7-phenyl quinolone compounds

A compound and solvate technology, applied in the field of medicine, can solve the problems of unsatisfactory antibacterial effect of Gram-positive bacteria and unsatisfactory safety

Active Publication Date: 2011-05-04
HAINAN SIHUAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the antibacterial effect of these drugs on Gram-positive bacteria, especially drug-resistant bacteria, is ...

Method used

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Examples

Experimental program
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Embodiment 1

[0135] Example 1 7-[4-[2-(1H-pyrazol-1-yl)ethoxy]phenyl]-1-cyclopropyl-8-(difluoromethoxy)-4-oxo- Preparation of 1,4-dihydroquinoline-3-carboxylic acid (compound 1)

[0136]

[0137] 7-Bromo-1-cyclopropyl-8-(difluoromethoxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 400mg (1mmol) was added to a dry reaction flask , 15mL toluene, stir to dissolve. Then 1-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl]-1H-pyridine was added Azole 314.2 mg (1 mmol), 0.5 mL of 2N sodium carbonate solution, Pd (PPh 3 ) 4 Cl 2 28mg. The reaction solution was stirred and refluxed under nitrogen atmosphere. After completion of the reaction of the raw materials, the reaction mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to dryness. Purified by column chromatography to obtain 0.36 g of solid product, yield: 71.4%.

[0138] 0.15 g (0.3 mmol) of 7-[4-[2-(1H-pyrazol-1-yl)ethoxy]phenyl]-1-cyclopropyl-8-(difluoromet...

Embodiment 2

[0141] Example 2 1-Cyclopropyl-8-(difluoromethoxy)-4-oxo-7-[4-[2-(pyrrolidin-1-yl)ethoxy]phenyl]-1, Preparation of 4-dihydroquinoline-3-carboxylic acid (compound 2)

[0142]

[0143] Under nitrogen protection, add 7-bromo-1-cyclopropyl-8-(difluoromethoxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester to the dry reaction flask 400 mg (1 mmol), 20 mL dioxane, 4-[2-(pyrrolidin-1-yl)ethoxy]phenylboronic acid 235 mg (1 mmol), Na 2 CO 3 106mg (1mmol) and catalyst Pd (PPh 3 ) 4 50 mg was stirred to dissolve and the reaction was stirred overnight at 100°C under nitrogen atmosphere. After the reaction was completed, a mixed solution of ethyl acetate and water (1:1) was added to the reaction system, and the organic layer was separated. The organic layer was dried with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated to dryness, and purified on a preparative chromatography column ( n-hexane:ethyl acetate=1:1) to obtain 307 mg of s...

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PUM

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Abstract

The invention belongs to the technical field of medicaments, and in particular relates to 7-phenyl quinolone compounds shown as a general formula (I), and pharmaceutically acceptable salt, solvate and stereoisomers thereof, wherein R<1>, R<2>, R<3>, R<4>, R<5> and n are defined in the specifications. The invention also relates to a method for preparing the compounds, medicinal preparations containing the compounds, and application of the compounds to the preparation of medicaments for treating and/or preventing infectious diseases.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to 7-phenylquinolones, pharmaceutically acceptable salts thereof, solvates or stereoisomers thereof, preparation methods of these compounds, pharmaceutical preparations containing these compounds, and these Use of compounds in the preparation of medicaments for treating and / or preventing infectious diseases. 2. Background technology [0002] Quinolone antibiotics are a class of synthetic antibacterial drugs, which have the characteristics of broad antibacterial spectrum, strong antibacterial activity, unique mechanism of action, wide tissue distribution, and good pharmacokinetic characteristics. Since the advent of nalidixic acid in 1962, after more than 40 years of development, thousands of quinolones have been synthesized. From the first generation of nalidixic acid, which can only be active against gram-negative bacteria such as Escherichia coli, it has developed ...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D215/56C07D405/12C07D409/12C07D417/12C07D413/12C07D487/10A61K31/4709A61K31/496A61K31/5377A61K31/501A61K31/506A61K31/497A61K31/47A61P31/00A61P31/04
Inventor 黄振华宋运涛
Owner HAINAN SIHUAN PHARMA
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