Beraprost-314d Monohydrate Crystals for Stability

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Solution Overview

Problem

The anhydrous form of Beraprost-314d is not stable at room temperature, leading to issues in storage, shipping, and formulation due to its tendency to form dimers and ester impurities with solvents or excipients.

Innovation Solution

The development of a stable monohydrated form of Beraprost-314d, which is characterized by specific FTIR, XRPD, and DSC patterns, and can exist in two crystalline forms (Form A and Form B) that are reversible with temperature changes, along with a method for preparation involving dissolution in solvents and addition of water to form a precipitate.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If anhydrous Beraprost-314d is used, then the compound can be stored and handled, but it forms dimers and ester impurities at room temperature, leading to instability

Engineering Contradiction:
Improvestability of Beraprost-314dVSAvoidformation of dimers and ester impurities
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The patent changes the physical and chemical parameters of Beraprost-314d by converting it from anhydrous form to monohydrate form. This parameter change (adding water of crystallization) fundamentally alters the chemical stability of the compound, preventing dimerization and esterification reactions that occur in the anhydrous form at room temperature.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite material system where Beraprost-314d is combined with water molecules in a specific stoichiometric ratio (monohydrate). This composite structure, stabilized by hydrogen bonding networks between water molecules and carbonyl groups, prevents the harmful reactions that occur in the pure anhydrous form.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If monohydrated form of Beraprost-314d is used, then stability at room temperature is improved, but additional steps for water control and crystallization are required in preparation

Engineering Contradiction:
Improvestability of Beraprost-314dVSAvoidcomplexity of preparation method
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent performs preliminary action by controlling the crystallization process to directly form the monohydrate structure during synthesis. By adjusting solvent composition and crystallization conditions, the monohydrate form is obtained directly without requiring subsequent hydration steps, thereby simplifying the overall preparation process despite the apparent complexity of water control.

Inventive Principle:
Principle #10Preliminary action

3Ease of manufacture

If anhydrous Beraprost-314d is used, then the formulation process can proceed, but handling difficulty increases due to static electrical charge

Engineering Contradiction:
Improveease of formulationVSAvoidease of handling
Core Design Contradiction:
Ease of manufactureVSEase of operation

Solution Approach 1:

The patent changes the electrical properties of Beraprost-314d by converting from anhydrous to monohydrate form. The presence of water molecules in the crystal structure alters the surface charge characteristics and reduces static electrical charge accumulation, making the material easier to handle during formulation and processing operations.

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 monohydrated form of Beraprost-314d is stable at room temperature, reducing the formation of unwanted dimers and impurities, making it suitable for commercial storage, shipping, and formulation, and is easier to handle due to reduced static electrical charge.

Implementation Method 1

the water molecules in the crystal lattice are hydrogen bonded to the carbonyl groups

Methodology Applied
Scientific EffectHydrogen bonding: Chemical Bonding

Implementation Method 2

the crystalline form transformation of Beraprost-314d monohydrate between Form A and Form B by increasing and decreasing temperature is reversible

Methodology Applied
Scientific EffectPhase transition: Phase Change

Data Source

PatentEP3656767A1Beraprost-314d monohydrate crystals and methods for preparation thereof
Publication Date: 2020.05.27 CHIROGATE INT
  • EP3656767A1 patent drawingFigure 1~2
  • EP3656767A1 patent drawingFigure 3~4
  • EP3656767A1 patent drawingFigure 5~6

AI summary

The present invention provides a monohydrated form of Beraprost-314d, and a novel crystalline form of Beraprost-314d monohydrate, and processes for the preparation thereof.