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Pennem derivates containing formamide heterocycle sulfonic acid amide sulfhydryl pyrrolidine

A sulfonylamino, methyl group technology, applied in the field of medicine, can solve the problems of poor antibacterial effect, long elimination half-life and the like

Active Publication Date: 2008-12-17
XUANZHU BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wide antibacterial spectrum, long elimination half-life, good tissue permeability, high bioavailability of intramuscular injection, used to treat abdominal infection, skin and skin soft tissue infection, urinary tract infection, gynecological infection and pneumonia, etc. Difference

Method used

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  • Pennem derivates containing formamide heterocycle sulfonic acid amide sulfhydryl pyrrolidine
  • Pennem derivates containing formamide heterocycle sulfonic acid amide sulfhydryl pyrrolidine
  • Pennem derivates containing formamide heterocycle sulfonic acid amide sulfhydryl pyrrolidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Example 1 (2S, 4S)-4-mercapto-2-formyl [(2-sulfonylamino-pyridin-6-yl) amino] -1- (tert-butoxycarbonyl) pyrrolidine preparation

[0100]Add (2S,4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 7.8g (27mmol) into the dry reaction flask, anhydrous tetrahydrofuran 100ml, under nitrogen protection, in Add 6.5g (40mmol) of 1,1-carbonyldiimidazole (CDI) at room temperature, react for 0.5h, add 8.7g of 6-aminopyridine-2-sulfonamide in tetrahydrofuran (50mmol / 100ml) below 0°C, and continue the reaction for 0.5 h, then add 40ml of 1mol / L hydrochloric acid dropwise, extract with ethyl acetate (50ml×2), wash the organic phase with water and saturated sodium chloride solution successively, concentrate under reduced pressure, add 100ml of 3mol / L hydrochloric acid to the residue, and stir for 2h , adjusted to basicity with a dilute alkaline solution, and a solid was precipitated, which was recrystallized from a mixed solution of ethyl acetate-cyclohexane (5:1) to obt...

Embodiment 2

[0101] Example 2 (2S, 4S) -4-mercapto-2-formyl [(4-sulfonylamino-thiazol-2-yl) amino] -1- (tert-butoxycarbonyl) pyrrolidine preparation

[0102] Refer to Example 1 for specific operations, throw (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 7.8g (27mmol), 2-aminothiazole-4-sulfonamide 9g (50mmol) to obtain 8.9g of (2S, 4S)-4-mercapto-2-formyl[(4-sulfonylamino-thiazol-2-yl)amino]-1-(tert-butoxycarbonyl)pyrrolidine, Yield: 81.2%.

Embodiment 3

[0103] Example 3 (2S, 4S)-4-mercapto-2-formyl [(4-sulfonylamino-oxazol-2-yl) amino] -1- (tert-butoxycarbonyl) pyrrolidine preparation

[0104] Refer to Example 1 for specific operations, throw (2S, 4S)-4-acetylthio-2-carboxy-1-(tert-butoxycarbonyl)pyrrolidine 7.8g (27mmol), 2-aminooxazole-4-sulfonyl Ammonia 8.2g (50mmol), to get (2S,4S)-4-mercapto-2-formyl[(4-sulfonylamino-oxazol-2-yl)amino]-1-(tert-butoxycarbonyl)pyrrolidine 8.4 g, yield: 78.9%.

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Abstract

The invention pertains to the technical field of medicines and particularly relates to a penem derivative containing formamide heterocyclic sulfonamide sulfhydryl pyrrolidine as showed in a general formula (1), a pharmaceutically acceptable salt thereof, easily hydrolyzable ester thereof and isomers thereof, wherein, R <1>, R<2>, R<3> and X are defined as in a specification. The invention also relates to a preparation method of the compounds, medical compositions containing the compounds and the application of the compounds in preparing medicines for curing and / or preventing infectious diseases.

Description

1. Technical field [0001] The present invention belongs to the technical field of medicine, and specifically relates to penem derivatives containing formamide heterocyclic sulfonamide mercaptopyrrolidine, pharmaceutically acceptable salts thereof, easily hydrolyzed esters thereof, isomers thereof, and methods for preparing these compounds. A pharmaceutical composition containing these compounds, and the use 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 penicillin and the conjugated dou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/20A61K31/407A61K31/454A61P31/04
Inventor 黄振华
Owner XUANZHU BIOPHARMACEUTICAL CO LTD
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