High-Purity Cyclopeptide Crystallization via pH Control

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Solution Overview

Problem

The compound of formula I is difficult to crystallize and typically exists in an amorphous state, making it challenging to achieve stability and purity necessary for storage and use as a drug intermediate, particularly for antifungal applications.

Innovation Solution

Crystals of the compound of formula I are formed by dissolving it in water or a mixture of water-miscible lower alcohols, maintaining the solution at saturated solubility and controlling the pH within a specified range, followed by in-vacuo drying to control crystal water content, resulting in various stable crystal forms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If the compound of formula I is crystallized using conventional methods, then the crystal form can be obtained, but the crystallization is difficult and the compound typically exists in an amorphous state with poor stability

Engineering Contradiction:
ImprovestabilityVSAvoidcrystallization difficulty
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by controlling pH within a specified range (pH 2.0-5.0, preferably pH 3.0-4.0) and controlling the solvent system composition (water-miscible lower alcohol content of 10-50% v/v) to enable successful crystallization of compound of formula I, transforming it from an amorphous state to stable crystal forms with defined XRPD patterns

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions by controlling the crystallization process to form specific crystal forms (Crystal Form A, B, C, D, E, F, G) from the amorphous state, where each crystal form has distinct X-ray powder diffraction patterns and stability characteristics, allowing selection of the most stable form for storage and use

Inventive Principle:
Principle #36Phase transitions

2Stability of the object's composition

If the compound is stored in amorphous state, then it can be easily handled, but it lacks stability and purity necessary for storage and use as drug intermediate

Engineering Contradiction:
ImprovestabilityVSAvoidpurity
Core Design Contradiction:
Stability of the object's compositionVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by optimizing crystallization conditions including pH control (pH 2.0-5.0), solvent system composition (water-miscible lower alcohol 10-50% v/v), and temperature control to achieve high-purity crystal forms with reduced impurities, meeting the purity requirements for drug intermediates

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies extraction by using solvent systems comprising water and water-miscible lower alcohols to selectively crystallize the compound of formula I from reaction mixtures, separating it from impurities and achieving high purity crystal forms suitable for pharmaceutical use

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If conventional crystallization methods are used, then the process is simple, but the yield and purity of the final product are insufficient

Engineering Contradiction:
ImproveyieldVSAvoidpurity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by optimizing multiple crystallization parameters including pH (2.0-5.0), solvent composition (water-miscible lower alcohol 10-50% v/v), and temperature to simultaneously achieve high yield and high purity crystal forms, resolving the contradiction between productivity and manufacturing precision

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies universality by developing a multi-functional crystallization method that can produce multiple stable crystal forms (A-G) with different characteristics from the same compound, allowing selection based on specific requirements for stability, purity, and downstream processing needs

Inventive Principle:
Principle #6Universality (Multi-functionality)

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

This method produces crystals with improved stability and high purity, suitable for storage and use, reducing impurities and simplifying the purification process for the compound, leading to enhanced yield and stability of the final product.

Implementation Method 1

crystals with different crystal forms can be prepared by using different solvent systems and drying methods

Methodology Applied
Scientific EffectCrystallisation: Crystallisation

Implementation Method 2

The crystal of compound of formula I will lose crystal water during in-vacuo drying

Methodology Applied
Scientific EffectVacuum drying: Vacuum Distillation

Data Source

PatentEP2832743B1High-purity cyclopeptide crystal as well as preparation method and use thereof
Publication Date: 2018.07.18 SHANGHAI TECHWELL BIOPHARMACEUTICALS CO LTD
  • EP2832743B1 patent drawingFigure 1~2
  • EP2832743B1 patent drawingFigure 3
  • EP2832743B1 patent drawingFigure 4~5

AI summary

A high purity cyclopeptide crystal has a structure shown by Formula I. R represents H or a cation forming a pharmaceutically acceptable salt. Also disclosed are a preparation method and a use of the high-purity cyclopeptide crystal.