Patent ID: 6340371
Filing Date: 2002-01-22
Classification: C07D

Abstract:
A compound of formula (1) below or an acid addition salt thereof: wherein:R1, R2 and R3, which may be identical or different, are chosen from a hydrogen atom; halogen atoms; Z groups; (C1-C6)alkylcarbonyls; amino(C1-C6)alkyl-carbonyls; Nâ€”Z-amino(C1-C6)alkylcarbonyls; Nâ€”(C1-C6)alkylamino(C1-C6)alkyl-carbonyls; N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyls; amino(C1-C6)alkylcarbonyl(C1-C6)alkyls; Nâ€”Z-amino(C1-C6)alkylcarbonyl-(C1-C6)alkyls; Nâ€”(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyls; N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyls; carboxyl; (C1-C6)alkylcarboxyls; (C1-C6)alkylsulphonyls; aminosulphonyls; Nâ€”Z-aminosulphonyls; (C1-C6)N-alkylaminosulphonyls; N,N-di(C1-C6)alkylaminosulphonyls; (C1-C6)aminosulphonylalkyls; (C1-C6)Nâ€”Z-aminosulphonylalkyls; Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyls; N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyls; carbamyl; Nâ€”(C1-C6)alkyl-carbamyls; N,N-di(C1-C6)alkylcarbamyls; carbamyl(C1-C6)alkyls; Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyls; N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyls; (C1-C6)alkyls; (C1-C6)monohydroxyalkyls; (C2-C6)polyhydroxyalkyls; (C1-C6)alkoxy(C1-C6)-alkyls; (C1-C6)trifluoroalkyls; cyano; OR6 and SR6 groups; amino groups protected with a radical chosen from (C1-C6)alkylcarbonyls, (C1-C6)alkylcarboxyls, trifluoro(C1-C6)alkylcarbonyls, amino(C1-C6)alkylcarbonyls, Nâ€”Z-amino(C1-C6)alkylcarbonyls, Nâ€”(C1-C6)alkylamino(C1-C6)alkylcarbonyls, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyls, (C1-C6)alkylcarboxyls, carbamyl, Nâ€”(C1-C6)alkylcarbamyls, N,N-di(C1-C6)alkylcarbamyls, (C1-C6)alkylsulphonyls, aminosulphonyls, Nâ€”Z-aminosulphonyls, (C1-C6)N-alkylaminosulphonyls, N,N-di(C1-C6)alkylaminosulphonyls, thiocarbamyl, formyl, and Z groups, in which the linker arm D of the Z group comprises a ketone function directly attached to the nitrogen atom of the amino group; and (C1-C6)aminoalkyl in which the amine is substituted with at least one, identical or different radical, chosen from (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, (C1-C6)alkylcarbonyls, carbamyl, Nâ€”(C1-C6)alkyl-carbamyls, N,N-di(C1-C6)alkylcarbamyls, (C1-C6)alkylsulphonyls, formyl, trifluoro (C1-C6)alkyl-carbonyls, (C1-C6)alkylcarboxyls, thiocarbamyl, and Z groups; R6 is a radical chosen from (C1-C6)alkyls; (C1-C6)monohydroxyalkyls; (C2-C6)polyhydroxyalkyls; Z groups; (C1-C6)alkoxy(C1-C6)alkyls; aryls; benzyl; carboxy(C1-C6)alkyls; (C1-C6)alkylcarboxy(C1-C6)alkyls; cyano(C1-C6)alkyls; carbamyl(C1-C6)alkyls; Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyls; N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyls; (C1-C6)trifluoroalkyls; (C1-C6)aminosulphonylalkyls; (C1-C6)Nâ€”Z-aminosulphonylalkyls; Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyls; N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyls; (C1-C6)alkylsulphinyl(C1-C6)alkyls; (C1-C6)alkylsulphonyl(C1-C6)alkyls; (C1-C6)alkylcarbonyl(C1-C6)alkyls; (C1-C6)aminoalkyls; (C1-C6)aminoalkyls in which the amine is substituted with one or two, identical or different, radicals chosen from (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, (C1-C6)alkylcarbonyls, formyl, trifluoro-(C1-C6)alkylcarbonyls, (C1-C6)alkylcarboxyls, carbamyl, Nâ€”(C1-C6)alkylcarbamyls, N,N-di-(C1-C6)alkylcarbamyls, thiocarbamyl and (C1-C6)alkylsulphonyls, and Z groups; R4, Râ€²4, R5 and Râ€²5, which may be identical or different, are substituents chosen from a hydrogen atom; Z groups; (C1-C6)alkyls; (C1-C6)monohydroxyalkyls; (C2-C6)polyhydroxyalkyls; (C1-C6)alkoxy(C1-C6)alkyls; aryls; benzyl; cyano(C1-C6)alkyls; carbamyl(C1-C6)alkyls; Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyls; N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyls; thiocarbamyl(C1-C6)alkyls; (C1-C6)trifluoroalkyls; (C1-C6)sulphoalkyls; (C1-C6)alkylcarboxy(C1-C6)alkyls; (C1-C6)alkylsulphinyl(C1-C6)alkyls; (C1-C6)aminosulphonylalkyls; (C1-C6)Nâ€”Z-aminosulphonylalkyls; Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyls; N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyls; (C1-C6)alkylcarbonyl(C1-C6)alkyls; (C1-C6)aminoalkyls; (C1-C6)aminoalkyls in which the amine is substituted with one or two, identical or different, radicals chosen from (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, (C1-C6)alkylcarbonyls, carbamyl, Nâ€”(C1-C6)alkylcarbamyls, N,N-di(C1-C6)alkylcarbamyls, (C1-C6)alkylsulphonyls, formyl, trifluoro(C1-C6)alkylcarbonyls, (C1-C6)alkylcarboxyls, thiocarbamyl, and Z groups; Z is chosen from unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below: â€ƒin which: D is a linker arm chosen from linear and branched alkyl chains, optionally interrupted by at least one hetero atom, such as oxygen, sulphur, and nitrogen