Cyclic Peptide Alpha4beta7 Integrin Antagonists

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Solution Overview

Problem

There is a need for improved α4β7 antagonists to effectively prevent or treat inflammatory and autoimmune diseases, as existing methods may not provide sufficient therapeutic benefits for conditions like Crohn's disease and ulcerative colitis.

Innovation Solution

Development of cyclic peptide compounds with specific structural formulas that inhibit α4β7 integrin, allowing for pharmaceutical compositions that can be administered orally, topically, or parenterally, exhibiting antagonistic activity against α4β7 integrin with selectivity over α4β1 integrin.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If monoclonal antibodies are used as α4β7 inhibitors, then therapeutic benefits are achieved for gastrointestinal diseases, but device complexity and manufacturing difficulty increase

Engineering Contradiction:
Improvetherapeutic benefitVSAvoidcomplexity of inhibitor structure
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent changes the molecular structure parameters from monoclonal antibodies to cyclic peptides with specific amino acid sequences and modifications (R1-R6 substituents), achieving simplified structure while maintaining therapeutic efficacy against α4β7 integrin for gastrointestinal diseases

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs small molecular weight cyclic peptide compounds that can be orally administered, replacing complex monoclonal antibodies with simpler, more manufacturable peptide-based inhibitors that maintain therapeutic effectiveness

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Reliability

If conventional α4β7 antagonists are used, then inflammatory conditions are treated, but manufacturing precision and synthesis difficulty increase

Engineering Contradiction:
Improveantiinflammatory activityVSAvoidsynthesis precision
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent divides the peptide into modular components with defined amino acid sequences (Ile-Leu-Asp-Val core) and variable substituents (R1-R6), enabling systematic synthesis and precise control over molecular structure while maintaining antiinflammatory activity

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent establishes specific structural parameters including cyclic peptide configuration, amino acid sequences, and substituent patterns that facilitate standardized synthesis procedures and improve manufacturing precision while preserving therapeutic activity

Inventive Principle:
Principle #35Parameter changes

3Reliability

If peptide inhibitors are developed, then selectivity over α4β1 integrin is achieved, but loss of time in development increases

Engineering Contradiction:
ImproveselectivityVSAvoiddevelopment time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent performs preliminary structural optimization and selectivity testing during the design phase, establishing the cyclic peptide framework with specific amino acid sequences before clinical development, thereby reducing later-stage development time while maintaining selectivity over α4β1 integrin

Inventive Principle:
Principle #10Preliminary action

Data Source

PatentEP3387004B1Cyclic peptides targeting alpha4 beta7 integrin
Publication Date: 2021.10.06 ZEALAND PHARMA AS
  • EP3387004B1 patent drawingFigure 1
  • EP3387004B1 patent drawingFigure 2
  • EP3387004B1 patent drawingFigure 3

AI summary

There is described herein antagonists of α4β7 integrin, and more particularly to cyclic peptide antagonists. Accordingly, there is described herein a compound of formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and R8 are various substituents; stereocentres 1*, 2* and 3* are each independently selected from R and S; n is 1, 2, 3, or 4 and where n is 2-4, Z is an amino terminus of an amino acid; -C=0- adjacent L is the carboxy terminus of an amino acid; and L along with Z and -C=0- is a peptide.