Patent ID: 6383230
Filing Date: 2002-05-07
Classification: C07C,C07D

Abstract:
A compound of formula (I) below, and acid addition salts thereof: in which:A1, A2 and A3, which may be identical or different, are chosen from a group â€”NR7R8 and a hydroxyl radical; one and only one of the groups A1, A2 and A3 may also represent a group R3 as defined below; R1, R2 and R3, which may be identical or different, are chosen from a hydrogen atom; a halogen atom; a group Z as defined below; a (C1-C6)alkylcarbonyl radical; an amino(C1-C6)alkylcarbonyl radical; an Nâ€”Z-amino(C1-C6)alkylcarbonyl radical; an Nâ€”(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical; an N,N-di(C1-C6)-alkylamino (C1-C6)alkylcarbonyl radical; an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a carboxyl radical; a (C1-C6)alkylcarboxyl radical; a (C1-C6)alkylsulphonyl radical; an aminosulphonyl radical; an Nâ€”Z-aminosulphonyl radical; a (C1-C6)N-alkylaminosulphonyl radical; an N,N-di(C1-C6)alkylaminosulphonyl radical; a (C1-C6)aminosulphonylalkyl radical; a (C1-C6)Nâ€”Z-aminosulphonylalkyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di (C1-C6)-alkylaminosulphonyl(C1-C6)alkyl radical; a carbamyl radical; an Nâ€”(C1C6)alkylcarbamyl radical, an N,N-di(C1-C6)alkylcarbamyl radical; a carbamyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a (C1-C6)alkyl radical; a (C1-C6)monohydroxyalkyl radical; a (C2-C6)polyhydroxyalkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; a (C1-C6)trifluoroalkyl radical; a cyano radical; a group OR6 or SR6; an amino group protected by a (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, trifluoro(C1-C6)alkylcarbonyl, amino(C1-C6)alkylcarbonyl, Nâ€”Z-amino(C1-C6)alkylcarbonyl, Nâ€”(C1-C6)alkylamino(C1-C6)alkylcarbonyl, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, carbamyl, Nâ€”(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, (C1-C6)alkylsulphonyl, aminosulphonyl, Nâ€”Z-aminosulphonyl, (C1-C6)N-alkylaminosulphonyl, N,N-di(C1-C6)alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z as defined below in which a linker arm D comprises a ketone function directly attached to the nitrogen atom of the amino group; and a (C1-C6)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; a (C1-C6)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two radicals, which may be identical or different, chosen from alkyl, (C1-C6)monohydroxyalkyl, (C2-C6)polyhydroxyalkyl, (C1-C6)alkylcarbonyl, cartamyl, Nâ€”(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, formyl, trifluoro (C1-C6)-alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocatamyl radicals, or from a group Z as defined below, or which may form, together with the nitrogen atom to which they are attached, a 5- or 6-membered ring which is carbon-based or which contains one or more hetero atoms; R6 is chosen from a (C1-C6)alkyl radical; a (C1-C6)monohydroxyalkyl radical; a (C2-C6)polyhydroxyalkyl radical; a group Z as defined below; a (C1-C6)alkoxy(C1-C6)alkyl radical; an aryl radical; a benzyl radical; a carboxy(C1-C6)alkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a (C1-C6)trifluoroalkyl radical; a (C1-C6)aminosulphonylalkyl radical; a (C1-C6)Nâ€”Z-aminosulphonylalkyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphinyl (C1-C6)alkyl radical; a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylcarbonyl (C1-C6)alkyl radical; a (C1-C6)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; and a (C1-C6)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two identical or different radicals chosen from (C1-C6)alkyl, (C1-C6)monohydroxyalkyl, (C2-C6)polyhydroxyalkyl, (C1-C6)allkylcarbonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, carbamyl, Nâ€”(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, thiocarbamyl and (C1-C6)alkylsulphonyl radicals, or from a group Z as defined below; or which may form, together with the nitrogen atom to which they are attached, a 5- or 6-membered ring which is carbon-based or which contains one or more hetero atoms; R4, R5, R7 and R8, which may be Identical or different, are chosen from a hydrogen atom; a group Z as defined below, in which the linker arm D contains no ketone functions directly linked to the nitrogen atom bearing the radicals R4 and R5; a (C1-C6)alkyl radical; a (C1-C6)monohydroxyalkyl radical; a (C2-C6)polyhydroxyalkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; an aryl radical; a benzyl radical; a cyano(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a thiocarbamyl(C1-C6)alkyl radical; a (C1-C6)trifluoroalkyl radical; a (C1-C6)sulphoalkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical, a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical; a (C1-C6)aminosulphonylalkyl radical; a (C1-C6)Nâ€”Z-aminosulphonylalkyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a (C1-C6)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; and a (C1-C6)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two identical or different radicals chosen from (C1-C6)alkyl, (C1-C6)monohydroxyalkyl, (C2-C6)polyhydroxyalkyl, (C1-C6)alkylcarbonyl, carbamyl, Nâ€”(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, (C1-C6)alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, or from a group Z as defined below; or which may form, together with the nitrogen atom to which they are attached, a 5- or 6-membered ring which is carbon-based