Patent ID: 6402791
Filing Date: 2002-06-11
Classification: A61K,A61Q,C07D

Abstract:
A compound of the following formula (I) an acid addition salt thereof: in which:B is a linking arm chosen from linear and branched alkyl chains, which may be uninterrupted or interrupted by at least one group chosen from a group Z as defined below, an unsubstituted heteroatom, and a heteroatom substituted with at least one radical chosen from a hydroxyl radical and a C1-C6 alkoxy radical, said alkoxy radical being chosen from an alkoxy radical not carrying at least one ketone functional group and an alkoxy radical carrying at least one ketone functional group; Ra, Rb, Râ€²a and Râ€²b, which are identical or different, are chosen from a hydrogen atom, a C1-C6 alkyl radical, a C1-C6 hydroxyalkyl radical, or formed in pairs, together with the carbon atom to which they are attached, a 5-, 6- or 7-membered saturated carbon ring; R1, Râ€²1, R2, Râ€²2, R3 and Râ€²3, which may be identical or different, are chosen from a hydrogen atom; a halogen atom; one valence of the divalent linking arm B, a group Z as defined below; a group A2 as defined below; a group A2â€² as defined a (C1-C6)alkylcarbonyl radical; an amino(C1-C6)alkylcarbonyl radical; an N-Z-amino(C1-C6)alkylcarbonyl radical; an N-(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical; an N,N-di(C1-C6 alkyl)amino(C1-C6)alkylcarbonyl radical; an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N-Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N-(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a carboxyl radical; a (C1-C6)alkylcarboxyl radical; a (C1-C6)alkylsulphonyl radical; an aminosulphonyl radical; an N-Z-aminosulphonyl radical; an N-(C1-C6 alkyl)aminosulphonyl radical; an N,N-di(C1-C6alkyl)aminosulphonyl radical; an aminosulphonyl(C1-C6)alkyl radical; an N-Z-aminosulphonyl(C1-C6)alkyl radical; an N-(C1-C6 alkyl)aminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)aminosulphonyl(C1-C6)alkyl radical; a carbamyl radical; an N-(C1-C6 alkyl)carbamyl radical; an N,N-di(C1-C6 alkyl)carbamyl radical; a carbamyl(C1-C6)alkyl radical; an N-(C1-C6 alkyl)carbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)carbamyl(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, ORâ€²6, SR6 or SRâ€²6; a C1-C6 aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; an amino(C1-C6)alkyl 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 are identical or different, chosen from an alkyl radical, a, C1-C6 monohydroxyalkyl radical, a, C2-C6 polyhydroxyalkyl radical, a, (C1-C6)alkylcarbonyl radical, a, carbamyl radical, an, N-(C1-C6 alkyl)carbamyl, an N,N-di(C1-C6 alkyl)carbamyl radical, a, (C1-C6)alkylsulphonyl radical, a, formyl radical, a, trifluoro(C1-C6)alkylcarbonyl radical, a, (C1-C6)alkylcarboxyl, a thiocarbamyl radical, a group Z as defined below; and, formed together with the nitrogen atom to which they are attached, a 5- or 6-membered ring comprising at least one of atom chosen from a carbon atom and a heteroatom; R6 and Râ€²6, which may be identical or different, denote one valence of the divalent linking arm B; 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 C1-C6 carboxyalkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical; a C1-C6 cyanoalkyl radical; a C1-C6 carbamylalkyl radical; an N-(C1-C6 alkyl)carbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)carbamyl(C1-C6)alkyl radical; a C1-C6 trifluoroalkyl radical; a C1-C6 aminosulphonylalkyl radical; a C1-C6 N-Z-aminosulphonylalkyl radical; an N-(C1-C6 alkyl)aminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)aminosulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphinyl(C1-C6)alkylradical; a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylcarbonyl-(C1-C6)alkyl radical; an amino(C1-C6)alkyl radical; an amino(C1-C6)alkyl 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 are identical or different, chosen from a (C1-C6)alkylmonohydroxy(C1-C6)alkyl radical, a, polyhydroxy(C2-C6)alkyl radical, a, (C1-C6)alkylcarbonyl radical, a, formyl radical, a, trifluoro(C1-C6)alkylcarbonyl radical, a, (C1-C6)alkylcarboxyl radical, a, carbamyl radical, a, N-(C1-C6 alkyl)carbamyl radical, a, N,N-di(C1-C6 alkyl)carbamyl radical, a, thiocarbamyl radical, a (C1-C6)alkylsulphonyl radical, a group Z as defined below; and formed together with the nitrogen atom to which they are attached, a 5- or 6-membered ring comprising at least one atom chosen from a carbon atom and a heteroatom; A is chosen from â€”NR4R5 and a hydroxyl radical; Aâ€² is chosen from â€”NRâ€²4Râ€²5 and a hydroxyl radical; A2 is chosen from â€”NRâ€³4Râ€³5 and a hydroxyl radical; Aâ€²2 is chosen from â€”NRâ€²â€³4Râ€²â€³5 and a hydroxyl radical; R4, R5, Râ€²4, Râ€²5, Râ€³4, Râ€³5, Râ€²â€³4 and Râ€²â€³5, which are identical or different, are chosen from one valence of the divalent linking arm B; a hydrogen atom; a group Z as defined below; 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 C1-C6 cyanoalkyl radical; a C1-C6 carbamylalkyl radical; an N-(C1-C6 alkyl)carbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)carbamyl(C1-C6)alkyl radical; a C1-C6 thiocarbamylalkyl 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 N-Z-aminosulphonylalkyl radical; an N-(C1-C6 alkyl)aminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6 alkyl)aminosulphonyl(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; 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 are identical or different, chosen from a C1-C6 alkyl