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US 8,772,544 B2Granted
Process for the production of bimatoprost
AssigneeSandoz Ltd.
InventorsDominic De Souza, Martin Albert, Hubert Sturm
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Abstract
The present invention relates to a process for the purification of crude bimatoprost to obtain pure bimatoprost comprising a chromatography, preferably a chromatography using an achiral stationary phase and an eluent comprising an alcohol and an apolar solvent; and crystallization of the product obtained the chromatography to obtain pure bimatoprost.
Claims7
A method for the purification of crude bimatoprost according to formula (I)
- comprising at least the steps of:
- (a) subjecting crude bimatoprost according to formula (I) to chromatography to form a product, wherein the chromatography is carried out using an achiral stationary phase comprising silica and an eluent comprising an alcohol and an apolar solvent, and wherein the alcohol is selected from methanol and ethanol and the apolar solvent is selected from heptane, hexane and cylcohexane;
- and
- (b) crystallizing the product obtained in step (a) from a solvent selected from ethers, acetonnitrile, alcohols, esters, or mixtures of any of these solvents to form pure bimatoprost containing less than 0.2% in total of any combination of 15R-bimatoprost and 5, 6-trans-bimatoprost.
1 more element
A method for the preparation of crude bimatoprost comprising at least step (i):
- (i) reacting a compound of formula (6)
- with a compound of general formula (IV)
- wherein A- represents a group selected from
- X represents a halide;
- and
- R represents a C6 to C10 aryl or C1 or C10 alkyl residue, to provide crude bimatoprost.
3 more elements
A method for the preparation of crude bimatoprost comprising at least step (x) and (y):
- (x) reacting a compound of formula (6)
- with a compound of general formula (V)
- wherein A- represents a group selected from
- X represents a halide;
- and
- R represents a C6 to C10 aryl or C1 or C10 alkyl residue, to provide a compound of formula (7)
- and
- (y) converting the compound of formula (7) obtained in step (x) to provide crude bimatoprost by activation of the carboxylic group of compound (7) as a mixed anhydride to form an activated intermediate, and reacting the activated intermediate with ethylamine.
5 more elements
Dependencies are inferred from the claim text.