Valsartanamide Dinitrate Sequential Nitric Oxide Release

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Solution Overview

Problem

Current treatments for vascular and metabolic diseases, such as hypertension and atherosclerosis, often lead to nitrate tolerance and vascular dysfunction due to the short half-life of nitrate esters, necessitating frequent dosing and adverse effects like oxidative stress.

Innovation Solution

Development of dinitrate esters of valsartanamide derivatives with nitrate functions attached to both the tetrazole unit and the amide substituent, which release nitrogen monoxide sequentially, enhancing vasodilatory potency and reducing oxidative stress.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If organic nitrates with short half-life are used for treatment, then fast-acting vasodilation effect is achieved, but nitrate tolerance develops requiring frequent dosing

Engineering Contradiction:
Improveonset of actionVSAvoidhalf-life
Core Design Contradiction:
SpeedVSDuration of action of moving object

Solution Approach 1:

The patent combines two nitrate ester groups onto the valsartanamide molecule to create a dinitrate derivative. This merging of multiple nitrate functions into a single molecular entity allows for sustained NO release over time, extending the duration of action while maintaining the fast-acting vasodilatory effect characteristic of nitrate esters.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention creates a composite molecular structure by attaching nitrate ester groups to the valsartanamide scaffold. This composite approach integrates the angiotensin II receptor blocking activity of valsartan with the vasodilatory properties of nitrate esters, producing a compound with both prolonged duration and enhanced pharmacodynamic effects.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional nitrate esters are used chronically, then vasodilatory effect is maintained, but oxidative stress and vascular dysfunction occur

Engineering Contradiction:
Improvetherapeutic effectVSAvoidoxidative stress
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent converts the potentially harmful rapid release of NO from conventional nitrates into a beneficial controlled sequential release pattern. The dinitrate structure allows for staged NO release, preventing the oxidative stress and vascular dysfunction associated with conventional nitrate esters while maintaining therapeutic vasodilatory effects.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If frequent dosing is administered to overcome nitrate tolerance, then therapeutic effect is maintained, but treatment complexity increases

Engineering Contradiction:
Improvetherapeutic effectVSAvoiddosing regimen
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The dinitrate derivative provides excessive NO release capacity compared to conventional mononitrates, with sequential release from two nitrate ester groups. This excessive action ensures sustained therapeutic effect throughout the dosing interval, allowing for less frequent dosing while maintaining reliable vasodilatory and antihypertensive effects.

Inventive Principle:
Principle #16Partial or excessive 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 dinitrate esters of valsartanamide demonstrate superior vasodilatory properties compared to valsartan and other nitrate esters, with reduced risk of nitrate tolerance and oxidative stress, effectively managing vascular and metabolic diseases with improved pharmacodynamic effects.

Implementation Method 1

dinitrate esters of valsartanamide derivatives with nitrate functions attached to both the tetrazole unit and the amide substituent, which release nitrogen monoxide sequentially

Methodology Applied
Scientific EffectNitrate ester decomposition: Decomposition (biological)

Data Source

PatentEP2377855B1A valsartanamide dinitrate derivative for the treatment of vascular and metabolic diseases
Publication Date: 2012.07.18 CARDIOLYNX
  • EP2377855B1 patent drawingFigure 1
  • EP2377855B1 patent drawingFigure 2
  • EP2377855B1 patent drawing

AI summary

A dinitrate ester of a valsartanamide is described. It has superior properties in the treatment of vascular and metabolic diseases.