Spirocyclic Amide Derivatives Dual Receptor Agonist Antagonist

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current treatments for pulmonary disorders like COPD and asthma often require co-administration of muscarinic-receptor antagonists and β-adrenoceptor agonists, which can be cumbersome and may not offer optimal efficacy and side-effect profiles.

Innovation Solution

Development of spirocyclic amide derivatives that act as dual adrenergic β receptor agonists and muscarinic receptor antagonists, providing a single molecule with combined bronchodilator effects to improve lung function and patient compliance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If co-administration of muscarinic-receptor antagonists and β-adrenoceptor agonists is used, then bronchodilator efficacy is improved, but treatment complexity and patient compliance deteriorate

Engineering Contradiction:
Improvebronchodilator efficacyVSAvoidpatient compliance
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent merges two separate therapeutic agents (muscarinic-receptor antagonist and β-adrenoceptor agonist) into a single dual-action molecule. This is achieved by designing a spirocyclic amide derivative structure that contains both pharmacophoric elements: a muscarinic antagonist moiety (typically a quaternary ammonium group) and a β-adrenergic agonist moiety (catecholamine structure with specific substituents), connected through a spirocyclic linker. The single molecule simultaneously binds to both muscarinic receptors and β-adrenoceptors, providing combined bronchodilator effects while simplifying administration to once-daily inhalation.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention creates a universal therapeutic agent that performs multiple functions: it acts as both a muscarinic-receptor antagonist and a β-adrenoceptor agonist within the same molecule. This multi-functionality allows the single compound to address multiple pathophysiological mechanisms in COPD and asthma (vagally-mediated bronchoconstriction and β-adrenergic tone) simultaneously, replacing the need for two separate medications while maintaining or enhancing clinical efficacy.

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

2Adaptability or versatility

If co-administration of two separate compounds is used, then therapeutic coverage is improved, but formulation complexity deteriorates

Engineering Contradiction:
Improvetherapeutic coverageVSAvoidformulation complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent combines two distinct therapeutic compounds into a single molecular entity through chemical synthesis. The dual-action molecule is formulated as a single substance for inhalation, eliminating the need for complex multi-component formulations, combination device assemblies, or coordinated delivery mechanisms required for co-administration of two separate medications.

Inventive Principle:
Principle #5Merging (Combining)

3Ease of operation

If single agent therapy is used, then ease of use is improved, but therapeutic efficacy deteriorates

Engineering Contradiction:
Improveease of useVSAvoidtherapeutic efficacy
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The single agent designed in this patent achieves multi-functionality by incorporating both muscarinic antagonist and β-adrenergic agonist activities within one molecule. This allows the compound to deliver broad therapeutic coverage (addressing multiple bronchoconstriction mechanisms) while maintaining simplicity of use (single inhalation device, once-daily dosing), thereby resolving the trade-off between ease of use and therapeutic efficacy.

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

Data Source

PatentEP2459572B1Spirocyclic amide derivatives
Publication Date: 2018.09.12 ASTRAZENECA AB
  • EP2459572B1 patent drawingFigure 1
  • EP2459572B1 patent drawingFigure 2
  • EP2459572B1 patent drawingFigure 3

AI summary

Spirocyclic amide derivatives of formula (I) wherein ArCH2CH2NH- represents a β-adrenoceptor binding group, processes for their preparation, pharmaceutical compositions containing them, a process for preparing such pharmaceutical compositions, their use in therapy, and intermediates for use in their preparation.