Solid Salt Forms of α-6-mPEG6-O-Hydroxycodone for Stable Opioid Formulations

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Solution Overview

Problem

Current opioid analgesics, despite being effective for pain management, are associated with serious central nervous system side effects such as respiratory depression and abuse liability, and α-6-mPEG 6-O-hydroxycodone exists only as a viscous liquid, lacking a solid form which could offer advantageous physicochemical properties for pharmaceutical processing.

Innovation Solution

Development of solid salt forms of α-6-mPEG 6-O-hydroxycodone, specifically phosphate and D-tartrate salts, which are crystalline or disordered crystalline forms, to provide a stable and handleable form for pharmaceutical compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If a solid form of α-6-mPEG 6-O-hydroxycodone is developed, then stability and ease of handling are improved, but the compound currently exists only as a viscous liquid which limits pharmaceutical processing advantages

Engineering Contradiction:
ImprovestabilityVSAvoidhandling
Core Design Contradiction:
Stability of the object's compositionVSEase of operation

Solution Approach 1:

The patent applies parameter changes by converting the physical state of α-6-mPEG 6-O-hydroxycodone from liquid to solid through salt formation. Specifically, the compound is converted into crystalline or disordered crystalline salt forms (such as hydrochloride, sulfate, phosphate, citrate, tartrate, and acetate salts), which fundamentally changes its physical parameters including melting point, solubility, and handling characteristics, thereby achieving both improved stability and ease of handling.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by forming salt compounds between α-6-mPEG 6-O-hydroxycodone and various counterions (e.g., hydrochloric acid, sulfuric acid, phosphoric acid, citric acid, tartaric acid, acetic acid). These composite salt forms combine the opioid agonist with acid counterions to create new materials that exhibit superior solid-state properties compared to the parent liquid compound, enabling better pharmaceutical processing and storage.

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If solid salt forms are prepared, then pharmaceutical processing advantages are achieved, but additional processing steps are required to convert the liquid freebase form to solid salt forms

Engineering Contradiction:
Improvepharmaceutical processingVSAvoidprocessing steps
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by performing salt formation early in the drug development and manufacturing process. The liquid freebase form of α-6-mPEG 6-O-hydroxycodone is converted to solid salt forms as a preliminary step before formulation and pharmaceutical processing. This advance conversion simplifies subsequent manufacturing operations by providing a stable, handleable solid material that can be directly incorporated into pharmaceutical compositions without requiring complex liquid handling equipment or procedures.

Inventive Principle:
Principle #10Preliminary action

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 solid salt forms of α-6-mPEG 6-O-hydroxycodone offer improved stability and handling, potentially reducing CNS side effects while maintaining analgesic properties, and can be used in pharmaceutical compositions for effective pain treatment.

Implementation Method 1

Development of solid salt forms of α-6-mPEG 6-O-hydroxycodone, specifically phosphate and D-tartrate salts, which are crystalline or disordered crystalline forms

Methodology Applied
Scientific EffectCrystallisation: Crystallisation

Data Source

PatentEP2914599B1Solid salt form of alpha-6-MPEG6-o-hydroxycodone as opioid agonists and uses thereof
Publication Date: 2017.11.22 NEKTAR THERAPEUTICS INC
  • EP2914599B1 patent drawingFigure 1
  • EP2914599B1 patent drawingFigure 2
  • EP2914599B1 patent drawingFigure 3

AI summary

Solid forms of certain opioid agonists are provided herein. Methods of preparing the solid forms, methods of using the solid forms, and pharmaceutical compositions comprising the solid forms are also provided herein.