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7-substituted-8-methoxy fluoroquinolone carboxylic derivatives, preparing process, preparation and use thereof

A methyl, representative technology, applied in the field of 7-substituted-8-methoxyfluoroquinolone carboxylic acid derivatives, can solve the problems of central nervous system toxicity and side effects, and achieve the effect of high antibacterial activity

Inactive Publication Date: 2005-10-19
南京澳新医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The drug is broad-spectrum and potent, and has almost no phototoxicity, but it has certain central nervous system side effects

Method used

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  • 7-substituted-8-methoxy fluoroquinolone carboxylic derivatives, preparing process, preparation and use thereof
  • 7-substituted-8-methoxy fluoroquinolone carboxylic derivatives, preparing process, preparation and use thereof
  • 7-substituted-8-methoxy fluoroquinolone carboxylic derivatives, preparing process, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] 1-cyclopropyl-6-fluoro-7-[(S)-3-methyl-4-methyl-1-piperazinyl]-1,4-dihydro-8-methoxy-4-oxo Dai-3-quinolinecarboxylic acid (No.1, supergafloxacin)

[0075] Mix 16.2g (22.3ml, 0.16mol) of triethylamine, 40.5ml of dimethylsulfoxide and 16.1g (0.16mol) of (S)-2-methylpiperazine, and add 33.92g (0.0802mol) of 1- Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate bisacetoxy borate (chelate), at about 50°C React for 5 hours, TLC detection, after the reaction is complete, distill under reduced pressure to dryness, add water and hydrolyze the residue, neutralize it with alkali, filter the precipitate, and recrystallize with ethanol to obtain light yellow crystals of levo-gatifloxacin hemihydrate 12.7g, yield 41.2%, mp189~191°C (dec).

[0076] Mix 18.5g (0.048mol) of levo-gatifloxacin hemihydrate and 108ml of 37% formaldehyde solution, heat slightly, add 180ml of formic acid, react at about 60°C for 6 hours, evaporate to dryness under reduced pressure, ...

Embodiment 2

[0084] 1-cyclopropyl-6-fluoro-7-[(S)-3-methyl-4-(5-methyl-2-oxo-1,3-dioxol-4-yl) Methyl-1-piperazinyl]-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (No.2, saprofloxacin)

[0085] Levo-gatifloxacin hemihydrate is obtained in the same way as example 1, 15.4g (0.04mol) levo-gatifloxacin hemihydrate, 12g (0.08mol) 4-chloromethyl-5-methyl-1, 3-dioxol-2-ketone and 200ml N, N-dimethylformamide are mixed, add 4.8 grams of KHCO 3 , reacted at 0°C for 9 hours, evaporated to dryness under reduced pressure, washed the residue with water to obtain a yellow crude product, and obtained 14 g of light yellow powder by column chromatography, yield 71.8%, mp 165.2~166.4°C.

[0086] MS(EI, 70V, M / Z): 488[M+H] +

[0087] IR (KBr, cm -1 ): 3446, 2845, 1727, 1623, 1461, 1329, 1063

[0088] 1 H-NMR (dimethylsulfoxide-d 6 , δ, ppm): 1.13 (4H, m, C a，a′ -H), 1.35(3H, m, C 13 -CH 3 ), 8.72 (1H, S, C 2 -H), 7.80 (1H, d, C 5 -H), 3.74 (3H, S, OCH 3 ), 4.35 (1H, m, C b -H), 3.46-3.3...

Embodiment 3

[0093] 1-cyclopropyl-6-fluoro-7-[(R)-3-methyl-4-methyl-1-piperazinyl]-1,4-dihydro-8-methoxy-4-oxo Substituent-3-quinolinecarboxylic acid (No.3)

[0094] Mix 16.2g (22.3ml, 0.16mol) of triethylamine, 40.5ml of dimethylsulfoxide and 16.1g (0.16mol) of (R)-2-methylpiperazine, and add 33.92g (0.0802mol) of 1- Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid diacetoxy borate (chelate) reacts at about 50°C After 5 hours, TLC detection, after the reaction was complete, distilled to dryness under reduced pressure, hydrolyzed the residue with water, neutralized to neutral with alkali, filtered the precipitate, and recrystallized with ethanol to obtain light yellow crystals of dextro-gatifloxacin hemihydrate 12.9g, yield 41.8%, mp187~189°C.

[0095] Dissolve 18.5g (0.048mol) of dextro-gatifloxacin hemihydrate in 200ml of acetonitrile, add 8.5ml of triethylamine, 6ml (0.096mol) of methyl iodide, react at room temperature for 10 hours, concentrate to dryn...

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Abstract

The present invention relates to medicine chemistry and discloses 7-substituent-8-methoxy fluoro quinolone carboxylic derivative, i. e. 7-substituent-1-cyclopropyl-6-fluoro-1, 4-dihydro-8-methoxy-4-oxo-3-quinolone carboxylic acid and its salt; their preparation process and medicine composition for human and animal. The compounds of the present invention has antiseptic activity and safety higher than gatifloxacin and similar medicine.

Description

technical field [0001] The present invention relates to 7-substituted-8-methoxyfluoroquinolone carboxylic acid derivatives, namely 7-substituted-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo Substituted-3-quinolinecarboxylic acid derivatives and their salts, their preparation methods, pharmaceutical compositions containing them as active ingredients, and their use as antibacterial drugs. Background technique [0002] Since the 1980s, fluoroquinolone antibacterial drugs have been developed rapidly. As we all know, ciprofloxacin, ofloxacin, etc. have become the first-line drugs for the treatment of various infectious diseases, but with the wide application of fluoroquinolone antibacterial agents, certain bacteria such as Staphylococcus The existing varieties headed by ciprofloxacin have developed drug resistance; drug reactions between some varieties and non-steroidal anti-inflammatory drugs, theophylline and antacids are becoming increasingly apparent; in addition, some...

Claims

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Application Information

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IPC IPC(8): A61K9/08A61K9/20A61K9/48A61K31/47A61P31/04C07D215/56
Inventor 王尔华吴葆金王新图
Owner 南京澳新医药科技有限公司
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