S1P Receptor Agonists via Local Quality Modifications

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Solution Overview

Problem

There is a need for novel, potent, and selective agonists of the S1P receptor with enhanced potency, selectivity, and oral bioavailability, as well as methods for their identification and synthesis.

Innovation Solution

The development of a compound of formula (I) with specific structural features, including various functional groups and bonds, which can act as a pharmaceutically acceptable salt or prodrug, and a method for its synthesis involving the use of a compound with a cycloalkyl or heterocyclyl group, to provide agonism of sphingosine 1-phosphate receptors for therapeutic applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing S1P agonists are used, then receptor activation is achieved, but potency and selectivity are insufficient

Engineering Contradiction:
Improvereceptor activation reliabilityVSAvoidpotency and selectivity
Core Design Contradiction:
ReliabilityVSMeasurement precision

Solution Approach 1:

The patent applies local quality by modifying specific regions of the S1P molecule structure. The compound features a sphingosine backbone with specific substitutions at defined positions (e.g., hydroxyl groups, amino groups, and side chains) to enhance binding affinity and selectivity for particular S1P receptor subtypes while maintaining overall receptor activation capability

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 functional group configurations in the S1P analog structure. These parameter modifications optimize the balance between potency (receptor binding strength) and selectivity (preference for specific receptor subtypes)

Inventive Principle:
Principle #35Parameter changes

2Reliability

If S1P agonist activity is enhanced, then therapeutic efficacy is improved, but oral bioavailability may be compromised

Engineering Contradiction:
Improvetherapeutic efficacyVSAvoidoral bioavailability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by modifying physicochemical properties of the S1P analog, such as adding polar groups or adjusting molecular weight, to improve oral bioavailability while preserving the core pharmacophore necessary for S1P receptor activation and therapeutic efficacy

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses intermediary structures such as prodrug moieties or solubilizing groups that facilitate oral absorption and distribution of the active compound, allowing the potent S1P agonist to reach its target receptors effectively after oral administration

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentEP2364089B1Heterobicyclic sphingosine 1-phosphate analogs
Publication Date: 2016.12.07 BIOGEN MA INC
  • EP2364089B1 patent drawingFigure 1~2
  • EP2364089B1 patent drawingFigure 3~4
  • EP2364089B1 patent drawingFigure 5~6

AI summary

Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.