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Glycopeptides compounds with anti-resistance bacterial activity, preparation method and application thereof

A technology of anti-drug-resistant bacteria and compounds, which is applied in the field of drugs for the treatment of infectious diseases and novel glycopeptide compounds, can solve the problems of reduced activity and achieve high safety and high inhibitory activity effects

Active Publication Date: 2018-08-17
SHANGHAI LAIYI BIOMEDICAL RES & DEV CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the clinical application, enterococci (VRE) resistant to vancomycin and MRSA bacteria with reduced activity of vancomycin have emerged.

Method used

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  • Glycopeptides compounds with anti-resistance bacterial activity, preparation method and application thereof
  • Glycopeptides compounds with anti-resistance bacterial activity, preparation method and application thereof
  • Glycopeptides compounds with anti-resistance bacterial activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, the preparation of compound 1

[0043] Mix compound II (0.5g, 0.3mmol) with 10mL DMF-methanol (1:1, v / v), add DIEA (0.1mL, 0.6mmol) and 4-benzyloxybenzaldehyde (0.085g, 0.4mmol ), stirred at 65°C for 2h and cooled to room temperature, added TFA (0.07mL, 0.9mmol) and borane tert-butylamine (0.05g, 0.6mmol) and continued to stir at room temperature for 2h, and added methyl tert-butyl ether to the reaction solution (50mL), the precipitate was collected by suction filtration, the residue was purified with a reverse-phase polymer filler, eluted with methanol-0.04% TFA aqueous solution (1:4, v / v), concentrated and dried to obtain compound 1 (white solid 0.28g, Yield 52%).

[0044] C 87 h 100 Cl 2 N 10 o 27 Molecular weight calculated value: 1786.61, measured value: m / z=1787.60 [M+H] + .

Embodiment 2

[0045] Embodiment two, the preparation of compound 2

[0046] Mix compound II (0.5g, 0.3mmol) with 10mL DMF-methanol (1:1, v / v), add DIEA (0.1mL, 0.6mmol) and 4-phenylethoxybenzaldehyde (0.09g, 0.4 mmol), stirred at 65°C for 2h and cooled to room temperature, added TFA (0.07mL, 0.9mmol) and borane tert-butylamine (0.05g, 0.6mmol) and continued to stir at room temperature for 2h, and added methyl tert-butyl to the reaction solution Ether (50mL), the precipitate was collected by suction filtration, the residue was purified by reverse phase polymer packing, eluted with methanol-0.04% TFA aqueous solution (1:4, v / v), concentrated and dried to obtain compound 2 (white solid 0.31g , yield 57%).

[0047] C 88 h 102 Cl 2 N 10 o 27 Molecular weight calculated value: 1800.63, measured value: m / z=1801.63 [M+H] + .

Embodiment 3

[0048] Embodiment three, the preparation of compound 3

[0049] Mix compound II (1.0g, 0.6mmol) with 15mL DMF-methanol (1:1, v / v), add DIEA (0.2mL, 1.2mmol) and 4-phenylpropoxybenzaldehyde (0.2g, 0.8 mmol), stirred at 65°C for 2h, cooled to room temperature, added TFA (0.14mL, 1.8mmol) and borane tert-butylamine (0.1g, 1.2mmol) and continued to stir at room temperature for 2h, then added methyl tert-butyl ether (70mL ), the precipitate was collected by suction filtration, the residue was purified by reverse phase polymer packing, eluted with methanol-0.04% TFA aqueous solution (1:4, v / v), concentrated and dried to obtain compound 3 (white solid 0.65g, yield 60%).

[0050] C 89 h 104 Cl 2 N 10 o 27 Molecular weight calculated value: 1814.64, measured value: m / z=1815.64 [M+H] + .

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Abstract

The invention discloses a group of glycopeptides compounds with anti-resistance bacterial activity. The glycopeptides compounds in accordance with a general formula (I) are as shown in the following specification. The invention further provides a preparation method and an application for the above glycopeptides compounds. Through testing, compared with a second-generation glycopeptides pharmaceutical oritavancin, the glycopeptides antibiotic compounds have the higher inhibitory activity to endurance strains, especially MRSA or VRE. Through further testing, the most of the glycopeptides compounds have the higher safety than the oritavancin, and can be used for preparing pharmaceuticals for treating or preventing various diseases, such as skin and soft tissue infection, cephalomeningitis, sepsis, pneumonia, arthritis, peritonitis, bronchitis, and empyema, caused by bacterial infection.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a group of novel glycopeptide compounds, which can be used as drugs for treating infectious diseases. The invention also relates to the preparation method and application of the compound. Background technique [0002] Infectious diseases have always been one of the major diseases faced by human beings. In our country, the treatment of infectious diseases has always been an important and thorny problem. The situation of bacterial drug resistance is even worse than that of developed countries. Demand is also higher than in developed countries. In fact, even if the use of antibiotics is well controlled clinically, drug-resistant bacteria will still gradually emerge. Therefore, the human struggle against bacterial infection is long and protracted. At the end of the last century, under the background that developed countries drastically cut R&D...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K9/00A61K38/14A61P31/04
CPCA61P31/04C07K9/006A61K38/00C07K9/008Y02A50/30C07K1/00A61K9/0019A61K38/14A61K47/02
Inventor 邵昌戈梅阮林高魏维夏兴饶敏孟庆前罗敏玉
Owner SHANGHAI LAIYI BIOMEDICAL RES & DEV CENT
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