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Oxazolidinone compound containing combined aromatic hydrazine and its preparation method

A compound, oxazolidine technology, applied in the field of medicinal chemistry

Inactive Publication Date: 2018-02-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, with their widespread use since their launch, drug resistance has emerged, requiring further optimization and the design of newer compounds to overcome drug resistance

Method used

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  • Oxazolidinone compound containing combined aromatic hydrazine and its preparation method
  • Oxazolidinone compound containing combined aromatic hydrazine and its preparation method
  • Oxazolidinone compound containing combined aromatic hydrazine and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Example 1 (S)-N-(3-{2-fluoro-4'-[(4-methylpiperazin-1-yl)iminomethyl]biphenyl-4-yl}-2-oxo Preparation of (1,3-oxazolidin-5-ylmethyl)acetamide (Ia)

[0109] 1.1(S)-N-[3-(2-fluoro-4'-formylbiphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-ylmethyl]acetamide Synthesis of (L4)

[0110] 1.1.1 Preparation of methyl (3-fluorophenyl) carbamate (L1)

[0111] Under an ice-salt bath, add 44.4g (0.40mol) of m-fluoroaniline and 31.6g (0.40mol) of pyridine into 266mL of dichloromethane, and stir until completely dissolved. Control the temperature at -5~0°C, add 41.4g (0.44mol) of methyl chloroformate in dichloromethane (50mL) dropwise to the reaction liquid, after 1.5h, react at room temperature for 2h. After the reaction, the reaction solution was washed with water (150mL×2), 1M hydrochloric acid (150mL) and saturated brine (150mL) successively, the organic layer was dried over anhydrous sodium sulfate, filtered with suction, the filtrate was concentrated to dryness under reduced pressure, a...

Embodiment 2

[0125] Example 2 (S)-N-{3-[2-fluoro-4'-(morpholin-4-yliminomethyl)biphenyl-4-yl]-2-oxo-1,3- Preparation of oxazolidin-5-ylmethyl}acetamide (Ib)

[0126] Using morpholine as a raw material, synthesize the key intermediate according to the synthesis method of 1.2 in Example 1, and then synthesize (S)-N-{3-[2-fluoro-4' according to the synthesis method of 1.3 in Example 1 -(morpholin-4-yliminomethyl)biphenyl-4-yl]-2-oxo-1,3-oxazolidin-5-ylmethyl}acetamide. Yield 78%. MS(ESI),m / z(%):441.1 [M+H] + ; 1 H-NMR (400MHz, DMSO-d6): δ8.27(t, J=5.7Hz, 1H), 7.74(s, 1H), 7.68(s, 1H), 7.66(s, 1H), 7.59(ddd, J=14.4,10.9,4.7Hz,4H),7.42(dd,J=8.6,2.0Hz,1H),4.77(m,1H),4.17(t,J=9.0Hz,1H),3.79(dd,J =10.7,6.2Hz,5H),3.44(t, J=5.4Hz,2H),3.20–3.07(m,4H),1.85(s,3H).

Embodiment 3

[0127] Example 3 (S)-N-{3-[2-fluoro-4'-(thiomorpholin-4-yliminomethyl)biphenyl-4-yl]-2-oxo-1, Preparation of 3-oxazolidin-5-ylmethyl}acetamide (Id)

[0128] Using thiomorpholine as a raw material, synthesize key intermediates according to the synthetic method of 1.2 in Example 1, and then synthesize (S)-N-{3-[2-fluoro- 4'-(thiomorpholin-4-yliminomethyl)biphenyl-4-yl]-2-oxo-1,3-oxazolidin-5-ylmethyl}acetamide. Yield 80%. MS(ESI),m / z(%):457.5[M+H] + .

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Abstract

The present invention relates to oxazolidinone compounds containing biarylhydrazone structures represented by general formula I, or optical isomers, pharmaceutically acceptable salts and / or solvates thereof, their preparation methods and compounds containing said compounds pharmaceutical composition. Wherein the substituents R1, R2, R3, X and ring A have the meanings given in the specification. The present invention also relates to the use of the compounds and their pharmaceutically acceptable salts, solvates or prodrugs as antibacterial drugs in treatment, especially the use in the treatment of Gram-positive bacteria infection and Mycobacterium tuberculosis infection.

Description

Technical field: [0001] The present invention relates to the field of medicinal chemistry, in particular to an oxazolidinone compound containing a biarylhydrazone structure, or its optical isomer, pharmaceutically acceptable salt and / or solvate, their preparation method and containing The pharmaceutical composition of said compound. The present invention also relates to the use of the compounds and their pharmaceutically acceptable salts, solvates or prodrugs as antibacterial drugs in treatment, especially the use in the treatment of Gram-positive bacteria infection and Mycobacterium tuberculosis infection. Background technique: [0002] In recent years, the widespread use and even abuse of antibacterial drugs has led to a sharp increase in the mortality rate of infectious diseases. Clinically, the problem of bacterial drug resistance has become increasingly serious, resulting in reduced efficacy or even ineffectiveness of some antibacterial drugs, such as methicillin-resist...

Claims

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Application Information

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IPC IPC(8): C07D263/20C07D413/12A61K31/496A61K31/5377A61K31/541A61K31/454A61K31/497A61P31/04A61P31/06
CPCC07D263/20C07D413/12
Inventor 赵燕芳宫平吴亚闯李颖修丁亮武国东洪岳
Owner SHENYANG PHARMA UNIVERSITY
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