2,4-Diphenyl-1,3-dioxane PPAR Modulators for Diabetic Complications

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Solution Overview

Problem

Current treatments for diabetes and insulin resistance, such as thiazolidinediones, have significant side effects like weight gain, hypertension, and liver toxicity due to their full-agonist properties, necessitating the development of novel compounds that modulate PPAR activity without being full-agonists and also address thromboxane receptor and thromboxane synthase activity.

Innovation Solution

Development of specific 2,4-diphenyl-1,3-dioxane compounds that act as PPAR modulators, TP receptor antagonists, and thromboxane synthase inhibitors, with specific stereochemistry and substitutions, to treat diabetic complications and other conditions like insulin resistance, metabolic syndrome, and inflammatory diseases, while minimizing adverse effects.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If thiazolidinediones are used to treat diabetes and insulin resistance, then insulin sensitivity is improved, but serious side effects occur including weight gain, hypertension, cardiac hypertrophy, liver toxicity and oedema

Engineering Contradiction:
Improveinsulin sensitivity improvementVSAvoidside effects (weight gain, hypertension, liver toxicity, oedema)
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of PPAR modulators from full-agonist thiazolidinediones to compounds with partial agonist or antagonist properties. This structural parameter change alters the pharmacological profile, reducing adverse effects while maintaining therapeutic benefit for insulin sensitivity and diabetic complications.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs partial action by developing PPAR modulators that are not full-agonists. These partial agonists or antagonists provide sufficient PPAR modulation to improve insulin sensitivity and treat diabetic complications, but with reduced activation of pathways leading to side effects like weight gain and oedema.

Inventive Principle:
Principle #16Partial or excessive action

2Reliability

If full-agonist PPAR modulators are used to treat metabolic disorders, then therapeutic efficacy is achieved, but adverse effects increase due to full-agonist properties

Engineering Contradiction:
Improvetherapeutic efficacyVSAvoidadverse effects
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the pharmacological parameter from full-agonist to partial agonist or antagonist activity. This parameter change maintains the ability to treat metabolic disorders while reducing the degree of PPAR activation that leads to adverse effects, achieving a balance between efficacy and safety.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses partial agonist action to achieve sufficient therapeutic effect without the excessive PPAR activation caused by full-agonists. This partial action provides the necessary modulation for treating insulin resistance and diabetic complications while avoiding the threshold for adverse effect generation.

Inventive Principle:
Principle #16Partial or excessive action

3Object-generated harmful factors

If novel PPAR modulators are developed to reduce side effects, then adverse reactions decrease, but the complexity of compound design increases

Engineering Contradiction:
Improveadverse reactionsVSAvoidcompound design complexity
Core Design Contradiction:
Object-generated harmful factorsVSDevice complexity

Solution Approach 1:

The patent systematically explores parameter changes in the 1,3-dioxane chemical scaffold, including substitutions at positions 2 and 4 with aromatic groups, varying chain lengths, and modifying functional groups. This structured parameter exploration allows identification of compounds with reduced adverse reactions while managing design complexity through focused chemical space investigation.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2150111B1Substituted 1,3-dioxanes useful as PPAR modulators
Publication Date: 2016.10.19 EVOLVA SA(CH)
  • EP2150111B1 patent drawingFigure 1
  • EP2150111B1 patent drawingFigure 2
  • EP2150111B1 patent drawingFigure 3

AI summary

Specifically useful stereoisomers of 1,3-dioxane derivatives are described and their use in the treatment of a disease or condition dependent on PPAR modulation, such as diabetes, cancer, inflammation, neurodegenerative disorders and infections as well as their use in the treatment of a disease related to TP, such as cardiovascular diseases.