Patent ID: 6464731
Filing Date: 2002-10-15
Classification: C07D

Abstract:
A compound chosen from cationic monobenzene nitrophenylenediamines of formula (I) and acid addition salts thereof: wherein:R1, R2, R3 and R4, which can be identical or different, are chosen from a hydrogen atom; a Z group as defined below; a (C1-C6)alkyl radical; a mono-hydroxy(C1-C6)alkyl radical; a polyhydroxy(C2-C6)alkyl 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(C1C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a thiocarbamyl(C1-C6)alkyl radical; a trifluoro(C1-C6)alkyl radical; a sulpho(C1-C6)alkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical; a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical; an aminosulphonyl(C1-C6)alkyl radical; an Nâ€”Z-aminosulphonyl(C1-C6)alkyl 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; an amino(C1-C6)alkyl radical, wherein the alkyl is unsubstituted or substituted by one or more hydroxyl radicals; and an amino(C1-C6)alkyl radical, wherein the alkyl is unsubstituted or substituted by one or more hydroxyl radicals and the amine is substituted by one or two identical or different radicals which may together form, with the nitrogen atom to which they are respectively attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more heteroatoms, or which are chosen from alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, carbamyl, Nâ€”(C1-C6)alkylcarbamyl or N,N-di(C1-C6)alkylcarbamyl, (C1-C6)alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, and from a Z group as defined below; R5 and R6, which can be identical or different, are chosen from a hydrogen atom; a halogen atom; a Z group 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; an Nâ€”(C1-C6)alkylaminosulphonyl radical; an N,N-di(C1-C6)alkylaminosulphonyl radical; an aminosulphonyl(C1-C6)alkyl radical; an Nâ€”Z-aminosulphonyl(C1-C6)alkyl 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€”(C1-C6)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 monohydroxy(C1-C6)alkyl radical; a polyhydroxy(C2-C6)alkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; a trifluoro(C1-C6)alkyl radical; a cyano radical; an OR7 or â€”SR7 group wherein R7 is as defined below; and an amino(C1-C6)alkyl radical, wherein the alkyl is unsubstituted or substituted by one or more hydroxyl radicals and the amine is unsubstituted or substituted by one or two identical or different radicals which may together form, with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more heteroatoms, or which are chosen from (C1-C6)alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (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, and from a Z group as defined below; R7 is chosen from a hydrogen atom; a (C1-C6)alkyl radical; a monohydroxy(C1-C6)alkyl radical: a polyhydroxy(C2-C6)alkyl radical; a Z group 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 trifluoro(C1-C6)alkyl radical; an aminosulphonyl(C1-C6)alkyl radical; an Nâ€”Z-aminosulphonyl(C1-C6)alkyl 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; an amino(C1-C6)alkyl radical, wherein the alkyl is unsubstituted or substituted by one or more hydroxyl radicals; and an amino(C1-C6)alkyl radical, wherein the alkyl is unsubstituted or substituted by one or more hydroxyl radicals and the amine is substituted by one or two identical or different radicals which may together form, with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more heteroatoms, or which are chosen from (C1-C6)alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, 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, and from a Z group as defined below; Z is chosen from the unsaturated cationic groups of following formulae (II) and (III) and the saturated cationic groups of following formula (IV): â€ƒwherein: D is a linking arm which is a linear or branched alkyl chain which can be interrupted by one or more heteroatoms, can be substituted by one or more hydroxyl or (C1-C6)alkoxy radicals and can carry one or more ketone functional groups; the E, G, J, L and M vertices, which are identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms; n is an integer ranging from 0 to 4; m is an integer ranging from 0 to 5; the R radicals, which are identical or different, are chosen from a second Z group identical to or different from the first Z group; a halogen atom; a hydroxyl radical; a (C1-C6)alkyl radical; a monohydroxy(C1-C6)alkyl radical; a polyhydroxy(C2-C6)alkyl radical; a nitro radical; a cyano radical; a cyano(C1-C6)alkyl radical; a (C1-C6)alkoxy radical; a tri(C1-C6)alkylsilyl(C1-C6)alkyl radical; an amido radical; a formyl radical; a carboxyl radical; a (C1-C6)alkylcarbonyl radical; a thio radical; a thio(C1-C6)alkyl radical; a (C1-C6)alkylthio radical; an amino radical; an amino radical protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; an