【药物名称】
化学结构式(Chemical Structure):
参考文献No.34375
标题:2-(3H)-Oxazolone derivs. and their use as COX-2 inhibitors
作者:Puig Duran, C.; Pujol Noguera, F.; Fernandez Forner, D. (Almirall Prodesfarma, SA)
来源:EP 0888316; ES 2125161; JP 2000506876; WO 9734882
合成路线图解说明:

The synthesis of the title compound has been reported by two related procedures. Cyclization of phenacyl N-(4-fluorophenyl)carbamate (I) in boiling HOAc gave rise to oxazolone (II). Chlorosulfonation of (II), followed by treatment of the resulting sulfonyl chloride (III) with ammonia, yielded the title sulfonamide.

参考文献No.563828
标题:Synthesis and biological evaluation of 3,4-diaryloxazolones: A new class of orally active cyclooxygenase-2 inhibitors
作者:Puig, C.; Crespo, M.I.; Godessart, N.; Feixas, J.; Ibarzo, J.; Jimenez, J.M.; Soca, L.; Cardelus, I.; Heredia, A.; Miralpeix, M.; Puig, J.; Beleta, J.; Huerta, J.M.; Lopez, M.; Segarra, V.; Ryder, H.; Palacios, J.M.
来源:J Med Chem 2000,43(2),214
合成路线图解说明:

In an alternative procedure, sodium 4-acetylbenzenesulfonate (IV) was refluxed with POCl3 and subsequently treated with dibenzylamine to afford sulfonamide (V). Bromination of (V) in chloroform yielded the bromo ketone (VI), which was hydrolyzed to phenacyl alcohol (VII) by treatment with ethanolic betaine, followed by aqueous NaHCO3. Addition of 4-fluorophenyl isocyanate (VIII) to (VII) and then cyclization in refluxing HOAc yielded the oxazolone (IX). Final debenzylation was achieved with concentrated H2SO4 to give the target sulfonamide.

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