Patent ID: 6379398
Filing Date: 2002-04-30
Classification: C07C,C07D

Abstract:
A compound of formula (I) below, or an acid addition salt thereof: in which:B is a linker arm chosen from linear and branched alkyl chains, which can be optionally interrupted with at least one group chosen from Z groups and hetero atoms, and which can be optionally substituted with at least one substituent chosen from hydroxyls and (C1-C6)alkoxys, and which can optionally bear at least one ketone function; R1, R2, R3, Râ€²1, Râ€²2 and Râ€²3, which may be identical or different, can be the point of attachment of a linker arm B, otherwise, they are chosen from a hydrogen atom; halogens; Z groups; (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; 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)alkylcarbamyls; 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-alkylaminosulphonyl, N,N-di(C1-C6)alkylaminosulphonyls, thiocarbamyl, formyl, and Z groups in which the linker arm B comprises a ketone function directly attached to the nitrogen atom of the amino group; R6 can be the point of attachment of a linker arm B, otherwise 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, (C1-C6)alkylsulphonyls, and Z groups; R4, R5, R7, R8, Râ€²4, Râ€²5, Râ€²7 and Râ€²8, which may be identical or different, can be the point of attachment of a linker arm B, otherwise they are 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, formyls, 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 saturated cationic groups of formula (IV) below: â€ƒin which: D is a linker arm chosen from linear and branched alkyl chains, which are optionally interrupted by at least one hetero atom, and which can optionally be substituted with at least one radical chosen from hydroxyls and (C1-C6)alkoxys, and which also 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, can be the point of attachment of a linker arm B, otherwise they are chosen from a second group Z which is identical to or different from the first group Z, halogen atoms, a hydroxyl group, (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, nitro, cyano, cyano(C1-C6)alkyls, (C1-C6)alkoxyls, tri(C1-C6)alkylsilane(C1-C6)alkyls, amidos, aldehydo, carboxyl, (C1-C6)alkylcarbonyls, thio, (C1-C6)thioalkyls, (C1-C6)alkylthios, amino, aminos protected with a radical chosen from (C1-C6)alkylcarbonyls, carbamyl, and (C1-C6)alkylsulphonyls; and NHRâ€³ and 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; R9 can be the point of attachment of a linker arm B, otherwise R9 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; R10, R11 and R12, which may be identical or different, can be the point of attachment of a linker arm B, otherwise they 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 R10, R11, and R12 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, it being possible for the ring to be unsubstituted or to be substituted with a substituent chosen from halogen atoms, a hydroxyl group, (C1-C6)alkyls, (C1-C6)monohydroxyalkyls, (C2-C6)polyhydroxyalkyls, nitro, 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 R10, R11 and R12 can also be chosen from a second group Z which is identical to or different from the first group Z; R13 can be the point of attachment of a linker arm B, otherwise R13 is a radical chosen from (C1-C6)alkyls; (C1-C6)monohydroxy-alkyls; (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)alkyl radical; a C1-C6 sulphonamidoalkyl radical; a (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 chosen from the integers 0 and 1; with the proviso 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: 1) when the ring members E, G, J and L simultaneously represent a carbon atom and when the radical R9 is borne 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 radical R9 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 R9 is borne by the nitrogen atom of the unsaturated ring; in the cationic groups of formula (IV): when x=0, then the linker arm D is attached to the nitrogen atom bearing the radicals R10 to R12, when x=1, then two of the radicals R10 to R12 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; it being understood that: the number of cationic groups Z is at least equal to 1; when at least one of R4, R5, Râ€²4, Râ€²5, R7, R8, Râ€²7, and Râ€²8 is chosen from Z groups in which the linker arm D is chosen from alkyl chains comprising a ketone function, then the ketone function is not directly attached to the nitrogen atom of the group â€”NR4R5, â€”NRâ€²4Râ€²5, â€”NR7R8 or â€”NRâ€²7Râ€²8; when at least one of R4, R5, Râ€²4, Râ€²5, R7, R8, Râ€²7, and Râ€²8 is the point of a attachment of linker arm B chosen from alkyl chains comprising a ketone function, then the ketone function is not directly attached to the nitrogen atom of the group â€”NR4R5, â€”NRâ€²4Râ€²5, â€”NR7R8 or â€”NRâ€²7Râ€²8.