NHRâ€³ group and an NRâ€³Râ€²â€³ group wherein Râ€³ and Râ€²â€³, which are identical or different, are chosen from a (C1-C6)alkyl radical, a monohydroxy(C1-C6)alkyl radical and a polyhydroxy(C2-C6)alkyl radical; R8 is chosen from a (C1-C6)alkyl radical; a monohydroxy(C1-C6)alkyl radical; a polyhydroxy(C2-C6)alkyl radical; a cyano(C1-C6)alkyl radical; a tri(C1-C6)alkylsilyl(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 identical to or different from the first Z group; R9, R10 and R11, which are identical or different, are chosen from a (C1-C6)alkyl radical; a monohydroxy(C1-C6)alkyl radical; a polyhydroxy(C2-C6)alkyl radical; a (C1-C6)alkoxy-(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; an aryl radical; a benzyl radical; an amido(C1-C6)alkyl radical; a tri(C1-C6)alkylsilyl(C1-C6)alkyl radical; and an amino(C1-C6)alkyl radical, wherein the amine is protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; or wherein two of the R9, R10 and R11 radicals together form, with the nitrogen atom to which they are attached, a saturated carbonaceous 5- or 6-membered ring or a saturated 5- or 6-membered ring which can comprise one or more heteroatoms, wherein said ring is unsubstituted or substituted by a halogen atom, a hydroxyl radical, a (C1-C6)alkyl radical, a monohydroxy(C1-C6)alkyl radical, a polyhydroxy(C1-C6)alkyl radical, a nitro radical, a cyano radical, a cyano(C1-C6)alkyl radical, a (C1-C6)alkoxy radical, a tri(C1-C6)alkylsilyl(C1-C6)alkyl radical, an amido radical, a formyl radical, a carboxyl radical, a keto(C1-C6)alkyl radical, a thio radical, a thio(C1-C6)alkyl radical, a (C1-C6)alkylthio radical, an amino radical or an amino radical protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; or wherein one of the R9, R10 and R11 radicals is a second Z group identical to or different from the first Z group: R12 is chosen from a (C1-C6)alkyl radical; a monohydroxy(C1-C6)alkyl radical; a polyhydroxy(C2-C6)alkyl radical; an aryl radical, a benzyl radical; an amino(C1-C6)alkyl radical; an amino(C1-C6)alkyl radical, wherein 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 trifluoro(C1-C6)alkyl radical; a tri(C1-C6)alkylsilyl(C1-C6)alkyl radical; a sulphonamido(C1-C6)alkyl 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; x and y are integers equal to 0 or 1, with the provisos that: in the unsaturated cationic groups of formula (II): when x=0, the D linking arm is attached to the nitrogen atom, when x=1, the D linking arm is attached to one of the E, G, J or L vertices, y can take the value 1 only when: â€ƒ1) the E, G, J and L vertices are all carbon atoms and when the R8 radical is carried by the nitrogen atom of the unsaturated ring; or â€ƒ2) at least one of the E, G, J and L vertices is a nitrogen atom to which the R8 radical is attached; in the unsaturated cationic groups of formula (III): when x=0, the D linking arm is attached to the nitrogen atom, when x=1, the D linking arm is attached to one of the E, G, J, L or M vertices, y can take the value 1 only when at least one of the E, G, J, L and M vertices is a divalent atom and when the R8 radical is carried by the nitrogen atom of the unsaturated ring; in the cationic groups of formula (IV): when y=0, the D linking arm is attached to the nitrogen atom carrying the R9, R10 and R11 radicals, when y=1, two of the R9, R10 and R11 radicals form, together with the nitrogen atom to which they are attached, a saturated carbonaceous 5- or 6-membered ring or a saturated 5- or 6-membered ring which can comprise one or more heteroatoms, wherein said ring is unsubstituted or substituted by a halogen atom, a hydroxyl radical, a (C1-C6)alkyl radical, a monohydroxy(C1-C6)alkyl radical, a polyhydroxy(C2-C6)alkyl radical, a nitro radical, a cyano radical, a cyano(C1-C6)alkyl radical, a (C1-C6)alkoxy radical, a tri(C1-C6)alkylsilyl(C1-C6)alkyl radical, an amido radical, a formyl radical, a carboxyl radical, a keto(C1-C6)alkyl radical, a thio radical, a thio(C1-C6)alkyl radical, a (C1-C6)alkylthio radical, an amino radical or an amino radical protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; and the D linking arm is carried by a carbon atom of the said saturated ring; Xâˆ’ is a monovalent or divalent anion; with the provisos that: in the compound of formula (I), at least one of R1, R2, R3, R4, R5, and R6 comprises at least one unsaturated cationic group Z of formula (II) wherein at least one of the E, G, J and L vertices is a nitrogen atom, and when only one of the R1, R2, R3, R4 or R7 radicals is a Z group wherein the D linking arm is an alkyl chain comprising a ketone functional group, then said ketone functional group is not directly attached to the nitrogen atom of the NR1R2 or NR3R4 group or to the oxygen atom of the OR7 group when R5 or R6 is OR7.