Crystalline Hemihydrate Solvent Selection for Pharmaceutical Stability

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Solution Overview

Problem

Obtaining a stable, pure, and crystalline form of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate from organic solvents has been difficult, hindering its commercial use and pharmaceutical applications due to issues with handling qualities, filtration, and long-term stability.

Innovation Solution

The compound is crystallized from a water-containing solvent, resulting in a reproducible crystalline hemihydrate form with improved handling qualities and stability, characterized by specific X-ray powder diffraction and infra-red spectra, and can be produced through a process involving precipitation or recrystallization.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Shape

If the compound is attempted to be crystallized from organic solvents, then the product should be obtained in crystalline form, but the crystallization is difficult and the product lacks good handling qualities

Engineering Contradiction:
Improvecrystalline formVSAvoidhandling qualities
Core Design Contradiction:
ShapeVSEase of operation

Solution Approach 1:

The patent changes the solvent system from organic solvents to water-containing solvents (aqueous systems). This parameter change in the crystallization medium enables the compound to form crystals with good handling qualities, including appropriate crystal habit, filterability, and drying characteristics that were not achievable with organic solvents.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces water as an intermediary solvent to mediate the crystallization process. The water-containing solvent system acts as a mediator that facilitates the formation of a crystalline form with desirable properties, including improved filterability and drying characteristics, while maintaining the compound's pharmaceutical integrity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If the product is to be produced in pure and crystalline form to meet pharmaceutical requirements, then the product quality is improved, but the manufacturing process becomes more difficult

Engineering Contradiction:
Improveproduct purity and crystallinityVSAvoidprocess difficulty
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the crystallization parameters by using water-containing solvents instead of organic solvents. This parameter change simplifies the manufacturing process while simultaneously achieving the required product purity and crystallinity, as aqueous systems generally offer better safety profiles, easier handling, and more straightforward purification steps.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs water-containing solvents which are generally safer, more environmentally friendly, and easier to dispose of compared to organic solvents. This approach reduces the complexity of waste handling and regulatory compliance while maintaining high product purity standards, thereby simplifying the overall manufacturing process.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Ease of operation

If the product should be readily filterable and easily dried, then the handling qualities are improved, but achieving this crystalline form from organic solvents has been difficult

Engineering Contradiction:
Improvefilterability and drying easeVSAvoidcrystallization process complexity
Core Design Contradiction:
Ease of operationVSDevice complexity

Solution Approach 1:

The patent changes the solvent parameter to water-containing systems, which produce crystals with morphology and physical properties that are inherently more filterable and easier to dry. The aqueous crystallization process yields a crystalline form with characteristics that naturally enhance downstream processing efficiency without requiring complex process modifications.

Inventive Principle:
Principle #35Parameter changes

4Stability of the object's composition

If the product should be stable for extended periods without specialized storage conditions, then the storage stability is improved, but obtaining the appropriate crystalline form has been difficult

Engineering Contradiction:
Improvestorage stabilityVSAvoidcrystallization process complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent changes the crystallization solvent system to water-containing solvents, which produce a crystalline form with enhanced storage stability. The aqueous crystallization process yields a stable polymorph that maintains its composition and potency over extended periods under normal storage conditions, eliminating the need for specialized storage while simplifying the overall process.

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 crystalline form is more stable, easier to isolate, and exhibits excellent blood glucose lowering effects, making it suitable for treating various diabetic and metabolic disorders, with enhanced pharmaceutical properties and extended storage capabilities.

Implementation Method 1

the compound of formula (I) hemihydrate can be produced in a crystalline form

Methodology Applied
Scientific EffectCrystallisation: Crystallisation

Implementation Method 2

crystalline form of hemihydrate of the compound of formula (I)

Methodology Applied
Scientific EffectHydrate formation: Hydrates

Data Source

PatentEP2102224B2CRYSTALLINE FORM OF 1- (ß-D-GLUCOPYRANOSYL) -4 -METHYL- 3- [5- (4 -FLUOROPHENYL) -2-THIENYLMETHYL]BENZENE HEMIHYDRATE
Publication Date: 2021.08.04 TANABE PHARMA CORP
  • EP2102224B2 patent drawingFigure 1
  • EP2102224B2 patent drawingFigure 2
  • EP2102224B2 patent drawing

AI summary

A novel crystal form of 1- (ß-D-glucopyranosyl) -4-methyl-3- [5- (4-f luorophenyl) -2-thienylmethyl] benzene hemihydrate, and having favorable characteristics, is characterized by its x-ray powder diffraction pattern and/or by its infra¬ red spectrum.