Crystalline AT2R Antagonist Salt Forms for Chronic Pain

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Solution Overview

Problem

Current AT2R antagonists for treating chronic pain lack stable and effective crystalline forms with optimal pharmacokinetic properties, which affects their biological activity and stability.

Innovation Solution

Development of specific crystalline forms 'A' and 'B' of a compound with defined X-ray powder diffraction patterns and thermal analysis profiles, prepared through controlled solvent mixtures and temperature conditions, enhancing stability and biological activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If AT2R antagonists are developed for treating chronic pain, then biological activity is improved, but stability and pharmacokinetic properties deteriorate due to lack of optimal crystalline forms

Engineering Contradiction:
Improvebiological activityVSAvoidstability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by discovering and characterizing different crystalline forms (Form A, Form B, and solvates) of the AT2R antagonist compound. Each crystalline form has distinct X-ray powder diffraction patterns, thermal properties, and stability characteristics. By changing the crystalline state parameter of the compound, the patent achieves both high biological activity and improved stability, resolving the technical contradiction between these two properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent develops composite crystalline structures by forming specific crystal lattices with defined molecular arrangements. The crystalline forms represent composite structures where the active pharmaceutical ingredient is organized in specific spatial configurations, resulting in enhanced stability while maintaining biological activity. This is evidenced by the distinct diffraction patterns and thermal properties of each crystalline form.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If crystalline forms are developed to improve stability, then pharmacokinetic properties are improved, but manufacturing complexity increases due to controlled solvent mixtures and temperature conditions

Engineering Contradiction:
ImprovestabilityVSAvoidmanufacturing complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent utilizes phase transitions by controlling the crystallization process from solution to solid state. By adjusting solvent composition (acetone-water mixtures at specific volume ratios) and temperature (30-50°C range), the patent directs the formation of specific crystalline phases with desired stability properties. The phase transition from dissolved state to crystalline state enables control over the final product's stability while providing reproducible manufacturing conditions.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The patent changes physical parameters during manufacturing, specifically temperature (30-50°C) and solvent composition (acetone-water volume ratios), to control crystalline form formation. These parameter changes enable the production of stable crystalline forms with defined characteristics while maintaining manageable manufacturing complexity through well-defined process conditions.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If specific crystalline forms are prepared through controlled solvent mixtures and temperature conditions, then stability and biological activity are enhanced, but production time increases due to extended stirring periods

Engineering Contradiction:
Improvebiological activityVSAvoidproduction time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent employs phase transition during crystallization to achieve the desired crystalline forms. By controlling the transition from solution to solid crystalline phase through temperature adjustment (30-50°C) and solvent composition, the patent enhances both stability and biological activity. The extended stirring time (10-30 hours) facilitates complete phase transition and uniform crystal formation, ensuring high product quality.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The patent applies preliminary action by conducting extended stirring (10-30 hours) at controlled temperatures before filtration and drying. This preliminary crystallization step ensures complete formation of the desired crystalline structure and uniform distribution of crystal particles, which is essential for achieving high biological activity and stability in the final product.

Inventive Principle:
Principle #10Preliminary action

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

The crystalline forms exhibit good biological activity, stability, and weak hygroscopicity, improving pharmacokinetic properties and effectiveness in treating chronic pain.

Implementation Method 1

an X-ray powder diffraction pattern of the crystalline form 'A' using Cu-Kα radiation with λ=1.54056Å has characteristic diffraction peaks

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

Implementation Method 2

The present disclosure provides a crystalline form 'A' of a compound represented by formula (I)

Methodology Applied
Scientific EffectCrystallisation: Crystallisation

Implementation Method 3

a differential scanning calorimetry curve of the crystalline form 'A' has an endothermic peak starting at 155.36°C±3°C

Methodology Applied
Scientific EffectMelting: Melting

Implementation Method 4

a differential scanning calorimetry curve of the crystalline form 'A' has an endothermic peak

Methodology Applied
Scientific EffectDifferential scanning calorimetry: Calorimetry

Implementation Method 5

a thermal gravimetric analysis curve of the crystalline form 'A' has a weight loss of 0.1489% at 100.00°C±3°C

Methodology Applied
Scientific EffectThermal gravimetric analysis:

Data Source

PatentEP3819293B1Angiotensin ii receptor 2 antagonist salt form and crystalline form, and preparation method therefor
Publication Date: 2023.03.29 SHANDONG DANHONG PHARMA
  • EP3819293B1 patent drawingFigure 1~2
  • EP3819293B1 patent drawingFigure 3~4
  • EP3819293B1 patent drawingFigure 5~6

AI summary

Disclosed are an angiotensin II receptor 2 (AT2R) antagonist salt form and crystalline form, a preparation method therefor, and an application of the salt form and crystalline form in preparing a drug which treats chronic pain.