Diazepane-Acetamide Derivatives Selective 11β-HSD1 Inhibition

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Solution Overview

Problem

Current therapies lack effective, selective inhibitors for 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) to treat various diseases associated with excessive cortisol levels, such as diabetes, obesity, hypertension, and cognitive disorders, with existing inhibitors often causing side effects or having limited specificity.

Innovation Solution

Development of diazepane-acetamide derivatives that act as selective inhibitors of 11β-HSD1, reducing cortisol levels in target tissues to treat metabolic syndrome, diabetes, obesity, glaucoma, osteoporosis, cognitive disorders, and other conditions with improved specificity and reduced side effects.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing 11β-HSD1 inhibitors are used, then cortisol levels are reduced, but side effects occur and specificity is limited

Engineering Contradiction:
ImprovespecificityVSAvoidside effects
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical structure of existing inhibitors by changing molecular parameters - specifically incorporating diazepane ring systems with varying substituents (R1-R6 groups) to optimize binding affinity and selectivity for 11β-HSD1, thereby reducing off-target effects while maintaining cortisol-lowering efficacy

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining diazepane core frameworks with various functional groups (carboxylic acid, ester, amide, urea, carbamate) to achieve selective inhibition of 11β-HSD1 while minimizing interaction with other biological targets, thus reducing side effects

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If non-specific 11β-HSD1 inhibitors are used, then cortisol levels decrease, but hypertension and other side effects occur due to inhibition of 11β-HSD2

Engineering Contradiction:
Improvecortisol reductionVSAvoidhypertension
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent achieves tissue-specific selectivity by designing molecules that preferentially bind to 11β-HSD1 in specific tissues (liver, adipose, brain) over 11β-HSD2 in other tissues (kidney, gut, placenta), thereby reducing cortisol in target tissues without causing systemic hypertension through 11β-HSD2 inhibition

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The invention optimizes the IC50 ratio between 11β-HSD1 and 11β-HSD2 by adjusting molecular parameters of the diazepane-acetamide derivatives, achieving selective inhibition of 11β-HSD1 at concentrations that do not significantly inhibit 11β-HSD2, thus preventing hypertension

Inventive Principle:
Principle #35Parameter changes

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 diazepane-acetamide derivatives effectively inhibit 11β-HSD1 activity, reducing cortisol levels and associated disease symptoms, offering a therapeutic approach with enhanced specificity and safety profiles compared to previous inhibitors.

Implementation Method 1

The present invention relates to diazepane-acetamide derivatives as selective inhibitors of the enzyme 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1)

Methodology Applied
Scientific EffectEnzyme inhibition: Enzyme

Data Source

PatentEP2078001B8Diazepane-acetamide derivatives as selective 11 -HSD1 inhibitors
Publication Date: 2010.12.15 MERCK PATENT GMBH

AI summary

The present invention relates to diazepane-acetamide derivatives of formula I as selective inhibitors of the enzyme 11-beta-hydroxysteroid dehydrogenase type 1 (11 ß-HSD-1 ) and the use of such compounds for the treatment and prevention of metabolic syndrome, diabetes, insulin resistance, obesity, lipid disorders, glaucoma, osteoporosis, cognitive disorders, anxiety, depression, immune disorders, hypertension and other diseases and conditions.