Patent ID: 6783557
Filing Date: 2004-08-31
Classification: A61K,A61Q,C07D

Abstract:
At least one chemical chosen from compounds of formula (I), and acid-addition salt thereof: in which:R1, R2 and R3, which may be identical or different, are each chosen from a hydrogen atom; a halogen atom; a group Z; a (C1-C6 alkyl)carbonyl radical; an amino(C1-C6 alkyl)carbonyl radical; an N-Z-amino(C1-C6 alkyl)carbonyl radical; an N-(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl radical; an N,N-di(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl radical; an amino(C1-C6 alkyl)carbonyl(C1-C6 alkyl) radical; an N-Z-amino(C1-C6 alkyl)carbonyl(C1-C6 alkyl) radical; an N-(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl(C1-C6 alkyl) radical; an N,N-di(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl(C1-C6 alkyl) radical; a carboxyl radical; a (C1-C6 alkyl)carboxyl radical; a (C1-C6 alkyl)sulphonyl radical; an aminosulphonyl radical; an N-Z-aminosulphonyl radical; an N-(C1-C6 alkyl)aminosulphonyl radical; an N,N-di(C1-C6 alkyl)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 alkylcarbamyl 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 hydroxyl radical; a nitro radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a C1-C6 (C1-C6 alkoxy)alkyl radical; a C1-C6 trifluoroalkyl radical; a cyano radical; a group OR6; a group SR6; an amino radical; an N-(C1-C6 alkyl)amino radical; an N,N-di(C1-C6 alkyl)amino radical, wherein the two alkyl substituents may form a ring chosen from 5- and 6-membered rings; an N-hydroxy(C1-C6 alkyl)amino radical; an N,N-bis(hydroxy(C1-C6 alkyl))amino radical; an N-polyhydroxy(C2-C6 alkyl)amino radical; an N,N-bis(polyhydroxy(C2-C6 alkyl))amino radical; an amino(C1-C6 alkyl)amino radical, in which the terminal amino group is unsubstituted or substituted by one or two C1-C6 alkyl radicals, where the alkyl radicals may form a ring chosen from saturated and unsaturated 5- and 6-membered rings; an amino group protected by at least one group chosen from a (C1-C6 alkyl)carbonyl, a trifluoro(C1-C6 alkyl)carbonyl, an amino(C1-C6 alkyl)carbonyl, an N-Z-amino(C1-C6 alkyl)carbonyl, an N-(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl, an N,N-di(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl radical, an N,N-di(C1-C6 alkyl)amino(C1-C6 alkyl) formyl radical, and a group Z; R6 is chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a group Z; a C1-C6 (C1-C6 alkoxy)alkyl radical; an aryl radical; a benzyl radical; a C1-C6 carboxyalkyl radical; a C1-C6 (C1-C6 alkyl)carboxyalkyl radical; a C1-C6 cyanoalkyl radical; a C1-C6 carbamylalkyl radical; a C1-C6 N-(C1-C6 alkyl)carbamylalkyl radical; a C1-C6 N,N-di(C1-C6 alkyl)carbamylalkyl radical; a C1-C6 trifluoroalkyl radical; a C1-C6 aminosulphonylalkyl radical; a C1-C6 N-Z-aminosulphonylalkyl radical; a C1-C6 N-(C1-C6 alkyl)aminosulphonylalkyl radical; a C1-C6 N,N-di(C1-C6 alkyl)aminosulphonylalkyl radical; a C1-C6 (C1-C6 alkyl)sulphinylalkyl radical; a C1-C6 (C1-C6 alkyl)sulphonylalkyl radical; a C1-C6 (C1-C6 alkyl)carbonylalkyl radical; a C1-C6 aminoalkyl radical; a C1-C6 aminoalkyl radical whose amine is substituted by one or two radicals chosen from C1-C6 alkyl, monohydroxy(C1-C76 alkyl), polyhydroxy(C2-C6 alkyl), (C1-C6 alkyl)carbonyl, formyl, trifluoro(C1-C6 alkyl)carbonyl, and (C1-C6 alkyl)sulphonyl radicals, and a group Z; A is chosen from â€”NR4R5 and a hydroxyl radical; R4 and R5, are independently chosen from a hydrogen atom; a group Z; a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a C1-C6 (C1-C6 alkoxy)alkyl radical; an aryl radical; a benzyl radical; a C1-C6 cyanoalkyl radical; a C1-C6 carbamylalkyl radical; a C1-C6 N-(C1-C6 alkyl)carbamylalkyl radical; a C1-C6 N,N-di(C1-C6 alkyl)carbamylalkyl radical; a C1-C6 thiocarbamylalkyl radical; a C1-C6 trifluoroalkyl radical; a C1-C6 sulphoalkyl radical; a C1-C6 (C1-C6 alkyl)carboxyalkyl radical; a C1-C6 (C1-C6 alkyl)sulphinylalkyl radical; a C1-C6 aminosulphonylalkyl radical; a C1-C6 N-Z-aminosulphonylalkyl radical; a C1-C6 N-(C1-C6 alkyl)-aminosulphonylalkyl radical; a C1-C6 N,N-di(C1-C6 alkyl)aminosulphonylalkyl radical; a C1-C6 (C1-C6 alkyl)carbonylalkyl radical; a C1-C6 aminoalkyl radical; and a C1-C6 aminoalkyl radical whose amine is substituted by one or two radicals chosen from C1-C6 alkyl, C1-C6 monohydroxyalkyl, C2-C6 polyhydroxyalkyl, (C1-C6 alkyl)carbonyl, (C1-alkyl)sulphonyl, formyl, and trifluoro(C1-C6 alkyl)carbonyl radicals, and a group Z; wherein one and only one of the radicals R4 and R5 may also be chosen from a (C1-C6 alkyl)carbonyl radical; a formyl radical; a trifluoro(C1-C6 alkyl)carbonyl radical; an amino(C1-C6 