Orbifloxacin, AT-4526, Victas
奥比沙星Chemical Name: 1-Cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-5,6,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
CAS No. 113617-63-3
项目整合开发状态: Launched-1994
项目研究机构: Dainippon Pharmaceutical (Originator), Schering-Plough (Licensee)
合成路线:The reaction of pentafluorobenzoylacetic acid ethyl ester (I) with triethyl orthoformate in refluxing acetic anhydride,followed by condensation with cyclopropylamine,gives 2-(pentafluorobenzoyl)-3-(cyclopropylamino)acrylic acid ethyl ester (II),which is cyclized by means of NaH in THF to yield 1-cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (III).The hydrolysis of (III) with H2SO4 /HOAc in refluxing water affords the corresponding carboxylic acid (IV),which is finally condensed with cis-2,6-dimethylpiperazine (V) in DMF to provide the target quinolone.
📌 参考资料/链接：
参考文献标题:Quinoline derivs.,pharmaceutical compsn.and method of use
文献作者:Matsumoto,J.-I.; Miyamoto,T.; Egawa,H.; Nakamura,S.(Dainippon Pharmaceutical Co.,Ltd.)
参考来源:EP 0242789; US 4886810
📄 详细内容
合成路线:The reaction of pentafluorobenzoylacetic acid ethyl ester (I) with triethyl orthoformate in refluxing acetic anhydride,followed by condensation with cyclopropylamine,gives 2-(pentafluorobenzoyl)-3-(cyclopropylamino)acrylic acid ethyl ester (II),which is cyclized by means of NaH in THF to yield 1-cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (III).The hydrolysis of (III) with H2SO4 /HOAc in refluxing water affords the corresponding carboxylic acid (IV),which is finally condensed with cis-2,6-dimethylpiperazine (V) in DMF to provide the target quinolone.
参考文献标题:Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones,including sparfloxacin,a new quinolone antibacterial agent with improved potency
文献作者:Miyamoto,T.; Matsumoto,J.; Chiba,K.; Egawa,H.; Shibamori,K.; Minamida,A.; Nishimura,Y.; Okada,H.; Kataoka,M.; Fujita,M.; et al.
参考来源:J Med Chem 1990,33(6),1645
产品链接: CAS No. 113617-63-3››