Phosphoramidate Nucleoside Prodrugs for Hepatitis Liver Targeting

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Solution Overview

Problem

Current treatments for hepatitis C and hepatitis B infections lack effective, low-toxicity pharmaceutical agents, with existing therapies often having adverse effects and limited efficacy, and there is a need for improved methods to target and concentrate therapeutic agents in the liver.

Innovation Solution

Development of phosphoramidate and phosphonoamidate compounds that can selectively concentrate in the liver, allowing for the accumulation of therapeutic agents, such as nucleosides, which are metabolized to their active forms to inhibit viral enzymes, thereby enhancing the treatment of hepatitis B and C infections.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing antiviral therapies are used to treat hepatitis C and hepatitis B infections, then viral replication is inhibited, but toxicity and adverse effects increase

Engineering Contradiction:
Improveefficacy of antiviral treatmentVSAvoidtoxicity and adverse effects
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies local quality by modifying nucleoside compounds with phosphoramidate or phosphonoamidate groups that enable selective accumulation in liver tissue. This localization ensures that the antiviral effect is concentrated where the virus replicates (in the liver) while reducing exposure and toxicity to other organs and tissues.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent uses phosphoramidate and phosphonoamidate derivatives as intermediary compounds that serve as prodrugs. These intermediaries are metabolized in the liver to release the active antiviral nucleoside form, allowing targeted delivery and reducing systemic toxicity while maintaining antiviral efficacy.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If antiviral agents are administered systemically to treat hepatitis infections, then viral replication is inhibited throughout the body, but drug concentration in the liver is insufficient

Engineering Contradiction:
Improveinhibition of viral replicationVSAvoiddrug concentration in liver
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent employs local quality by designing phosphoramidate and phosphonoamidate nucleoside compounds that exhibit preferential accumulation in liver tissue. This structural modification enables the drug to concentrate locally in the target organ (liver) where hepatitis viruses replicate, thereby achieving higher effective concentrations at the site of infection.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent utilizes phosphoramidate and phosphonoamidate derivatives as intermediary prodrugs that are metabolized specifically in the liver. These intermediaries facilitate targeted delivery by being converted to active antiviral forms preferentially in liver tissue, ensuring high local drug concentration while maintaining systemic safety.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Adaptability or versatility

If conventional antiviral compounds are used to treat hepatitis infections, then treatment coverage is broad, but selectivity for liver targeting is poor

Engineering Contradiction:
Improvebroad treatment coverageVSAvoidselectivity for liver targeting
Core Design Contradiction:
Adaptability or versatilityVSLength of moving object

Solution Approach 1:

The patent applies local quality by incorporating phosphoramidate or phosphonoamidate functional groups into nucleoside compounds. These modifications confer liver-selective accumulation properties to the antiviral agents, enabling them to maintain broad antiviral activity while specifically concentrating in liver tissue where hepatitis viruses are present.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent uses phosphoramidate and phosphonoamidate derivatives as intermediary prodrugs that facilitate selective liver targeting. These intermediaries are designed to be metabolized preferentially in the liver, thereby converting a broadly active antiviral compound into a liver-targeted therapeutic with enhanced selectivity and reduced off-target effects.

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentEP2120566B1Compounds and pharmaceutical compositions for the treatment of viral infections
Publication Date: 2019.05.08 INDENIX PHARM LLC
  • EP2120566B1 patent drawingFigure 1
  • EP2120566B1 patent drawingFigure 2
  • EP2120566B1 patent drawing

AI summary

Provided herein are compounds, compositions and methods for the treatment of liver disorder, including HCV and/or HBV infections. Specifically, compound and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents.