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Fexofenadine hydrochloride compound of novel crystal form and preparation method of fexofenadine hydrochloride compound

A technology of fexofenadine hydrochloride and fexofenadine, which is applied in the directions of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc. Solubility and bioavailability issues

Active Publication Date: 2014-10-01
KUSN ROTAM REDDY PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Different crystal forms of the same compound have the same chemical composition but different microscopic crystal structures, which lead to differences in their appearance, physicochemical properties and biological activities
These characteristics directly affect the preparation performance of the drug, and will affect the stability, solubility and bioavailability of the drug, which in turn will affect the quality, safety, effectiveness and application of the drug
It has been found through research that the above-mentioned existing crystal forms of fexofenadine hydrochloride cannot meet the actual needs of pharmaceuticals due to reasons such as stability or bioavailability. Therefore, in drug research and development, the problem of polymorphic forms of drugs should be fully considered

Method used

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  • Fexofenadine hydrochloride compound of novel crystal form and preparation method of fexofenadine hydrochloride compound
  • Fexofenadine hydrochloride compound of novel crystal form and preparation method of fexofenadine hydrochloride compound
  • Fexofenadine hydrochloride compound of novel crystal form and preparation method of fexofenadine hydrochloride compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Suspend 10 g of fexofenadine amorphous (from WO2009034582A2) in a mixed solution of 60 ml of pentanone and tetrahydrofuran (the volume ratio of pentanone to tetrahydrofuran is 5:1), heat to reflux for 5 hours, and add 10% Ethyl acetate solution of HCl, adjust the pH value of the reaction material to 2, stir at ambient temperature for 14 hours, filter, and dry the obtained solid at 80°C, then suspend the solid in acetone and heat to reflux for 5 hours, stir at room temperature, filter the obtained solid, 100-120 °C and vacuum-dried to obtain fexofenadine hydrochloride crystal form J9.2g of the present invention.

Embodiment 2

[0029] Suspend 10g of fexofenadine crystal form A (from CN100390145C) in a mixed solution of 62.5ml of pentanone and tetrahydrofuran (the volume ratio of pentanone to tetrahydrofuran is 7:1), heat to reflux for 5h, and add 10 % HCl in ethyl acetate solution, adjust the pH value of the reaction material to 2, stir at ambient temperature for 14 hours, filter, and dry the obtained solid at 80°C, then suspend the solid in acetone and heat to reflux for 5 hours, stir at room temperature, filter the obtained solid, 110°C Dry under vacuum to obtain fexofenadine hydrochloride crystal form J9.6g.

Embodiment 3

[0031] Suspend 10 g of fexofenadine crystal form A in a mixed solution of 100 ml of pentanone and tetrahydrofuran (the volume ratio of pentanone to tetrahydrofuran is 8:1), heat to reflux for 5 h, and add ethyl acetate containing 10% HCl to the solution. Ester solution, adjust the pH value of the reaction material to 2, stir at ambient temperature for 14 hours, filter, and dry the obtained solid at 80°C, then suspend the solid in acetone and heat to reflux for 5 hours, stir at room temperature, filter the obtained solid, and vacuum dry at 110°C, thereby Obtained fexofenadine hydrochloride crystal form J9.3g.

[0032] The XRPD diffraction data of fexofenadine hydrochloride crystalline form J prepared in Examples 1-3 are consistent with those in Table 2. DSC detection shows that crystalline form J has an obvious endothermic peak at 172±3°C.

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Abstract

The invention relates to the field of medicinal chemistry, in particular to novel crystal form of fexofenadine hydrochloride and a preparation method of the novel crystal form, and particularly discloses a fexofenadine hydrochloride crystal form J which is favorable in stability, better in solubility in a normal solvent, convenient to store, and stable in treatment during preparation of preparation formulation, thereby improving in-vivo bioavailability.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a new crystal form of fexonafildine hydrochloride and a preparation method thereof. Background technique [0002] Fexofenadine hydrochloride, the English name is Fexofenadine Hydrochloride, the chemical name is 4-[4-[4-(hydroxydiphenylmethyl)-l-piperidinyl]-1-hydroxybutyl]-.-di Methylphenylacetic acid hydrochloride, fexofenadine hydrochloride is a new generation of anti-allergic drugs, and similar products astemizole (astemizole, withdrawn from the US market in 1999 due to easy to cause cardiotoxicity), cetirizine Compared with oxazine, loratadine, etc., fexofenadine hydrochloride has the advantages of fast action, high curative effect, and small toxic and side effects, and its structure is as shown in formula I: [0003] [0004] At present, fexofenadine hydrochloride is known to exist in various crystal forms, as detailed in the table below: [0005] Table 1 [0006] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22A61K31/445A61P37/08
CPCC07D211/22
Inventor 朱炳跃刘颖辉曹俊章刘火
Owner KUSN ROTAM REDDY PHARMA