Sulfhydryl oxo heterocycle substituted penem derivates

A technology of alkyl and methyl groups, applied in the field of compositions, can solve the problems of increasing glycopeptide-resistant bacteria, large side effects, increased bacterial resistance and the like

Active Publication Date: 2008-12-24
XUANZHU BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Due to the continuous increase of bacterial resistance due to the abuse of antibiotics and the limitation of digestive tract absorption, the currently marketed carbapenems can only be administered as injections in clinical practice, and the clinical utilization is not high. The antibacterial activity is weak, which can no longer meet the clinical needs
[0008] At present, although vancomycin has been widely used in infectious diseases caused by MRSA, its side effects are relatively large, and its use will further increase glycopeptide-resistant bacteria

Method used

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  • Sulfhydryl oxo heterocycle substituted penem derivates
  • Sulfhydryl oxo heterocycle substituted penem derivates
  • Sulfhydryl oxo heterocycle substituted penem derivates

Examples

Experimental program
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Effect test

Embodiment 1

[0104] The preparation of embodiment 1 (S)-5-mercapto-2-oxo-N-(3-fluorophenyl)-oxazolidine

[0105] In a dry reaction flask, add 16.2g (100mmol) of (S)-5-acetylthio-2-oxooxazolidine, add 150ml of toluene, heat to reflux, then slowly add 17.5g (100mmol) of 3-bromo - 50ml of toluene solution of 1-fluorobenzene, reflux and stir for 6h, after the reaction is completed, cool, add 100ml of water, separate the water layer after stirring, dry the organic layer with anhydrous sodium sulfate, cool to -30°C, slowly add 4.92mol dropwise / L sodium methoxide / methanol solution 40ml, stirred at -20°C for 1h, added 50ml of ice water to dilute, acidified with concentrated hydrochloric acid, separated the water phase, washed the organic phase with water, dried and concentrated, and the residue was treated with ethyl acetate-cyclohexane The alkane was recrystallized to obtain 11.1 g of white solid, yield: 52.1%.

Embodiment 2

[0106] The preparation of embodiment 2 (S)-4-mercapto-2-oxo-N-(3-fluorophenyl-1-yl)-pyrrolidine

[0107] Refer to Example 1 for specific operations, throw (S)-4-acetylthio-2-oxopyrrolidine 15.9g (100mmol), 3-bromo-1-fluorobenzene 17.5g (100mmol), get (S)- 12.7 g of 4-mercapto-2-oxo-N-(3-fluorophenyl-1-yl)-pyrrolidine, yield: 60.2%.

Embodiment 3

[0108] The preparation of embodiment 3 (S)-5-mercapto-2-oxo-N-(2-fluoropyridin-4-yl)-oxazolidine

[0109] Refer to Example 1 for specific operation, throw (S)-5-acetylthio-2-oxooxazolidine 16.2g (100mmol), 4-bromo-2-fluoropyridine 17.6g (100mmol), get (S) - 13.8 g of 5-mercapto-2-oxo-N-(2-fluoropyridin-4-yl)-oxazolidine, yield: 64.3%.

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Abstract

The invention relates to a sulfhydryl oxo heterocycle-substituted penem derivate as shown in a general formula (I), an easily hydrolyzed ester thereof, a salt thereof acceptable in pharmacology, an isomer thereof, a hydrate thereof, a hydrate of the ester or the salt thereof, a preparation method of the compounds as shown in the formula (I), an application of the compounds as medicine active substances, particularly an application of the compounds in preparing medicines used to treat and / or prevent infectious diseases as well as a medicine combination containing the compounds as shown in the formula (I), wherein the definition of each group is detailed in a specification.

Description

1. Technical field [0001] The present invention relates to penem derivatives substituted by mercapto oxo heterocycles, easily hydrolyzed esters thereof, pharmaceutically acceptable salts thereof, isomers thereof, hydrates thereof, and hydrates of esters or salts thereof, these compounds The preparation method, the pharmaceutical composition containing these compounds, and the application of these compounds in the preparation of medicines for treating and / or preventing infectious diseases belong to the field of medical technology. 2. Background technology [0002] In 1974, carbapenems were isolated from fermentation media and found to have broad-spectrum antibacterial activity, which can be used to treat infectious diseases including Gram-positive and negative bacteria, aerobic and anaerobic bacteria infections. [0003] Drugs of this type currently on the market include imipenem, meropenem, doripenem, biapenem, ertapenem, etc. The first to be marketed is imipenem, which has...

Claims

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Application Information

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IPC IPC(8): C07D477/20A61K31/422A61K31/407A61K31/5377A61K31/4439A61P31/04
CPCY02P20/55
Inventor 黄振华
Owner XUANZHU BIOPHARMACEUTICAL CO LTD
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