CB2 Receptor Selective Modulators via Local Quality Structural Design

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Solution Overview

Problem

Current CB2 receptor agonists often exhibit significant CB1 activity, leading to adverse effects, and there is a need for compounds that selectively activate the CB2 receptor with minimized CB1 activity for therapeutic applications such as inflammation and pain treatment.

Innovation Solution

Development of novel compounds with specific structural features that bind to the CB2 receptor, reducing CB1 activity, including specific alkyl, cycloalkyl, and heterocyclic substitutions, and their use in pharmaceutical compositions for therapeutic administration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If CB2 receptor agonist compounds are used to treat inflammation and pain, then therapeutic benefits are achieved, but CB1 receptor activation occurs causing adverse effects

Engineering Contradiction:
Improvetherapeutic efficacyVSAvoidadverse effects from CB1 activation
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies local quality by introducing specific substituents at particular positions on the cannabinoid molecule structure. Different substituents (R1-R10) are placed at specific locations to modulate receptor selectivity, ensuring the compound interacts preferentially with CB2 over CB1 receptors while maintaining therapeutic efficacy.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by systematically varying chemical parameters such as substituent types, chain lengths, and molecular weight within specific ranges. These parameter adjustments optimize the compound's receptor binding profile to achieve high CB2 selectivity while minimizing CB1 activation, directly resolving the technical contradiction.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If dual CB1/CB2 agonists are used, then both CB1 and CB2 effects are achieved, but adverse effects increase due to lack of selectivity

Engineering Contradiction:
Improvereceptor activity profileVSAvoidadverse effects
Core Design Contradiction:
Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

The patent uses local quality by placing specific functional groups at defined positions on the molecular scaffold. This localized structural modification creates steric and electronic properties that favor CB2 binding over CB1, enabling selective activation without requiring dual agonist activity, thus eliminating adverse effects while maintaining versatility.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent applies inversion by designing compounds that achieve therapeutic effects through selective CB2 activation rather than dual CB1/CB2 activation. This inverted approach reverses the conventional strategy of broad-spectrum cannabinoid activity, demonstrating that selectivity can be achieved through careful structural design rather than requiring multiple receptor interactions.

Inventive Principle:
Principle #13The other way round (Inversion)

Data Source

PatentEP2716635B1Compounds which selectively modulate the CB2 receptor
Publication Date: 2017.02.01 BOEHRINGER INGELHEIM INT GMBH
  • EP2716635B1 patent drawingFigure 1
  • EP2716635B1 patent drawingFigure 2

AI summary

Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.