Buprenorphine Ester Derivatives for Opiate Dependence

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Solution Overview

Problem

Current buprenorphine treatments for opiate abuse and dependence have limitations, including low bioavailability, potential for misuse, and restrictive administration routes, which hinder effective and safe management of opiate dependence and pain relief.

Innovation Solution

Development of buprenorphine ester derivatives with modified phenolic hydroxyl groups, which can be administered in various forms, including solid dosage forms, to enhance bioavailability, duration of action, and reduce misuse potential, allowing for convenient and flexible administration routes such as oral, sublingual, and transdermal delivery.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If buprenorphine is administered orally, then it is easy to administer, but bioavailability is low (approximately 5%)

Engineering Contradiction:
Improveease of administrationVSAvoidbioavailability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of buprenorphine through esterification of the phenolic hydroxyl group. This chemical modification changes the physicochemical parameters of the molecule, specifically improving its lipophilicity and enabling it to bypass first-pass metabolism, thereby achieving high oral bioavailability (greater than 50%) while maintaining ease of oral administration.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If buprenorphine is administered sublingually, then bioavailability is high (approximately 50%), but administration is restrictive and requires patient compliance

Engineering Contradiction:
ImprovebioavailabilityVSAvoidease of administration
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The ester derivatives modify the absorption parameters of buprenorphine, allowing it to be effectively administered orally with bioavailability exceeding 50%, eliminating the need for restrictive sublingual administration and improving patient compliance while maintaining high bioavailability.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If buprenorphine is used for treatment, then it provides effective pain relief and opiate dependence treatment, but it has potential for misuse

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidmisuse potential
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies preliminary action by incorporating disulfiram or its metabolites into the pharmaceutical composition before administration. This preliminary inclusion creates a deterrent effect against misuse, as co-administration of opioids with disulfiram produces unpleasant reactions, thereby reducing misuse potential while preserving the therapeutic effectiveness of buprenorphine for legitimate medical use.

Inventive Principle:
Principle #10Preliminary action

4Duration of action of moving object

If buprenorphine has long duration of action, then dosing interval can be extended, but this requires sufficient duration to enable single daily dose

Engineering Contradiction:
Improveduration of actionVSAvoiddosing frequency
Core Design Contradiction:
Duration of action of moving objectVSProductivity

Solution Approach 1:

The ester derivatives of buprenorphine modify the pharmacokinetic parameters of the drug, extending its duration of action. This allows for extended dosing intervals, enabling treatment to be administered as a single daily dose or even less frequently, thereby improving productivity by reducing the number of dosing events while maintaining therapeutic effectiveness.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2001891B1Buprenorphine derivatives and uses thereof
Publication Date: 2013.07.24 RB PHARMA
  • EP2001891B1 patent drawingFigure 1A~1B
  • EP2001891B1 patent drawingFigure 2A~2B
  • EP2001891B1 patent drawingFigure 3A~3B

AI summary

Ester derivatives of the phenolic hydroxyl group of buprenorphine are described that can be used in the treatment of opiate dependency and/or moderate to severe pain. The esters have an enhanced bioavailability, an enhanced duration of action, and a reduced abuse potential.