Dimeric Avermectin Linkers for Resistant Parasite Control

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Solution Overview

Problem

There is a need for novel endectocides and anthelmintic treatments in veterinary medicine due to increasing resistance among veterinary parasites, and existing avermectin and milbemycin compounds have limited effectiveness against certain parasitic infections.

Innovation Solution

Development of novel dimeric avermectin/milbemycin compounds where two monomeric units are linked by a chemical linker at the 13-, 4'-, or 4"-positions, allowing further substitution at the 4-, 5-, 23-, and 25-positions, creating compounds with enhanced parasiticidal activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional avermectin and milbemycin compounds are used, then they provide basic antiparasitic activity, but they have limited effectiveness against resistant parasites

Engineering Contradiction:

Improveeffectiveness against resistant parasitesVSAvoidbroad-spectrum activity

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent combines two avermectin or milbemycin monomer units through a chemical linker at the 13-position to create dimeric compounds. This merging of two active units into a single molecular structure enhances parasiticidal activity while maintaining broad-spectrum effectiveness against both resistant and susceptible parasites

Inventive Principle:

Principle #5Merging (Combining)

Solution Approach 2:

The dimeric compounds represent composite molecular structures where two macrocyclic lactone units are linked together. This composite architecture integrates the properties of individual monomers while creating new emergent properties that overcome parasite resistance mechanisms

Inventive Principle:

Principle #40Composite materials

2Reliability

If dimeric structures are created by linking two monomeric units, then parasiticidal activity is enhanced, but molecular complexity increases

Engineering Contradiction:

Improveparasiticidal activityVSAvoidmolecular structure complexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The dimeric molecules are segmented into two distinct macrocyclic lactone monomer units connected by a linker. Each monomer retains its characteristic structure and activity, while the linker provides flexibility and enables the enhanced parasiticidal effect through cooperative action of both units

Inventive Principle:

Principle #1Segmentation

3Adaptability or versatility

If further substitution is allowed at multiple positions, then compound versatility is improved, but manufacturing complexity increases

Engineering Contradiction:

Improvecompound substitution optionsVSAvoidsynthesis complexity

Core Design Contradiction:

Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The dimeric compound structure provides universal reactivity at multiple positions (4-, 5-, 23-, and 25-positions), allowing various substituents to be introduced. This multi-functional capability enables the development of a series of derivatives with tailored properties while using a common synthetic platform

Inventive Principle:

Principle #6Universality (Multi-functionality)

Data Source

PatentEP2376513B1Dimeric avermectin and milbemycin derivatives

Publication Date: 2015.02.25 MERIAL LTD

AI summary

This invention provides for novel antiparasitic and pesticidal derivatives of avermectin and milbemycin compounds in which two avermectin or milbemycin members are linked together by a chemical linker. The resulting compounds may be used in veterinary compositions which are used in treating, controlling and preventing of endo- and ectoparasite infections and infestations in animals or for combating pests in plants or plant propagation material.