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Carbapenem derivative containing sulfhydryl pyrrolidine formamide benzyl

A technology of aminosulfonyl and alkyl groups, applied in the field of carbapenem derivatives containing mercaptopyrrolidine carboxamide benzyl group, can solve the problems of low clinical availability, short half-life and the like

Active Publication Date: 2009-02-25
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 external half-life of penem is relatively short, which can no longer meet the clinical needs. The structural formula of ertapenem sodium is as follows:

Method used

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  • Carbapenem derivative containing sulfhydryl pyrrolidine formamide benzyl
  • Carbapenem derivative containing sulfhydryl pyrrolidine formamide benzyl
  • Carbapenem derivative containing sulfhydryl pyrrolidine formamide benzyl

Examples

Experimental program
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Effect test

Embodiment 1

[0102] Example 1 (2S, 4S)-4-mercapto-2-formyl [[4-methoxyphen-1-ylmethyl] amino] -1- (tert-butoxycarbonyl) pyrrolidine preparation

[0103] 14.5 g (50 mmol) of (2S,4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine and 200 ml of anhydrous tetrahydrofuran were added to the dry reaction flask. Under the protection of nitrogen, 9.8g (60mmol) of 1,1-carbonyldiimidazole (CDI) was added at room temperature, reacted for 2h, and an acetone solution of 7.5g (55mmol) of 4-methoxybenzylamine was added below 0°C, and continued Reaction 1h. Then 100ml of 1mol / L hydrochloric acid was added dropwise, extracted with ethyl acetate (50ml×2), the organic phase was washed with water and saturated sodium chloride solution successively, concentrated under reduced pressure, the residue was added with 200ml of 5mol / L hydrochloric acid, stirred for 2h, and The dilute alkali solution was adjusted to be alkaline, and a solid was precipitated and recrystallized to obtain 15.9 g of a solid...

Embodiment 2

[0104] Example 2 (2S, 4S)-4-mercapto-2-formyl[[4-aminosulfonylphen-1-ylmethyl]amino]-1-(tert-butoxycarbonyl)pyrrole Preparation of alkane

[0105] Operation Reference Example 1, cast (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 14.5g (50mmol), 4-sulfonylamino-benzylamine 10.2g ( 55mmol), to obtain the product 16.8g, yield: 81.1%.

Embodiment 3

[0106] Example 3 (2S, 4S)-4-mercapto-2-formyl[[3-(propionic acid-3-yl)phen-1-ylmethyl]amino]-1-(tert-butoxycarbonyl)pyrrole alkyl preparation of

[0107] Operation Reference Example 1, cast (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 14.5g (50mmol), 3-(3-(aminomethyl)benzene Base) 9.3g (52mmol) of propionic acid to obtain 16.4g of product, yield: 80.3%.

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Abstract

The invention belongs to the technical field of medicine, and more particularly relates to carbapenem derivatives which are shown in general formula (I) and contain hydrosulphonyl pyrrolidine methanamide phenmethyl, salt which can be accepted by the derivatives on pharmacy, ester of the derivatives that is easy to hydrolyze, isomer of the derivatives, hydrate of the derivatives, and hydrate of the ester or the salt of the derivatives; wherein, R1, R2, R3 and R4 are defined as instruction; the invention also relates to a method used for preparing the compounds, medicine combinations containing the compounds, and the application of the compounds in the preparation of the medicine for treating and / or preventing infectious diseases.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to carbapenem derivatives containing mercaptopyrrolidinecarboxamide benzyl, pharmaceutically acceptable salts thereof, easily hydrolyzed esters, isomers thereof, hydrates thereof, and Hydrates of esters or salts, 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...

Claims

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Application Information

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IPC IPC(8): C07D477/20A61K31/407A61P31/00
CPCC07D405/12C07D477/20A61P31/00A61P31/04
Inventor 黄振华
Owner XUANZHU BIOPHARMACEUTICAL CO LTD
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