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项目整合精选>>>Sparfloxacin, CP-103826, RP-64206, CI-978, PD-131501, AT-4140, Zagam, Spara
Sparfloxacin, CP-103826, RP-64206, CI-978, PD-131501, AT-4140, Zagam, Spara
司帕沙星 司帕沙星 Chemical Name: 5-Amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS No. 110871-86-8, 111542-93-9 (undefined stereoch.)
项目整合开发状态: Launched-1993
项目研究机构: Dainippon Pharmaceutical (Originator), Aventis Pharma (Licensee), Bertek (Licensee)
合成路线:The reaction of ethyl pentafluorobenzoylacetate (I) with ethyl orthoformate in refluxing acetic anhydride and then with cyclopropylamine (II) in ether gives the aminomethylene derivative (III),which is cyclized by means of NaH in THF yielding ethyl 5,6,7,8-tetrafluoro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (IV).The reaction of (IV) with benzylamine (V) by means of K2CO3 in refluxing acetonitrile affords the benzylamino derivative (VI),which is deprotected by hydrogenation with H2 over Pd/C in ethanol giving ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (VII).The hydrolysis of (VII) with hot H2SO4 yields the free acid (VIII),which is finally condensed with cis-2,6-dimethylpiperazine (IX) in DMF.
📌 参考资料/链接：
参考文献标题:Novel quinoline derivatives and processes for preparation thereof
文献作者:Matsumoto,J.; Miyamoto,T.; Egawa,H.; Nakamura,S.(Dainippon Pharmaceutical Co.,Ltd.)
参考来源:AU 8664277; EP 0221463; JP 87277362
📄 详细内容
合成路线:The reaction of ethyl pentafluorobenzoylacetate (I) with ethyl orthoformate in refluxing acetic anhydride and then with cyclopropylamine (II) in ether gives the aminomethylene derivative (III),which is cyclized by means of NaH in THF yielding ethyl 5,6,7,8-tetrafluoro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (IV).The reaction of (IV) with benzylamine (V) by means of K2CO3 in refluxing acetonitrile affords the benzylamino derivative (VI),which is deprotected by hydrogenation with H2 over Pd/C in ethanol giving ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (VII).The hydrolysis of (VII) with hot H2SO4 yields the free acid (VIII),which is finally condensed with cis-2,6-dimethylpiperazine (IX) in DMF.
参考文献标题:AT-4140
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1989,14(5),413
产品链接: CAS No. 110871-86-8›› 产品链接: CAS No.111542-93-9››