Amide Substituted Imidazoquinoline Compounds for Immune Response Modulation

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Solution Overview

Problem

Current immune response modifiers (IRMs) lack effective compounds that can induce cytokine biosynthesis and modulate the immune response for treating viral diseases and tumors, and there is a need for new vaccine adjuvants with enhanced immunomodulatory capabilities.

Innovation Solution

Development of new compounds of Formula I and Formula VI, which are immune response modifiers that induce cytokine biosynthesis and can be used as vaccine adjuvants, comprising specific structural elements such as R, R1, R2, R3, R4, X, and n, and their pharmaceutically acceptable salts, for administering to humans or animals to treat viral and neoplastic diseases.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing immune response modifiers are used, then immune modulation is achieved, but effective cytokine biosynthesis induction is lacking

Engineering Contradiction:

Improveimmune modulation effectivenessVSAvoidcytokine biosynthesis induction

Core Design Contradiction:

ReliabilityVSQuantity of substance

Solution Approach 1:

The patent modifies the chemical structure of existing imidazo[4,5-c]quinoline compounds by introducing specific substituent patterns (R1, R2, R3, R4 groups) and linkage variations (X, n parameters) to enhance cytokine biosynthesis induction while maintaining immune response modification capabilities

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates composite chemical structures combining the core imidazo[4,5-c]quinoline scaffold with various amide-substituted side chains and branched chain linking groups, resulting in compounds that simultaneously achieve immune modulation and cytokine induction

Inventive Principle:

Principle #40Composite materials

2Reliability

If new compounds with enhanced immunomodulatory capabilities are developed, then vaccine adjuvant effectiveness is improved, but compound structural complexity increases

Engineering Contradiction:

Improvevaccine adjuvant effectivenessVSAvoidcompound structural complexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The patent divides the molecule into distinct functional segments: a core imidazo[4,5-c]quinoline pharmacophore, amide-substituted side chains with specific R groups, and branched chain linking groups, allowing systematic optimization of each segment's contribution to immunomodulatory activity

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The invention introduces specific local structural features (R1, R2, R3, R4 substituents and X linkages) at particular positions on the core scaffold to enhance vaccine adjuvant effectiveness without requiring complete redesign of the entire molecular structure

Inventive Principle:

Principle #3Local quality

Data Source

PatentUS11306083B2Amide substituted imidazo[4,5-C]quinoline compounds with a branched chain linking group for use as an immune response modifier

Publication Date: 2022.04.19 SOLVENTUM INTELLECTUAL PROPERTIES CO

AI summary

Imidazo[4,5-c]quinoline compounds having an alkylamide substituent that is attached at the N-1 position by a branched chain linking group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in humans and animals, and in the treatment of diseases including infectious and neoplastic diseases are also disclosed. Formula (I):