3-carboxy-2-oxo-1-pyrrolidine derivatives and their uses
AssigneeUCB Pharma S.A.
InventorsCelal Ates, Arnaud Schule
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Abstract
The present invention relates to 3-carboxy-2-oxo-1-pyrrolidine derivatives of formula (I), geometrical isomers, enantiomers, diastereoisomers, pharmaceutically acceptable salts and all possible mixtures thereof, and processes using them.
Claims30
A compound of formula (I), or a geometrical isomer, enantiomer, or diastereoisomer thereof,
- wherein,
- R1 is —COOH, —COOM or —COOR4,
- R2 is hydrogen or C1-10 alkyl,
- R3 is C1-10 alkyl or C2-6 alkenyl,
- X is —CONR5R6, —COOH, —COOR4 or —CN,
- M is an alkali metal,
- R4 is C1-10 alkyl,
- R5 is hydrogen or C1-10 alkyl,
- R6 is hydrogen or C1-10 alkyl,
- 1* and 2* denote a stereogenic center,
- provided that compound of formula (I) is not 1-((1S)-1-carbamoyl-propyl)-2-oxo-pyrrolidone-3-carboxylic acid or 2(S)(3-carboxy-2-oxo-1-pyrrolidinyl)-4-methyl pentanoic acid methyl ester.
A process for the preparation of a compound of formula (IV), a geometrical isomer, enantiomer, diastereoisomer, or pharmaceutically acceptable salt thereof,
- said process comprising decarboxylating a compound of formula (Ia), a geometrical isomer, enantiomer, or diastereoisomer thereof,
- wherein
- R1 is —COOH or —COOM,
- R2 is hydrogen or C1-10 alkyl,
- R3 is C1-10 alkyl or C2-6 alkenyl,
- X is —CONR5R6, —COOH, —COOR4 or —CN,
- M is an alkali metal,
- R4 is C1-10 alkyl,
- R5 is hydrogen or C1-10 alkyl,
- R6 is hydrogen or C1-10 alkyl.
A process for the preparation of a compound of formula (IV), a geometrical isomer, enantiomer, diastereoisomer, or pharmaceutically acceptable salt thereof,
- said process comprising decarboalkoxylating a compound of formula (Ib)), a geometrical isomer, enantiomer, or diastereoisomer thereof,
- wherein
- R2 is hydrogen or C1-10 alkyl,
- R3 is C1-10 alkyl or C2-6 alkenyl,
- X is —CONR5R6, —COOH, —COOR4 or —CN,
- R4 is C1-10 alkyl,
- R5 is hydrogen or C1-10 alkyl,
- R6 is hydrogen or C1-10 alkyl.
A process for the preparation of levetiracetam, said process comprising decarboxylating or decarbalkoxylating a compound of formula (Ic),
- wherein R7 is hydrogen, an alkali metal or C1-10 alkyl.
A process for the preparation of brivaracetam, said process comprising decarboxylating or decaralkoxylating a compound of formula (Id),
- wherein R7 is hydrogen, an alkali metal or C1-10 alkyl.
Dependencies are inferred from the claim text.