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Novel crystal form of lubiprostone and preparation method of crystal form

A lubiprostone and crystal form technology, which is applied to medical preparations containing active ingredients, pharmaceutical formulas, digestive systems, etc., can solve the problems of inconvenient production and storage of preparations, and achieve easy operation, simple preparation methods, and high purity Effect

Inactive Publication Date: 2015-06-17
QILU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, the lubiprostone product obtained by most processes is an oily substance, which brings inconvenience to the production and storage of preparations, so it is necessary to develop a lubiprostone crystal form suitable for pharmaceutical use

Method used

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  • Novel crystal form of lubiprostone and preparation method of crystal form
  • Novel crystal form of lubiprostone and preparation method of crystal form
  • Novel crystal form of lubiprostone and preparation method of crystal form

Examples

Experimental program
Comparison scheme
Effect test

preparation example

[0037] Preparation example: Preparation of lubiprostone oily substance

[0038] (Z)-7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]heptanoic acid-5 -Enbenylate (2.5g) is added to 20mL of ethanol, palladium hydroxide charcoal is added, 3g of triethylsilane is added to 20mL of ethanol, diluted and added to the above solution, and reacted at 20-25℃ for 30 minutes After filtration, the filtrate is concentrated to obtain 2.0 g of oily substance, which is lubiprostone oily substance. The reaction formula is as follows:

[0039]

Embodiment 1

[0040] Example 1 Preparation of new crystal form of lubiprostone

[0041] 1g of lubiprostone oil prepared by the method of Preparation Example 1 was dissolved in 5mL of isopropyl acetate, stirred to dissolve, cooled to 0-10°C, 75mL of n-heptane was added dropwise, stirred for 2h, and a white solid precipitated slowly. Filtration with suction, drying under reduced pressure, to obtain 0.9g of white solid, which is a new crystal form of lubiprostone, with a purity of 99.96% and a yield of 90.0%. The X-RPD spectrum is as follows figure 1 As shown, its infrared absorption spectrum is as figure 2 As shown, its DSC spectrum is as image 3 Shown.

Embodiment 2

[0042] Example 2 Preparation of new crystal form of lubiprostone

[0043] 0.5g of lubiprostone oil obtained according to the method of Preparation Example 1 was dissolved in 2mL of propyl acetate, stirred to dissolve, cooled to 0~10℃, 25mL of n-hexane was added dropwise, stirred for 2h, a white solid precipitated slowly, and filtered with suction And dried under reduced pressure to obtain 0.44 g of white solid, which is a new crystal form of lubiprostone, with a purity of 99.88% and a yield of 88.0%. After determination, its X-RPD spectrum is figure 1 The infrared spectrum is basically the same as figure 2 Basically the same, its DSC spectrum is image 3 Basically the same.

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Abstract

The invention belongs to the technical field of pharmaceutical chemical engineering and particularly relates to a novel crystal form of lubiprostone, a preparation method of the crystal form and the application of the crystal form to medicine preparation. The crystal form is represented through X-ray powder diffraction, infrared spectrography and differential scanning calorimetry, has the advantages of high purity, high stability and easy preparation, is more suitable for storage and use, and can be better applied to preparation of lubiprostone drug substances and preparations.

Description

Technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and specifically relates to a new crystal form of lubiprostone and a preparation method thereof, and the application of the crystal form in the preparation of medicines. Background technique [0002] Lubiprostone was jointly developed by Sucampo Pharmaceuticals, Abbott and Takeda, and was first launched in the United States in 2006. It is used to treat adult chronic idiopathic constipation and constipation-type irritable bowel syndrome in women over 18 years old. . Lubiprostone is a prostaglandin compound, namely (-)-7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxoocta Hydrocyclopentapyran-5-yl]heptanoic acid, the compound often exists in the following tautomeric forms: [0003] [0004] Lubiprostone is a localized chloride channel activator, which can selectively activate the type 2 chloride channel (CIC-2) located on the luminal cell membrane of the epithelial tip of ...

Claims

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Application Information

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IPC IPC(8): C07D311/94C07C405/00A61K31/558A61K31/5575A61P1/10A61P1/00
Inventor 潘雷张贵岭高源周晓东
Owner QILU PHARMA
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