TBN Crystal Form A Stabilization via Solvent Crystallization

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing tetramethylpyrazine nitrone (TBN) formulations lack stability and consistency, leading to potential polymorphism transformations and reduced efficacy in treating neurological and cardiovascular diseases.

Innovation Solution

Development of a specific crystal form A of TBN with characteristic XRPD peaks and a preparation method using solvents like n-hexane and n-heptane, which stabilizes the compound and enhances its solubility and bioavailability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If conventional TBN formulations are used, then the compound can be administered for therapeutic effect, but the formulations lack stability and undergo polymorphism transformations

Engineering Contradiction:
Improvecrystal form stabilityVSAvoidformulation consistency
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent applies parameter changes by selecting specific crystallization conditions including solvent type (n-hexane, n-heptane, ethyl acetate, cyclohexane), temperature ranges (60-80°C for dissolution, 2-12°C for crystallization), and concentration ratios (1:5-20 API to solvent). These parameter optimizations lead to the formation of Crystal Form A with consistent XRPD characteristics and eliminate polymorphism transformations, thereby improving both stability and reliability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs preliminary action through a two-step preparation process: first dissolving the API in hot solvent to ensure complete dissolution and homogeneity, then cooling to induce controlled crystallization of the stable Crystal Form A. This preliminary dissolution step prevents subsequent polymorphic transformations during storage and administration

Inventive Principle:
Principle #10Preliminary action

2Ease of operation

If conventional TBN formulations are used, then the compound provides therapeutic activity, but the solubility and bioavailability are insufficient

Engineering Contradiction:
ImprovesolubilityVSAvoidbioavailability consistency
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent improves solubility and bioavailability by optimizing crystallization parameters including selecting specific solvents (n-hexane, n-heptane, ethyl acetate, cyclohexane) and controlling temperature (60-80°C dissolution, 2-12°C crystallization). These parameter changes produce Crystal Form A with enhanced solubility characteristics while maintaining consistent bioavailability through reproducible crystal structure

Inventive Principle:
Principle #35Parameter changes

3Productivity

If simple crystallization methods are used, then the preparation process is quick, but the crystal form consistency and purity are compromised

Engineering Contradiction:
Improvepreparation speedVSAvoidcrystal form consistency
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent employs preliminary action through a systematic two-step process: first heating to 60-80°C to dissolve the API completely in the selected solvent, then cooling to 2-12°C to induce controlled crystallization. This preliminary dissolution ensures homogeneous distribution before crystallization, guaranteeing consistent Crystal Form A formation while maintaining efficient preparation speed

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent optimizes manufacturing precision through specific parameter control: solvent selection (n-hexane, n-heptane, ethyl acetate, cyclohexane), temperature parameters (60-80°C for dissolution, 2-12°C for crystallization), and concentration ratios (1:5-20). These controlled parameters ensure reproducible Crystal Form A with consistent XRPD characteristics and high purity, while the straightforward two-step process maintains productivity

Inventive Principle:
Principle #35Parameter changes

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 crystal form A of TBN exhibits improved stability, solubility, and bioavailability, ensuring consistent drug quality and rapid action in treating neurological and cardiovascular diseases.

Implementation Method 1

having characteristic diffraction peaks in the XRPD pattern of the crystal form at 2θ°: 10.60±0.2, 11.03±0.2, 15.31±0.2, 15.55±0.2, 17.14±0.2, 17.93±0.2, and 23.81±0.2

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

the melting point of the crystal form A of TBN is 76-78°C

Methodology Applied
Scientific EffectMelting: Melting

Implementation Method 3

a preparation method using solvents like n-hexane and n-heptane, which stabilizes the compound and enhances its solubility and bioavailability

Methodology Applied
Scientific EffectSolubility: Solvation

Data Source

PatentEP3950679B1Crystal form of tetramethylpyrazine nitrone, preparation method and use thereof
Publication Date: 2025.04.02 GUANGZHOU MAGPIE PHARMA
  • EP3950679B1 patent drawingFigure 1~2
  • EP3950679B1 patent drawingFigure 3
  • EP3950679B1 patent drawingFigure 4~5

AI summary

The present invention discloses a crystal form of TBN, and a preparation method and use thereof. The present invention provides a crystal form A of TBN, having characteristic diffraction peaks in the XRPD pattern at 2θ°: 10.60±0.2, 11.03±0.2, 15.31±0.2, 15.55±0.2, 17.14±0.2, 17.93±0.2, and 23.81±0.2. The crystal form A has low risk of polymorphism transformation and good stability, which contribute to the stability of the preparations during the production and storage processes, and effectively guarantee the consistency of the content of the crystal form in the preparations. Therefore, the preparations are safe, effective, and controllable in quality. Also, the crystal form A has high biological activity, good druggability, and high bioavailability, fast onset of action.