Pyrazolopyrimidine Sigma Ligands Selectivity

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Solution Overview

Problem

There is a need for compounds with pharmacological activity towards sigma receptors that are both effective and selective, and possess good pharmaceutical properties such as administration, distribution, metabolism, and excretion, which are currently lacking in existing sigma receptor ligands.

Innovation Solution

Development of novel pyrazolo[3,4-d]pyrimidine compounds with specific structural formulas that exhibit high affinity for sigma receptors, including sigma-1 and sigma-2 receptors, and their use in pharmaceutical compositions for various therapeutic applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing sigma receptor ligands are used, then pharmacological activity towards sigma receptors is achieved, but pharmaceutical properties such as administration, distribution, metabolism, and excretion are insufficient

Engineering Contradiction:
Improvepharmacological activityVSAvoidpharmaceutical properties
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by systematically modifying the chemical structure of pyrazolo[3,4-d]pyrimidine compounds through varying substituents at different positions (R1-R6 groups). These structural parameter changes optimize both the pharmacological activity towards sigma receptors and the pharmaceutical properties including administration, distribution, metabolism, and excretion characteristics.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the pyrazolo[3,4-d]pyrimidine core with various functional groups and substituents. This composite approach allows the molecule to simultaneously achieve high affinity for sigma receptors while incorporating pharmacophores that improve pharmaceutical properties such as solubility, metabolic stability, and tissue distribution.

Inventive Principle:
Principle #40Composite materials

2Reliability

If known sigma receptor ligands like rimcazole are used, then treatment of psychosis is achieved, but selectivity and effectiveness are limited

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidreceptor selectivity
Core Design Contradiction:
ReliabilityVSMeasurement precision

Solution Approach 1:

The patent applies local quality by introducing specific substituents at particular positions on the pyrazolo[3,4-d]pyrimidine ring system. Each substituent position (R1-R6) can be independently optimized to enhance selectivity for sigma-1 versus sigma-2 receptors, allowing precise control over which receptor subtype is primarily activated or blocked.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The molecular structure is segmented into distinct functional regions: the pyrazolo[3,4-d]pyrimidine core provides the basic sigma receptor binding capability, while separate substituent groups (R1-R6) can be independently optimized for selectivity, pharmacokinetic properties, and specific receptor subtype preference, allowing modular optimization of the ligand.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP2734524B1PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS, THEIR PREPARATION AND USE AS SIGMA LIGANDS
Publication Date: 2017.01.11 LABORATORIOS DEL DR ESTEVE SA

AI summary

The present invention relates to new pyrazolo[3,4-d]pyrimidine compounds having a great affinity for sigma receptors, especially sigma-1 receptors as well as to the process for the preparation thereof, to composition comprising them and to their use as medicaments.