Fluoro-carbostyril derivative as well as preparation method and application thereof

A fluoroquinolone and fluoroquinolone technology, which is applied in the field of novel fluoroquinolone derivatives and their preparation, can solve the problems of inconvenient industrial production, difficult post-processing, and high reaction temperature, and achieve low price of raw materials, convenient post-processing, and total yield. high rate effect

Inactive Publication Date: 2010-08-04
BEIJING OKEANOS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The main disadvantage of this method is that the reaction temperature is too high (250°C) during the ring closure step, the overall steps are too long, and because the intermediate c has a ketone form and an enol

Method used

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  • Fluoro-carbostyril derivative as well as preparation method and application thereof
  • Fluoro-carbostyril derivative as well as preparation method and application thereof
  • Fluoro-carbostyril derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0051] Example 1: 2-(2,6-Dichloro-3-fluoronicotinoyl)-3-naphthylaminoethyl acrylate (S1)

[0052] Fluorochloronicotinic acid ester (4g, 14.3mmol) was dispersed in a mixed solution of acetic anhydride (10mL) and triethyl orthoformate (2.7mL, 16.3mmol) and reacted under reflux for 1 hour. Remove excess acetic anhydride and orthoformic acid under vacuum Triethyl ester, the resulting brown oil was diluted with 15 ml of absolute ethanol, and then naphthylamine (16 mmol) was added and stirred at room temperature until a large amount of precipitation appeared. The resulting precipitate was filtered and the filter cake was washed with a small amount of methanol. After the filter cake was dried, intermediate S1 (5.35 g) was obtained. The total yield of the two steps was 86.3% (calculated as chlorofluoronicotinate).

Example Embodiment

[0053] Example 2: 7-chloro-6-fluoro-1-naphthyl-4-oxo-1,4-dihydro-1,8-naphthyridinyl-3-carboxylic acid ethyl ester (1)

[0054] Disperse S1 (500 mg) in 2.5 mL of acetonitrile, then add 0.5 g of anhydrous potassium carbonate, and react under reflux conditions until the raw material reaction is completed by thin layer chromatography. After cooling, the reaction system was poured into 50 mL of water and fully stirred for 30 minutes and then filtered. The filter cake was washed with a small amount of methanol and then dried to obtain compound 1 (275 mg) with a yield of 58.9%. 1 H NMR(300MHz, CDCl 3 ): δ8.63 (s, 1H), 8.52 (d, 1H), 8.09-7.99 (dd, 2H), 7.66-7.24 (m, 4H), 7.23 (t, 1H), 4.40-4.33 (m, 2H) ), 1.36(t, 3H).

Example Embodiment

[0055] Example 3: 2-(2,6-Dichloro-3-fluoronicotinoyl)-3-phenylaminoethyl acrylate (S2)

[0056] Aniline (16 mmol) was added to the oil obtained in the first step to react, and the reaction operation was the same as in Example 1. After filtration and drying, intermediate S 2 (4.07 g) was obtained. The total yield of the two steps was 74.2%.

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Abstract

The invention provides a novel fluoro-carbostyril derivative which is expressed as the following formula (1) and has antibacterial activity and a preparation method thereof. The preparation method has mild reaction condition, few reaction step, high total yield and convenient postprocessing and can realize the purification of a product just by simple filtering and recrystallization, therefore, the method is suitable for industrialized production.

Description

technical field [0001] The present invention relates to a class of novel fluoroquinolone derivatives, a preparation method and application thereof. Background technique [0002] As a new generation of broad-spectrum antibiotics, quinolones have been widely used at home and abroad in recent years. They have the characteristics of strong antibacterial effect, wide antibacterial spectrum, high bioavailability, and good tissue permeability. Therefore, they have attracted more and more attention from various countries. It has become a hot drug that is competing for production and application. Enoxacin is an excellent representative of the third-generation quinolone antibiotics. [0003] [0004] At present, the mainstream process for synthesizing enoxacin both at home and abroad is to use 3-chloro-4-aminopyridine as the starting material, which is cyclized with triethyl orthoformate and diethyl malonate and then ethylated, hydrolyzed, Piperazine condensation and other steps ...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/4375A61K31/444A61K31/506A61K31/4545A61K31/541A61K31/5377A61K31/496A61P31/04
Inventor 刘迎春牟应科高源
Owner BEIJING OKEANOS TECH
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