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US 5,965,752 AGranted
Preparative scale isolation and purification of taxanes
AssigneeInstitut National De La Recherche Scientifique
InventorsLolita Zamir, Gaetan Caron
Life of this patent
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Abstract
This invention relates to an improved method for isolating taxanes by using a preparative scale technique amenable to commercial production. This method provides high yields of known taxanes in addition to new taxanes.
Claims14
A process for the purification of taxanes from plant material of a taxus genus which comprises the following steps:
- (i) extracting organic matter from a Taxus genus into an organic solvent to form an extract;
- (ii) washing said extract with one or more aqueous phases to yield a washed organic extract;
- (iii) contacting said washed organic extract with charcoal;
- (iv) substantially removing solvent from said organic extract to form a residue;
- (v) substantially taking up said residue in a volume of a first organic solvent to form a solution and whilst agitating the solution gradually adding a second organic solvent, wherein said second solvent is of lower polarity than said first solvent, precipitating a solid;
- (vi) recrystallizing said precipitated solid to form a crystalline product;
- and
- (vii) separating said crystalline product from its mother liquor.
5 more elements
A process for the purification of taxanes from an extract of plant material of a taxus genus which comprises the following steps:
- (i) substantially taking up the extract of plant material of a taxus genus in a volume of a first organic solvent to form a solution and whilst agitating the solution gradually adding a second organic solvent, wherein said second solvent is of lower polarity than said first solvent, precipitating a solid;
- (ii) recrystallizing said precipitated solid to form a crystalline product;
- and
- (iii) separating said crystalline product from its mother liquor.
1 more element
A process for obtaining taxanes from Taxus canadensis which comprises
- (a) drying the vegetal material obtained from the Taxus plant at a temperature of between 20.degree. C. and 70.degree. C. to form dried plant matter;
- (b) contacting the dried plant matter from step (a) with an organic solvent that is, or an equivalent organic solvent whose polarity is equivalent to, a solution of methanol:dichloromethane ranging in concentration from 1:5 to 1:15 so as to extract a crude taxane mixture in the extracting solvent mixture;
- (c) washing the extract of (b) with water;
- (d) filtering the extract over charcoal;
- (e) evaporating the filtered extract of (d) to remove organic solvent leaving a residue;
- (f) dissolving the residue of (e) in toluene, or an equivalent organic solvent, to which petroleum ether, or an equivalent organic solvent, is added under fast uninterrupted stir to form a residue-solution;
- (g) filtering the residue-solution of (f) to accumulate a solid;
- (h) drying the solid of (g);
- and
- (i) dissolving the dried solid of (h) in methanol or an equivalent organic solvent to crystallize 9-dihydro-13-acetylbaccatin III out of said dissolved dried solid and filtering to separate into a solid and a filtrate A.
7 more elements
Dependencies are inferred from the claim text.