atoms, and optionally substituted with at least one radical chosen from a hydroxyl group and (C1-C6)alkoxys, and which can optionally bear at least one ketone function; the ring members E, G, J, L and M, which may be identical or different, are chosen from carbon, oxygen, sulphur, and nitrogen atoms; n is chosen from the integers 0, 1, 2, 3, and 4; m is chosen from the integers 0, 1, 2, 3, 4, and 5; the radicals R, which may be identical or different, are chosen from a second group Z which is identical to or different from the first group Z, a halogen atom, a hydroxyl, (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, a nitro, a cyano, cyano(C1-C6,)alkyls, (C1-C6)alkoxys, tri(C1-C6)alkylsilane(C1-C6)alkyls, amido, aldehydo, carboxyl, (C1-C6)alkylcarbonyls, thio, (C1-C6)thioalkyls, (C1-C6)alkylthios, amino, aminos protected with a radical chosen from (C1-C6)alkylcarbonyls, carbamyls and (C1-C6)alkylsulphonyls; NHRâ€³ groups, NRâ€³Râ€²â€³ groups in which Râ€³ and Râ€²â€³, which may be identical or different, are chosen from (C1-C6)alkyl radicals, (C1-C6)monohydroxyalkyl radicals, and (C2-C6)polyhydroxyalkyl radicals; R7 is a radical chosen from (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, cyano(C1-C6)alkyls, tri(C1-C6)alkylsilane(C1-C6)alkyls, (C1-C6)alkoxy(C1-C6)alkyls, carbamyl-(C1-C6)alkyls, (C1-C6)alkylcarboxy(C1-C6)alkyls, benzyl and a second group Z which is identical to or different from the first group Z; R8, R9 and R10, which may be identical or different, are radicals chosen from (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, (C1-C6)alkoxy(C1-C6)alkyls, cyano(C1-C6)alkyls, aryls, benzyl, (C1-C6)amidoalkyls, tri(C1-C6)alkylsilane(C1-C6)alkyls, and (C1-C6)aminoalkyls in which the amine is protected with a radical chosen from (C1-C6)alkylcarbonyls, carbamyl, and (C1-C6)alkylsulphonyls; two of the radicals R8, R9 and R10 can together also form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring or a ring containing at least one additional hetero atom, the ring being optionally substituted with a substituent chosen from halogen atoms, a hydroxyl group, (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, a nitro, a cyano, cyano(C1-C6)alkyls, (C1-C6)alkoxys, tri(C1-C6)alkylsilane(C1-C6)alkyls, amido, aldehydo, carboxyl, keto(C1-C6)alkyls, thio, (C1-C6)thioalkyls, (C1-C6)alkylthios, amino, and aminos protected with a radical chosen from (C1-C6)alkylcarbonyls, carbamyl, and (C1-C6)alkylsulphonyls; one of the radicals R8, R9 and R10 can also be chosen from a second group Z which is identical to or different from the first group Z; R11 is a radical chosen from (C1-C6)alkyls; (C1-C6)monohydroxyalkyls; (C2-C6)polyhydroxyalkyls; aryls; benzyl; (C1-C6)aminoalkyls, (C1-C6)aminoalkyls in which the amine is protected with a radical chosen from (C1-C6)alkylcarbonyls, carbamyl, and (C1-C6)alkylsulphonyls; carboxy(C1-C6)alkyls; cyano(C1-C6)alkyls; carbamyl(C1-C6)alkyls; (C1-C6)trifluoroalkyls; tri(C1-C6)alkylsilane(C1-C6)alkyls; (C1-C6)sulphonamidoalkyls; (C1-C6)alkylcarboxy(C1-C6)alkyls; (C1-C6)alkylsulphinyl(C1-C6)alkyls; (C1-C6)alkylsulphonyl(C1-C6)alkyls; (C1-C6)alkylketo(C1-C6)alkyls; Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyls; Nâ€”(C1-C6)alkylsulphonamido(C1-C6)alkyls; x and y are integers chosen from 0 and 1; with the provision that: in the unsaturated cationic groups of formula (II): when x=0, the linker arm D is attached to the nitrogen atom, when x=1, the linker arm D is attached to one of the ring members E, G, J or L, y can take the value 1 only: â€ƒ1) when the ring members E, G, J and L simultaneously represent a carbon atom and when the radical R7 is borne by the nitrogen atom of the unsaturated ring; or alternatively â€ƒ2) when at least one of the ring members E, G, J and L represents a nitrogen atom to which the radical R7 is attached; in the unsaturated cationic groups of formula (III): when x=0, the linker arm D is attached to the nitrogen atom, when x=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 is chosen from divalent atoms and when the radical R7 is borne by the nitrogen atom of the unsaturated ring; in the cationic groups of formula (IV): when x=0, then the linker arm is attached to the nitrogen atom bearing the radicals R8 to R10, when x=1, then two of the radicals R8 to R10 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm D is borne by a carbon atom of the saturated ring; Xâˆ’ is chosen from monovalent and divalent anions; â€ƒit being understood that: the number of unsaturated cationic groups Z of formula (II) or (III) is at least equal to 1; when at least one of R4, R5, Râ€²4, and Râ€²5, is chosen from Z groups in which the linker arm D represents an alkyl chain comprising a ketone function, then the ketone function is not directly attached to the nitrogen atom of the group â€”NR4R5 or â€”NRâ€²4Râ€²5.