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Macrolide compound and preparation method and application thereof

A compound and composition technology, applied in the field of macrolide compounds, can solve problems such as clinical treatment difficulties

Inactive Publication Date: 2014-12-31
PU LIKE BIO ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, with the widespread use of antibiotics, especially the continuous and improper use, drug resistance to the currently widely used macrolide antibiotics such as azithromycin and telamycin have developed, which has brought great challenges to clinical treatment. difficulty
And the acute toxicity test proves that telamycin has certain toxicity

Method used

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  • Macrolide compound and preparation method and application thereof
  • Macrolide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] Open the low-temperature tank and set the temperature to -12°C; add 500mL of dichloromethane into a 1.0L three-neck flask with a 1L graduated cylinder, place it in the low-temperature tank and stir to cool down, and use a tray balance to take 50g (0.068mol) of compound 2 into the reaction flask Add 300mL of dichloromethane into the reaction flask with a 1L graduated cylinder, stir to dissolve, and cool down; cool to an internal temperature of 0-5°C, keep the temperature of the reaction solution at 0-5°C, and slowly add 11.98mL of benzyl chloroformate and dichloroformate A mixed solution of 60mL of methane was added, and the reaction was incubated for 1 hour; the progress of the reaction was monitored by thin-layer chromatography (developing solvent: dichloromethane / methanol=10:1, and two drops of ammonia water were added). After the reaction is completed, the reaction solution is concentrated under reduced pressure at a temperature ≤ 50°C and a vacuum degree ≤ -0.086Mpa ...

Embodiment 2

[0120] Turn on the low-temperature refrigeration equipment, adjust the temperature to -75°C, and lower the temperature to -70~-60°C; transfer about 300mL of compound 3 liquid obtained from the concentration of Example 1 to a 1.0L three-necked reaction flask, and store at room temperature (25~30°C) Add 106.46 mL (117.11 g, 1.498 mol) of dimethyl sulfoxide; after the addition of dimethyl sulfoxide, place the reaction bottle in a low-temperature bath and stir to cool down to -70~-60 °C, and take 21.55 mL of trifluoroacetic anhydride ( 0.152mol, 31.865g) to control the rate of addition to maintain the temperature of the reaction solution at -65~-60°C, slowly drop it, and keep it warm for 0.5 hours; then keep the temperature of the reaction solution at -65~-60°C and slowly drop triethylamine 47.3mL (0.339mol, 34.35g), after dripping, keep stirring for 0.5 hours; after the reaction, the reaction solution rises to room temperature. Transfer the reaction solution raised to room temper...

Embodiment 3

[0124] Add 50g (0.0456mol) of the compound 4 obtained in Example 2 and 80ml of dichloromethane into a 3.0L beaker. After stirring and mixing, the solution is dried with 15g of anhydrous magnesium sulfate for 20min, filtered with suction, and the filtrate is then washed with 7g of anhydrous magnesium sulfate. Secondary drying for 20 minutes, suction filtration, filter residue washed with dichloromethane, dichloromethane added to the filtrate to 160ml, (the water content of the filtrate should be less than 0.3%) for later use. Turn on the low-temperature refrigeration equipment, and adjust the temperature to -8°C; add 170 mL of tetrahydrofuran (dried over anhydrous magnesium sulfate for 30 minutes, and suction filter) into a 1.0L three-necked bottle, place it in a low-temperature tank and stir to cool down to -5-0°C, Add 20 g (0.1273 mol) of trimethylsulfur bromide, add 20 g (0.1786 mol) of potassium tert-butoxide under temperature control, use a circulating water pump to evacuat...

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Abstract

The invention provides an anti-infection pharmaceutical composition. The pharmaceutical composition contains an effective amount of a compound shown as a formula (I). The composition and pharmaceutically acceptable salt, ester, amide, stereoisomer or racemic mixture thereof can effectively prevent and treat various bacterial and protozoal infections, and have effect better than that of tulathromycin. The invention also relates to a preparation method and application of the compound.

Description

technical field [0001] The invention belongs to the field of veterinary medicine, and in particular relates to a macrolide compound, a preparation method and an application of the compound. Background technique [0002] As an important class of anti-infective drugs, macrolides have become the second only to β-lactams in clinical application because of their good antibacterial activity, no allergic reaction, few side effects and high safety. Antibiotics, the second largest class of anti-infective drugs, play an important role in clinical treatment. As the first generation of macrolide antibiotics, erythromycin has been widely used to treat infections caused by Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus hemolyticus and Mycoplasma pneumoniae, especially for those who are allergic to penicillin. Instability limits its application. The second-generation macrolide antibiotics represented by azithromycin have solved this problem and have greatly improved their...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7052A61P31/04A61P33/02C07H17/00C07H1/00
CPCY02P20/55
Inventor 张许科郭德祥刘兴金
Owner PU LIKE BIO ENG
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