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Penem derivative containing sulfhydryl formamide benzenesulfonyl pyrrolidine

A methyl and amino technology, applied in the field of penem derivatives containing mercaptopyrrolidine carboxamide benzenesulfonyl, which can solve the problems of low clinical utilization and short half-life

Active Publication Date: 2009-02-04
XUANZHU BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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 half-life of penem is relatively short, which can no longer meet the clinical needs

Method used

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  • Penem derivative containing sulfhydryl formamide benzenesulfonyl pyrrolidine
  • Penem derivative containing sulfhydryl formamide benzenesulfonyl pyrrolidine
  • Penem derivative containing sulfhydryl formamide benzenesulfonyl pyrrolidine

Examples

Experimental program
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Effect test

Embodiment 1

[0099] The preparation of embodiment 1 (2S, 4S)-4-acetylthio-2-formyl [(4-sulfonylguanidino-phen-1-yl) amino]-pyrrolidine

[0100] Add 5.7 g (30 mmol) of (2S, 4S)-4-acetylthio-2-carboxy-1-pyrrolidine and 100 ml of anhydrous tetrahydrofuran into a dry reaction flask, and add 1,1- Carbonyldiimidazole 6.5g (40mmol), react for 0.5h, add 10.7g (50mmol) 1-(4-aminobenzenesulfonyl) guanidine solution in 100ml of tetrahydrofuran below 0°C, continue to react for 0.5h, then add 1mol / L dropwise 40ml of hydrochloric acid was extracted with ethyl acetate (50ml×2), the organic phase was washed with water and saturated sodium chloride solution successively, concentrated under reduced pressure, and the solid was recrystallized from acetone solution to obtain 12.6g of solid, yield: 65.3%.

Embodiment 2

[0101] Example 2 (2S, 4S)-4-acetylthio-2-formyl [[4-sulfonyl (2-amino-pyrimidin-2-yl)-benzene-1-yl]amino]-pyrrolidine preparation of

[0102] Referring to the preparation method of Example 1, 8.7 g (30 mmol) of (2S,4S)-4-acetylthio-2-carboxy-pyrrolidine and 12.5 g (50 mmol) of 2-(4-aminobenzenesulfonylamino)pyrimidine were cast. Obtained product: 8.9 g, yield: 70.6%.

Embodiment 3

[0103] Example 3 (2S, 4S)-4-acetylthio-2-formyl[(4-sulfonyl(2-amino-thiazol-2-yl)-benzene-1-yl)amino]-pyrrolidine preparation of

[0104]Referring to the preparation method of Example 1, 8.7 g (30 mmol) of (2S,4S)-4-acetylthio-2-carboxy-pyrrolidine and 12.8 g (50 mmol) of 2-(4-aminobenzenesulfonylamino)thiazole were cast. Obtained product: 9.4 g, yield: 73.5%.

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Abstract

The invention belongs to the medicine technology field, which particularly relates to an ertapenem derivative containing hydrosulphonyl pyrrolidine formamide benzenesulfonyl, the salt thereof acceptable in pharmacy, the ester which is easy to be hydrolyzed, the isomer thereof, the hydrate thereof and the hydrate of ester or salt thereof shown in the formula (I) and a preparing method of the compound shown in the formula (I); wherein, the definitions of R<1>, R<2>, R<3>, R<4>, R<5> and R<6> are elaborately described in an introduction. The invention also relates to preparing methods of compounds and the drug combination containing the compounds and the applications of the compounds in preparing the medicine for curing or preventing infectious diseases.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to penem derivatives containing mercaptopyrrolidine carboxamide benzenesulfonyl group, its pharmaceutically acceptable salt, its easily hydrolyzed ester, its isomer, its hydrate, and its ester or salt hydrates, preparation methods of these compounds, pharmaceutical compositions containing these compounds, and uses of these compounds in the preparation of medicaments for treating and / or preventing infectious diseases. 2. Background technology [0002] Carbapenem antibiotics are a class of β-lactam antibiotics developed in the 1970s. It has attracted much attention because of its broad antibacterial spectrum, strong antibacterial activity, and stability to β-lactamase. Its structural feature is that the sulfur at the 1-position of the penicillane core is replaced by carbon, and the 2-position has a double bond, which combines the five-membered ring of penicillin and t...

Claims

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Application Information

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IPC IPC(8): C07D477/20A61K31/407A61K31/427A61K31/506A61P31/00
Inventor 黄振华
Owner XUANZHU BIOPHARMACEUTICAL CO LTD
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