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Sulfonyl substituted carbpenems compounds

A technology of compounds and hydrates, applied in organic chemistry, drug combinations, medical preparations containing active ingredients, etc., can solve problems that cannot meet clinical needs, increase bacterial resistance, etc.

Inactive Publication Date: 2009-02-11
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the excessive clinical application, bacterial drug resistance is increasing continuously, and at the same time, due to the limitation of injection administration, it can no longer meet the clinical needs.

Method used

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  • Sulfonyl substituted carbpenems compounds
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  • Sulfonyl substituted carbpenems compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1 Preparation of 3-mercapto-N-sulfonamido-azetidine

[0075] In a dry reaction flask, add 13.1g (100mmol) of 3-acetylthio-azetidine, 100ml of carbon tetrachloride, stir and cool down to -20°C, add 11.1g (110mmol) of triethylamine, After the solution is clarified, add 12.8g (110mmol) sulfuryl chloride carbon tetrachloride solution dropwise very slowly, keep stirring for 0.5h, then slowly rise to room temperature, stir for 0.5h, stop the reaction, drop below -10°C, and drop 50ml After stirring, the water layer was separated, and the solution of 3-acetylthio-N-sulfonyl-azetidine was dried for later use.

[0076] In the dry reaction flask, add the carbon tetrachloride solution of 3-acetylthio-N-sulfonyl-azetidine prepared in the previous step, and add 11.9 g (100 mmol) of thionyl chloride under stirring, Then heat up to 60°C, slowly add 15.2g (150mmol) triethylamine dropwise, keep stirring for 0.5h, then slowly lower the solution to 0°C, wash with water, saturate...

Embodiment 2

[0077] The preparation of embodiment 2 (3S)-3-mercapto-N-sulfonamido-pyrrolidine

[0078] Referring to the preparation method of Example 1, 14.5 g (100 mmol) of 3-acetylthio-pyrrolidine was cast. Obtained product: 12.8 g, yield: 70.5%.

Embodiment 3

[0079] Example 3 Preparation of 3-mercapto-N-sulfonamido-azidine

[0080] Referring to the preparation method of Example 1, 16 g (100 mmol) of 3-acetylthio-azacyclohexane was cast. Obtained product: 14.5 g, yield: 74.3%.

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Abstract

The invention pertains to the technical field of medicine and particularly relates to a compound shown as general formula (I), and pharmaceutically acceptable salts, easily hydrolysable ester, isomers and hydrates of the compound, as well as hydrates of the ester or the salt of the compound; wherein, R<1>, R<2>, R<3> and A are defined as the specification. The invention also relates to a preparation method of the compounds, medicine composition containing the compounds as well as application of the compounds to the preparation of medicines 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 sulfonyl-substituted carbapenem compounds, their pharmaceutically acceptable salts, their easily hydrolyzed esters, their isomers, their hydrates, and the hydration of their esters or salts substances, preparation methods of these compounds, pharmaceutical compositions 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 have attracted much attention because of their broad antibacterial spectrum, strong antibacterial activity, and stability to β-lactamase. Imipenem, meropenem, panipenem, biapenem, and doripenem have been used clinically. Donipenem is a penem antibiotic developed by Shionogi Co., Ltd. of Japan. Its structural formula is as follows: [0003] [0004] The antibacterial effect of doripenem on gram-posi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/20A61K31/506A61K31/407A61P31/04
CPCC07D477/20A61P31/00A61P31/04
Inventor 黄振华
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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