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Macrolide compound, synthetic method of macrolide compound, pharmaceutical composition and application

A technology of macrolides and macrolides, which is applied in the field of macrolides and can solve problems such as defects

Active Publication Date: 2019-12-27
SHANGHAI INST OF PHARMA IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the defect that clinical methicillin-resistant Staphylococcus aureus produces drug resistance to β-lactam antibiotics, and provides a macrolide compound, a synthesis method, and a drug combination things and their applications

Method used

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  • Macrolide compound, synthetic method of macrolide compound, pharmaceutical composition and application
  • Macrolide compound, synthetic method of macrolide compound, pharmaceutical composition and application
  • Macrolide compound, synthetic method of macrolide compound, pharmaceutical composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 19

[0111] Example 1 9-hydrazone clarithromycin (compound 2)

[0112] Clarithromycin (10g, 13.38mmol) was dissolved in methanol (80mL), hydrazine acetate (36.9g, 0.4mol) was added, and heated to reflux for 46h. After removing part of the methanol by rotary evaporation, water (200 mL) was added, the pH was adjusted to 9-10 with 3N NaOH aqueous solution, filtered, the filter cake was washed with water, and dried to obtain 10.7 g of crude white solid, 105.0%.

Embodiment 2

[0113] Example 2 9-isopropylidene hydrazone clarithromycin (compound 3)

[0114]9-Hydrazone clarithromycin (11.6g, 15.2mmol) was dissolved in 50mL of acetone, heated to reflux for 4h. Add 100 mL of water and 50 mL of dichloromethane, adjust the pH to 9-10 with 3N NaOH aqueous solution, separate the layers, extract the aqueous layer with dichloromethane (20 mL*2), combine the dichloromethane layers, wash with water (50 mL*2), Washed with saturated brine and spin-dried to obtain 11.1 g of a white solid with a yield of 90.1%.

Embodiment 3

[0115] Example 3 2'-O-acetyl-9-isopropylidene hydrazone clarithromycin (compound 4)

[0116] Dissolve 11.1 g (13.8 mmol) of 9-isopropylidene hydrazone clarithromycin in 40 mL of dichloromethane, add 1.9 mL (20 mmol) of acetic anhydride, and stir at room temperature for 4 h. Add 50 mL of water, adjust the pH to 9-10 with 3N NaOH aqueous solution, separate the layers, extract the aqueous layer with dichloromethane (20 mL*2), combine the dichloromethane layers, wash with water (50 mL*2), wash with saturated saline, and spin dry 11.5 g of white solid was obtained.

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Abstract

The invention discloses a macrolide compound, a synthetic method of the macrolide compound, a pharmaceutical composition and application. The macrolide compound or pharmaceutically acceptable salt thereof shows certain separate anti-MRSA (methicillin-resistant staphylococcus aureus) activity and can further remarkably increase the MRSA inhibiting function of beta-lactam antibiotics when jointly used with the beta-lactam antibiotics. Test results show that the macrolide compound or pharmaceutically acceptable salt has good in-vitro synergism, is a novel synergist, can relieve drug resistance ofthe MRSA to oxacillin and is a drug with good market development prospects.

Description

technical field [0001] The invention relates to a macrolide compound, a synthesis method, a pharmaceutical composition and application. Background technique [0002] The problem of bacterial drug resistance is becoming more and more severe, and the prevalence of drug-resistant bacteria is becoming wider and wider, especially Staphylococcus aureus (MRSA). MRSA is defined as: staphylococcus aureus resistant to methicillin, oxacillin, cephradine or mec gene positive. Since MRSA was first isolated in 1961, its infection rate and isolation rate have gradually increased around the world. Grundmann et al. believe that as many as 53 million people around the world may carry MRSA. my country is an area with high prevalence of MRSA, and the prevention and control situation is very severe. The survey on the current situation of MRSA infection in general hospitals in Shanghai showed that the MRSA infection rate of inpatients in 2008 was 2.68%, accounting for 81.85% of the detected Sta...

Claims

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Application Information

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IPC IPC(8): C07H17/04C07H1/00A61P31/04A61K31/7048A61K31/706A61K31/7056A61K31/7042
CPCC07H17/04C07H1/00A61P31/04Y02A50/30
Inventor 沈舜义樊钱永华楠刘珊张芸徐屹军
Owner SHANGHAI INST OF PHARMA IND
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