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US 2015/0307468 A1Published application
Process for the preparation of cabazitaxel and its intermediates
AssigneeIntas Pharmaceuticals Ltd.
InventorsMettilda Lourdusamy, Ioan Iosif Radu, Rahul Chandrashayi Saxena, Raghvendra Jayantibhai Patel, Sandeep Bachubhai Shah
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Abstract
The present invention relates to a novel process for preparation of cabazitaxel (I) starting from 10-Deacetyl baccatin or derivative that involves methylation of 7, 10 —OH groups. Also provided is a novel process using chiral bis-lactam linker for the synthesis of cabazitaxel.
Claims20
A process to prepare cabazitaxel (I) comprising a step of:
- reacting a compound of formula II
- in which X represents H or side chain of formula (III)
- Z represents a hydroxy protecting group, R1 is C(O)OC(CH3)3 with methyl trifluoromethansulfonate to get compound of formula (IV)
A process to prepare cabazitaxel comprising:
- reacting compound of formula II
- wherein X represents side chain of formula (III), Z=triethyl silyl
- with methyl trifluoromethansulfonate to get a compound of formula (XII)
A process to prepare cabazitaxel comprising:
- selective 2′ deprotection of compound of formula (XIII)
A process to prepare cabazitaxel (I) comprising:
- reacting compound of formula (V)
- wherein R1 as defined, Ar is a phenyl group and L is a cleavable linker with a suitable taxane precursor of formula
- to get compound of formula (VII)
A process to prepare cabazitaxel comprising:
- a. reacting a compound of formula (VIII) with methyl trifluoromethansulfonate
- to get compound of formula (VI)
- b. reacting compound of formula (VI) with compound of formula (IX)
- to get compound of formula (X)
- wherein w=alkyl having C1-C30
- c. treating compound of formula (X) in presence of solvent and base to obtain cabazitaxel (I)
3 more elements
Dependencies are inferred from the claim text.