Stable Pyrimido Azacyclo Crystal Forms for RET Inhibitor Delivery

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Solution Overview

Problem

Current RET kinase inhibitors, such as Carbotinib and Vandetanil, suffer from low targeting specificity and cause serious toxicity due to off-target VEGFR inhibition, necessitating the development of novel compounds with better pharmacodynamic and pharmacokinetic properties for treating RET-related cancers like thyroid cancer and non-small cell lung cancer.

Innovation Solution

The development of stable crystal forms of a pyrimido azacyclo compound, specifically free base crystal form III, fumarate crystal form I, and malate crystal form I, which exhibit characteristic X-ray powder diffraction patterns and are suitable for pharmaceutical use, ensuring drug stability, solubility, and bioavailability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If multi-kinase inhibitors (Carbotinib, Vandetanil) are used to treat RET gene mutations, then broad anti-tumor activity is achieved, but serious toxicity occurs due to off-target VEGFR inhibition

Engineering Contradiction:
Improvebroad anti-tumor activityVSAvoidtoxicity from off-target inhibition
Core Design Contradiction:
Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies local quality by designing the pyrimido azacyclo compound with specific structural features (formula A) that provide selective binding to RET kinase while avoiding off-target VEGFR inhibition. The molecular structure is locally optimized with specific substituents and core framework to achieve targeted action at the RET site without affecting other kinases, thereby maintaining anti-tumor activity while reducing toxicity.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by modifying chemical parameters of the inhibitor molecule - specifically the structural parameters of the pyrimido azacyclo core and its substituents - to alter the binding affinity and selectivity profile. By changing molecular parameters such as substituent types, positions, and configurations, the compound achieves high RET selectivity while maintaining potent inhibition, thus resolving the contradiction between broad activity and low toxicity.

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If stable crystal forms are developed for the pyrimido azacyclo compound, then drug stability and quality consistency are improved, but additional development time and resources are required

Engineering Contradiction:
Improvedrug stabilityVSAvoidcrystal form development time
Core Design Contradiction:
Stability of the object's compositionVSLoss of time

Solution Approach 1:

The patent applies preliminary action by conducting comprehensive crystal form screening and characterization during the early drug development stage. Multiple crystal forms (including free base form III, fumarate form I, and malate form I) are identified, isolated, and characterized in advance with their stability profiles, solubility characteristics, and manufacturing properties established before clinical development begins. This preliminary work ensures drug stability is secured early, preventing later formulation problems and reducing overall development time despite the initial investment.

Inventive Principle:
Principle #10Preliminary action

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 crystal forms provide improved drug stability, solubility, and bioavailability, reducing toxicity and enhancing therapeutic efficacy in treating RET-related cancers by maintaining consistent drug quality and absorption.

Implementation Method 1

the X-ray powder diffraction pattern of the free base crystal form III exhibits characteristic peaks at the following 2θ values: 5.1±0.2°, 5.8±0.2°, 7.3±0.2°, 8.2±0.2°, 9.3±0.2°, 10.4±0.2°, 10.7±0.2°, 13.0±0.2°, 13.3±0.2°, 14.7±0.2°, 16.7±0.2°, 18.4±0.2°, 19.0±0.2° and 23.4±0.2°

Methodology Applied
Scientific EffectX-ray powder diffraction: X-Ray

Data Source

PatentEP4714947A1Crystal form of pyrimido azacyclo compound, and preparation method therefor and use thereof
Publication Date: 2026.03.25 TYK MEDICINES INC
  • EP4714947A1 patent drawingFigure 1
  • EP4714947A1 patent drawingFigure 2
  • EP4714947A1 patent drawingFigure 3

AI summary

The present invention relates to a crystal form of a pyrimido azacyclo compound, and a preparation method therefor and a use thereof. Particularly, disclosed in the present invention are a series of crystal forms of a compound of formula A, wherein the crystal forms have excellent stability. Further disclosed in the present invention are a preparation method for the crystal forms and a use of the crystal forms in the prevention and/or treatment of tumors.