Dapoxetine Chemische Eigenschaften,Einsatz,Produktion Methoden
Verwenden
Dapoxetine-d7 Hydrochloride is a Labelled Dapoxetine (D185700). A selective serotonin reuptake inhibitor (SSRI).
Clinical Use
Dapoxetine is a selective serotonin re-uptake inhibitor (SSRI)
which has been approved in Finland and Sweden for the treatment
of premature ejaculation.Dapoxetine was discovered and developed
by Lilly and was licensed to Alza, a wholly-owned subsidiary
of Johnson & Johnson.
Synthese
Several synthetic routes for the preparation of dapoxetine have been disclosed, all on gram scale. Based on
the routes and yields, the most likely process route is described
in the scheme 4. Commercially available (R)-(+)-3-chloro-1-phenyl-
1-propanol (19) was reacted with 1-naphthol in the presence of
50% aqueous sodium hydroxide in DMF to give ether 20 in 90%
yield. Activation of the secondary alcohol was accomplished
through treatment of 20 with methane sulfonyl chloride and triethylamine
with catalytic DMAP. Upon complete conversion to
the corresponding mesylate, dimethylamine was added to the
reaction mixture. The addition of hydrochloric acid in ethyl acetate
to the resultant crude product gave dapoxetine hydrochloride (IV)
in 67% yield. Purification of this material by re-crystallization from
isopropanol provided IV in 86% yield and in 99.6% ee.
Dapoxetine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
