Crystalline PI3K Inhibitor Forms for Scalable Manufacturing

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Solution Overview

Problem

Current manufacturing methods for pyrimidine derivatives, specifically PI3K inhibitors like Compound A, are not scalable, safe, simple, high-yielding, or economical, and there is a need for new solid forms for effective cancer treatment.

Innovation Solution

Development of a crystalline form of the monohydrochloride salt of Compound A, including polymorphs, and processes for forming these solid forms, which offer improved pharmacokinetic properties and stability for pharmaceutical compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional manufacturing methods are used for pyrimidine derivatives, then the compound can be synthesized, but the process is not scalable, safe, simple, high-yielding, or economical

Engineering Contradiction:
Improvemanufacturing yield and scalabilityVSAvoidmanufacturing process complexity and safety
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the physical state parameter of the product from conventional forms to specific crystalline polymorph forms ( Forms A, B, C, D, E with different hydration states). This parameter change enables improved manufacturing scalability, safety, and economy while maintaining compound identity, as different polymorph forms can be obtained through controlled crystallization processes that are more suitable for industrial production.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transition processes (crystallization from solution or melt) to obtain specific polymorph forms of the pyrimidine derivative. By controlling phase transition conditions (temperature, solvent selection, cooling rates), the process achieves high yield and scalability while improving safety and economic viability compared to conventional methods.

Inventive Principle:
Principle #36Phase transitions

2Reliability

If new solid forms are developed for cancer treatment, then pharmacokinetic properties and stability are improved, but manufacturing complexity increases

Engineering Contradiction:
Improvepharmacokinetic properties and stabilityVSAvoidsolid form development complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies physical parameters (crystalline structure, hydration state) of the solid form to achieve improved pharmacokinetic properties and stability. Multiple polymorph forms (A-E) with different physical parameters are developed, each offering enhanced reliability for cancer treatment while maintaining manageable manufacturing complexity through systematic crystallization protocols.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If multiple polymorph forms are produced, then pharmacokinetic properties are enhanced, but manufacturing process complexity increases

Engineering Contradiction:
Improvepharmacokinetic propertiesVSAvoidpolymorph production complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent segments the product into different polymorph forms (A, B, C, D, E) with distinct pharmacokinetic properties. Each form can be produced through specific crystallization conditions, allowing selective production based on therapeutic requirements. This segmentation enables enhanced pharmacokinetic properties while managing complexity through standardized protocols for each form.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent develops a universal crystallization methodology that can produce multiple polymorph forms (A-E) using similar process principles (solvent selection, temperature control, seeding). This multi-functional approach enables enhanced pharmacokinetic properties across different forms while avoiding proportional increase in manufacturing complexity, as the same fundamental process framework applies to all forms.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 crystalline forms of Compound A's monohydrochloride salt provide enhanced stability, purity, and pharmacokinetic properties, making them suitable for scalable and economical production, and effective in treating various cancers by inhibiting PI3K-mediated disorders.

Implementation Method 1

The invention provides a crystalline form of the monohydrochloride salt of the compound of formula A

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP3040333B1Crystalline forms of 5-(2,6-di-4-morpholinyl-4-pyridmidinyl)-4-trifluoromethylpyridin-2-amine, a pik3 inhibitor
Publication Date: 2018.09.12 NOVARTIS AG
  • EP3040333B1 patent drawingFigure 1
  • EP3040333B1 patent drawingFigure 2
  • EP3040333B1 patent drawingFigure 3

AI summary

The invention relates to processes for manufacturing a compound of formula 5, or a stereoisomer, tautomer or a salt thereof, wherein the substituents are as defined in the specification. The invention further relates to new manufacturing processes for specific solid forms of Compound A and its salts, to such solid forms and to use of said solid forms for the therapeutic treatment of warm-blooded animals.