N-chlorinated Cationic Compounds for Selective Antimicrobial Action

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Solution Overview

Problem

Current N-halogenated and N,N-dihalogenated compounds used as antimicrobial agents often exhibit toxicity to mammalian cells, limiting their therapeutic applications due to their broad disinfectant properties.

Innovation Solution

Development of specific compounds represented by Formula I, which include various N-halogenated and N,N-dihalogenated structures with improved antimicrobial efficacy while minimizing toxicity, suitable for use as antibacterial, anti-infective, disinfectant, antifungal, and antiviral agents, along with methods for their preparation and application in treating microbial infections and disinfecting surfaces and medical devices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If chlorinating agents are used as antimicrobial agents, then antimicrobial efficacy is improved, but toxicity to mammalian cells increases

Engineering Contradiction:
Improveantimicrobial efficacyVSAvoidtoxicity to mammalian cells
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of N-halogenated compounds through specific substituents (A1, A2, R1, R2, R3 groups) and halogenation patterns to alter the balance between antimicrobial efficacy and mammalian cell toxicity. By systematically varying these chemical parameters, the invention achieves compounds with improved therapeutic index.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs local quality by introducing specific functional groups and substituents at particular positions in the molecular structure (indicated by the detailed variable definitions in Formula I). This localized modification of molecular regions allows selective enhancement of antimicrobial activity while minimizing toxicity to mammalian cells.

Inventive Principle:
Principle #3Local quality

2Adaptability or versatility

If broad-spectrum disinfectant properties are achieved, then antimicrobial coverage is improved, but selectivity against mammalian cells deteriorates

Engineering Contradiction:
Improveantimicrobial coverageVSAvoidlack of selectivity
Core Design Contradiction:
Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

The patent uses parameter changes to achieve broad-spectrum antimicrobial activity while maintaining selectivity. The detailed structural parameters (n, m, Z1, Z2, Y, X, A1, A2, R1, R2, R3) provide multiple degrees of freedom for optimizing the compound's interaction with different microbial targets while preserving mammalian cell selectivity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent achieves universality by designing compounds with broad-spectrum antimicrobial activity against bacteria, fungi, and viruses while simultaneously maintaining selectivity for microbial targets over mammalian cells. The versatile molecular framework can target multiple types of microorganisms through different mechanisms.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Data Source

PatentUS8278482B2Antimicrobial N-chlorinated compositions
Publication Date: 2012.10.02 NOVABAY PHARMACEUTICALS INC
  • US8278482B2 patent drawing
  • US8278482B2 patent drawing
  • US8278482B2 patent drawing

AI summary

The present application relates to N-chlorinated cationic compounds of Formula Ior a salt thereof, and associated compositions and methods of use as antimicrobial agents.