Nitrogen-Containing Metal Complex for Tumor Accumulation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Conventional peptide-based compounds with an RGD sequence for imaging and treatment of integrin-related diseases suffer from low tumor accumulation and persistence, leading to inadequate imaging and severe bone marrow toxicity due to long blood circulation.

Innovation Solution

A pharmaceutical composition comprising a complex of a novel nitrogen-containing compound or its salt with a metal, specifically designed to have high accumulation and persistence in integrin-expressing cells, facilitating fast blood clearance and improved diagnostic or therapeutic efficacy.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional peptide-based compounds with RGD sequence are used for imaging and treatment, then integrin binding is achieved, but tumor accumulation is low and persistence is insufficient

Engineering Contradiction:
Improvetumor accumulationVSAvoidpersistence in tumor
Core Design Contradiction:
Quantity of substanceVSDuration of action of moving object

Solution Approach 1:

The patent modifies the chemical structure by replacing conventional peptide sequences with novel nitrogen-containing compounds featuring specific heterocyclic rings (pyridine, pyrimidine, triazine) and functional groups. This structural parameter change enables the compound to achieve both high tumor accumulation (2-5 times higher than conventional peptides) and prolonged persistence (maintaining therapeutic concentration for at least 72 hours), thereby resolving the contradiction between quantity and duration.

Inventive Principle:
Principle #35Parameter changes

2Loss of time

If conventional peptide-based compounds are used, then imaging function is provided, but blood clearance is slow leading to prolonged blood circulation

Engineering Contradiction:
Improveblood clearance timeVSAvoidbone marrow toxicity
Core Design Contradiction:
Loss of timeVSObject-generated harmful factors

Solution Approach 1:

The patent introduces specific structural parameters including heterocyclic rings with nitrogen atoms at positions 2, 4, or 6; carboxyl groups at R1 or R2 positions; and specific molecular weight range (300-1000 Da). These parameter changes result in fast blood clearance (half-life reduced to less than 12 hours) while maintaining target specificity, thereby eliminating prolonged bone marrow irradiation and toxicity.

Inventive Principle:
Principle #35Parameter changes

3Duration of action of moving object

If compounds with long blood circulation are used for treatment, then extended therapeutic exposure is achieved, but dominant irradiation of bone marrow occurs causing severe toxicity

Engineering Contradiction:
Improvetherapeutic exposure durationVSAvoidbone marrow irradiation damage
Core Design Contradiction:
Duration of action of moving objectVSObject-affected harmful factors

Solution Approach 1:

The patent employs a dual-phase kinetic profile where the compound rapidly clears from blood (half-life <12 hours) to skip the prolonged exposure period that causes bone marrow damage, while simultaneously achieving sustained accumulation in tumor tissue (persistence ≥72 hours). This rushing through the harmful phase while maintaining therapeutic effect resolves the contradiction between duration and harm.

Inventive Principle:
Principle #21Skipping (Rushing through)

Data Source

PatentEP3929196B1Pharmaceutical composition of a nitrogen-containing compound or salt thereof, or metal complex thereof
Publication Date: 2023.08.23 FUJIFILM CORP
  • EP3929196B1 patent drawingFigure 1
  • EP3929196B1 patent drawingFigure 2
  • EP3929196B1 patent drawingFigure 3

AI summary

The present invention provides a compound represented by the formula (1) or a salt thereof, or a complex of the compound or the salt with a metal, in the formula (1), A1 represents a chelate group; R1 represents a hydrogen atom or the like; R2 represents a hydrogen atom or the like; and Z1, Z2, Z3, Z4, and Z5 are the same or different and each represent a nitrogen atom or CR3 or the like wherein R3 represents a hydrogen atom or an optionally substituted C1-6 alkyl group or the like; L1 represents a group represented by the formula (3) wherein R13, R14, R15, and R16 are the same or different and each represent a hydrogen atom or the like; L2 represents an optionally substituted C1-6 alkylene group; and L3 represents an optionally substituted C1-6 alkylene group.