Stable Crystal Form I for 1,4-Bisbenzisoselenazolone Butane

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Solution Overview

Problem

Existing crystalline forms of 1,4-bis[1,2-benzisoselenazol-3(2H)-one]-butane lack stability and uniformity, affecting the solubility, bioavailability, and efficacy of drugs used for treating fibrosis and inflammatory diseases, particularly liver cancer.

Innovation Solution

Development of a crystalline form I with specific X-ray diffraction peaks and monoclinic monocrystalline properties, prepared by dissolving the compound in solvents like DMSO and adding antisolvents such as water or acetonitrile, ensuring stability and high solubility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing crystalline forms are used, then the compound can be applied in medicaments, but the lack of stability and uniformity affects solubility, bioavailability, and efficacy

Engineering Contradiction:
ImprovestabilityVSAvoiduniformity
Core Design Contradiction:
ReliabilityVSDifficulty of detecting and measuring

Solution Approach 1:

The patent applies parameter changes by systematically varying crystallization conditions including solvent type (DMSO, ethanol, isopropanol, acetonitrile), temperature (4°C, room temperature, refrigeration), and concentration to obtain different crystalline forms with distinct stability and uniformity characteristics. This allows selection of optimal crystalline form parameters for reliable drug performance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions through controlled crystallization processes where the compound transitions from solution phase to solid crystalline phase. By controlling cooling rates, solvent evaporation, and crystallization temperature, the patent achieves uniform crystalline structures with improved stability and predictable bioavailability

Inventive Principle:
Principle #36Phase transitions

2Ease of operation

If different crystalline forms are developed, then solubility and bioavailability can be improved, but the complexity of identifying and characterizing stable forms increases

Engineering Contradiction:
ImprovesolubilityVSAvoidcrystalline form characterization
Core Design Contradiction:
Ease of operationVSDevice complexity

Solution Approach 1:

The patent employs X-ray diffraction (XRD) technology to replace complex manual characterization methods. The XRD system automatically identifies crystalline forms through diffraction patterns, providing rapid and accurate characterization of solubility-related crystalline properties without requiring complex manual analysis

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

Solution Approach 2:

The patent creates reference crystalline forms with characterized properties that serve as templates for future developments. Once a crystalline form with desirable solubility is identified and characterized, it can be replicated using the same crystallization parameters, simplifying subsequent work without requiring re-characterization

Inventive Principle:
Principle #26Copying

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 form I exhibits good stability, high solubility, reasonable bioavailability, and excellent tumor inhibitory activity, particularly against HBV-associated liver cancer, with improved therapeutic activity and safety for pharmaceutical use.

Implementation Method 1

dissolving 1,4-bis[1,2-benzisoselenazol-3(2H)-one]-butane in a solvent S1, and adding an antisolvent S2 to give the crystalline form I

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 2

having characteristic peaks at 2θ angles of 6.15±0.20°, 12.28±0.20°, 18.44±0.20°, 19.09±0.20°, 22.20±0.20°, 23.68±0.20°, 25.92±0.20°, 30.95±0.20° and 32.45±0.20° by X-ray powder diffraction using Cu-Kα radiation

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Data Source

PatentEP3974418B1Crystal form of 1,4-[bis(1,2-benzisoselenazol-3(2H)-one)]butane, preparation method therefor, and application thereof
Publication Date: 2025.12.10 SHANGHAI YUANXI MEDICINE CORP
  • EP3974418B1 patent drawingFigure 1~2
  • EP3974418B1 patent drawingFigure 3~4
  • EP3974418B1 patent drawingFigure 5~6

AI summary

Disclosed herein is a crystalline form I of 1,4-BIS[1,2-BENZISOSELENAZOL-3(2H)-one]-butane having characteristic peaks at 2θ angles of 6.17±0.20°, 12.28±0.20°, 18.44±0.20°, 25.92±0.20° and 30.95±0.20° by X-ray powder diffraction using Cu-Kα radiation. The crystalline form has good stability, is not susceptible to polymorphic transition, is beneficial to the preparation, use, shipping and preservation of pharmaceutical compositions and preparations, and fully ensures the safety of medication and the quality of medicaments. In addition, the crystalline form features high solubility, reasonable bioavailability, low toxicity and excellent tumor inhibitory activity.