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US 8,466,297 B2Granted
Manufacturing process for (S)-Pregabalin
OwnerMilan Soukupinventor
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Abstract
The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compounds of general formula I used for treatment of epilepsy, neuropathic pain, anxiety and social phobia. The invention describes preparation of enantiomerically pure (S)-Pregabalin from chiral pyrrolidin-2-one of formula IV.
Claims5
A compound of general formula III, having the (S)-configuration as given in formula,
- wherein R3 represents hydrogen and
- R4 represents counter cation as alkali or earth alkali metal cation, or hydrogen, or O-protective group, which together with O forms an ester or carbonate, or —SO2Cl or alkyl- or arylsulfonyl, or thiocarbonyl derivative such as —C(S)Oalkyl or —C(S)Oaryl or —C(S)imidazolyl, and a salt thereof,
- in either enantiomerically enriched or enantiomerically pure form.
A process for preparation of a compound of general formula III, having the (S)-configuration as given in formula,
- wherein
- R3 represents hydrogen and
- R4 represents counter cation as alkali or earth alkali metal cation, or hydrogen, or O-protective group, which together with O forms an ester or carbonate, or alkyl- or arylsulfonyl, or thiocarbonyl derivative such as —C(S)Oalkyl or —C(S)Oaryl or —C(S)imidazolyl,
- comprising following steps:
- a) reaction of the compound of formula IV,
- wherein R represents hydrogen, linear or brunched C1-6-alkyl, aryl, arylalkyl, alkylaryl, and
- R3 is the same as defined for compound of formula III;
- with a reagent containing CH3-organometallic reagent such as Me-alkali metal or Me-earth alkali metal halide,
- b) followed by activation of tert.-hydroxy group according to the definition for R4.
6 more elements
Dependencies are inferred from the claim text.