2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses

  • US 6,784,197 B2
  • Filed: 08/20/2002
  • Issued: 08/31/2004
  • Est. Priority Date: 02/23/2000
  • Status: Active Grant
First Claim
Patent Images

1. A compound having the formula I or a pharmaceutically acceptable salt thereof, embedded imagewhereinX is —

  • CA1NR5R6 or —



    A1 and A2 are independently oxygen, sulfur or —


    R1 is hydrogen, alkyl, aryl or —


    R1a wherein R1a is aryl, halogen, hydroxy, amino, nitro or cyano;

    R3 is hydrogen, halogen, thiol, nitro, nitrooxy, cyano, azido, carboxy, amido, sulfonic acid, sulfonamide, alkyl, alkenyl, alkenyl, ester, ether, aryl, tetrazolyl, thiazolyl, thienyl, furyl, pyrrolyl, pyridinyl, alkynyloxy, acyloxy, oxyester, oxyamido, alkylsulfonyloxy, alkylsulfinyloxy, arylsulfonyloxy, arylsulfinyloxy, aryloxy, aralkoxy, alkythio, alkenylthio, alkynylthio, arylthio, formyl, acetyl, propionyl, isobutyryl, valeryl, lauroyl, heptanedioyl, cyclohexanecarbonyl, crotonoyl, furmaroyl, arcyrloyl, benzoyl, naphthoyl, 4-carboxybutanoyl, oxalyl, ethoxalyl, cysteinyl, oxamoyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, arylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsufinyl or arylsulfinyl, R3a is hydrogen, halogen, alkyl, alkenyl, alkynyl or aryl;

    R5, R6 and R9 are the same or different and each is independently hydrogen, hydroxy, alkyl, aryl, alkoxy, alkenyloxy, alkynyloxy, acyloxy, oxyester, oxyamido, alkylsufonyloxy, alkylsulfinyloxy, arylsulfonyloxy, arylsufinyloxy, aryloxy or arylalkoxy and R8 is hydrogen, hydroxy, thiol, halogen, alkyl, aryl, alkylthio, alkenylthio, alkynylthio or with the provisos that at least one of as R3 and R3a is other than hydrogen; and

    that when the compound is a mixture of all possible isomers , X is —

    CONR5R6, A2 is oxygen and R1is hydrogen, methyl, ethyl or propyl then substitution on the pyrrolidine ring is other than mono-, di-methyl or mono-ethyl; and

    that when R1 and R3a are both hydrogen, A2 is oxygen and X is —

    CONR5R6 then R3 is different from carboxy, ester, amido, substituted oxo-pyrrolidine, alkynyloxy, acyloxy, oxyester, oxyarmido, alkylsulfonyloxy, alkylsulfinyloxy, arylsulfonyloxy, arylsulfinyloxy, aryloxy, aralkoxy, methyl, naphthyl, phenyl optionally substituted by oxy derivatives or in the para position by an halogen atom.

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