Clathrate of azithromycin hydrate with 1,2-propyleneglycol, method for the manufacture thereof and pharmaceutical composition comprising same

A technology of azithromycin and propylene glycol, applied in the field of pharmaceutical compositions comprising this inclusion compound, can solve problems such as being insufficient to remove toxic aliphatic hydrocarbon solvents, undesired water content azithromycin dihydrate and the like

Inactive Publication Date: 2004-06-16
HANMI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this water content control procedure is not sufficient to remove the toxic aliphatic hydrocarbon solvents strictly used in the recrystallization procedure
On the other hand, vacuum drying at high temperature may lead to the formation of azithromycin dihydrate with undesired water content

Method used

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  • Clathrate of azithromycin hydrate with 1,2-propyleneglycol, method for the manufacture thereof and pharmaceutical composition comprising same
  • Clathrate of azithromycin hydrate with 1,2-propyleneglycol, method for the manufacture thereof and pharmaceutical composition comprising same
  • Clathrate of azithromycin hydrate with 1,2-propyleneglycol, method for the manufacture thereof and pharmaceutical composition comprising same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 100 g of azithromycin anhydride was dissolved in 300 ml of acetone, and 100 ml of 1,2-propanediol was added thereto. The solution was stirred at room temperature for 10 minutes, and 500 ml of water was added dropwise thereto to induce precipitation of azithromycin crystals. The solution was stirred at room temperature for 2 hours, and the precipitate was filtered, washed strictly with water, and then dried at 40° C. for 20 hours to obtain 96 g of an inclusion compound of azithromycin hydrate and 1,2-propanediol.

[0040] m.p.: 129~131℃,

[0041] Moisture content measured by Karl Fischer water analyzer: 3.5wt%,

[0042] 1,2-Propanediol content determined by gas chromatography: 3.3% by weight.

Embodiment 2

[0044] 20 g of azithromycin monohydrate was dissolved in 100 ml of acetone, and 15 ml of 1,2-propanediol was added thereto. The solution was stirred at room temperature for 10 minutes, and 200 ml of water was added dropwise thereto to induce precipitation of azithromycin crystals. The solution was stirred at 0-5° C. for 2 hours, and the precipitate was filtered, washed strictly with water, and then dried at 40° C. for 20 hours to obtain 18.2 g of an inclusion compound of azithromycin hydrate and 1,2-propanediol.

[0045] m.p.: 130~132℃,

[0046] Moisture content: 3.4wt%,

[0047] 1,2-propanediol content: 3.2 wt%.

Embodiment 3

[0049]20 g of azithromycin monohydrate was dissolved in 120 ml of acetone, and 15 ml of 1,2-propanediol was added thereto. The solution was stirred at room temperature for 10 minutes, and 180 ml of water was added dropwise thereto to induce precipitation of azithromycin crystals. The solution was stirred at 0-5° C. for 3 hours, and the precipitate was filtered, washed strictly with water, and then dried at 40° C. for 20 hours to obtain 17.6 g of an inclusion compound of azithromycin hydrate and 1,2-propanediol.

[0050] m.p.: 130~132℃,

[0051] Moisture content: 3.4wt%,

[0052] 1,2-propanediol content: 3.5 wt%.

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Abstract

A clathrate of azithromycin hydrate with 1,2-propyleneglycol is much less hygroscopic than azithromycin hydrate or crystals known in the art, therefore, it can be useful for the preparation of a medicine for treating various microbial infections.

Description

technical field [0001] The present invention relates to a new clathrate of azithromycin hydrate and 1,2-propanediol, a preparation method thereof, and a pharmaceutical composition containing the clathrate. Background technique [0002] Azithromycin, 9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin A (homoerythromycin A) (N-methyl-11- Aza-10-deoxy-10-dehydroerythromycin A: IUPAC), a semisynthetic macrolide antibiotic of the azanidazole type, can be used in the treatment of bronchial infections, sexual contact infections and skin infections (see Kirste and Sides; Antimicrob. Agents Chemother., 33, 1419 (1989)). [0003] [0004] Azithromycin is known to exist in three forms, the anhydride form, the monohydrate form and the dihydrate form. These forms have been identified by powder X-ray diffraction and differential scanning calorimetry studies. [0005] Azithromycin anhydride disclosed in US Pat. No. 4,517,359 is a non-crystalline product and thus its high hygroscopicity is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00A61K31/7028A61K31/7052A61P31/04C07D413/14
CPCC07D413/14A61K31/7028A61P31/00A61P31/04
Inventor 徐贵贤金基净尹相旼成美罗李宽淳
Owner HANMI PHARMA
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