C-20 Modified Macrolide Compounds for Resistant Animal Pathogens
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Solution Overview
Problem
Existing macrolide antibiotics, such as tylosin, face challenges in effectively treating pathogen infections in animals due to potential resistance and limited efficacy against certain bacteria and mycoplasma.
Innovation Solution
Development of new macrolide compounds with specific structural modifications, including varying substituents at the 20-position, and their pharmaceutically acceptable salts, synthesized through specific reaction routes involving amino alcohols and reducing agents, followed by purification using silica gel chromatography.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional macrolide antibiotics such as tylosin are used, then they provide basic antibacterial activity, but they face challenges in effectively treating pathogen infections due to antibiotic resistance and limited efficacy
Solution Approach 1:
The patent modifies the chemical structure of tylosin by changing parameters at specific positions (C-20 amino group modification) to create derivatives with enhanced antibacterial activity and reduced resistance. The general formula I allows systematic variation of chemical groups to optimize efficacy against resistant pathogens.
Solution Approach 2:
The invention creates composite macrolide structures by combining the core tylosin molecule with various amino alcohol derivatives at the C-20 position. This composite approach integrates the antibacterial properties of tylosin with the enhanced activity of modified amino groups to overcome resistance mechanisms.
2Reliability
If structural modifications are made to tylosin to enhance antibacterial activity, then efficacy against pathogen infections is improved, but the complexity of synthesis and purification increases
Solution Approach 1:
The synthesis process is divided into distinct segments: (1) reaction of tylosin with amino alcohols to form intermediate compounds, (2) purification via silica gel chromatography, and (3) final product isolation. This segmentation allows each step to be optimized independently and facilitates scalability.
Solution Approach 2:
The patent employs amino alcohol compounds as intermediary substances that react with tylosin to form the modified macrolide derivatives. These intermediaries serve as bridges between the starting material and final product, enabling controlled structural modification through well-defined chemical reactions.
3Adaptability or versatility
If multiple derivatives are synthesized through reactions with various amino alcohols, then the range of antibacterial activities is expanded, but the time and resources required for synthesis increase
Solution Approach 1:
The patent establishes a universal synthesis approach where a single reaction framework (tylosin + amino alcohol) can generate multiple derivatives by simply changing the amino alcohol substituent. This multi-functional template allows rapid exploration of different antibacterial activities without requiring entirely new synthetic routes for each derivative.
Solution Approach 2:
The method performs preliminary structural modification at the C-20 position during the synthesis stage, preparing the compound for subsequent biological testing. By pre-establishing the modified amino group structure, the patent eliminates the need for time-consuming post-synthesis modifications and allows parallel evaluation of multiple derivatives.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The new macrolide compounds demonstrate superior or equivalent antibacterial activity against Gram-positive and Gram-negative bacteria, including Mycoplasma, compared to tylosin, providing enhanced treatment options for animal infections.
Implementation Method 1
reacting the tylosin A with the amino alcohol in a polar solvent to obtain an imine solution
Implementation Method 2
adding a reducing agent to the imine solution, and reacting to obtain a hydroxyl secondary amino-modified macrolide compound
Implementation Method 3
adding an acid to the reaction mixture obtained in step (A), and reacting to obtain a hydroxyl tertiary amino-modified macrolide compound
Implementation Method 4
adjusting the pH of the aqueous phase obtained after the separation of liquid to 9-11 with a base
Implementation Method 5
extracting the aqueous solution with an organic solvent
Implementation Method 6
drying it over anhydrous sodium sulfate
Implementation Method 7
purification using silica gel chromatography
Data Source
AI summary
A macrolide compound and a preparation method and application thereof are provided. The macrolide compound has a structure represented by Formula I. A pharmaceutical composition or a veterinary pharmaceutical composition, which includes the macrolide compound with a structure represented by Formula I, is also provided. Moreover, a pharmaceutical preparation, which includes the macrolide compound with a structure represented by Formula I, is provided. The macrolide compound, veterinary pharmaceutical composition and pharmaceutical preparation can be used to treat pathogen infections, especially to treat pathogen infections in animals, with a significant effect.