TRPA1 Modulators Potency Metabolic Stability

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Solution Overview

Problem

Current TRPA1 modulators lack enhanced potency, metabolic stability, and solubility, which are essential for effective treatment of TRPA1-mediated disorders.

Innovation Solution

Development of novel TRPA1 modulators with specific structural formulas, such as 5-fluoro-N-(2-methylbut-3-yn-2-yl)-2-(3,3,3-trifluoropropylamino)nicotinamide, that improve potency and metabolic stability, and offer improved solubility, as part of pharmaceutical compositions for treating TRPA1-related diseases.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current TRPA1 modulators are used, then treatment of TRPA1-mediated disorders is achieved, but potency, metabolic stability, and solubility are insufficient

Engineering Contradiction:
ImprovepotencyVSAvoidmetabolic stability
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by systematically modifying chemical structures of TRPA1 modulators through varying substituents (R1-R6) at different positions on the core molecular framework. This includes changing atomic composition (fluorine, chlorine, methyl groups), molecular weight, and spatial arrangement to optimize the balance between potency, metabolic stability, and solubility parameters simultaneously

Inventive Principle:
Principle #35Parameter changes

2Reliability

If current TRPA1 modulators are used, then treatment of TRPA1-mediated disorders is achieved, but solubility is insufficient

Engineering Contradiction:
ImproveeffectivenessVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies local quality by introducing specific functional groups and substituents at particular positions on the molecular structure (e.g., fluorine at R4 or R5 positions, methyl groups at R1-R3 positions) to locally modify properties such as polarity, hydrogen bonding capacity, and hydrophobicity, thereby improving overall solubility while maintaining target binding effectiveness

Inventive Principle:
Principle #3Local quality

Data Source

PatentEP2903965B1N-prop-2-ynyl carboxamide derivatives and their use as TRPA1 antagonists
Publication Date: 2017.03.01 ORION CORP(FI)

AI summary

Compounds of formula I, wherein A, B, X, Z and R1-R6, are as defined in the claims, exhibit TRPA 1 activity and are thus useful as TRPA1 modulators.