Sulfonamide Crystal Forms for Stability and Anti-Agglomeration

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Solution Overview

Problem

Existing crystal forms of the sulfonamide derivative N-(5-((1H-pyrazol-1-yl)methyl)-3,4-dihydro-2H-benzopyran[8,7-d]isoxazol-9-yl)-2,6-dimethoxybenzenesulfonamide exhibit poor stability and agglomeration, posing challenges in production and storage, and require improved polymorphs for better clinical efficacy.

Innovation Solution

Development of six distinct crystal forms (A, B, C, D, E, F, G, and H) characterized by specific X-ray powder diffraction patterns, each prepared through various solvent-based crystallization methods, including trituration, stirring, and antisolvent crystallization, to enhance stability and clinical prospects.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If amorphous drug products are used, then the compound can be obtained without crystallization, but the product stability is poor and agglomeration occurs

Engineering Contradiction:
Improvecrystallization processVSAvoidproduct stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies parameter changes by systematically varying crystallization conditions including solvent type (water, organic solvents), temperature (room temperature, refrigeration, heating), and concentration to obtain different crystal forms with improved stability. This resolves the contradiction by transforming the amorphous product into structured crystal forms through controlled parameter changes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions by inducing crystallization from amorphous or dissolved states to ordered crystal structures. The transformation from amorphous compound to crystalline forms (Forms I-X) through controlled crystallization processes eliminates agglomeration and improves product stability while maintaining manufacturability.

Inventive Principle:
Principle #36Phase transitions

2Manufacturing precision

If conventional crystallization conditions are used, then the compound can be crystallized, but fine particles are generated and filtration is difficult

Engineering Contradiction:
Improvecrystal form structureVSAvoidfiltration process
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent optimizes crystallization parameters including solvent selection, temperature control, and concentration to produce crystal forms with appropriate particle size and morphology. This enables easier filtration while maintaining defined crystal structures, resolving the contradiction between manufacturing precision and ease of manufacture.

Inventive Principle:
Principle #35Parameter changes

3Duration of action of stationary object

If crystal form variations occur due to storage conditions, then the compound can be stored, but other crystal forms are generated causing product inconsistency

Engineering Contradiction:
Improvestorage periodVSAvoidcrystal form consistency
Core Design Contradiction:
Duration of action of stationary objectVSStability of the object's composition

Solution Approach 1:

The patent employs preliminary action by pre-selecting and characterizing stable crystal forms (Forms I-X) that are resistant to polymorphic transformation during storage. By establishing the most stable crystal forms beforehand and optimizing storage conditions, the patent prevents generation of other crystal forms during the storage period, ensuring product consistency.

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 new crystal forms exhibit improved stability and flowability, addressing the issues of agglomeration and enhancing the drug's suitability for pharmaceutical applications, particularly in the treatment of cancers such as breast, ovarian, pancreatic, and lung cancer.

Implementation Method 1

adding the compound of formula 1 to a solvent (I), and triturating for crystallization

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 2

an X-ray powder diffraction pattern represented by diffraction angles 2θ having characteristic peaks

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Data Source

PatentEP4663635A1Crystalline form of sulfonamide derivative and preparation method therefor
Publication Date: 2025.12.17 JIANGSU HENGRUI MEDICINE CO LTD
  • EP4663635A1 patent drawingFigure 1~2
  • EP4663635A1 patent drawingFigure 3~4
  • EP4663635A1 patent drawingFigure 5~6

AI summary

The present disclosure relates to a crystalline form of a sulfonamide derivative and a preparation method therefor. Specifically, the present disclosure provides a new crystalline form of a compound as represented by formula (1) and a preparation method therefor.