Enantiomerically Enriched Hydroxybutyrate Ester Precursor
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Solution Overview
Problem
Direct administration of (R)-3-hydroxybutyrate or acetoacetate can cause acidosis and sodium overload, making it impractical and dangerous for elevating ketone body levels, while existing derivatives are unpalatable and difficult to administer orally.
Innovation Solution
Enantiomerically enriched 3-hydroxybutyl 3-hydroxybutyrate, specifically (3R,3R') enantiomer, is used as a precursor to (3R)-hydroxybutyrate, providing a palatable and effective means to elevate ketone body levels through oral administration, with a favorable pharmacokinetic profile.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If direct administration of (R)-3-hydroxybutyrate or acetoacetate is used to elevate ketone body levels, then the desired therapeutic effect is achieved, but acidosis and sodium overload occur making it dangerous and impractical
Solution Approach 1:
The patent uses esters of (R)-3-hydroxybutyrate as intermediary compounds that serve as precursors to ketone bodies. These esters can be administered orally and are metabolized in the body to release ketone bodies, thereby elevating their blood levels without causing the harmful effects of direct acid administration. The ester serves as a safe mediator that delivers the active substance indirectly.
Solution Approach 2:
The patent changes the chemical form of (R)-3-hydroxybutyrate from its free acid form to ester form, altering its pharmacological properties. This parameter change allows the compound to be administered orally without causing acidosis, while still achieving the desired elevation of ketone body levels after metabolism in the body.
2Reliability
If sodium salt of hydroxybutyrate is administered to achieve therapeutic levels, then ketone body elevation is achieved, but sodium overload occurs making it unsuitable
Solution Approach 1:
The patent employs ester compounds as intermediaries that do not contain high levels of sodium. These esters are metabolized to release ketone bodies without introducing excessive sodium into the system, thus avoiding sodium overload while achieving the desired therapeutic effect.
Solution Approach 2:
The patent changes the chemical formulation from sodium salt to ester form, fundamentally altering the composition. This parameter change eliminates the sodium overload issue while preserving the ability to elevate ketone body levels through metabolic conversion.
3Reliability
If existing derivatives of hydroxybutyrate are used to elevate ketone bodies, then the desired effect is achieved, but they are unpalatable and difficult to administer orally
Solution Approach 1:
The patent optimizes the chemical structure by selecting specific ester derivatives with favorable taste properties and bioavailability. This parameter change in the molecular structure makes the compound palatable and suitable for oral administration, resolving the issue of poor acceptability while maintaining effectiveness.
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 compound effectively raises blood levels of (3R)-hydroxybutyrate, promoting rapid and sustained effects, improving physical performance, weight management, and cognitive function, while being well-tolerated and easily ingested.
Implementation Method 1
3-hydroxybutyl 3-hydroxybutyrate enantiomerically enriched with respect to (3R)-hydroxybutyl (3R)-hydroxybutyrate
Data Source
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AI summary
A compound which is 3-hydroxybutyl 3-hydroxybutyrate enantiomerically enriched with respect to (3?)»hydroxybutyl (3i?)-hydroxybutyrate of formula (I): is an effective and palatable precursor to the ketone body (3?)-hydroxybutyrate and may therefore be used to treat a condition which is caused by, exacerbated by or associated with elevated plasma levels of free fatty acids in a human or animal subject, for instance a condition where weight loss or weight gain is implicated, or to promote alertness or improve cognitive function, or to treat, prevent or reduce the effects of, neuro degeneration, free radical toxicity, hypoxic conditions or hyperglycaemia.