Crystalline 6-OH CBDV Forms for Stable Pharmaceutical Processing

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Solution Overview

Problem

Existing forms of 6-hydroxy cannabidivarin (6-OH CBDV) are difficult to handle and process due to their amorphous nature, lacking stability under stress conditions such as compression and milling, which complicates pharmaceutical formulation.

Innovation Solution

The development of crystalline forms of 6-OH CBDV, specifically Forms A, B, C, D, and E, which exhibit enhanced chemical stability and processability, characterized by distinct X-ray powder diffraction patterns and thermal analysis profiles, allowing for improved handling and formulation into pharmaceutical products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If 6-OH CBDV is produced by reduction of 6-oxo-CBDV diacetate and purified by column chromatography, then the compound can be obtained, but it forms glassy (amorphous) solid or semi-solid material that is difficult to handle and process

Engineering Contradiction:

Improveease of handling and processingVSAvoidstability under stress conditions

Core Design Contradiction:

Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by transforming the physical state of 6-OH CBDV from amorphous to crystalline form. This phase transition fundamentally alters the material properties, providing a defined melting point, improved stability under compression and milling, and enhanced ease of handling compared to the glassy amorphous material obtained through conventional purification methods

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention directly utilizes phase transitions by inducing crystallization of 6-OH CBDV from its amorphous state. The patent describes obtaining crystalline forms with specific X-ray diffraction patterns, which represent a distinct phase transition that confers superior mechanical stability, defined thermal properties, and improved processability for pharmaceutical formulation

Inventive Principle:

Principle #36Phase transitions

2Stability of the object's composition

If crystalline forms of 6-OH CBDV are developed, then stability and processability are improved, but multiple crystal forms (polymorphs) need to be characterized and controlled

Engineering Contradiction:

Improvechemical stabilityVSAvoidcomplexity of crystal form characterization

Core Design Contradiction:

Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the crystalline forms of 6-OH CBDV into distinct polymorphic categories (Form A, Form B, Form C, etc.), each with unique X-ray diffraction patterns and properties. This systematic classification allows for individual characterization and control of each crystal form, managing the complexity through structured organization rather than treating all crystalline forms as a single entity

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The invention replaces complex mechanical handling and stability assessment with X-ray powder diffraction (XRPD) characterization. By using diffraction patterns as a fingerprint for each crystal form, the patent provides a non-destructive, rapid method to identify and control polymorphs, substituting physical stability testing with analytical characterization

Inventive Principle:

Principle #28Mechanics substitution (Replace mechanical system)

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 forms provide excellent stability and processability, facilitating easier handling and formulation into pharmaceutical compositions, particularly for treating epilepsy.

Implementation Method 1

Form A 6-OH CBDV is characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.83, 12.50, 13.01, 14.64, 18.30, 20.79, 23.90, 24.60, 25.43, and 26.22±0.2 (° 2θ)

Methodology Applied

Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

Form A 6-OH CBDV is characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.83, 12.50, 13.01, 14.64, 18.30, 20.79, 23.90, 24.60, 25.43, and 26.22±0.2 (° 2θ)

Methodology Applied

Scientific EffectBragg diffraction: Bragg Diffraction

Implementation Method 3

Form A material may have a differential scanning calorimetry (DCS) thermogram comprising a peak with an onset temperature (Tonset) of between 142° C. and 153° C., such as about 151° C.

Methodology Applied

Scientific EffectDifferential scanning calorimetry: Calorimetry

Implementation Method 4

Form B material may have a thermogravimetric differential thermal analysis (TG/DTA) thermogram comprising a peak with a Tonset of about 78±2° C.

Methodology Applied

Scientific EffectThermogravimetric analysis:

Implementation Method 5

Form B material may have a thermogravimetric differential thermal analysis (TG/DTA) thermogram comprising a peak with a Tonset of about 78±2° C.

Methodology Applied

Scientific EffectDifferential thermal analysis:

Data Source

PatentUS20250289774A1Crystaline forms of a cannabidiol-like cannabinoid

Publication Date: 2025.09.18 GW RES LTD

AI summary

The present invention relates to crystalline forms of 6-hydroxy cannabidivarin (6-OH CBDV), methods for their production, and their use in therapy. The crystalline forms are easier to handle than other solid forms, such as glass amorphous material, and will useful in the manufacture of medicaments for the treatment of conditions associated with seizure.