An improved process for the preparation of quinolone...

Details An improved process for the preparation of quinolone... An improved process for the preparation of quinolone...

C - Chemistry, Metallurgy

07

D

C07D 215/56 (2006.01) C07C 225/16 (2006.01)

Patent

CA 2415040

This invention relates to an improved process for the preparation of quinolone drugs of the formula (I), wherein R=C¿1?-C¿6? alkyl, C¿3?-C¿6? cycloalklyl, aryl, substituted aryl, NR?1¿R?2¿=diarylamino, arylalkylamino, C¿1?-C¿6?-dialkylamino, piprazinyl, N or C alkyl (C¿1?-C¿6?) substituted piperazinyl, morpholino, pyrrolidinyl, substituted pyrrolidinyl, aralkyl, substituted aralkyl etc. Some of the compounds falling within the formula (I) are ciprofloxacin, enrofloxin, pefloxacin, etc. These compounds are useful as antibacterial drugs. The process of the present invention for preparation of compound of formula (I) comprises in enhancing the reactivity of the displaceable halogen (X) in the compound of the formula (II) towards various amines of formula (III) wherein R = as defined for compound of formula (I), R?3¿=COOR?6¿ (R?6¿=C¿1?-C¿6? alkyl, aryl, aralkyl), nitrile a carboxamide (-CONR?7¿R?8¿, R?7¿ and R?8¿ = C¿1?-C¿6? alkyl, C¿3?-C¿6? cycloalkyl, aralkyl), X = Cl, Br, F; NR?1¿R?2¿ = as defined above by introducing a nitro group ortho to the displaceable halo group and subsequently removing the nitro group in a conventional manner. The process of the present invention enhances the yield of the compound of the formula (I) and also improves the quality of the prepared compound.

La présente invention concerne un procédé amélioré de préparation de médicaments à base de quinolone de formule I dans laquelle R= alkyle en C¿1?-C¿6?, cycloalklyle en C¿3?-C¿6?, aryle, aryle substitué, NR?1¿R?2¿= diarylamino, arylalkylamino, dialkylamino en C¿1?-C¿6?, piprazinyle, N ou C alkyl (C¿1?-C¿6?) piperazinyl substitués, morpholine, pyrrolidinyle, pyrrolidinyle substitué, aralkyle, aralkyle substitué, etc. Quelques-uns parmi les composés de formule I sont des ciprofloxacine, enrofloxine, pefloxacine, etc. Ces composés sont utilisés comme médicaments antibactériens. Le procédé selon la présente invention destiné à la préparation de composés de formule I consiste à accroître la réactivité de l'halogène mobile (X) dans le composé de formule II vers différentes amines de formule III dans laquelle R = tel que défini dans le composé de formule I, R?3¿=COOR?6¿(R?6¿= alkyle, aryle, aralkyle en C¿1?-C¿6?), nitrile, un carboxamide (-CONR?7¿R?8¿,R?7¿ et R?8¿ = alkyle, cycloalkyle, aralkyle en C¿1?-C¿6?, C¿3?-C¿6?), X = Cl, Br, F; NR?1¿R?2¿ = tel que défini précédemment, caractérisé en ce qu'on introduit un groupe nitré en ortho par rapport au groupe halo mobile et en ce qu'on élimine ensuite le groupe nitré de façon classique. Le procédé selon la présente invention accroît le rendement du composé de formule I et améliore également la qualité du composé préparé.

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