1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】22103

【品名】1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid

【CA登记号】85721-33-1

【分子式】C₁₇H₁₈FN₃O₃

【分子量】331.3467432

【元素组成】C 61.62% H 5.48% F 5.73% N 12.68% O 14.49%

与该中间体有关的原料药合成路线共 4 条

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

该中间体在本合成路线中的序号：(XII)

2) The condensation of quinoline (IX) with piperazine (XI) by heating at 140 C as before gives 1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-3-carboxylic acid (XII), which is finally treated with ethyl iodide and triethylamine in hot DMF.

参考文献中间体

合成目标

【1】 Grohe, K.; Petersen, U.; Kuck, K.-H. (Bayer AG); Antimicrobial agent of quinolone-carboxylic acid b. DE 3248507; US 4563459 .
【2】 Grohe, K.; Klimetzek, V.; Metzger, K.G.; Stunkel, K.G.; Zeiler, H.-J. (Bayer AG); Immunostimulant agent. AU 8542762; DE 3420116; EP 0165474; ES 8607020; JP 1985258163; US 4659603 .
【3】 Castaner, J.; Prous, J.; Enrofloxacin. Drugs Fut 1988, 13, 4, 305.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	10925	Iodoethane;ethyl iod	75-03-6	C₂H₅I	详情	详情
(IX)	22101	7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid	86393-33-1	C₁₃H₉ClFNO₃	详情	详情
(XI)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(XII)	22103	1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid	85721-33-1	C₁₇H₁₈FN₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The title compound was synthesized by condensation of cyprofloxacin (I) with tetraethyl ethenylidenebisphosphonate (II) in the presence of Et3N in CH2Cl2

参考文献中间体

合成目标

【1】 Herczegh, P.; Buxton, T.B.; McPherson, J.C. III.; Kovács-Kulyassa, A.; Brewer, P.D.; Sztaricskai, F.; Stroebel, G.G.; Plowman, K.M.; Farcasiu, D.; Hartmann, J.F.; Osteoadsorptive bisphosphonate derivatives of fluoroquinolone antibacterials. J Med Chem 2002, 45, 11, 2338.
【2】 Herczegh, P.; Sztaricskai, F.J.; Farcasiu, D.; Hartmann, J.F. (ElizaNor Biopharmaceuticals, Inc.); Diphosphonate derivs. of therapeutic agents. US 5880111; WO 9640190 .

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)	22103	1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid	85721-33-1	C₁₇H₁₈FN₃O₃	详情	详情
(II)	28428	diethyl 1-(diethoxyphosphoryl)vinylphosphonate		C₁₀H₂₂O₆P₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

The condensation of 1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid (I) with methylenediphosphonic acid tetraethyl ester (II) by means of TEA gives the addition product (III), which is finally hydrolyzed with trimethylsilyl bromide and water to afford the target diphosphonic acid.

参考文献中间体

合成目标

【1】 Herczegh, P.; Buxton, T.B.; McPherson, J.C. III.; Kovács-Kulyassa, A.; Brewer, P.D.; Sztaricskai, F.; Stroebel, G.G.; Plowman, K.M.; Farcasiu, D.; Hartmann, J.F.; Osteoadsorptive bisphosphonate derivatives of fluoroquinolone antibacterials. J Med Chem 2002, 45, 11, 2338.

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)	22103	1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid	85721-33-1	C₁₇H₁₈FN₃O₃	详情	详情
(II)	28428	diethyl 1-(diethoxyphosphoryl)vinylphosphonate		C₁₀H₂₂O₆P₂	详情	详情
(III)	63172	7-{4-[2,2-bis(diethoxyphosphoryl)ethyl]-1-piperazinyl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid		C₂₇H₄₀FN₃O₉P₂	详情	详情

合成路线4

该中间体在本合成路线中的序号：(I)

The alkylation of ciprofloxacin (I) with bis(chloromethyl)benzene (II) afforded the monosubstituted adduct (III). This was further condensed with norfloxacin (IV) to yield the title heterodimer compound.

参考文献中间体

合成目标

【1】 Grucz, R.G.; Kerns, R.J.; Kaatz, G.W.; Vaka, F.; Rybak, M.J.; Synthesis and antibacterial activity of novel piperazinyl-linked fluoroquinolones. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-565.

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)	22103	1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid	85721-33-1	C₁₇H₁₈FN₃O₃	详情	详情
(II)	55918	1,4-Bis(chloromethyl)benzene; alpha,alpha'-Dichloro-p-xylene; p-Xylylene dichloride	623-25-6	C₈H₈Cl₂	详情	详情
(III)	55919	7-{4-[4-(chloromethyl)benzyl]-1-piperazinyl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid		C₂₅H₂₅ClFN₃O₃	详情	详情
(IV)	11290	1-Ethyl-6-fluoro-4-oxo-7-piperazino-1,4-dihydro-3-quinolinecarboxylic acid; Norfloxacin	70458-96-7	C₁₆H₁₈FN₃O₃	详情	详情

Extended Information