CELECOXIB Chemische Eigenschaften,Einsatz,Produktion Methoden
Originator
Celact,Sun Pharmaceuticals
Industries Ltd.,India
Manufacturing Process
4-(5-(4-Methylphenyl)-3-trifluoromethyl-N-pyrazol-1-yl)benzenesulfonamide
To a solution of ethyl trifluoroacetate (1.90 ml, 16.0 mmol) in 7 ml of methyl
tert-butyl ether was added 25% NaOMe (3.62 ml, 16.8 mmol). Next 4-
chloroaceteophenone (2.08 ml, 16.0 mmol) in 2 ml of methyl tert-butyl ether
was added. The mixture was stirred at room temperature overnight. To above
solution was added 100 ml of 90% EtOH, followed by 4 N HCl (4.0 ml, 16
mmol) and 4-sulphonamidophenylhydrazine hydrochloride (3.58 g, 16 mmol).
The mixture was heated to reflux for 3 hours. The mixture was concentrated.
When 30 ml of water was added, a solid formed. The solid was filtered and
washed with 20 ml of 60% EtOH to give 4.50 g of white solid. The filtrate was
evaporated and taken up in ethyl acetate (100 ml), washed with saturated
NaHCO3, and brine, dried over MgSO4, and concentrated. Heptane was added
at boiling point of the mixture. After cooling down to 0°C, 1.01 g more
product was obtained. The combined yield of the 4-(5-(4-methylphenyl)-3-
trifluoromethyl-N-pyrazol-1-yl)benzenesulfonamide (Celecoxib) was 86%.
Therapeutic Function
Antiinflammatory
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