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US 8,912,325 B2Granted
Process for preparation of imatinib and its mesylate salt
AssigneeInd-Swift Laboratories Limited
InventorsBhaskar Bhirud Shekhar, Kumar Jain Anshul, Kumar Sharma Ajay
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Abstract
Disclosed is a process for the preparation of imatinib of formula (I), or its mesylate salt with controlled level of genotoxic impurity of formula (II), a key intermediate for imatinib.
Claims21
A process for the preparation of imatinib mesylate of formula Ia, comprising:
- a) reacting an amine intermediate of formula II
- with an intermediate of formula III in the presence of a base in an organic solvent, in a ratio of at least 1.5 molar equivalents of the intermediate of formula III per molar equivalent of the intermediate of formula II;
- wherein X is selected from the group consisting of —OH and halogen;
- b) isolating imatinib of formula I from the reaction mixture,
- wherein said imatinib of formula I contains less than 50 ppm of the amine intermediate of formula II;
- c) optionally, purifying imatinib of formula I;
- and
- d) reacting imatinib with methanesulfonic acid to form imatinib mesylate of formula Ia,
- wherein said imatinib mesylate produced in step (d) contains less than 20 ppm of the intermediate of formula II.
6 more elements
A process for the preparation of imatinib, comprising:
- a) admixing an intermediate of formula III with a base and an organic solvent to form a reaction mixture;
- wherein X is selected from the group consisting of —OH and halogen;
- b) reacting the intermediate of formula III in the reaction mixture with an amine intermediate of formula II,
- wherein at least 1.5 molar equivalents of the intermediate of formula III is used per molar equivalent of the intermediate of formula II;
- and
- c) isolating imatinib of formula I from the reaction mixture;
- wherein said imatinib of formula I contains less than 50 ppm of the amine intermediate of formula II;
- and
- d) optionally, purifying imatinib of formula I.
6 more elements
A process for the preparation of an α form of imatinib mesylate,
- said α form having 2% or less of other polymorphic forms,
- said α form showing a thermal event by DSC at 226° C.;
- said method comprising the steps of:
- a) combining imatinib and dimethylsulfoxide;
- b) adding methanesulfonic acid to the resulting mixture;
- c) adding a second solvent with optional seeding;
- d) stirring the reaction mixture for a time sufficient till complete crystallization;
- and
- e) isolating α form of imatinib mesylate therefrom.
6 more elements
Dependencies are inferred from the claim text.