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Mercapto azacycloalkyl acidamide alcohol substituted penem derivates

An azabicyclic, representative technology, applied in the field of preparation of drugs for the treatment and/or prevention of infectious diseases, can solve the problems of not meeting clinical needs, increasing bacterial resistance, etc.

Active Publication Date: 2011-05-18
XUANZHU BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the increase of clinical application of penem antibiotics, the bacterial drug resistance is increasing continuously, and the currently marketed penem antibiotics can only be administered clinically by injection, which cannot meet the clinical needs

Method used

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  • Mercapto azacycloalkyl acidamide alcohol substituted penem derivates
  • Mercapto azacycloalkyl acidamide alcohol substituted penem derivates
  • Mercapto azacycloalkyl acidamide alcohol substituted penem derivates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1 Preparation of 2-chloro-N-(3-amino-2-propanol-1-yl)-acetamide

[0091] In a dry reaction flask, add 9.1g (100mmol) of 1,3-diamino-2-propanol, 100mL of dichloromethane, then dropwise add 10mL of triethylamine, stir for 5min to dissolve, then add 5.6g (50mmol) of chlorine Acetyl chloride solution in 50 mL dichloromethane was stirred for 1 h. After the reaction was completed, the reaction was stopped, and the solid was removed by filtration. The filtrate was washed with dilute lye, dilute acid, and water respectively, dried and then concentrated under reduced pressure to obtain 6.9 g of the product. Rate: 83.1%.

Embodiment 2

[0092] Example 2 Preparation of (S)-3-acetylthio-1-[N-(3-amino-2-propanol-1-yl)-acetamide-1-yl]-pyrrolidine

[0093] Dissolve 8.3g (50mmol) 2-chloro-N-(3-amino-2-propanol-1-yl)-acetamide in 100mL dry DMF in a dry reaction flask, then add (S)-3-acetyl Sulfuryl-pyrrolidine 7.3g (50mmol), after the addition, add 1.5g (60mmol) of sodium hydride at 0°C, keep the temperature for 2h, then raise the temperature to 40°C and stir for 1h, stop the reaction, cool to room temperature and add 100mL Ethyl acetate and 100 mL of water were extracted, the aqueous layer was extracted twice with ethyl acetate (50 mL×2), the organic layers were combined, washed with saturated NaCl aqueous solution, dried over anhydrous sodium sulfate, and the solvent was recovered under reduced pressure to obtain 9.0 g of the product. Yield: 65.6%.

Embodiment 3

[0094] Example 3 Preparation of 3-acetylthio-1-[N-(3-amino-2-propanol-1-yl)-acetamido-1-yl]-azetidine

[0095] Preparation method reference example 2, cast 3-acetylthio-azetidine 6.6g (50mmol), 8.3g (50mmol) 2-chloro-N-(3-amino-2-propanol-1-yl) -Acetamide, 8.2g of the product was obtained, yield: 62.4%.

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PUM

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Abstract

The invention belongs to a field of medicine technology, concretely relating to mercapto azacycloalkyl acidamide alcohol substituted penem derivates represented by general formula (1), pharmaceutically acceptable salts thereof, easy hydrolytic esters thereof and isomers thereof, wherein R<1>, R<2>, R<3>, R<4>, R<5>, R<6> and n are defined in the description; the invention also relates to a methodfor producing these compounds, medicament compositions containing the compounds, and use of the compounds for preparing medicaments for treating 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 substituted by mercaptoazacycloalkanoamide alcohols, pharmaceutically acceptable salts thereof, easily hydrolyzed esters or isomers thereof, and methods for preparing these compounds, including these The pharmaceutical composition of the compounds, and the use of these compounds in the preparation of medicines for treating and / or preventing infectious diseases. 2. Background technology [0002] Penem 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 in the 1-position of the penicillane core is replaced by carbon, and the 2-position has a double bond, which is a structure that combines the five-membered ring of penicillin and the conjugated ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D477/20A61K31/407A61P31/00A61P31/04
CPCY02P20/55
Inventor 黄振华
Owner XUANZHU BIOPHARMACEUTICAL CO LTD