Darunavir Crystalline Forms for Stability and Bioavailability

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Solution Overview

Problem

Current antiretroviral therapies for HIV-1 face challenges such as drug resistance, toxicity, and complex treatment regimens, necessitating the development of stable and effective formulations of darunavir that minimize drug interactions and maintain long-term safety and adherence.

Innovation Solution

The development of novel crystalline forms of darunavir, including Form I, Hydrate I, Solvate I, and their characterization through XRPD, DSC, and TGA analysis, which provide enhanced stability, bioavailability, and manufacturability, thereby addressing the challenges of drug resistance and treatment complexity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If multiple different drugs are used to suppress HIV and treat other conditions, then viral suppression is achieved, but the potential for drug interactions increases

Engineering Contradiction:
Improveviral suppressionVSAvoiddrug interactions
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the physical form parameter of darunavir from amorphous to crystalline, which modifies its dissolution rate and bioavailability characteristics. This allows for optimized dosing that may reduce drug interactions while maintaining viral suppression efficacy.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If potent and well-tolerated anti-retroviral therapy is used, then viral suppression is achieved, but mutations of the HIV-1 virus continue to occur

Engineering Contradiction:
Improveviral suppressionVSAvoiddrug resistance
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the physical form parameter of darunavir from amorphous to crystalline, which modifies its dissolution rate and bioavailability characteristics. This allows for optimized dosing that may reduce drug interactions while maintaining viral suppression efficacy.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If stable forms of darunavir are developed, then chemical and physical stability is improved, but manufacturing and storage requirements become more complex

Engineering Contradiction:
Improvechemical and physical stabilityVSAvoidmanufacturing and storage requirements
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent changes the physical form parameter of darunavir from amorphous to crystalline, which modifies its dissolution rate and bioavailability characteristics. This allows for optimized dosing that may reduce drug interactions while maintaining viral suppression efficacy.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3532478B1Crystalline form of darunavir free base
Publication Date: 2021.05.26 GILEAD SCIENCES INC
  • EP3532478B1 patent drawingFigure 1
  • EP3532478B1 patent drawingFigure 2
  • EP3532478B1 patent drawingFigure 3

AI summary

The present invention relates to crystalline forms of darunavir free base, hydrate, acetic acid solvate, esylate, besylate, hemisulfate, napsylate, hemiedisylate, tosylate, methyl ethyl ketone (MEK) solvate, methyl tetrahydrofuran (MeTHF) solvate, methyl acetate (MeOAc) solvate and ethyl formate solvate, and to pharmaceutical formulations thereof for treating viral infections.