Piperazine derivatives and process for the preparation thereof

Details Piperazine derivatives and process for the preparation thereof Piperazine derivatives and process for the preparation thereof

C - Chemistry, Metallurgy

07

D

C07D 295/108 (2006.01) C07D 213/65 (2006.01) C07D 213/74 (2006.01) C07D 241/20 (2006.01) C07D 241/28 (2006.01) C07D 295/13 (2006.01) C07D 295/215 (2006.01) C07D 401/12 (2006.01) C07D 403/12 (2006.01)

Patent

CA 2330942

The present invention relates to a novel compound of the general formula (I) and its pharmaceutically acceptable acid addition salt, and process for the preparation thereof, which have strong antitumor activities and very low toxicity, (see formula I) wherein R1 and R2 are independently hydrogen, C1-C4 alkyl, C1-C4 alkylcarboxyl, C1-C4 alkylcarbonyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl, C1-C4 aminoalkyl or C1-C4 hydroxyiminoalkyl, or R1 and R2 are fused to form C3-C4 unsaturated ring; R3, R4, R5, R6 and R7 are independently hydrogen, halogen, hydroxy, nitro, amino, C1-C4 alkyl, C1-C4 alkylcarboxyl, C1-C4 alkylcarbonyl, C1-C4 alkoxy or C1-C4 thioalkoxy; R8 is C1-C4 alkyl; Y is oxygen, sulphur, amino, substituted amino or C1-C4 thioalkyl; Z is C1-C4 alkoxy, C1-C4 alkyl, C1-C4 alkylamino or C1-C4 thioalkoxy; X1 and X2 are independently CH or nitrogen; and ~N~C~ and ~C~Y~ may form a single bond or a double bond provided that if ~N~C~ forms a single bond, ~C~Y~ forms a double bond, and if ~C~Y~ forms a single bond, ~N~C~ forms a double bond and R8 is nonexistent.

L'invention concerne un nouveau composé de formule générale (I) et son sel d'addition acide pharmaceutiquement acceptable ainsi que son procédé de préparation présentant des activités anticancéreuses marquées et une très faible toxicité, dans laquelle R1 et R2 représentent indépendamment un hydrogène, C1-C4 alkyle, C1-C4 alkylcarboxyle, C1-C4 alkylcarbonyle, C1-C4 alcoxy, C1-C4 hydroxyalkyle, C1-C4 aminoalkyle ou C1-C4 hydroxyiminoalkyle, ou R1 et R2 sont fusionnés pour former un noyau insaturé C3-C4; R3, R4, R5, R6 et R7 représentent pris séparément un hydrogène, halogène, hydroxy, nitro, amino, C1-C4 alkyle, C1-C4 alkylcarboxyle, C1-C4 alkylcarbonyle, C1-C4 alcoxy ou C1-C4 thioalkoxy; R8 représente C1-C4 alkyle; Y représente un oxygène, soufre, amino, amino substitué ou C1-C4 thioalkyle; Z représente C1-C4 alcoxy, C1-C4 alkyle, C1-C4 alkylamino ou C1-C4 thioalkoxy; X1 et X2 représentent pris séparément un carbone ou azote; et -N--C- et -C--Y- peuvent former une seule liaison ou une double liaison à condition que, lorsque -N--C- forme une seule liaison, -C--Y- forme une double liaison, et que lorsque -C--Y-, -N--C- forme une double liaison et que R8 ne soit pas présent.

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