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Novel oxazolidinone compound as well as preparation method and medical application thereof

A technology of oxazolidinones and compounds, applied in chemical instruments and methods, active ingredients of heterocyclic compounds, compounds of Group 5/15 elements of the periodic table, etc., can solve the problem that the antibacterial spectrum cannot fully cover upper respiratory tract infections

Inactive Publication Date: 2017-11-28
HC SYNTHETIC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, a variety of oxazolidinone derivatives have been disclosed, but so far, only linezolid (ZYVOX) has been approved for the treatment of microbial infections, but it has been used for a long time In the latter part, reversible thrombocytopenia and other myelosuppressive reactions appeared, and the antibacterial spectrum of the drug could not sufficiently cover the upper respiratory tract infections caused by Haemophilus influenzae, Moraxella catarrhalis and atypical pathogens, so the new anti-infection agents are still in great demand

Method used

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  • Novel oxazolidinone compound as well as preparation method and medical application thereof
  • Novel oxazolidinone compound as well as preparation method and medical application thereof
  • Novel oxazolidinone compound as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: N-(((S)-3-(3-fluoro-4-((4aR,7aR)-octahydropyrrolo[3,4-b]pyridin-6-yl)phenyl)-2 Preparation of -oxooxazolidin-5-yl)methyl)acetamide (Compound A)

[0037]

[0038] Compound A

[0039] Take (4aR,7aR)-6-(4-bromo-2-fluorophenyl)-octahydro-1H-pyrrolo[3,4-b]pyridine 10g, add 200ml of ethyl acetate to dissolve, and lower the temperature of the solution to below 5°C, then add 6.5g of N-(((S)-2-oxooxazolidin-5-yl)methyl)acetamide in batches, control the internal temperature not to exceed 10°C, and let the bath The temperature was naturally raised to room temperature, and the reaction was stirred for 8 hours, then the insoluble matter was filtered off, washed with a small amount of chloroform, combined with the chloroform solution, washed twice with water, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was separated by HPLC to obtain 3.5 g of compound A.

Embodiment 2

[0040] Example 2: (S)-3-(3-fluoro-4-((4aR,7aR)-octahydropyrrolo[3,4-b]pyridin-6-yl)phenyl)-5-((form Preparation of (amino)methyl)oxazolidin2-one (compound B)

[0041]

[0042] Compound B

[0043] Prepared according to the method of Example 1, except that N-(((S)-2-oxooxazolidin-5-yl)methyl)acetamide is replaced by (S)-5-((dimethyl amino)methyl)oxazolidin-2-one.

Embodiment 3

[0044] Example 3: N-(((S)-3-(4-((R)-3-aminoazepan-1-yl)-3-fluorophenyl)-2-oxooxazolidine Preparation of -5-yl)methyl)acetamide (Compound C)

[0045]

[0046] Compound C

[0047]Take 10g of (R)-1-(4-bromo-2-fluorophenyl)azepan-3-amine, add 200ml of dichloromethane to dissolve, lower the temperature of the solution to below 5°C, and then add in batches N-(((S)-2-oxooxazolidin-5-yl)methyl)acetamide 7.5g, control the internal temperature not to exceed 10°C, after the addition, let the bath temperature naturally rise to room temperature, and stir the reaction 8h, then filter out the insoluble matter, wash with a small amount of chloroform and combine the chloroform solution, then wash twice with water, dry over anhydrous sodium sulfate, and concentrate to dryness. The residue was separated by HPLC to obtain 4.2 g of compound C.

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Abstract

The invention relates to a novel oxazolidinone compound as well as a preparation method and a medical application thereof, and in particular relates to a novel oxazolidinone compound which is of formula (I) as shown in the specification, a preparation method of the compound, a medicinal composition with the compound, and an application of the compound as a treatment agent, particularly an application of the compound in preparing medicines for treating microorganism infection. Substituent groups of the formula (I) are defined same as those in claims.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a novel oxazolidinone derivative, a preparation method, a pharmaceutical composition containing the derivative, and the use of the derivative in anti-infective diseases. Background technique [0002] The rapid development of drug-resistant bacteria of various antibiotics and antibacterial drugs has seriously threatened the life and health of patients with infectious diseases. Exploring new drugs against drug-resistant Gram-positive bacteria has become a research hotspot in the medical field at home and abroad. Oxazolidinone antibacterial drugs are a new class of chemically fully synthetic antibacterial drugs developed after sulfonamides and fluoroquinolones in the past 30 years. They can kill Gram-positive pathogens by inhibiting protein synthesis at a very early stage. Efficacy of multidrug-resistant Gram-positive bacteria. [0003] In the prior art, a variety of oxazolidinone ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D263/20C07D263/24C07D413/10C07D413/12C07D413/14C07F9/6561C07F9/6558A61K31/437A61K31/422A61K31/421A61K31/496A61K31/454A61K31/55A61K31/675A61P31/00
CPCC07D263/20C07D263/24C07D413/10C07D413/12C07D413/14C07D471/04C07F9/65586C07F9/6561
Inventor 陆华龙
Owner HC SYNTHETIC PHARMA CO LTD
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