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Crystal and deforming shaped smilagenin

A technology of smilagenin and smilagenin, which is applied in the directions of medical preparations containing active ingredients, steroids, organic chemistry, etc., can solve the problem that smilagenin is not described.

Inactive Publication Date: 2007-11-21
PHYTOPHARM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art does not describe any amorphous smilagenin

Method used

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  • Crystal and deforming shaped smilagenin
  • Crystal and deforming shaped smilagenin
  • Crystal and deforming shaped smilagenin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140] Form I

[0141] A. Crystallization from acetone

[0142] Smilagenin (10.0 g) was suspended in acetone (250 ml) and the mixture was heated to reflux. The resulting solution was decanted, separated from some insoluble solids, and reheated to reflux to yield a clear solution. The solution was allowed to cool to 29°C for about 3.5 hours and further cooled gradually to 2°C with ice / water. The resulting solid was collected by filtration, washed with cold (5°C) acetone (50 ml) and dried in a vacuum oven for 3 days to obtain 7.4 g of pure smilagenin, which was characterized by XRPD as Form I according to our nomenclature .

[0143] B. Crystallization from Acetonitrile

[0144] A suspension of smilagenin (1.05 g) in acetonitrile (10 ml) was stirred overnight at ambient temperature. The solid was collected by filtration and dried in a vacuum oven at 80° C. to yield smilagenin Form I (0.92 g, 88% yield).

Embodiment 2

[0146] Form II

[0147] Smilagenin was produced by stereospecific reduction of diosgenin according to the method described in PCT Patent Application No. PCT / GB2003 / 001780 (WO-A-2004 / 037845).

[0148] XRPD was performed on smilagenin, and the pattern was found to be substantially similar to that shown in Figure 1 . On this basis, the material was characterized as Form II according to our nomenclature.

Embodiment 3 and 4

[0150] Form III

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PUM

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Abstract

The invention provides smilagenin in novel amorphous, crystalline, hydrated and solvated forms, and the use thereof in manufacturing pharmaceutical or edible grade smilagenin and its derivatives.

Description

technical field [0001] The present invention relates to novel amorphous and crystalline forms of smilagenin and its hydrates. Background technique [0002] It is well understood that certain organic compounds are capable of crystallization in a variety of different polymorphic forms or crystallization habits, which may include the compound itself, solvates of the compound, hydrates of the compound, or combinations thereof. Alternatively, the compound, solvate or hydrate may precipitate as an amorphous solid. [0003] The stability and bioavailability of a drug product can vary depending on the polymorphic forms present. Therefore, the choice of crystal form is a key aspect of drug development (Brittain, Pharm.Tech.pp.50-52, 1994; Yu et al., Pharm.Sci.Technol.Today, 1, pp.118-127, 1998; Byrn et al., Chem.Mater.6, pp.1148-1158, 1994; Byrn et al., Pharm.Res., 12, pp.945-954, 1995; Henk et al., Pharm.Ind.59, pp .165-169, 1997). [0004] Smilagenin...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/58A61P19/10A61P25/28
CPCC07J71/0005A61P19/10A61P21/00A61P25/16A61P25/28A61P3/04A61P3/06A61P3/10C07J71/00
Inventor 彼得·大卫·蒂芬
Owner PHYTOPHARM LTD