7-[4-(aminomethyl)-4-fluoro-3-(alkoxyimine) pyrrolidine-1-yl] substituted quinoline carboxylic acid derivative and preparation thereof

A technology of alkoxyimino and pyrrolidine, applied in the field of new quinoline carboxylic acid derivatives and its preparation, to achieve strong antibacterial activity

Inactive Publication Date: 2009-01-28
NANJING MESE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, quinolone drug resistance and easy cross-resistanc

Method used

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  • 7-[4-(aminomethyl)-4-fluoro-3-(alkoxyimine) pyrrolidine-1-yl] substituted quinoline carboxylic acid derivative and preparation thereof
  • 7-[4-(aminomethyl)-4-fluoro-3-(alkoxyimine) pyrrolidine-1-yl] substituted quinoline carboxylic acid derivative and preparation thereof
  • 7-[4-(aminomethyl)-4-fluoro-3-(alkoxyimine) pyrrolidine-1-yl] substituted quinoline carboxylic acid derivative and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1: Synthesis of 4-(N-tert-butoxycarbonyl)aminomethyl-4-fluoro-1-(N-tert-butoxycarbonyl)-pyrrolidin-3-alcohol (4) lithium aluminum tetrahydride (3.6 g, 94.7mmol) was dissolved in anhydrous THF (150ml), and the solution formed by dissolving 2 (11g, 47.6mmol) in anhydrous THF (100ml) was added dropwise in an ice-salt bath (-5°C). , continue to react at the same temperature for 0.5h, then add water (3.6ml), 15% sodium hydroxide (3.6ml) and water (10.8ml) to the reaction system successively, stir the mixture at room temperature for 1h, then add anhydrous Magnesium sulfate continued to stir for 0.5h, filtered, and the filtrate was concentrated to obtain the crude product of 3. The resulting product was dissolved in chloroform (200ml), and added in batches to (t-BOC) 2 O (12.3g, 56.4mmol), the mixture was stirred for 30min to complete the reaction, then concentrated, diluted with ethyl acetate, washed with water, dried and filtered. The filtrate was concentrated, and...

Embodiment 2

[0089] Example 2: Synthesis of 4-(N-tert-butoxycarbonyl)aminomethyl-4-fluoro-1-(N-tert-butoxycarbonyl)-pyrrolidin-3-one (5)4(5.2g, 15.8 mmol) was dissolved in acetone (100ml), and newly prepared Jones reagent (6.9ml) was added dropwise under an ice bath, and stirring was continued for 0.5h at the same temperature, then methanol (5ml) was added, stirred for a while, filtered, and the residue was obtained after the filtrate was concentrated. Dilute with chloroform, wash with saturated brine, dry, filter, and concentrate the filtrate to obtain 4.5 g (crude yield: 90.0%). This product does not need to be refined, and is directly carried out to the next step reaction.

Embodiment 3

[0090] Example 3: Synthesis of 4-(N-tert-butoxycarbonyl)aminomethyl-4-fluoro-1-(N-tert-butoxycarbonyl)-pyrrolidin-3-one-O-methyloxime (6)

[0091] 5 (4.2g, 12.7mmol) was dissolved in pyridine (50ml), and methoxyamine hydrochloride (2.2g, 25.4mmol) was added. The reaction mixture was stirred at 50°C for 0.5h, and the solvent was evaporated. Analysis and purification yielded 3.7 g (yield 80.2%).

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PUM

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Abstract

The invention discloses quinolinecarboxylic acid derivative substituted by 7-[4-(aminomethyl)-4-fluorine-3-(alkoxyimine) pyrrolidine-1-group] and a preparation method thereof. The invention discloses a compound with a structure as the formula (I) or an acceptable salt hydrate for the drugs thereof, and also discloses the application thereof on the preparation of antibacterium drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a novel quinolinecarboxylic acid derivative with excellent antibacterial activity and a preparation method thereof. Background technique [0002] Quinolones began with the discovery of nalidixic acid (J. Med. Chem. 1962, 5, 1063) in 1962, and have now developed into a class of broad-spectrum, high-efficiency, and low-toxic synthetic chemotherapy drugs. Early quinolones have stronger antibacterial activity to Gram-negative bacteria, but lower activity to Gram-positive bacteria, although newly listed quinolones such as gatifloxacin (Drug, 1999,58 (4) : 683) and moxifloxacin (EP 550903) have improved antibacterial activity, but in general, the activity against Gram-positive bacteria needs to be further enhanced, and at the same time it is necessary to enhance the antibacterial activity against some specific bacteria such as Streptococcus pneumoniae, Enterococcus etc. ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D401/04C07D207/22A61K31/4375A61K31/4709A61P31/04
CPCC07D207/22C07D471/04C07D401/04A61P31/04Y02P20/55
Inventor 陈萍季子为
Owner NANJING MESE PHARMA
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