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US RE40,901 E1Granted
Taxane derivatives and processes for the preparation thereof
AssigneeIndena S.p.A.
InventorsEzio Bombardelli, Bruno Gabetta, Alessandro Pontiroli
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Abstract
A novel taxane derivative with anticancer activity, a process for its preparation and a process for the preparation of 14-β-hydroxy-1,14-carbonate-baccatine III and V derivatives 13-substituted by an isoserine residue.
Claims34
A compound of Formula I,
A process for preparing a compound of Formula I,
- comprising reacting 13-(N-Boc-β-isobutylisoserinyl)-14β-hydroxy-baccatine III 1,14-carbonate with diazabicyclo[5,4,0]7-undecene in methanol or THF.
A process for preparing a compound of Formula I,
- comprising preparing (4S, 5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-isobutyl-1-oxazolidine-5-carboxylic acid, comprising the steps of:
- a. protecting the amino group of a leucinol with Boc to form N-Boc-L-leucinol;
- b. converting the N-Boc-L-leucinol into N-Boc-L-leucinal;
- c. preparing a cyanhydrin nitrile from the N-Boc-L-leucinal;
- d. transforming the cyanhydrin nitrile into a carboxylic acid;
- e. forming a methyl ester of the carboxylic acid;
- f. purifying the methyl ester of the carboxylic acid;
- g. condensing the product of step (f) with 2,4-dimethoxybenzaldehyde dimethyl acetal to form (4S, 5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-isobutyl-1-oxazolidine-5-carboxylic acid methyl ester;
- h. transforming the (4S, 5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-isobutyl-1-oxazolidine-5-carboxylic acid methyl ester into the (4S, 5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-isobutyl-1-oxazolidine-5-carboxylic acid;
- and
- i. using the (4S, 5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-isobutyl-1-oxazolidine-5-carboxylic acid to prepare the compound of Formula I.
8 more elements
Dependencies are inferred from the claim text.