Fandofloxacin hydrochloride, DW-116
泛斗沙星 Chemical Name: 6-Fluoro-1-(5-fluoropyridin-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
CAS No. 164150-85-0, 164150-99-6 (free base)
项目整合开发状态: Phase II
项目研究机构: Dong-Wha (Originator)
合成路线:Condensation of ethyl 2,4,5-trifluorobenzoylacetate (I) with triethyl orthoformate in refluxing Ac2O produced the benzoyl ethoxyacrylate (II),which was further condensed with 2-amino-5-fluoropyridine (III) to afford enamine (IV).Cyclization of (IV) in the presence of K2CO3 gave rise to the quinolone (V).The 7-fluoride group of (V) was then displaced by N-methylpiperazine (VI) in cold pyridine to furnish the piperazinyl quinolone (VII).Finally,ester hydrolysis in (VII) under acidic conditions yielded the target compound.In a closely related procedure,ester (V) was hydrolyzed to acid (VIII) using HCl.Subsequent displacement of the 7-fluoride of (VIII) with N-methylpiperazine (VI) provided the desired piperazinyl quinolone.
📌 参考资料/链接：
参考文献标题:Leukotriene B4 derivs.,methods of preparing them and their use as drugs
文献作者:Skuballa,W.; Buchmann,B.; Heindl,J.; Fr鰄lich,W.; Ekerdt,R.; Giesen,C.(Schering AG)
参考来源:EP 0741687; JP 1997511487; WO 9520564
📄 详细内容
合成路线:Condensation of ethyl 2,4,5-trifluorobenzoylacetate (I) with triethyl orthoformate in refluxing Ac2O produced the benzoyl ethoxyacrylate (II),which was further condensed with 2-amino-5-fluoropyridine (III) to afford enamine (IV).Cyclization of (IV) in the presence of K2CO3 gave rise to the quinolone (V).The 7-fluoride group of (V) was then displaced by N-methylpiperazine (VI) in cold pyridine to furnish the piperazinyl quinolone (VII).Finally,ester hydrolysis in (VII) under acidic conditions yielded the target compound.In a closely related procedure,ester (V) was hydrolyzed to acid (VIII) using HCl.Subsequent displacement of the 7-fluoride of (VIII) with N-methylpiperazine (VI) provided the desired piperazinyl quinolone.
参考文献标题:Synthesis,pharmacokinetics,and biological activity of a series of new pyridonecarboxylic acid antibacterial agents bearing a 5-fluoro-2-pyridyl group or a 3-fluoro-4-pyridyl group at N-1
文献作者:Yoon,S.J.; et al.
参考来源:J Heterocycl Chem 1997,34(3),1021
产品链接: CAS No. 164150-85-0›› 产品链接: CAS No.164150-99-6››