or which contains one or more hetero atoms; Z is chosen from the unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below: in which:D is a linker arm which represents a linear or branched alkyl chain, which can be interrupted by one or more hetero atoms, and which can be substituted with one or more hydroxyl or C1-C6 alkoxy radicals, and which can bear one or more ketone functions; the ring members E, G, J, L and M, which may be identical or different, are chosen from a carbon, oxygen, sulphur and nitrogen; n is an integer ranging from 0 to 4; m is an integer ranging from 0 to 5; the R radical, which may be identical or different, are chosen from a second Z group, which is identical to or different from the first Z group, a halogen atom, a hydroxyl radical, a (C1-C6)alkyl radical, a (C1-C6)monohydroxyalkyl radical, a (C2-C6)polyhydroxyalkyl radical, a nitro radical, a cyano radical, a cyano(C1-C6)alkyl radical, a (C1-C6)alkoxy radical, a tri(C1-C6)alkylsilane(C1-C6)alkyl radical, an amido radical, a formyl radical, a carboxyl radical, a (C1-C6)alkylcarbonyl radical, a thio radical, a (C1-C6)thioalkyl radical, a (C1-C6)alkylthio radical, an amino radical, an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; a group NHRO or NRORâ€³ in which RO and Râ€³, which may be identical or different, are chosen from a (C1-C6)alkyl radical, a (C1-C6)monohydroxyalkyl radical and a (C2-C6)polyhydroxyalkyl radical; R9 is chosen from a (C1-C6)alkyl radical, a (C1-C6)monohydroxyalkyl radical, a (C2-C6)polyhydroxyalkyl radical, a cyano(C1-C6)alkyl radical, a tri(C1-C6)alkylsilane(C1-C6)alkyl radical, a (C1-C6)alkoxy(C1-C6)alkyl radical, a carbamyl-(C1-C6)alkyl radical, a (C1-C6)alkylcarboxy(C1-C6)-alkyl radical, a benzyl radical and a second Z group, which is identical to or different from the first Z group; R10, R11 and R12, which may be identical or different, are chosen from a (C1-C6)alkyl radical, a (C1-C6)monohydroxyalkyl radical, a (C2-C6)polyhydroxyalkyl radical, a (C1-C6)alkoxy(C1-C6)alkyl radical, a cyano(C1-C6)alkyl radical, an aryl radical, a benzyl radical, a (C1-C6)amidoalkyl radical, a tri(C1-C6)alkylsilane(C1-C6)alkyl radical and a (C1-C6)aminoalkyl radical in which the amine is protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; two of the R10, R11 and R12 radicals may also together form, with the nitrogen atom to which they are attached, a carbonaceous saturated 5- or 6-membered ring or which contains one or more hetero atoms, wherein said ring may be unsubstituted or substituted with a halogen atom, a hydroxyl radical, a (C1-C6)alkyl radical, a (C1-C6)monohydroxyalkyl radical, a (C2-C6)polyhydroxyalkyl radical, a nitro radical, a cyano radical, a cyano(C1-C6)alkyl radical, a (C1-C6)alkoxy radical, a tri(C1-C6)alkylsilane(C1-C6)alkyl radical, an amido radical, a formyl radical, a carboxyl radical, a keto(C1-C6)alkyl radical, a thio radical, a (C1-C6)thioalkyl radical, a (C1-C6)alkylthio radical, an amino radical or an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; one of the R10, R11 and R12 radicals may also be chosen from a second Z group which is identical to or different from the first Z group; R13 is chosen from a (C1-C6)alkyl radical; a (C1-C6)monohydroxy-alkyl radical; a (C2-C6)polyhydroxyalkyl radical; an aryl radical; a benzyl radical: a (C1-C6)aminoalkyl radical, a (C1-C6)aminoalkyl radical in which the amine is protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; a carboxy(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical a (C1-C6)trifluoroalkyl radical; a tri(C1-C6)alkyolsilane-(C1-C6)alkyl radical; a (C1-C6)sulphonamidoalkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical, a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylketo(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyl radical, and an Nâ€”(C1-C6)alkylsulphonamido(C1-C6)alkyl radical; a and y are integers equal to 0 or 1; with the following conditions, in the unsaturated cationic groups of formula (II): when a 0, the linker arm D is attached to the nitrogen atom, when a=1, the linker arm D is attached to one of the ring members E, G, J or L vertices, y can take the value 1 only: 1) when the ring members E, G, J and L simultaneously represent a carbon atom and when the R9 radical is carried by the nitrogen atom of the unsaturated ring; or alternatively 2) when at least one of the ring members E, G, J and L represents a nitrogen atom to which the R9 radical is attached; in the unsaturated cationic groups of formula (III): when a=0, the linker arm D is attached to the nitrogen atom, when a=1, the linker arm D is attached to one of the ring members E, G, J, L or M, y can take the value 1 only when at least one of the ring members E, G, J, L and M represents a divalent atom and when the R9 radical is carried by the nitrogen atom of the unsaturated ring; in the cationic groups of formula (IV): when a=0, then the linker arm D is attached to the nitrogen atom carrying the R10 to R12 radicals, when a=1, then two of the R10 to R12 radicals form, together with the nitrogen atom to which they are attached, a saturated 5- or 6membered ring as defined above, and the linker arm D is carried by a carbon atom of the saturated ring; Xâˆ’ is a monovalent or divalent anion; with the proviso that the number of cationic Z groups in the compound of formula (I) is at least equal to 1.