Trientine Tetrahydrochloride Crystallization for Stable Drug Storage

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Solution Overview

Problem

Existing methods for preparing trientine tetrahydrochloride (TETA • 4HCl) suffer from stability issues and complex processes, particularly with TETA • 4HCl Form B, which is less faded and more stable but requires low-temperature crystallization and seeding, making it inconvenient.

Innovation Solution

A method involving dissolving crude TETA • 4HCl in purified water, adding an anti-solvent like methanol at controlled temperatures for crystallization, and stirring for specific durations to produce TETA • 4HCl crystals (Form N), with steps to ensure low loss on drying and using a pharmaceutically acceptable vehicle for formulation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If TETA·4HCl is prepared by low-temperature crystallization and seeding as disclosed in TW202002956A, then the stability of the crystalline form is improved, but the process complexity and operational inconvenience increase

Engineering Contradiction:
Improvestability of TETA·4HCl crystalline formVSAvoidprocess complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent changes the crystallization temperature parameter from low-temperature (prior art) to room temperature or higher, and modifies the crystallization method from seeding-dependent to spontaneous crystallization, thereby simplifying the process while maintaining stability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent performs preliminary acidification of the TETA·2HCl solution with hydrochloric acid before crystallization to ensure complete conversion to TETA·4HCl, which prevents stability issues during storage without requiring complex seeding procedures

Inventive Principle:
Principle #10Preliminary action

2Manufacturing precision

If TETA·4HCl Form A is used in tablet manufacturing, then the initial crystalline form is obtained, but faded debris appear after six-month storage at 40°C and 75% RH indicating degradation

Engineering Contradiction:
Improvecrystalline form consistencyVSAvoidstorage stability
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent changes the crystallization parameters (temperature, solvent ratio, acidification) to produce a more stable crystalline form that resists degradation under storage conditions, eliminating the faded debris issue observed with Form A

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies preliminary acidification and controlled crystallization conditions to pre-stabilize the TETA·4HCl crystals before manufacturing, providing a buffer against degradation during storage and preventing the formation of degraded products

Inventive Principle:
Principle #11Beforehand cushioning (Prior cushioning)

3Productivity

If conventional methods are used to prepare TETA·4HCl, then the basic product is obtained, but the yield and purity are insufficient for pharmaceutical applications

Engineering Contradiction:
Improveyield of TETA·4HClVSAvoidpurity of TETA·4HCl
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent performs preliminary acidification with hydrochloric acid to ensure complete conversion of TETA·2HCl to TETA·4HCl before crystallization, which maximizes both yield and purity by preventing incomplete reactions and impurity formation

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses methanol as an intermediary anti-solvent to facilitate the crystallization of TETA·4HCl from the aqueous solution, enabling high-yield precipitation of pure crystals that can be easily separated and dried

Inventive Principle:
Principle #24Intermediary (Mediator)

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 method yields TETA • 4HCl crystals with high stability and anti-moisture absorption, simplifying the preparation process and improving yield rates without the drawbacks of previous methods.

Implementation Method 1

an anti-solvent at a feeding temperature is added into a trientine tetrahydrochloride solution and stirred for crystallization wherein the feeding temperature ranges from 50°C to 75°C

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 2

the step 1 further comprises drying crystals for LOD (loss on drying) of crystals

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP4234532B1Trientine tetrahydrochloride and a method of preparation and a pharmaceutical composition thereof
Publication Date: 2026.05.20 YU JET CO LTD
  • EP4234532B1 patent drawingFigure 1
  • EP4234532B1 patent drawingFigure 2
  • EP4234532B1 patent drawingFigure 3

AI summary

A method of preparation of trientine tetrahydrochloride crystals in which an anti-solvent at a feeding temperature is added into a trientine tetrahydrochloride solution and stirred for crystallization wherein the feeding temperature ranges from 50°C to 75°C and the anti-solvent is an alcohol solvent. A novel trientine tetrahydrochloride featuring XRPD peaks detected at 21.9, 24.8, 25.2, 28.0 and 35.6±0.1° 20 for stable storage of a pharmaceutical composition manufactured with the trientine tetrahydrochloride.