Pyrimidine Derivatives for Selective TLR7 Activation

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Solution Overview

Problem

Current immunomodulatory agents targeting toll-like receptors (TLRs) have limitations in effectively treating viral or allergic diseases and cancers, as they may not specifically activate TLR7, a crucial receptor for modulating immune responses.

Innovation Solution

Development of a class of pyrimidine derivatives that act via TLR7, characterized by specific structural formulas, allowing for the modulation of immune responses in treating viral, allergic, and cancerous conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current immunomodulatory agents targeting TLRs are used, then immune response modulation is achieved, but specificity for TLR7 activation is insufficient

Engineering Contradiction:
Improvespecificity of TLR7 activationVSAvoidbroad immune response modulation
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies local quality by designing pyrimidine derivatives with specific structural features (substituents at positions 4, 5, and 6 of the pyrimidine ring) that are optimized for TLR7 binding. The molecular structure incorporates specific functional groups (such as amino, hydroxyl, and alkyl groups) at defined positions to enhance affinity and selectivity for TLR7 while maintaining the ability to modulate immune responses.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by systematically varying molecular parameters of the pyrimidine derivatives, including substituent types (halogen, hydroxyl, methyl, cyano, trifluoromethyl, S(O)h-methyl, methoxy groups), chain lengths (m=1 or 2, j=1 or 2), and functional group configurations. These parameter variations enable optimization of TLR7 binding affinity and specificity while preserving broad immune modulatory capabilities.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If pyrimidine derivatives with specific structural formulas are developed, then TLR7 activation specificity is improved, but molecular complexity increases

Engineering Contradiction:
Improvespecificity of TLR7 activationVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the pyrimidine derivative structure into distinct functional segments: the core pyrimidine ring (positions 4, 5, 6), substituent groups (R1, R3, R5, R5a, R6, R7), and linkage elements (Z1, Y1). This modular segmentation allows for systematic optimization of TLR7 binding while maintaining synthetic feasibility and manageable molecular complexity.

Inventive Principle:
Principle #1Segmentation

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The pyrimidine derivatives effectively modulate immune responses by activating TLR7, providing therapeutic benefits in treating viral, allergic, and cancerous conditions, enhancing cytokine production and immune function.

Implementation Method 1

The pyrimidine derivatives effectively modulate immune responses by activating TLR7, providing therapeutic benefits in treating viral, allergic, and cancerous conditions, enhancing cytokine production and immune function.

Methodology Applied
Scientific EffectToll-like receptor activation:

Data Source

PatentEP2222648B1Pyrimidine derivatives for the treatment of asthma, COPD, allergic rhinitis, allergic conjunctivitis, atopic dermatitis, cancer, hepatitis b, hepatitis c, HIV, HPV, bacterial infections and dermatosis
Publication Date: 2013.01.09 ASTRAZENECA AB
  • EP2222648B1 patent drawingFigure 1A
  • EP2222648B1 patent drawingFigure 1B
  • EP2222648B1 patent drawing

AI summary

The present invention provides compounds of formula (I) wherein R 1, R2, R3 and R4 are as defined in the specification, and pharmaceutically acceptable salts thereof, as well as processes for their preparation, pharmaceutical compositions containing them and their use in therapy.