9-Substituted-8-Oxoadenine Compounds for TLR7 Modulation

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Solution Overview

Problem

Current immunomodulators for treating viral and allergic diseases, as well as cancers, have limitations in specificity and efficacy, particularly in modulating TLR7 activity effectively.

Innovation Solution

Development of 9-substituted-8-oxoadenine compounds with specific structural modifications that act via TLR7, allowing for targeted immune modulation in treating viral, allergic, and cancerous conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current immunomodulators are used to treat viral and allergic diseases and cancers, then therapeutic coverage is provided, but specificity and efficacy in modulating TLR7 activity are limited

Engineering Contradiction:
ImprovespecificityVSAvoidTLR7 modulation capability
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies local quality by introducing specific substituents at defined positions on the adenine core structure. The 9-substituted-8-oxoadenine framework with specific R1 groups (hydroxyl, alkoxy, alkoxycarbonyl, aryl, heteroaryl, or cycloalkyl) creates localized functional modifications that enhance TLR7 binding affinity and selectivity, thereby improving both specificity and modulation capability simultaneously

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by systematically varying the chemical structure parameters of the immunomodulators. By modifying the R1 substituent types, Y1 linker lengths, and X1 atom identities (O, S, or NR4), the patent optimizes molecular properties to achieve superior TLR7 activity while maintaining the desired therapeutic effects for viral, allergic, and cancer treatments

Inventive Principle:
Principle #35Parameter changes

2Reliability

If 9-substituted-8-oxoadenine compounds are developed with specific structural modifications, then TLR7 modulating activity is enhanced, but structural complexity increases

Engineering Contradiction:
ImproveTLR7 modulating activityVSAvoidstructural complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the immunomodulator into distinct functional modules: a core 8-oxoadenine structure, variable R1 substituents at the 9-position, and optional Y1 linkers. This modular architecture allows systematic optimization of TLR7 activity through targeted modifications of individual segments while maintaining overall structural manageability

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent achieves universality by designing a core adenine structure that serves multiple functions: it provides the essential immunomodulatory activity, allows for diverse substituent attachment (R1 groups), and maintains pharmacokinetic properties. This multi-functional core structure enables the compounds to address multiple therapeutic indications (viral, allergic, and cancer diseases) without proportionally increasing complexity

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

Data Source

PatentEP2132209B89-substituted-8-oxo-adenine compounds as toll-like receptor (TLR7 ) modulators
Publication Date: 2014.04.16 ASTRAZENECA AB

AI summary

The present invention provides compounds of formula (I): wherein R1, Y1, X1, L and R2 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 as modulation of toll-like receptor (especially TLR7).