Oxazolidinone compound containing thiadiazoles groups and preparation method thereof

A compound, thiadiazole technology, applied in the application field of oxazolidinone compounds and/or hydrates to prepare and treat microorganisms, especially bacterial infectious diseases, can solve ineffective, such as methicillin-resistant Staphylococcus aureus , Methicillin-resistant Staphylococcus epidermidis and vancomycin-resistant Enterococcus, reduced efficacy of antibacterial drugs, difficult treatment, etc.

Inactive Publication Date: 2008-01-02
SHENYANG J & HEALTH PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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; Bacteria become conditional pathogens, such as Proteus, Pseudomonas aeruginosa, etc.
The formation and development of all these drug-resistant strains have led to difficulties in treatment. The current antibacterial drugs can no longer meet the clinical needs, and there is an urgent need for antibacterial drugs with new mechanisms of action.

Method used

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  • Oxazolidinone compound containing thiadiazoles groups and preparation method thereof
  • Oxazolidinone compound containing thiadiazoles groups and preparation method thereof
  • Oxazolidinone compound containing thiadiazoles groups and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 (S)-N-[[3-[3-fluoro-4-[4-(5-amino-[1,3,4]thiadiazol-2-ylmethyl)-1-piperazine Preparation of base]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

[0052] [1] Preparation of 1-(2-fluoro-4-nitrophenyl)piperazine

[0053] Dissolve 25.8g (0.3mol) of anhydrous piperazine in 250ml of acetonitrile, stir and raise the temperature to 40°C, slowly add 11.4ml (0.1mol) of 3,4-difluoronitrobenzene dropwise, heat to reflux for 3h, and cool , evaporated to dryness under reduced pressure, 100 ml of water was added to the residue, extracted with ethyl acetate, the organic layers were combined, washed with water, dried, and evaporated to dryness under reduced pressure to obtain 18.9 g of yellow solid (yield 84%).

[0054] [2] Preparation of N-benzyloxycarbonyl-3-fluoro-4-(N-benzyloxycarbonyl-1-piperazinyl)aniline

[0055] Dissolve 18.9g (0.084mol) of 1-(2-fluoro-4-nitrophenyl)piperazine in 200ml of tetrahydrofuran, add 1.8g of 10% palladium carbon, hydrogenate and reduce under ...

Embodiment 2

[0072] Example 2 (S)-N-[[3-[3-fluoro-4-[4-(5-amino-[1,3,4]thiadiazol-2-ylethyl)-1-piperazine Base]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide hydrochloride

[0073]

[0074](S)-N-[[3-[3-fluoro-4-[4-cyanoethyl-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl ] Add 3.9g (0.01mol) of acetamide to 10ml of toluene, add 4ml of concentrated hydrochloric acid to the reaction solution, stir, add 0.9g (0.01mol) of thiosemicarbazide, and heat to reflux for 5h. After the reaction is complete, cool, adjust the pH to 8 with saturated sodium carbonate solution at 0-5°C, extract with toluene, combine the organic layers, wash with water, dry, evaporate to dryness, add the obtained solid to acetone, and adjust the pH to 1- 2. Heating to reflux for 0.5h, cooling, standing overnight, crystallization, suction filtration, drying to obtain (S)-N-[[3-[3-fluoro-4-[4-(5-amino-[1, 3,4] Thiadiazol-2-ylmethyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide hydrochloride 4.2g, yield w...

Embodiment 3-6

[0076] Example 3-6 compound

[0077] Table 2 is the compound prepared by embodiment 3-6

[0078] Example

structural formula

Chemical Name

yield

[0079] The preparation of the tablet of embodiment 7 embodiment 1 compound

[0080] Get Example 1 compound 250g, starch 30g, 2% HPMC aqueous solution 80ml, carboxymethyl starch sodium 15g, magnesium stearate 2g, follow the steps below:

[0081] a. Prepare an appropriate amount of 2% HPMC solution and set aside;

[0082] b. Properly dry the raw materials and auxiliary materials, pass through a 100-mesh sieve respectively, and set aside;

[0083] c. Weigh the raw and auxiliary materials according to the prescription quantity. After mixing the compound of Example 1, starch, and sodium starch glycolate evenly, add 2% HPMC solution to make soft material, and use a 20-mesh sieve to make wet granules;

[0084] d. Dry the wet granules at 55°C for about 3 hours, let cool slightly after drying, add magnesi...

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PUM

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Abstract

The invention discloses an oxazolidinone compound with thiadiazole group as formula I and making method, wherein R 1 is H or F; m is integral between 1 and 4. The invention also provides the application to treat microbe, especially for bacteria infection disease.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to oxazolidinone compounds and / or hydrates of formula I, and pharmaceutical compositions containing them. The present invention also provides a preparation method of the compound of formula I and its application in the preparation and treatment of microorganisms, especially bacterial infectious diseases. 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; Bacteria become conditional pathogens, such as Proteus, Pseudomonas aeruginosa and so on. The formation and development...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14A61K31/497A61P31/04
Inventor 史秀兰
Owner SHENYANG J & HEALTH PHARMA
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