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3,5-substituted oxazolidinone derivative and its preparing process and application

A technology of oxazolidinone and derivatives, applied in 3 fields, can solve problems such as difficult clinical treatment

Inactive Publication Date: 2002-06-26
广东赛法洛药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, various types of antibiotics have been continuously developed and released, so that there are many targeted drugs for the treatment of bacterial infectious diseases. While affirming their positive effects, a large number of drug-resistant bacteria against antibacterial agents are also developing rapidly, such as , methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Staphylococcus epidermidis (MRSE), penicillin-resistant Streptococcus pneumoniae (PRSP), multidrug-resistant Mycobacterium tuberculosis, especially vancomycin-resistant Enterococcus (VRE ), these bacteria mutate through plasmids or chromosomes after being exposed to antibacterial drugs, and acquire drug resistance, which has caused new difficulties for clinical treatment
Since the reported antimicrobial drugs are still difficult to effectively control these drug-resistant bacterial infections, medicinal chemists are making great efforts to develop new anti-drug-resistant bacterial drugs, design and screen drugs with new chemical structures, new mechanisms of action or new targets of action. new antimicrobials

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0051] The preparation of embodiment 13-fluoro-4-morpholino nitrobenzene (1)

[0052] In a 500ml four-neck flask, add ethyl acetate (110ml), morpholine (19.07ml, 0.218mol), diisopropylethylamine (37.4ml, 0.215mol), mechanically stir at room temperature, slowly drop 3, 4-Difluoronitrobenzene (22.0ml, 0.199mol), stirred for 72 hours, the reactant was extracted with ethyl acetate (250ml), washed with saturated NaCl solution (250ml×3), washed over anhydrous MgSO 4 After drying and evaporating to dryness, a yellow solid was obtained, which was recrystallized from acetone-water to obtain a yellow crystal (42.70 g), with a yield of 95.0%.

[0053] m.p.112-113°C (literature, 98%, 111-112°C)

[0054] 1 H-NMR (CDCl 3 , 300MHz) δ: 7.982(dd, 1H), 7.894(dd, 1H), 6.921(t, 1H), 3.874(t, 4H), 3.279(t, 4H)

Embodiment 23

[0055] Preparation of embodiment 23-fluoro-4-morpholinylaniline (2)

[0056] In a 500ml three-necked flask, add reduced iron powder (8.40g, 0.150mol), water (30ml, 1.67mol), glacial acetic acid (1.4ml, 24.27mmol), stir mechanically, activate under reflux for 30min, and slowly add compound (1) dropwise (12.305g, 50mmol) of absolute ethanol solution, react for about 30min after adding, filter while hot, and evaporate to dryness to obtain a light white solid, wash the filter cake (50ml×3) with ethyl acetate, combine the filtrates, wash with acetic acid Extract with ethyl ester (250ml×3), wash with saturated NaCl solution (250ml×3), wash with anhydrous MgSO 4 After drying and evaporating to dryness, a pale white solid (9.71 g) was obtained with a yield of 90.98%, which was directly used in the next reaction.

[0057] 1 H-NMR (CDCl 3 , 300MHz) δ: 6.784(t, 1H), 6.456(d, 1H), 6.393(d, 1H), 3.851(t, 4H), 3.023(t, 4H)

Embodiment 3

[0058] Embodiment 3N-benzyloxycarbonyl-3-fluoro-4-morpholinylaniline (3)

[0059] In a 1000ml four-necked flask, add compound (2) (9.71g, 49.47mmol), acetone (166ml), water (84ml), and add NaHCO at 0°C 3 (7.77g, 92.50mmol), stirred mechanically, added dropwise benzyl chloroformate (6.63ml, 50.95mmol), stirred for 16h, and filtered with suction to obtain a white solid (5.47g), poured the filtrate into an ice-water mixture (550ml, Ice / water=1 / 2, v / v), a light red floc was precipitated, and was filtered by suction to obtain a solid (6.83g). All the obtained solids were recrystallized by acetone-water, and the combined yield was 76.10%.

[0060] m.p.123-124.5°C (literature, 70%, 123-124°C)

[0061] FAB-MS: 330[M + ]

[0062] IR(film)cm -1 : 3321, 2848, 1705, 1591, 1533, 1435, 1238, 930, 744

[0063] 1 H-NMR (CDCl 3 , 300MHz) δ: 7.362 (m, 5H), 6.957 (t, 2H), 6.669 (s, 1H), 5.189 (s, 2H), 3.873 (t, 4H), 3.043 (t, 4H) Example 4 ( Preparation of R)-[N-3-(3'-fluoro-4'-morpholin...

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Abstract

An antibacterial 3,5-substituted oxazolidione derivative and its salt with strong activity to resist gram-position bacteria, their preparing process, their application in preparing antibacterial agents and the antibacterial medicine containing them as active components are disclosed.

Description

technical field [0001] The present invention relates to 3,5-substituted oxazolidinone derivatives and salts thereof with antibacterial effect. The present invention also relates to the preparation method of the 3,5-substituted oxazolidinone derivative and its salt. In addition, the present invention also relates to the application of the 3,5-substituted oxazolidinone derivatives and their salts in the preparation of antibacterial agents, and the 3,5-substituted oxazolidinone derivatives and their salts as active ingredients Antimicrobials. Background technique [0002] In recent years, various types of antibiotics have been continuously developed and released, so that there are many targeted drugs for the treatment of bacterial infectious diseases. While affirming their positive effects, a large number of drug-resistant bacteria against antibacterial agents are also developing rapidly, such as , methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Stap...

Claims

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Application Information

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IPC IPC(8): A01N43/74A61K31/21C07D263/22
Inventor 刘浚孟庆国金洁武燕彬
Owner 广东赛法洛药业有限公司
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