radical, a, C1-C6 monohydroxyalkyl radical, a, C2-C6 polyhydroxyalkyl radical, a, (C1-C6)alkylcarbonyl radical, a, carbamyl radical, a, N-(C1-C6 alkyl)carbamyl radical, a, N,N-di(C1-C6 alkyl)carbamyl radical, a, (C1-C6)alkylsulphonyl radical, a, formyl radical, a, trifluoro(C1-C6alkyl)carbonyl radical, a, (C1-C6)alkylcarboxyl thiocarbamyl radical, a group Z as defined below; and formed together with the nitrogen atom to which they are attached a 5- or 6-membered ring comprising at least one atom chosen from a carbon atom and a heteroatom; Z is chosen from the unsaturated cationic groups of the following formulae (II) and (III), and the saturated cationic groups of the following formula (IV): â€ƒin which: D is a linking arm chosen from a linear or branched alkyl chain, which may be interrupted by one or more heteroatoms, and which may be unsubstituted or substituted with at least one of radical chosen from a hydroxyl radical and a C1-C6 alkoxy radicals, and which may carry one or more ketone functions; the members E, G, J, L and M, which are identical or different, are independently chosen from carbon, oxygen, sulphur and nitrogen atoms; n is an integer between 0 and 4 inclusive; m is an integer between 0 and 5 inclusive; the radicals R, which are identical or different, are chosen from one valence of the divalent linking arm B; a second group Z which is identical to or different from the first group Z; 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 C1-C6 cyanoalkyl radical; a C1-C6 alkoxy radical; a tri(C1-C6 alkyl)silane(C1-C6)alkyl radical; an amido radical; an aldehydo 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 NHRâ€³, and a group NRâ€³Râ€²â€³, in which Râ€³ and Râ€²â€³, which are identical or different, represent a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical or a C2-C6 polyhydroxyalkyl radical; R7 is chosen from a C1-C6 alkyl radical; one valence of the divalent linking arm B; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a C1-C6 cyanoalkyl radical; a tri(C1-C6 alkyl)silane(C1-C6)alkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; a C1-C6 carbamylalkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical; a benzyl radical; and a second group Z which is identical or different from the first group Z; R8, R9 and R10, which are identical or different, are chosen from one valence of the divalent linking arm B; 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 cyanoalkyl radical; an aryl radical; a benzyl radical; a C1-C6 amidoalkyl radical; a tri(C1-C6 alkyl)silane(C1-C6)alkyl radical; or 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 radicals R8, R9 and R10 may also form together, with the nitrogen atom to which they are attached, a 5- or 6-membered saturated ring comprising at least one atom chosen from a carbon atom and a heteroatom, it being possible for the said ring to be unsubstituted or substituted with at least one of 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 C1-C6 cyanoalkyl radical, a C1-C6 alkoxy radical, a tri(C1-C6 alkyl)silane(C1-C6)alkyl radical, an amido radical, an aldehydo radical, a carboxyl radical, a C1-C6 ketoalkyl radical, a thio radical, a 1-C6 thioalkyl radical, a (C1-C6)alkylthio radical, and an amino radical, and an amino radical protected by a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; â€ƒone of the radicals R8, R9 and R10 can be chosen from a second group Z which is identical to or different from the first group Z; R11 is chosen from one valence of the divalent linking arm B; a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl 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 with a (C1-C6)alkylcarbonyl, carbamyl or (C1-C6)alkylsulphonyl radical; a C1-C6 carboxyalkyl radical; a C1-C6 cyanoalkyl radical; a C1-C6 carbamylalkyl radical; a C1-C6 trifluoroalkyl radical; a tri(C1-C6 alkyl)silane(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 N-(C1-C6 alkyl)carbamyl(C1-C6)alkyl radical; and an N-(C1-C6 alkyl)sulphonamido(C1-C6)alkyl radical; a and y are integers equal to 0 or 1; with the following conditions: â€ƒin the unsaturated cationic groups of formula (II): when a=0, the linking arm D is attached to the nitrogen atom, when a=1, the linking arm D is attached to one of the members E, G, J or L, y can only take the value 1: 1) when the members E, G, J and L simultaneously represent a carbon atom and when the radical R7 is carried by the nitrogen atom of the unsaturated ring; or alternatively 2) when at least one of the members E, G, J and L represents a nitrogen atom to which the radical R7 is attached; â€ƒin the unsaturated cationic groups of formula (III): when a=0, the linking arm D is attached to the nitrogen atom, when a=1, the linking arm D is attached to one of the members E, G, J, L or M, y can only take the value 1 when at least one of the members E, G, J, L and M represents a divalent atom, and when the radical R7 is carried by the nitrogen atom of the unsaturated ring; â€ƒin the cationic groups of formula (IV): when a=0, then the linking arm D is attached to the nitrogen atom carrying the radicals R8 to R10, when a=1, then two of the radicals R8 to R10 form together with the nitrogen atom to which they are attached a 5- or 6-membered saturated ring as defined above, and the linking arm D is carried by a carbon atom of the said saturated ring; and Xâˆ’ is chosen from a monovalent anion and a divalent anion; it being understood that:the number of cationic groups Z is at least equal to 1.