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Alatrofloxacin parenteral compositions

A composition, gastrointestinal technology, applied in the field of 96/00756, nalididone antibiotic profloxacin mesylate, can solve problems such as insufficient removal of weak polar impurities

Inactive Publication Date: 2000-09-06
PFIZER PRODS ETAT DE CONNECTICUT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As noted above, treatment of profloxacin mesylate with diatomaceous earth did not adequately remove less polar impurities

Method used

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  • Alatrofloxacin parenteral compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Batch Resin Processing of Profloxacin Mesylate

[0045] Profloxacin mesylate (50 g), which contained 700 ppm oligomer impurities in addition to other weakly polar impurities, was dissolved in 0.05% aqueous methanesulfonic acid (714 ml), and Mitsubishi Diacon HP-20® hydrophobic resin ( 50g). After stirring the resin suspension for 24 hours in the dark, the suspension was filtered and the solution was analyzed by high performance liquid chromatography (HPLC) (HPLC conditions as described above). The filtered solution contained 19 ppm of oligomeric impurities and the yield of profloxacin mesylate was 80%. The oligomer has the following NMR: ( 1NMR DMSO d

[0046] 6) δ: 9.98(d, 1H); 8.79(s, 1H); 8.51(s, 1H), 8.45(d, 1H), 8.16(d 1H), 8.03(d 1H), 7.92(d

[0047] 1H), 7.76(m 2H), 7.61(m 2H), 7.33(m 2H), 4.18(q 1H), 3.77(q 1H), 3.60(m 8H), 2.54(s 1H),

[0048] 2.34(s 1H), 2.27(s 3H), 1.92(b.s.2H), 1.72(b.s.2H), 1.28(d 3H), 1.17(d 3H).

Embodiment 2

[0050] Resin Column Treatment of Profloxacin Mesylate

[0051] Profloxacin mesylate is dissolved in 10 to 40 liters of water per kilogram of drug substance at ambient temperature. The solution was filtered and then passed through a column containing hydrated Amberchrom CG-161(R) polystyrene resin (approximately 10-12 kg of crude reaction product per kg of dry resin) (3-5 bed volumes per hour). The column was washed with water (3 L / kg crude reaction product), then the eluate and wash were combined. The treated profloxacin mesylate solution was analyzed by HPLC. After being treated with a polystyrene resin column, the impurity content of formula II is reduced from 500ppm to below 30ppm, calculated as a drug substance. Additionally, the drug was recovered from the resin in 95% yield.

Embodiment 3

[0053] Separation of Zwitterions

[0054] Add 10% aqueous caustic agent dropwise to the solution containing profloxacin mesylate (10g) (prepared by embodiment 1 or 2), deionized water (154ml) and ethanol (31ml) that has been processed with resin, Neutralize to pH 6.5-7.5. After granulating the suspension for 30 minutes at 24°C, it was filtered. After the filtered solid was rinsed with ethanol (30ml), the zwitterions were dried under vacuum at 40°C for about 16 hours. Profloxacin (800 g) was recovered as white trapezoidal crystals with a yield of 95%.

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Abstract

The present invention relates to alatrofloxacin mesylate substantially free of less polar impurities, to parenteral compositions of alatrofloxacin mesylate and to processes for purifying alatrofloxacin mesylate.

Description

Background of the invention [0001] The present invention relates to the naphthyridone antibiotic alatrofloxacin (alatrofloxacin) mesylate substantially free of weakly polar impurities, the composition for parenteral use of said alatrofloxacin mesylate and purified alatrofloxacin The method of star mesylate. [0002] Profloxacin mesylate is a salt of the mesylate prodrug of the related nalidinone antibiotic trovafloxacin. The purity of profloxacin mesylate prepared by the current method is very high. However, the profloxacin mesylate salts prepared by these current methods contain traces of weakly polar impurities which precipitate out of parenteral compositions over an indeterminate period of time. These less polar impurities cannot be adequately removed by commercially available methods such as recrystallization, standard chromatography using flash silica gel, solvent / solvent extraction, or treatment with diatomaceous earth. The present inventors have found that treatment ...

Claims

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Application Information

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IPC IPC(8): A61K38/00A61P31/04C07D519/00C07K5/06C07K5/062
CPCA61K38/00C07D519/00C07K5/06191A61P31/04C07K5/06017
Inventor 罗伯特·M·吉恩约翰·F·兰伯特萨布拉玛尼恩·S·古汉斯坦利·W·瓦林斯基
Owner PFIZER PRODS ETAT DE CONNECTICUT
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