Crystalline TLR-8 Modulator Solid Forms

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Solution Overview

Problem

There is a need for potent and selective modulators of Toll-like receptor 8 (TLR-8) with reduced off-target liabilities to effectively treat various diseases involving autoimmunity, inflammation, and viral infections, as existing modulators may have unwanted side effects.

Innovation Solution

The development of crystalline forms of (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol gentisic acid, hippuric acid, and succinic acid, characterized by specific X-ray powder diffraction patterns, which serve as novel modulators of TLR-8, potentially offering improved therapeutic efficacy with minimized off-target effects.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing TLR-8 modulators are used to stimulate immune response, then therapeutic benefit is achieved, but off-target liabilities and unwanted side effects occur

Engineering Contradiction:
Improvetherapeutic benefitVSAvoidoff-target liabilities
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by developing new chemical compounds with modified molecular structures (diamino pyrido[3,2-d]pyrimidine core with specific substituents) to achieve selective TLR-8 modulation. The structural parameters including R1-R6 groups, X1-X6 linkers, and Y1-Y6 substituents are optimized to enhance TLR-8 binding affinity while reducing off-target interactions, thereby improving therapeutic reliability without increasing harmful effects

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements local quality by introducing specific functional groups and structural features at particular positions on the pyrido[3,2-d]pyrimidine core. The differentiated substitution patterns at R1-R6 positions and the specific configurations of X1-X6 and Y1-Y6 groups create localized interaction zones that selectively engage TLR-8 receptors, enabling potent immune stimulation with minimized off-target liabilities

Inventive Principle:
Principle #3Local quality

2Productivity

If TLR-8 activation is enhanced to treat viral infections and autoimmune diseases, then immune response is improved, but selectivity and reduced side effects become challenging

Engineering Contradiction:
Improveimmune responseVSAvoidmolecular selectivity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the TLR-8 modulator into distinct functional modules: the pyrido[3,2-d]pyrimidine core structure, R1-R6 substituent groups, X1-X6 linker regions, and Y1-Y6 terminal groups. Each segment contributes specific binding interactions with TLR-8, allowing the molecule to achieve high affinity and selectivity through modular assembly, thereby enhancing immune response while maintaining molecular selectivity

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent implements composite materials by creating hybrid molecular structures that combine the pyrido[3,2-d]pyrimidine scaffold with diverse substituent combinations. The composite nature of these compounds, integrating multiple functional groups and structural elements, enables simultaneous optimization of TLR-8 binding affinity, selectivity, and pharmacological properties, achieving enhanced immune response with reduced complexity challenges

Inventive Principle:
Principle #40Composite materials

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

These crystalline forms provide effective modulation of TLR-8, enhancing immune responses and treating conditions like hepatitis B, HIV, and other immune-related disorders with reduced off-target liabilities, thereby improving treatment outcomes.

Implementation Method 1

characterized by an X-ray powder diffraction (XRPD) pattern comprising three or more peaks at 4.4°, 8.7°, 12.9°, 14.9°, 17.3°, 19.5°, 24.8°, 25.7°, or 26.3° 2θ (± 0.2° 2θ), Compound I gentisic acid

Methodology Applied
Scientific EffectX-ray powder diffraction: X-Ray

Data Source

PatentEP3956329B9Solid forms of a toll-like receptor modulator
Publication Date: 2024.04.17 GILEAD SCIENCES INC
  • EP3956329B9 patent drawingFigure 1
  • EP3956329B9 patent drawingFigure 2~3
  • EP3956329B9 patent drawingFigure 4~5

AI summary

The present disclosure provides solid forms, solvates and hydrates of (R)-2-((2- amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-l-ol, and methods of making.