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【结 构 式】

【药物名称】Amifloxacin, Win-493753(mesylate), Win-49375

【化学名称】6-Fluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

【CA登记号】86393-37-5, 88036-80-0 (mesylate)

【 分 子 式 】C16H19FN4O3

【 分 子 量 】334.35323

【开发单位】Sanofi-synthélabo (Originator), Yamanouchi (Licensee)

【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Quinolones

合成路线1

The reaction of ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (I) with O-(2,4-dinitrophenyl)hydroxylamine (II) by means of K2CO3 in DMF gives ethyl 1-amino-6-fluoro-7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (III), which is formylated with HCOOH in acetic anhydride yielding the corresponding 1-(formylamino) compound (IV). The methylation of (IV) with MeI and K2CO3 in DMF affords the 1-(formylmethylamino) compound (V), which is hydrolyzed with NaOH in refluxing water to give 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-(methylamino)quinoline-3-carboxylic acid (VI). Finally, this compound is condensed with N-methylpiperazine (VII) in refluxing pyridine.

1 Powles, R.G.; Wentland, M.P.; Wagner, R.B.; Dobson, .A.; Bailey, D.M.; Cornett, J.B.; Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: Synthesis and stucture-activity relationships. J Med Chem 1984, 27, 9, 1103.
2 Wentland, M.P.; Bailey, D.M. (Sterling Winthrop Inc.); New quinolone compounds and preparation thereof. EP 0090424; JP 8401468 .
3 Castaner, J.; Serradell, M.N.; Burnie, J.; Matthews, R.; Amifloxacin. Drugs Fut 1985, 10, 3, 183.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 19904 ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate C12H9ClFNO3 详情 详情
(II) 29034 1-(aminooxy)-2,4-dinitrobenzene C6H5N3O5 详情 详情
(III) 29035 ethyl 1-amino-7-chloro-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate C12H10ClFN2O3 详情 详情
(IV) 29036 ethyl 7-chloro-6-fluoro-1-(formylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylate C13H10ClFN2O4 详情 详情
(V) 29037 ethyl 7-chloro-6-fluoro-1-[formyl(methyl)amino]-4-oxo-1,4-dihydro-3-quinolinecarboxylate C14H12ClFN2O4 详情 详情
(VI) 29038 7-chloro-6-fluoro-1-(methylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C11H8ClFN2O3 详情 详情
(VII) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
Extended Information