Avibactam Sodium Form C Crystallization Process

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Solution Overview

Problem

Current crystalline forms of avibactam sodium, such as forms A, B, D, and E, are unstable and difficult to produce on an industrial scale due to their tendency to convert to other physical forms during pharmaceutical processing and storage, making them unsuitable for reliable use in pharmaceutical compositions.

Innovation Solution

Development of anhydrous crystalline form C of avibactam sodium, which is polymorphically stable and can be produced on an industrial scale using a process involving the addition of 2-butanol or isobutanol to an aqueous solution followed by azeotropic distillation, ensuring stability against moisture and temperature stress.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing crystalline forms (A, B, D, E) of avibactam sodium are used, then the compound can be produced, but they are unstable and convert to other physical forms during pharmaceutical processing and storage

Engineering Contradiction:
Improvepolymorphic stabilityVSAvoidphysical form stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The invention changes the physical parameters of avibactam sodium by establishing a new crystalline form (form C) with specific lattice structure and hydration state. This new form exhibits polymorphic stability by having a different molecular packing arrangement that resists conversion to other forms under pharmaceutical processing conditions, including temperature stress, moisture, and pH variations.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention provides beforehand cushioning against polymorphic transformation by pre-establishing form C as a thermodynamically stable or kinetically stable form that resists conversion to other forms. The specific crystalline structure of form C acts as a protective state that prevents degradation into unstable forms during storage and processing.

Inventive Principle:
Principle #11Beforehand cushioning (Prior cushioning)

2Ease of manufacture

If anhydrous forms (B, D) are produced, then moisture stability is improved, but they are difficult to prepare in the absence of seed crystals and require narrow water activity ranges

Engineering Contradiction:
ImprovemanufacturabilityVSAvoidprocess robustness
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention changes the manufacturing parameters by establishing a new crystalline form (form C) that can be produced through controlled crystallization processes without requiring seed crystals. The form exhibits stability across a broader range of water activity and processing conditions, making the manufacturing process more robust and reliable for industrial production.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If hydrated forms (A, E) are used, then ease of crystallization is improved, but they are prone to dehydration and hydrolysis during storage and processing

Engineering Contradiction:
Improvecrystallization easeVSAvoidchemical stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The invention changes the hydration state parameter by establishing form C as a crystalline form with a specific, stable hydration level that resists both dehydration and hydrolysis. This form maintains its chemical composition stability under pharmaceutical processing conditions while being accessible through controlled crystallization methods.

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

Form C maintains stability under ambient conditions and during pharmaceutical processing, preventing conversion to other forms, thus ensuring the reliability and effectiveness of avibactam sodium in pharmaceutical compositions for treating bacterial infections.

Implementation Method 1

The process comprises a crystallization by adding a solvent containing 2-butanol and/or isobutanol into an aqueous solution of avibactam sodium

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 2

followed by at least partially removing the water, preferably by means of azeotropic distillation

Methodology Applied
Scientific EffectAzeotropic distillation: Distillation

Implementation Method 3

The present invention relates to anhydrous crystalline form C of avibactam sodium and to an industrially applicable, reliable and robust process for its preparation

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP3334734B1Form c of avibactam sodium
Publication Date: 2020.01.01 SANDOZ LTD
  • EP3334734B1 patent drawingFigure 1
  • EP3334734B1 patent drawingFigure 2
  • EP3334734B1 patent drawingFigure 3

AI summary

The present invention relates to crystalline form C of avibactam sodium and to a process for its preparation. The invention also concerns a pharmaceutical composition comprising form C and one or more antibacterial agents, wherein at least one antibacterial agent is a beta-lactam antibiotic. The pharmaceutical composition of the present invention can be used as medicament, in particular for treatment and/or prevention of bacterial infections.