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Pseudo-polymorphic form of desloratadine citrate disodium and preparation method thereof

A technology for loratadine and pseudopolymorphism, which is applied to the field of pseudopolymorphism of desloratadine citrate and its preparation, can solve the problems of impossible prediction of drug formation, different crystal forms and the like, and achieves good stability And the effect of solubility, high stability and good solubility

Active Publication Date: 2015-03-25
JIANGSU HAICI BIOLOGICAL PHARMA CO LTD OF YANGTZE RIVER PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, it is usually not possible to predict whether a particular drug will form different crystalline forms, only the structure and properties of the crystalline forms themselves
In conclusion, the discovery of new crystalline forms of pharmaceutically useful compounds may have the opportunity to improve certain performance characteristics of pharmaceutical products

Method used

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  • Pseudo-polymorphic form of desloratadine citrate disodium and preparation method thereof
  • Pseudo-polymorphic form of desloratadine citrate disodium and preparation method thereof
  • Pseudo-polymorphic form of desloratadine citrate disodium and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of 8-chloro-6,11-dihydro-11-(4-piperidinylene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

[0031] Add 100g of loratadine to a 500mL three-neck flask, add 300mL of hydrochloric acid with a mass fraction of 50%, heat up to 90°C, stir, and react for 3-4 hours. After the reaction, take a sample TLC to track the reaction process. After the reaction of the raw materials is completely stopped, cool to room temperature. Add 300mL of ice water to the solution, and slowly add 20% sodium hydroxide aqueous solution under ice bath conditions to adjust the pH value to 10. At this time, a large amount of white precipitates are precipitated in the solution, and the precipitates are filtered under reduced pressure with 300mL of acetic acid Ethyl ester dissolves. The filtrate was extracted twice with 200 mL ethyl acetate, the organic phase was mixed with the above ethyl acetate solution in which the precipitate was dissolved, dried with anhydrous sodium sulfate,...

Embodiment 2

[0032] Example 2 Preparation of 8-chloro-6,11-dihydro-11-(4-piperidinylene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

[0033] Add 100g of loratadine to a 500mL three-neck flask, add 300mL of sulfuric acid with a mass fraction of 50%, heat up to 90°C, stir, and react for 5-6 hours. After the reaction, take a sample TLC to track the reaction process. After the reaction of the raw materials is completely stopped, cool to room temperature. Add 300mL ice water to the solution, and slowly add potassium hydroxide aqueous solution with a mass fraction of 20% under ice bath conditions to adjust the pH value to 12. At this time, a large amount of white precipitates are precipitated in the solution, and the precipitates are filtered under reduced pressure with 300mL toluene. dissolve. The filtrate was extracted twice with 200 mL of toluene, the organic phase was mixed with the above-mentioned toluene solution in which the precipitate was dissolved, dried with anhydrous sodium sulfat...

Embodiment 3

[0034] Example 3 Preparation of polymorphic compounds of desloratadine citrate

[0035] Add 28g of citric acid and 41g of 8-chloro-6,11-dihydro-11-(4-piperidinylene)-5H-benzo-[5,6] prepared in Example 1 into a 1000mL three-necked flask Add 300mL of methanol to -cycloheptane-[1,2-b]-pyridine, and slowly drop in NaOH aqueous solution (11g, 200mL of pure water) at 25°C with stirring, adjust the pH to 6-7, and continue stirring for 30min , a white solid appeared, continued to stir for 3-4h, more solids were precipitated, filtered under reduced pressure, and the filter cake was washed with 300mL. The obtained solid was dried under vacuum at 50° C. for 4 h to obtain 70 g of white solid. The yield is 75%.

[0036] The crystal is used as a sample, and powder X-ray diffraction is measured to obtain figure 1 The X-ray powder diffraction pattern shown, wherein at about 4.378°, 8.208°, 8.483°, 11.050°, 14.184°, 16.742°, 17.430°, 19.365°, 21.558°, 23.367°, 25.084°, 27.104°, 32...

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Abstract

The invention provides a pseudo-polymorphic form of desloratadine citrate disodium. Under the conditions of Cu-Ka radiation, the compound of the pseudo-polymorphic form has an X-ray powder diffractogram which is shown as Figure 1 and is represented by a diffraction angle 2theta, wherein characteristic peaks exist at approximately 4.378 degrees, 8.208 degrees, 8.483 degrees, 11.050 degrees, 14.184 degrees, 16.742 degrees, 17.430 degrees, 19.365 degrees, 21.558 degrees, 23.367 degrees, 25.084 degrees, 27.104 degrees, 32.335 degrees and 38.992 degrees. The invention also provides a preparation method of the pseudo-polymorphic form of desloratadine citrate disodium. Compared with the parent body desloratadine, the pseudo-polymorphic form of desloratadine citrate disodium has better stability and solubility.

Description

technical field [0001] The invention relates to a pseudopolymorph of desloratadine citrate and a preparation method thereof, belonging to the technical field of pharmaceutical production. Background technique [0002] Desloratadine citrate is 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine citrate Disodium hydrogen acid dihydrate has the following structure: [0003] [0004] III [0005] Desloratadine is a nonsedating, long-acting histamine antagonist. US Patent No. 4,659,716 first described desloratadine in detail. However, desloratadine is unstable, sensitive to acids and sugars, and easily oxidized by air. Patent US6100274 discloses that desloratadine is unstable in normal storage conditions in the presence of conventional filler lactose. Patent CN02128998 discloses a method of reacting desloratadine with an inorganic acid or an organic acid to form a compound salt to improve its stability. On the other hand, the solubility ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07C51/41C07C59/265
Inventor 史登健孙会王庆辉冯建鹏陈元龙朱圣红陆良喆
Owner JIANGSU HAICI BIOLOGICAL PHARMA CO LTD OF YANGTZE RIVER PHARMA GRP
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