Manifaxine
Source: Wikipedia, the free encyclopedia.
Chemical compound
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Other names | GW-320,659 |
Routes of administration | Oral |
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Manifaxine (developmental code name GW-320,659) is a
structural modification of radafaxine, an isomer of hydroxybupropion and one of the active metabolites of bupropion.[1] 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.[2][3] However, no results were reported following these initial trials and development was discontinued.[1]
Synthesis
The Grignard reaction between 3,5-difluorobenzonitrile [64248-63-1] (1) and ethylmagnesium bromide gives 3,5-difluoropropiophenone [135306-45-5] (2). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone [135306-46-6] (3). Intermolecular ring formation with DL-Alaninol (2-Aminopropanol) [6168-72-5] completed the synthesis of Manifaxine (4).
See also
References
- ^ a b "Manifaxine - AdisInsight".
- PMID 12162627.
- S2CID 40809351.
- PMID 8558500.
- ^ James Leroy Kelley, et al. EP0426416 (1991 to Wellcome Foundation Ltd).
- ^ Frank Ivy Carroll, et al. US9562001 (2012 to Research Triangle Institute).
- ^ Frank Ivy Carroll, et al. US20180215701 (Research Triangle Institute).