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Cyanopyridyl-replaced oxazolidinone compound

A technology of oxazolidinones and compounds, applied in the field of medicinal chemistry

Inactive Publication Date: 2010-01-06
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, no one has prepared oxazolidinone compounds containing cyanopyridyl substitution, and conducted research on their antibacterial activity, especially anti-drug-resistant bacteria activity

Method used

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  • Cyanopyridyl-replaced oxazolidinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1 (S)-N-[[3-[3-fluoro-4-(2-amino-3-cyano-4-pyridyl)phenyl]-2-oxo-5-oxazolidinyl ]methyl]acetamide

[0084] Step 1 Preparation of (S)-1-amino-3-chloro-2-propanol hydrochloride

[0085] Dissolve 59.0g (0.56mol) of benzaldehyde in 150ml of ethanol, add dropwise 58.0ml (0.55mol) of ammonia water to the reaction solution, stir, and dropwise add 58ml (0.88mol) of (S)-epichlorohydrin to the reaction solution , Control the rate of addition to keep the reaction temperature below 40°C. After dropping, react at 35-40°C for 6h, then lower the reaction solution to room temperature and continue to react for 12h. Most of the solvent was distilled off under reduced pressure, and 100 ml of toluene was added. After stirring, the solution was raised to 35-40°C, and an aqueous hydrochloric acid solution (68ml hydrochloric acid, 77ml water) was added dropwise, and the solution was stirred at 35-40°C for 3h. Stand still, separate the water layer, wash the organic layer with water...

Embodiment 2

[0102] Example 2 (S)-N-[[3-[3-fluoro-4-(2-amino-3-cyano-6-pyridyl)phenyl]-2-oxo-5-oxazolidinyl ]methyl]acetamide

[0103] Step 1: (S,E)-N-[[3-[3-fluoro-4-[(3-dimethylamino-2-propenyl)yl]phenyl]-2-oxo-5-oxazolidine base] methyl] acetamide

[0104] S-N-[[3-(4-acetyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide 5.0g (17mmol) and DMF- DMA13.6ml (102mmol) was added to 50ml of acetonitrile, heated to reflux and stirred for 7h. After the reaction was completed, the reaction solution was cooled to room temperature, suction filtered, and washed with acetonitrile to obtain 5.1 g of a yellow solid, with a yield of 86%, [M+H + ]: 350.1

[0105] Step 2: (S)-N-[[3-[3-fluoro-4-(2-amino-3-cyano-6-pyridyl)phenyl]-2-oxo-5-oxazolidinyl ]methyl]acetamide

[0106](S, E)-N-[[3-[3-fluoro-4-[(3-dimethylamino-2-propenyl)yl]phenyl]-2-oxo-5-oxazolidinyl] Add 5g (14.3mmol) of methyl]acetamide, 1.1g (17.2mmol) of malononitrile and 5.5g (71.6mmol) of ammonium acetate into 20ml of ethan...

Embodiment 3

[0108] Example 3 (S)-N-[[3-[3-fluoro-4-[2-(1-piperidinyl)-3-cyano-4-pyridyl]phenyl]-2-oxo- 5-Oxazolidinyl]methyl]acetamide

[0109] Step 1: (S)-N-[[3-[3-fluoro-4-(2-bromo-3-cyano-4-pyridyl)phenyl]-2-oxo-5-oxazolidinyl ]methyl]acetamide

[0110] Add 1.0 g (2.7 mmol) of the compound of Example 1 to 10 mL of pyridine, stir, cool to -10°C, and dropwise add 0.94 g (13.5 mmol) of sodium nitrite and 6.8 mL of concentrated sulfuric acid to the reaction solution in 6 mL of aqueous solution , Control the rate of addition so that the temperature of the reaction solution is -10°C. After dropping, the temperature of the reaction solution was raised to 0° C. for 1 h. After the reaction was completed, 1.94 g (16.2 mmol) of KBr in 3.5 mL aqueous solution was added to the reaction liquid, and the reaction was carried out at room temperature for 16 h. After the reaction is completed, filter with suction and wash the filter cake with water to obtain (S)-N-[[3-[3-fluoro-4-[2-(1-piperidyl)-3-c...

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Abstract

The invention relates a cyanopyridyl-replaced oxazolidinone compound with a general formula (I); wherein, R1 is hydrogen, fluorine, chlorine or trifluoromethyl and R is shown in the right structural formula. The invention also provides a preparation method of the compound shown in general formula (I) and medicinal salts of the compound and an application thereof for curing microbial infections, in particular to bacterial infection diseases. Preliminary antibacterial activity tests in vitro show that the compound of the invention has better antibacterial activity compared with linezolid and obvious antibacterial activity to drug-resistant bacteria.

Description

Technical field: [0001] The invention relates to the field of medicinal chemistry, in particular to a cyanopyridyl oxazolidinone compound or a pharmaceutically acceptable salt thereof, as well as a pharmaceutical composition containing them, a preparation method and an application. Background technique: [0002] In recent decades, the abuse of antimicrobial drugs has led to a sharp increase in the mortality rate of infectious diseases. Clinically, the drug resistance of cells is increasing year by year, resulting in the reduction of the efficacy of some antibacterial drugs, or even ineffective, such as methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis and vancomycin-resistant enterococci; Pathogenic bacteria become conditional pathogens, such as Proteus, Pseudomonas aeruginosa and so on. The formation and development of all these drug-resistant strains have led to difficulties in treatment. The current antibacterial drugs can no l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10A61K31/4439A61K31/496A61K31/5377A61P31/00A61P31/04
Inventor 宫平赵燕芳翟鑫刘亚婧
Owner SHENYANG PHARMA UNIVERSITY
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