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Anhydrous Crystalline form of (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

IP.com Disclosure Number: IPCOM000247644D
Publication Date: 2016-Sep-22
Document File: 3 page(s) / 857K

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The IP.com Prior Art Database

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Anhydrous Crystalline form of (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-

yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

The present document relates to anhydrous crystalline form of (2S,3R,4R,5S,6R)-2-(3-((5-(4- fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran- 3,4,5-triol designated as form T4. This crystalline form is useful for the preparation of pharmaceutical compositions.

(2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol from which the crystalline form of the present document is prepared, may be obtained according to processes known in the art, including but not limited to the processes described in WO 2005/012326, WO 2008/069327 and WO 2009/035969.

Example 1: Preparation of anhydrous crystalline form T4 of (2S,3R,4R,5S,6R)-2-(3-((5-(4-

fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-

3,4,5-triol.

Amorphous (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (10.0 g, 22.50 mmol) was suspended in 50 ml of methyl formate. The suspension was heated at 35ºC and stirred until complete dissolution and further precipitation of the solid. The new suspension was cooled to 20-25ºC and 30 ml of methyl formate was added. After stirring for 72 hours at 20-25ºC the product was filtered and dried...