Dinucleotide Compounds for HCV Treatment

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Solution Overview

Problem

Current treatments for hepatitis C virus (HCV) infections lack effective and low-toxicity pharmaceutical agents, and there is a need for new treatments that can address the rising threat of flaviviridae infections.

Innovation Solution

Development of dinucleotide compounds, specifically those according to Formula I (N1-L-N2), which are 2'-methyl nucleotides linked by a divalent linker, offering remarkable efficacy and bioavailability for treating HCV and other flaviviridae infections, including chronic liver inflammation, cirrhosis, and acute hepatitis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current treatments for HCV infections are used, then treatment is provided, but effectiveness is insufficient and toxicity is high

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of nucleoside analogs through specific substitutions (2'-methyl groups, 2'-fluoro groups, O-alkyl modifications) to optimize the balance between antiviral effectiveness and host toxicity. These structural parameter changes enable the compound to achieve remarkable efficacy against HCV while maintaining low toxicity profiles.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining modified nucleoside units with specific divalent linkers (L) to form dinucleotide compounds. This composite approach, where two nucleoside moieties are connected through defined linker structures, produces a molecule with enhanced antiviral activity and improved safety profile compared to monomeric nucleoside analogs.

Inventive Principle:
Principle #40Composite materials

2Reliability

If existing nucleoside derivatives are used, then some antiviral activity is achieved, but bioavailability and efficacy are limited

Engineering Contradiction:
Improveantiviral efficacyVSAvoidbioavailability
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent merges two nucleoside analog units into a single dinucleotide compound through a divalent linker, creating a bivalent antiviral agent. This merging strategy increases the quantity of active antiviral moieties delivered to the target, thereby enhancing efficacy and bioavailability while maintaining favorable pharmacokinetic properties.

Inventive Principle:
Principle #5Merging (Combining)

3Reliability

If new effective agents are developed, then treatment efficacy improves, but complexity of compound structure increases

Engineering Contradiction:
Improvetreatment efficacyVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The complex dinucleotide compound is segmented into recognizable and systematic components: modified nucleoside units with specific substituents (2'-methyl, 2'-fluoro, O-alkyl groups) connected through defined divalent linkers. This segmentation approach allows the complex structure to be designed, synthesized, and characterized in a modular fashion, making the complexity manageable while achieving superior efficacy.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP2909223B1Dinucleotide compounds for HCV infection
Publication Date: 2017.03.22 INDENIX PHARM LLC

AI summary

Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds comprise two 2 '-methyl nucleotides linked according to Formula (I): N1 - L - N2 or a pharmaceutically acceptable salt, ester, solvate, stereoisomer, isomeric form, tautomeric form or polymorphic form thereof; wherein N1, L and N2 are as described herein.