KRAS G12C Inhibitor Crystal Forms for Stability

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Solution Overview

Problem

Existing KRAS G12C inhibitors face challenges with chemical stability due to variations in crystallization and storage conditions, leading to issues like poor product stability, agglomeration, and poor flowability, necessitating the development of stable crystal forms with improved properties.

Innovation Solution

The development of multiple crystal forms of the KRAS G12C inhibitor, each with distinct X-ray powder diffraction patterns, is achieved through various crystallization methods using different solvents and temperature cycles, ensuring stability and improved clinical efficacy.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the compound is crystallized using conventional methods, then the drug can be produced, but the chemical stability is poor and product aggregation occurs

Engineering Contradiction:
Improvechemical stabilityVSAvoidproduct aggregation
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by systematically varying crystallization conditions including solvent types (ethyl acetate, n-heptane, their mixtures), temperatures (4℃, room temperature, 60℃), and pH values (adjusted with ammonium hydroxide or hydrochloric acid) to obtain different crystal forms with improved stability and reduced aggregation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transitions through controlled crystallization processes where the compound transitions from solution phase to solid crystal phase under specific conditions, generating distinct crystal forms (Form A, Form B, Form C, Form D, Form E) with different stability characteristics and physical properties

Inventive Principle:
Principle #36Phase transitions

2Ease of operation

If amorphous drug products are used, then the drug can be formulated, but poor product stability and difficult filtration occur

Engineering Contradiction:
Improvefiltration difficultyVSAvoidproduct stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent transforms the amorphous phase to crystalline phase through controlled crystallization, converting the unstable amorphous drug product into stable crystal forms that are easier to filter and handle while maintaining or improving therapeutic efficacy

Inventive Principle:
Principle #36Phase transitions

3Reliability

If polymorphs are generated due to storage conditions, then the drug remains stable, but different storage requirements and production complexities arise

Engineering Contradiction:
Improvestorage stabilityVSAvoidstorage requirements
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent identifies and characterizes multiple polymorphic forms (Form A through Form E) with distinct XRPD patterns, DSC, and TGA characteristics, establishing specific storage conditions for each form to maintain stability while understanding their respective requirements

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 new crystal forms exhibit enhanced stability and better clinical prospects, addressing the issues of chemical instability and improving the pharmaceutical properties of KRAS G12C inhibitors.

Implementation Method 1

adding the compound of formula 1 to a solvent a and stirring for crystallization, wherein the solvent a is selected from the group consisting of one or more of ethyl acetate and n-heptane

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP4700027A1Crystalline form of nitrogen-containing tetracyclic compound and preparation method therefor
Publication Date: 2026.02.25 JIANGSU HENGRUI MEDICINE CO LTD
  • EP4700027A1 patent drawingFigure 1~2
  • EP4700027A1 patent drawingFigure 3~4
  • EP4700027A1 patent drawingFigure 5~6

AI summary

The present disclosure relates to a crystalline form of a nitrogen-containing tetracyclic compound and a preparation method therefor. Specifically, provided in the present disclosure are a crystal form C, a crystal form F, a crystal form G, a crystal form H, a crystal form L, a crystal form M, a crystal form N, a crystal form R and a crystal form S of (S)-4-((S)-10-acryloyl-4-chloro-2-fluoro-14-oxo-8,8a,9,10,11,12-hexahydro-7H,14H-pyrazino[1',2':5,6][1,5]diazocin[3,2,1-hi]indazol-3-yl)-2-amino-7-fluorobenzo[b]thiophene-3-carbonitrile (formula 1), which crystal forms have good stability and can be better used in clinical treatment.