CEM-101 Crystalline Forms for Polymorph Control

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The existing macrolide antibiotic compound CEM-101 exhibits polymorphism, leading to variations in physical properties such as solubility and stability, which complicates its manufacturing and formulation into stable pharmaceutical forms.

Innovation Solution

The development of crystalline forms of CEM-101, specifically Form I and Form II, characterized by distinct X-ray powder diffraction patterns and differential scanning calorimetry profiles, which can be prepared and formulated to be substantially free of other physical forms, enhancing stability and handling properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If CEM-101 is manufactured without controlling crystalline form, then production process is simpler, but physical properties such as solubility and stability vary

Engineering Contradiction:
Improvephysical stabilityVSAvoidmanufacturing complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by controlling specific crystallization conditions including temperature ranges (cooling from 50-80°C to 4-25°C), pH values (adjusting to 2-7), and solvent compositions to selectively produce desired crystalline forms of CEM-101 with consistent physical properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs preliminary action by pre-adjusting solution parameters before crystallization occurs, including setting initial pH, temperature, and solvent composition to ensure formation of the desired crystalline form, thereby preventing formation of unwanted polymorphs

Inventive Principle:
Principle #10Preliminary action

2Adaptability or versatility

If multiple crystalline forms are present, then more physical forms are available for different applications, but manufacturing and formulation become more difficult

Engineering Contradiction:
Improvephysical form varietyVSAvoidformulation ease
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent applies the extraction principle by isolating and separating specific crystalline forms (Form I, Form II, Form III) from mixture to obtain substantially pure forms, each with distinct and consistent physical properties suitable for specific pharmaceutical applications

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent applies local quality by providing different crystalline forms with specific, localized properties - Form I with particular solubility characteristics, Form II with different stability profiles, allowing selection of the optimal form for each specific pharmaceutical application

Inventive Principle:
Principle #3Local quality

3Reliability

If amorphous form is used, then manufacturing is simpler, but stability and bioavailability are reduced

Engineering Contradiction:
Improvebioavailability consistencyVSAvoidmanufacturing simplicity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent transforms the amorphous form into crystalline forms by changing physical parameters including temperature control during crystallization, pH adjustment, and solvent selection, thereby improving stability and bioavailability while maintaining manufacturing feasibility

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 crystalline forms of CEM-101 provide improved stability, solubility, and manufacturing advantages, ensuring consistent pharmaceutical compositions and effective treatment of bacterial and protozoal infections.

Implementation Method 1

an X-ray powder diffraction pattern including peaks at 2θ = 8.8, 10.5, 13.2, and 18.6, each ± 0.2 2θ, where each of said peaks is detected from an incident beam of Cu Kα radiation

Methodology Applied
Scientific EffectX-ray diffraction: X-Ray

Implementation Method 2

characterized by an X-ray powder diffraction pattern including peaks

Methodology Applied
Scientific EffectDiffraction: Diffraction

Implementation Method 3

characterized by differential scanning calorimetry having an endotherm at 170°C, an endotherm in the range from 194°C to 199°C, an endotherm in the range from 219°C to 225°C, or an endotherm at 225°C

Methodology Applied
Scientific EffectCalorimetry: Calorimetry

Data Source

PatentEP3009442B1Crystalline forms of a macrolide, and uses therefor
Publication Date: 2019.06.19 CEMPRA PHARMACEUTICALS INC
  • EP3009442B1 patent drawingFigure 1
  • EP3009442B1 patent drawingFigure 2
  • EP3009442B1 patent drawing

AI summary

New crystalline forms of macrolide compounds, and pharmaceutical compositions thereof, are described herein. In addition, processes for preparing the crystalline forms are described herein.