Antibacterial Compounds with Aromatic Unit and Anionic Group

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Solution Overview

Problem

The rise of antibiotic-resistant bacteria necessitates the development of new antibacterial agents that can effectively target both Gram-positive and Gram-negative bacteria without easily inducing resistance, as existing antibiotics have limited new classes since the 1960s and struggle with Gram-negative bacteria in particular.

Innovation Solution

Development of a new class of antibacterial compounds with an aromatic unit and an oxygen-containing anionic group, designed to facilitate bactericidal activity against Gram-positive bacteria and bacteriostatic activity against Gram-negative bacteria, using a simplified one-pot synthesis method to enable easy modification and reduce the risk of resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing antibiotics are used, then they have been available since the 1940s-1960s, but they struggle with Gram-negative bacteria and antibiotic-resistant bacteria have emerged

Engineering Contradiction:
Improveantibacterial effectivenessVSAvoidantibiotic resistance
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of antibacterial compounds to create a new class with a fundamentally different core structure from known antibiotics. The specific parameters changed include the core aromatic structure, substitution patterns, and functional groups to achieve novel mechanisms of action that bypass existing resistance mechanisms while maintaining effectiveness against both Gram-positive and Gram-negative bacteria

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by combining multiple structural elements into a new antibacterial compound class. The compounds integrate a core aromatic structure with specific substitution patterns and functional groups, creating a composite molecular architecture that provides both broad-spectrum activity and novel resistance profiles distinct from existing antibiotics

Inventive Principle:
Principle #40Composite materials

2Reliability

If new classes of antibiotics are developed, then they can target bacteria via new mechanisms, but the synthesis process becomes complex and time-consuming

Engineering Contradiction:
Improvenovel antibacterial mechanismVSAvoidsynthesis process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the synthesis into modular stages with clearly defined intermediate structures. The multi-step synthesis process is organized into discrete transformations that build the complex molecular architecture systematically, allowing for easier optimization and scaling while maintaining the novel structural features required for new antibacterial mechanisms

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs preliminary action by preparing and characterizing intermediate compounds in advance of the final assembly. This approach allows for optimization of each synthetic step independently, ensures availability of pure intermediates for structure-activity relationship studies, and facilitates scaling by establishing reliable preparative procedures before final compound production

Inventive Principle:
Principle #10Preliminary action

3Adaptability or versatility

If comprehensive structural modification is performed to investigate antimicrobial properties, then activity against different bacteria can be assessed, but preparation time and cost increase

Engineering Contradiction:
Improveantimicrobial activity rangeVSAvoidpreparation time
Core Design Contradiction:
Adaptability or versatilityVSLoss of time

Solution Approach 1:

The patent applies segmentation by organizing structural modifications into systematic series that vary one parameter at a time while keeping others constant. This modular approach to structure-activity relationship studies allows efficient assessment of antimicrobial properties across different bacterial targets while reducing redundant synthesis and enabling focused investigation of structure-function relationships

Inventive Principle:
Principle #1Segmentation

Data Source

PatentUS11701333B2Antibacterial compounds
Publication Date: 2023.07.18 KENT INNOVATION & ENTERPRISE UNIV OF KENT
  • US11701333B2 patent drawing
  • US11701333B2 patent drawing
  • US11701333B2 patent drawing

AI summary

The present invention relates to certain compounds of formula (I) wherein—Ar is (Ar1) or (Ar2) and to their uses as antibacterial agents. The invention further relates to methods of treatment of bacterial infection with such compounds, optionally in combination with other antimicrobials and to compositions and pharmaceutical formulations containing such compounds. The invention additionally relates to coatings containing such compounds and to items having such coatings.