Oxa Acid Compounds Tuning Polarity for Drug Delivery

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Solution Overview

Problem

There is a need for oxa acid compounds with varying molecular weights and hydrophile-lipophile balances to enhance polarity control in drug delivery systems and cosmetics, as existing compounds lack diversity in these aspects.

Innovation Solution

The development of oxa acid compounds with specific structural formulas, including linear or branched hydrocarbon groups and functional groups capable of chemical reactions, allowing for varying molecular weights and hydrophile-lipophile balances, which can be used as absorption promoters or prodrug producers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing oxa acid compounds are used, then absorption promotion and prodrug production capabilities are achieved, but diversity in molecular weights and hydrophile-lipophile balances is insufficient

Engineering Contradiction:
Improvediversity in molecular weights and hydrophile-lipophile balancesVSAvoidcompound structure variety
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by systematically varying the molecular weight and hydrophile-lipophile balance (HLB) of oxa acid compounds through modification of the alkyl chain length (n = 1-20) and ether oxygen content (m = 1-10) in the general formula (I). This allows tuning of the compounds' polarity and solubility characteristics to match different drug properties and delivery requirements, thereby achieving diverse absorption promotion and prodrug production capabilities without increasing structural complexity unnecessarily.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent establishes a universal oxa acid compound structure (formula I) that can serve multiple functions: as absorption promoters for orally administered pharmaceuticals, as promoters of percutaneous absorption, and as prodrug components. By adjusting parameters n and m within specified ranges, the same basic structure adapts to different application scenarios and drug types, achieving versatility without requiring entirely different molecular frameworks for each application.

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Manufacturing precision

If polarity control is enhanced through diverse oxa acid compounds, then drug delivery system effectiveness is improved, but compound synthesis and selection complexity increases

Engineering Contradiction:
Improvepolarity control precisionVSAvoidcompound selection complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent provides a systematic approach to polarity control by defining specific ranges for parameters n (1-20) and m (1-10) in formula (I), which directly determine the hydrophile-lipophile balance. This parameter-based control system allows precise adjustment of polarity characteristics to match the solubility and permeability requirements of different drugs, achieving manufacturing precision in polarity control while maintaining a manageable selection framework through the generalized formula structure.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3441382B1Oxa acid compound
Publication Date: 2023.08.30 MORESCO
  • EP3441382B1 patent drawingFigure 1~2
  • EP3441382B1 patent drawingFigure 3~4
  • EP3441382B1 patent drawingFigure 5~6

AI summary

A compound, comprising a structure represented by a formula (1) where R1 represents a linear or branched hydrocarbon group having 1 to 36 carbon atoms, one or more but not all carbon atoms of which hydrocarbon group have each optionally been substituted by an oxygen atom, a nitrogen atom, or a sulfur atom; m represents an integer of 0 to 35; n represents an integer of 2 to 5; and -C(=O)-X represents a functional group capable of chemical reaction, or a formula (2) where R2 represents a linear or branched hydrocarbon group having 1 to 36 carbon atoms, one or more but not all carbon atoms of which hydrocarbon group have each optionally been substituted by an oxygen atom, a nitrogen atom, or a sulfur atom; p represents an integer of 0 to 30; q represents an integer of 2 to 5; and -C(=O)-X represents a functional group capable of chemical reaction.