Synthetic Triterpenoids Nrf2 Activation Renal Function

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Solution Overview

Problem

Current treatments for renal/kidney disease, insulin resistance, diabetes, endothelial dysfunction, and cardiovascular disease are inadequate in halting or reversing the progression of these conditions, with existing therapies failing to effectively improve compromised renal function and addressing underlying oxidative stress and inflammation.

Innovation Solution

Administration of synthetic triterpenoids, such as CDDO-Me and related compounds, which activate the Keap1/Nrf2/ARE pathway to induce antioxidant and anti-inflammatory proteins, reducing serum creatinine levels and improving glomerular filtration rate by suppressing NF-κB and STAT3 activities and enhancing Phase 2 responses.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional treatments are used for renal/kidney disease, diabetes, and cardiovascular disease, then current standard of care is maintained, but progression of disease is not halted or reversed and renal function is not improved

Engineering Contradiction:
Improvedisease progression controlVSAvoidrenal function improvement
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of triterpenoid compounds (changing molecular parameters) to enhance their biological activity. Specifically, the synthesis of CDDO and its derivatives involves altering functional groups and molecular configurations to improve potency in activating Nrf2 and suppressing inflammatory pathways, thereby resolving the contradiction between maintaining standard care reliability and achieving improved renal function outcomes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by combining multiple pharmacological mechanisms into a single compound class. The synthetic triterpenoids simultaneously activate antioxidant pathways (Nrf2/ARE), suppress inflammatory mediators (NF-κB, STAT3), and modulate multiple disease processes, creating a multi-functional therapeutic agent that addresses both disease progression control and renal function improvement

Inventive Principle:
Principle #40Composite materials

2Reliability

If naturally-occurring triterpenoids like ursolic and oleanolic acids are used, then anti-inflammatory and anti-carcinogenic activity is provided, but biological activity is relatively weak

Engineering Contradiction:
Improveanti-inflammatory activityVSAvoidbiological activity potency
Core Design Contradiction:
ReliabilityVSPower

Solution Approach 1:

The patent directly applies parameter changes by systematically modifying the chemical parameters of naturally-occurring triterpenoids. The synthesis of CDDO involves adding functional groups (cyano group at C-2, dioxo groups at C-3 and C-12) to the oleanolic acid skeleton, which dramatically enhances the compound's ability to activate Nrf2 and suppress inflammatory pathways, thereby resolving the contradiction between maintaining anti-inflammatory reliability and achieving higher biological potency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by introducing specific functional groups at particular positions on the triterpenoid molecular structure. The cyano group at C-2 and the dioxo groups at C-3 and C-12 are strategically placed to enhance interaction with nuclear receptors and enzymatic targets, creating localized regions of high chemical reactivity and binding affinity that amplify the overall biological activity while preserving the core anti-inflammatory mechanism

Inventive Principle:
Principle #3Local quality

3Productivity

If no new treatment mechanisms are developed, then current treatment limitations are maintained, but significant advance in treating renal failure cannot be achieved

Engineering Contradiction:
Improverenal function improvementVSAvoidtreatment effectiveness
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent employs the intermediary mechanism by utilizing the Nrf2 protein as a molecular mediator. The synthetic triterpenoids act as upstream activators that trigger the Nrf2/ARE signaling pathway, which in turn activates a cascade of downstream antioxidant and anti-inflammatory genes. This intermediary approach allows a single compound to regulate multiple protective pathways simultaneously, achieving both improved renal function and reliable treatment effectiveness through coordinated molecular signaling

Inventive Principle:
Principle #24Intermediary (Mediator)

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 use of synthetic triterpenoids like CDDO-Me effectively reduces serum creatinine levels, improves renal function, and alleviates endothelial dysfunction, offering a significant advancement in treating and preventing renal/kidney disease, insulin resistance, diabetes, and cardiovascular disease by targeting oxidative stress and inflammation.

Implementation Method 1

RTA 402 has also been reported to activate the Keap1/Nrf2/ARE signaling pathway resulting in the production of several anti-inflammatory and antioxidant proteins

Methodology Applied
Scientific EffectNrf2/ARE pathway activation:

Implementation Method 2

enhancing Phase 2 responses

Methodology Applied
Scientific EffectPhase 2 response induction:

Implementation Method 3

suppressing NF-κB and STAT3 activities

Methodology Applied
Scientific EffectNF-κB suppression:

Implementation Method 4

suppressing NF-κB and STAT3 activities

Methodology Applied
Scientific EffectSTAT3 suppression:

Data Source

PatentEP3492077A1Synthetic triterpenoids and methods of use in the treatment of disease
Publication Date: 2019.06.05 REATA PHARMACEUTICALS HOLDINGS LLC
  • EP3492077A1 patent drawingFigure 1a~1d
  • EP3492077A1 patent drawingFigure 2a~2c
  • EP3492077A1 patent drawingFigure 3a~3d

AI summary

The present invention concerns methods for treating and preventing renal/kidney disease, insulin resistance/diabetes, fatty liver disease, and/or endothelial dysfunction/cardiovascular disease using synthetic triterpenoids, optionally in combination with a second treatment or prophylaxis.