Asymmetric synthesis of pregabalin
AssigneeWarner-Lambert Company
InventorsMark Joseph Burk, Omprakash Goel, Marvin Simon Hoekstra, Thomas Frederick Mich, Thomas Mulhern, James A. Ramsden
Life of this patent
Estimating the term…
Abstract
This invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid (pregabalin) or a salt thereof via an asymmetric hydrogenation synthesis. Pregabalin is useful for the treatment and prevention of seizure disorders, pain, and psychotic disorders. The invention also provides intermediates useful in the production of pregabalin.
Claims26
A method for preparing an (S)-3-cyano-5-methylhexanoic acid derivative of the formula
- 29
- wherein X is CO2H or CO2—Y. and where Y is a cation;
- the method comprising asymmetric catalytic hydrogenation of an alkene of the formula
- 30
- in the presence of a chiral catalyst.
A compound of the formula
- 34
- wherein X is CO2H or CO2—Y, and where Y is a cation.
A compound of the formula
- 35
- wherein R1 is alkyl.
A method for preparing a compound of the formula
- 36
- wherein R1 is alkyl
- the method comprising asymmetric catalytic hydrogenation of an alkene of the formula
- 37
- in the presence of a chiral catalyst.
A compound of the formula
- 39
- wherein Y is a cation.
A process for preparing pregabalin comprising asymmetrically hydrogenating
- 40
- where Y is a cation, in the presence of a chiral catalyst, followed by reduction of the cyano group, and protonation to the free acid.
Dependencies are inferred from the claim text.