alkyl)carbonyl radical; an N-Z-amino(C1-C6 alkyl)carbonyl radical; an N-(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl radical; and an N,N-di(C1-C6 alkyl)amino(C1-C6 alkyl)carbonyl radical; 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 which is chosen from linear and branched alkyl chains and may be interrupted by at least one heteroatom atom and may be substituted by at least one of a hydroxyl and a C1-C6 alkoxy radical, and may carry at least one ketone function; the ring members E, G, J, L and M, 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 radicals R, which are identical or different, may be chosen from a 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 C1-C6 tri(C1-C6 alkyl)silanealkyl 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 alkyl)thio radical; an amino radical; an amino radical protected by a group chosen from (C1-C6 alkyl)carbonyl, carbamyl, and (C1-C6 alkyl)sulphonyl; and groups NHRâ€³ and NRâ€³Râ€²â€³ in which Râ€² and Râ€²â€³, which are identical or different, are chosen from a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical and a C2-C6 polyhydroxyalkyl radical; R7 is chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a C1-C6 cyanoalkyl radical; a C1-C6 tri(C1-C6 alkyl)silanealkyl radical; a C1-C6 (C1-C6 alkoxy)alkyl radical; a carbamyl(C1-C6 alkyl) radical; a C1-C6 (C1-C6 alkyl)carboxyalkyl radical; a benzyl radical; and a group Z; R8, R9 and R10, which are identical or different, are chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a C1-C6 (C1-C6 alkoxy)alkyl radical; a C1-C6 cyanoalkyl radical; an aryl radical; a benzyl radical; a C1-C6 amidoalkyl radical; a C1-C6 tri(C1-C6 alkyl)silanealkyl radical; and a C1-C6 aminoalkyl radical whose amine is protected by at least one of a (C1-C6 alkyl)carbonyl, amido, carboxyl and (C1-C6 alkyl)sulphonyl radical; two of the radicals R8, R9 and R10 may form, together with the nitrogen to which they are attached, a ring chosen from saturated 5- and 6-membered carbon-containing rings which may contain at least one heteroatom, wherein said rings may contain a substituent chosen from 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 C1-C6 tri(C1-C6 alkyl)silanealkyl radical; an amido radical; an aldehydo radical; a carboxyl radical; a C1-C6 ketoalkyl radical; a thio radical; a C1-C6 thioalkyl radical; a (C1-C6 alkyl)thio radical; an amino radical; and an amino radical protected by a group chosen from (C1-C6 alkyl)carbonyl; carbamyl and (C1-C6 alkyl)sulphonyl radical; one of the radicals R8, R9 and R10 may be chosen from a second group Z, identical to or different from the first group Z; R11 may be chosen from 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 whose amine is protected by at least one of a (C1-C6 alkyl)carbonyl, a carbamyl, and a (C1-C6 alkyl)sulphonyl radical; a C1-C6 carboxyalkyl radical; a C1-C6 cyanoalkyl radical; a C1-C6 carbamylalkyl radical; a C1-C6 trifluoroalkyl radical; a C1-C6 tri(C1-C6 alkyl)silanealkyl radical; a C1-C6 sulphonamidoalkyl radical; a C1-C6(C1-C6 alkyl)carboxyalkyl radical; a C1-C6(C1-C6 alkyl)sulphinylalkyl radical; a C1-C6 (C1-C6 alkyl)sulphonylalkyl radical; a C1-C6 (C1-C6 alkyl)ketoalkyl radical; a C1-C6 N-(C1-C6 alkyl)carbamylalkyl radical; and a C1-C6 N-(C1-C6 alkyl)sulphonamidoalkyl 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 D is attached to the nitrogen atom, when a=1, the linker D is attached to one of the ring members E, G, J or L, y can adopt the value 1 only 1) when the ring members E, G, J and L are simultaneously a carbon atom and when the radical R7 is carried by the nitrogen atom of the unsaturated ring; or 2) when at least one of the ring members E, G, J and L is chosen from a nitrogen atom to which the radical R7 is attached; in the unsaturated cationic groups of formula (III): when a=0, the linker D is attached to the nitrogen atom, when a=1, the linker D is attached to one of the ring members E, G, J, L or M, y can adopt the value 1 only 1) when at least one of the ring members E, G, J, L and M is chosen from a divalent atom and 2) when the radical R7 is carried by the nitrogen atom of the unsaturated ring; in the saturated cationic groups of formula (IV): when a=0, then the linker D is attached to the nitrogen atom which carries the radicals R8 to R10, when a=1, then two of the radicals R8 to R10, together with the nitrogen atom to which they are attached, form a ring chosen from 5- and 6-membered saturated rings, and the linker D is carried by a carbon atom of the said ring; Xâˆ’ is chosen from monovalent and divalent anions; with the proviso that at least one of R1, R2 and R3 is a group Z.