Crystalline forms of 9-aminomethyl-substituted tetracycline compound and a method for their production

RU2865380C2Active Publication Date: 2026-07-01KBP BIOSCIENCES CO LTD
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Patent Information

Authority / Receiving Office
RU · RU
Patent Type
Patents
Current Assignee / Owner
KBP BIOSCIENCES CO LTD
Filing Date
2017-06-22
Publication Date
2026-07-01

AI Technical Summary

Technical Problem

The amorphous form of the tigecycline compound represented by formula (1) produced by existing methods has low purity, stability, and content, making it unsuitable for pharmaceutical use.

Method used

Development of stable crystalline forms I, II, and VII of the tigecycline compound, characterized by specific X-ray diffraction peaks and differential scanning calorimetry profiles, along with methods to produce these forms using specific solvent systems, ensuring high purity and stability.

Benefits of technology

The crystalline forms I and II exhibit improved stability, purity, and reduced residual solvent content, making them suitable for pharmaceutical applications with enhanced therapeutic efficacy against tetracycline-sensitive and resistant bacteria.

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Abstract

FIELD: pharmaceutical compositions.SUBSTANCE: crystalline form I of the compound represented by formula (1), (4S,4aS,5aR,12aS)-9-(3-azabicyclo[3.1.0]hexan-3-ylmethyl)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, which is characterized by the presence of a powder X-ray diffraction pattern having the following characteristic peaks, expressed in degrees 2θ when measured using Cu-K irradiationα: 10.6°±0.2°, 13.3°±0.2°, 15.9°±0.2°, 24.0°±0.2°. The invention relates to a pharmaceutical composition having antibacterial activity, which contains crystalline form I of the compound represented by formula (1) according to the invention and pharmaceutically acceptable carrier(s). The invention relates to a pharmaceutical composition having antibacterial activity, containing crystalline form I of the compound represented by formula (1), according to the invention, and one or more pharmaceutically acceptable carriers and / or diluents, which is in any pharmaceutically acceptable dosage form. The crystalline form of the compound represented by formula (1) is used in the production of a medicament for the treatment and / or prevention of a disease caused by tetracycline-sensitive and / or tetracycline-resistant bacteria, wherein said disease caused by tetracycline-sensitive and / or tetracycline-resistant bacteria is selected from infection, cancer and diabetes, wherein said crystalline form is crystalline form I.EFFECT: crystalline form of (4S,4aS,5aR,12aS)-9-(3-azabicyclo[3.1.0]hexan-3-ylmethyl)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide with high purity, high content, good stability and pharmacokinetics.8 cl, 14 dwg, 2 tbl, 9 exFormula (1)
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