinol: A Novel Antidepressant Agent and Selective Inhibitor of Norepinephrine Uptake". Journal of Medicinal Chemistry.
  5. James Leroy Kelley, et al. EP0426416 (1991 to Wellcome Foundation Ltd).
  6. Frank Ivy Carroll, et al. US9562001 (2012 to Research Triangle Institute).
  7. Frank Ivy Carroll, et al. US20180215701 (Research Triangle Institute).
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

abandoned-drugs beta-hydroxyamphetamines fluoroarenes drugs-developed-by-gsk-plc norepinephrine–dopamine-reuptake-inhibitors phenylmorpholines stimulants tertiary-alcohols
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