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US 11,767,317 B1Granted
Methods of synthesizing enantiopure deuterium-enriched pioglitazone
AssigneePoxel
InventorsLaure Françoise Valérie Navarre, Vincent Jacques, Sébastien Bolze
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Abstract
The invention provides methods of synthesis of enantiopure deuterium enriched R-pioglitazone with structure of compound (IV), or a pharmaceutically acceptable salt thereof: The invention further provides chemical intermediates useful in the synthesis of compound (IV), and methods of synthesizing those intermediates.
Claims20
A method of producing compound (IV) or salt thereof, the method comprising the steps:
- a) reacting compound (I) or salt thereof with D2O and DCl at a temperature from about 80° C. to about 100° C. to produce compound (II) or salt thereof
- b) reacting compound (II) or salt thereof with L-dibenzoyl tartaric acid in a first solvent comprising at least 90% by volume of MeOD and/or MeOH, or at least 90% by volume of a mixture of MeOD and/or MeOH, and D2O to produce compound (III)
- c) recrystallizing compound (III) one or more times in a second solvent comprising at least 90% by volume of a mixture of D2O, DCl and/or HCl, and MeOH and/or MeOD to produce recrystallized compound (III′)
- and
- d) reacting recrystallized compound (III′) with DCl and/or HCl, in a third solvent which comprises deuterated and/or non-deuterated solvent, to produce compound (IV), or salt thereof, which is obtained by crystallization
2 more elements
Dependencies are inferred from the claim text.