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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

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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 form, it will generate during the ethylation process. Ethylation product d and o-ethylation by-product d 1 , resulting in low yield and difficulty in post-processing, which brings inconvenience to industrial production

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
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Effect test

Embodiment 1

[0051] Example 1: Ethyl 2-(2,6-dichloro-3-fluoronicotinoyl)-3-naphthylaminoacrylate (S1)

[0052] Fluclonicotinate (4g, 14.3mmol) was dispersed in a mixed solution of acetic anhydride (10mL) and triethyl orthoformate (2.7mL, 16.3mmol) for reflux reaction for 1 hour, and excess acetic anhydride and orthoformic acid were removed under vacuum Triethyl ester, the resulting brown oil was diluted with 15 mL of absolute ethanol, then naphthylamine (16 mmol) was added and stirred at room temperature until a large amount of precipitation occurred. After filtering the resulting precipitate, the filter cake was washed with a small amount of methanol, and the filter cake was dried to obtain intermediate S1 (5.35 g). The two-step total yield was 86.3% (based on flunicotinate).

Embodiment 2

[0053] Example 2: Ethyl 7-chloro-6-fluoro-1-naphthyl-4-oxo-1,4-dihydro-1,8-naphthyridinyl-3-carboxylate (1)

[0054] Take S1 (500 mg) and disperse it in 2.5 mL of acetonitrile, then add 0.5 g of anhydrous potassium carbonate, and react under reflux until the reaction of raw materials is detected by thin layer chromatography. After cooling, the reaction system was poured into 50 mL of water and fully stirred for 30 minutes before filtration. The filter cake was washed with a small amount of methanol and dried to obtain Compound 1 (275 mg). The yield was 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).

Embodiment 3

[0055] Example 3: Ethyl 2-(2,6-dichloro-3-fluoronicotinoyl)-3-phenylaminoacrylate (S2)

[0056] Aniline (16mmol) was added to react in the oily matter obtained in the first step, and the reaction operation was the same as in Example 1. After filtration and drying, the intermediate S 2 (4.07 g) was obtained, and 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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