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【结 构 式】

【药物名称】Fandofloxacin hydrochloride, DW-116

【化学名称】6-Fluoro-1-(5-fluoropyridin-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

【CA登记号】164150-85-0, 164150-99-6 (free base)

【 分 子 式 】C20H19ClF2N4O3

【 分 子 量 】436.84923

【开发单位】Dong-Wha (Originator)

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

合成路线1

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.

1 Yoon, S.J.; et al.; 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. J Heterocycl Chem 1997, 34, 3, 1021.
2 Skuballa, W.; Buchmann, B.; Heindl, J.; Frohlich, W.; Ekerdt, R.; Giesen, C. (Schering AG); Leukotriene B4 derivs., methods of preparing them and their use as drugs. EP 0741687; JP 1997511487; WO 9520564 .
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) 55875 Ethyl 2,4,5-trifluorobenzoylacetate C11H9F3O3 详情 详情
(II) 55876 ethyl (Z)-3-ethoxy-2-(2,4,5-trifluorobenzoyl)-2-propenoate C14H13F3O4 详情 详情
(III) 55877 5-fluoro-2-pyridinamine; 5-fluoro-2-pyridinylamine C5H5FN2 详情 详情
(IV) 55878 ethyl (Z)-3-[(5-fluoro-2-pyridinyl)amino]-2-(2,4,5-trifluorobenzoyl)-2-propenoate C17H12F4N2O3 详情 详情
(V) 55879 ethyl 6,7-difluoro-1-(5-fluoro-2-pyridinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate C17H11F3N2O3 详情 详情
(VI) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(VII) 55880 ethyl 6-fluoro-1-(5-fluoro-2-pyridinyl)-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate C22H22F2N4O3 详情 详情
(VIII) 55881 6,7-difluoro-1-(5-fluoro-2-pyridinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C15H7F3N2O3 详情 详情
Extended Information