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Penem derivant containing sulfhydryl pyrrolidine formhydrazide

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

Active Publication Date: 2009-02-18
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 derivant containing sulfhydryl pyrrolidine formhydrazide
  • Penem derivant containing sulfhydryl pyrrolidine formhydrazide
  • Penem derivant containing sulfhydryl pyrrolidine formhydrazide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1 (2S, 4S)-4-mercapto-2-formyl [(2-amino-2-oxoacetyl) hydrazino] -1- (tert-butoxycarbonyl) pyrrolidine preparation

[0084] Add (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 8.7g (30mmol) and 100ml of anhydrous tetrahydrofuran to the dry reaction flask, under nitrogen protection, in Add 6.5g (40mmol) of 1,1-carbonyldiimidazole at room temperature, react for 0.5h, add 4.1g (40mmol) of 2-amino-2-oxoacetylhydrazine in 100ml of tetrahydrofuran solution below 0°C, and continue the reaction for 0.5h, Then 40ml 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 100ml of 3mol / L hydrochloric acid, stirred for 2h, and The dilute alkaline solution was adjusted to be basic, and a solid was precipitated, which was recrystallized to obtain 6.1 g of a solid, with...

Embodiment 2

[0085] Example 2 Preparation of (2S, 4S)-4-mercapto-2-formyl [(4-methyl-thiourea-1-yl) amino]-1-(tert-butoxycarbonyl)pyrrolidine

[0086] Refer to Example 1 for the specific preparation method. Throw (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 8.7g (30mmol) and 4-methylthiosemicarbazide 4.2g (40mmol). 6.3 g of the product was obtained, yield: 63.2%.

Embodiment 3

[0087] Example 3 Preparation of (2S, 4S)-4-mercapto-2-formyl (guanidine-1-yl) amino-1-(tert-butoxycarbonyl) pyrrolidine

[0088] Refer to Example 1 for the specific preparation method. Throw (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 8.7g (30mmol) and aminoguanidine 3.0g (40mmol). 5.9 g of the product was obtained, yield: 65.1%.

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Abstract

The present invention belongs to the technical field of medicine, in particular to a penem derivative containing mercaptopyrrolidine formylhydrazine shown in the formula (1) and a pharmaceutically acceptable salt, an easily hydrolyzed ester, an isomer, a hydrate and a hydrate of the ester or the salt thereof: wherein, R<1>, R<2>, R<3>, R<4>, R<5>, R<6> and X are defined in the description. The present invention also relates to preparation methods of the compounds, drug combinations and applications of the compounds in the preparation of drugs for treating and / or preventing infective diseases.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to penem derivatives containing mercaptopyrrolidine carbohydrazide, their pharmaceutically acceptable salts, their easily hydrolyzed esters, their isomers, their hydrates, and their esters or salts Hydrates of these compounds, preparation methods of these compounds, pharmaceutical compositions containing these compounds, and uses of these compounds in the preparation of medicines 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 pe...

Claims

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Application Information

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