Solid Forms of Kinase Modulating Compound I

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Solution Overview

Problem

Current treatments for c-Kit and/or c-Fms and/or Flt3 mediated diseases lack effective solid forms and crystalline forms of Compound I and Compound II, which are essential for therapeutic applications.

Innovation Solution

The development of solid forms, polymorphic forms, and crystalline forms of Compound I and Compound II, including specific forms like Compound I Form A, B, C, and D, and Compound II, characterized by unique X-ray powder diffractograms, differential scanning calorimetry, and thermogravimetric analysis, are provided, along with processes for their preparation and use in pharmaceutical compositions for treating c-Kit and/or c-Fms and/or Flt3 mediated diseases.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If Compound I and Compound II are developed for therapeutic applications, then therapeutic efficacy is improved, but lack of effective solid forms and crystalline forms limits their practical use

Engineering Contradiction:
Improvetherapeutic efficacyVSAvoidavailability of solid forms
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by developing multiple polymorphic forms (Forms A, B, C, D) of Compound I and crystalline forms of Compound II, each with distinct crystal structures characterized by unique X-ray powder diffractograms. These different solid forms exhibit varying physical properties such as solubility, stability, and bioavailability, allowing optimization of therapeutic efficacy while providing manufacturing flexibility through multiple viable solid forms

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite pharmaceutical compositions that incorporate specific crystalline forms of Compound I and Compound II with excipients and carriers. These composite materials combine the active compounds in optimized crystal forms with formulation components to enhance stability, solubility, and delivery, thereby resolving the contradiction between therapeutic efficacy and ease of manufacture

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If multiple crystalline forms (Forms A-D) are developed, then solubility and bioavailability are improved, but characterization and quality control become more complex

Engineering Contradiction:
Improvesolubility and bioavailabilityVSAvoidcharacterization complexity
Core Design Contradiction:
Ease of operationVSDifficulty of detecting and measuring

Solution Approach 1:

The patent employs characteristic X-ray powder diffractogram patterns as unique identifiers for each polymorphic form (Forms A, B, C, D). Each form displays distinct diffraction peaks at specific 2θ angles, serving as a fingerprint for identification and quality control. This approach simplifies differentiation and characterization of the various crystalline forms through a reliable, standardized analytical method

Inventive Principle:
Principle #32Color changes

Solution Approach 2:

The patent replaces complex physical characterization methods with X-ray powder diffraction analysis for identifying and differentiating polymorphic forms. This substitution provides a non-destructive, rapid, and highly specific method for characterizing crystal structures, reducing the complexity of quality control while enabling precise identification of each form based on its unique diffraction pattern

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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

These forms demonstrate therapeutic efficacy in treating conditions such as tenosynovial giant cell tumor, pigmented villonodular synovitis, malignant peripheral nerve sheath tumors, breast cancer, acute myeloid leukemia, and other diseases by effectively inhibiting c-Kit and c-Fms protein kinases, offering improved treatment options.

Implementation Method 1

Compound I Form A is characterized by an X-ray powder diffractogram comprising the following peaks (± 0.2°): at 7.1, 22.9 and 27.6 °2θ, as determined on a diffractometer using Cu-Kα radiation

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

as determined on a diffractometer using Cu-Kα radiation

Methodology Applied
Scientific EffectBragg diffraction: Bragg Diffraction

Implementation Method 3

characterized by an X-ray powder diffractogram comprising the following peaks (± 0.2°): at 7.1, 22.9 and 27.6 °2θ, as determined on a diffractometer using Cu-Kα radiation

Methodology Applied
Scientific EffectCalorimetry: Calorimetry

Implementation Method 4

characterized by an X-ray powder diffractogram comprising the following peaks (± 0.2°): at 7.1, 22.9 and 27.6 °2θ, as determined on a diffractometer using Cu-Kα radiation

Methodology Applied
Scientific EffectThermogravimetric analysis:

Data Source

PatentEP3292123B1Solid forms of a compound modulating kinases
Publication Date: 2020.07.22 PLEXXIKON INC
  • EP3292123B1 patent drawingFigure 1
  • EP3292123B1 patent drawingFigure 2
  • EP3292123B1 patent drawingFigure 3~4

AI summary

Solid forms of the compound, [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]- (6-trifluoromethyl-pyridin-3-ylmethyl)-amine HC1 salt (Compound I) and its free base, active on the receptor protein kinases c-Kit and/or c-Fms and/or Flt3, were prepared and characterized. Also provided are methods of using the solid forms.