Glycosylated Hydroxytryptamine Compounds for Serotonin Modulation

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Solution Overview

Problem

There is a need for new compounds that act as modulating agents at serotonin receptors for the prevention and treatment of diseases and disorders such as depression, anxiety, pain, inflammation, addiction, eating disorders, and autoimmune diseases.

Innovation Solution

Development of glycosylated hydroxytryptamine compounds, including 4-HO-MET, 4-HO-MPT, and their analogues, which act on serotonin receptors and can be administered to treat various diseases and disorders by modulating serotonin receptor function.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional serotonin receptor modulators are used, then therapeutic effects are achieved, but side effects and limited efficacy remain

Engineering Contradiction:

Improvetherapeutic efficacyVSAvoidside effects

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of hydroxytryptamine compounds through glycosylation at different positions (4-OH, 5-OH, N-alkyl groups) and using various sugar moieties. This structural parameter modification creates analogues with different pharmacological profiles, enabling optimized therapeutic efficacy and reduced side effects compared to conventional non-glycosylated serotonin modulators

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining hydroxytryptamine core structures with glycosyl groups to form glycosylated analogues. This composite approach integrates the serotonin receptor affinity of the hydroxytryptamine core with the modified pharmacokinetic and pharmacodynamic properties of the glycosylated moiety, achieving improved therapeutic profiles

Inventive Principle:

Principle #40Composite materials

2Reliability

If new glycosylated compounds are developed, then therapeutic benefits are improved, but synthesis complexity increases

Engineering Contradiction:

Improvetherapeutic benefitsVSAvoidsynthesis complexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The synthesis approach segments the glycosylation process into distinct stages: (1) preparation of glycosyl donors with appropriate protecting groups, (2) selective glycosylation of hydroxytryptamine derivatives under controlled conditions, and (3) deprotection to reveal the active glycosylated compound. This segmentation simplifies the overall synthesis by breaking down complex transformations into manageable steps with standardized protocols

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent employs glycosyl donors as intermediary reagents that facilitate the transfer of sugar moieties to hydroxytryptamine derivatives. These intermediaries enable controlled glycosylation through well-established glycosylation chemistry, avoiding the need for complex direct coupling methods and simplifying the synthesis of glycosylated analogues

Inventive Principle:

Principle #24Intermediary (Mediator)

Data Source

PatentUS20250305018A1Synthesis of glycosylated hydroxytryptamine compounds and methods of their use

Publication Date: 2025.10.02 CY BIOPHARMA AG

AI summary

Provided herein is a method of treating a disorder (e.g. depression, anxiety, pain, inflammation, or addiction), or symptoms thereof, by administering an effective amount of a glycosylated hydroxytryptamine compound, such as compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 is a glycosyl group and the other variables are as defined herein. Also provided herein is a method of enzymatically synthesizing the glycosylated hydroxytryptamine compounds.