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GSK plc brands
Manifaxine
Другие языки:

Manifaxine

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Manifaxine
Manifaxine.svg
Clinical data
Other names GW-320,659
Routes of
administration		 Oral
ATC code
  • none
Identifiers
  • (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H15F2NO2
Molar mass 243.254 g·mol−1
3D model (JSmol)
  • C[C@@H]1CO[C@]([C@@H](N1)C)(C2=CC(=CC(=C2)F)F)O
  • InChI=1S/C12H15F2NO2/c1-7-6-17-12(16,8(2)15-7)9-3-10(13)5-11(14)4-9/h3-5,7-8,15-16H,6H2,1-2H3/t7-,8+,12-/m1/s1 ☒N
  • Key:OZGPVYJHWWPEFT-RGNHYFCHSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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

Synthesis: Patent: See also:

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




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