10h-benzo[g]pteridine-2,4-dione derivatives, method for the production thereof, and use thereof

A compound having the formula (1):

• where I) only 1 R1, R2, R3, R4, R5 or R6 radical is an organic radical having:
• a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or
• a) at least two positively charged, preferably quaternary, nitrogen atoms not bonded directly to the isoalloxazine ring,
• and where each of the R1, R2, R3 and R4 radicals which is not an organic radical having a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or b) at least two positively charged, preferably quaternary, nitrogen atoms not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, and
• where each of the R5 and R6 radicals which is not an organic radical having a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or b) at least two positively charged, preferably quaternary, nitrogen atoms not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms,
• with the proviso that the R3 radical is not an aminomethyl radical, where the nitrogen atom may be unsubstituted or substituted, and
• excluding compounds in which the R1, R4 and R10 radicals are hydrogen, the R2 radical is hydrogen, alkyl having 1 to 8 carbon atoms or cycloalkyl having 3 to 7 carbon atoms, the R3 radical is hydrogen, halogen, alkyl having 1 to 8 carbon atoms, O-alkyl having 1 to 8 carbon atoms or a heterocyclic radical having 4 to 7 carbon atoms, and the R5 radical is an alkyl radical which has 1 to 8 carbon atoms and is substituted by at least by a radical of the formula —N(R35)(R36) or a radical of the formula —OR35, where the R35 radical is a radical of the formula —C1-8alkyl(amine)-OR37 or a 7,8-dimethylisoalloxazin-10-yl-C1-8alkyl radical and where the R36 radical is hydrogen or a radical of the formula —C1-8alkyl, which may be unsubstituted or substituted, and where the R37 radical is hydrogen, aryl having 6 to 7 carbon atoms or alkyl which may be unsubstituted or substituted and has 1 to 8 carbon atoms, and
• additionally excluding compounds in which the R1 and R4 radicals are hydrogen, the R10 radical is hydrogen or a radical having the general formula —C1-4alkyl-OC(O)CH3, the R2 radical is hydrogen or alkyl having 8 to 8 carbon atoms and the R5 radical is a radical having the general formula —C1-6alkyl-N(R31)—C0-3alkyl-(R32), where R31 is hydrogen or a radical having the formula —C1-4alkyl and where R32 is a radical having the formula —C1-4alkyl-N(R33)(R34), a radical having the formula —C0-4alkyl-aryl, a radical having the formula —C0-4alkylheterocycloalkyl or a radical having the formula —C0-4alkylheteroaryl, and where the R33 and R34 radicals are each independently hydrogen or —C1-4alkyl, and
• excluding 10-butyl-7,8-dimethyl-3-[2-oxo-2-(1,4,7,10-tetrazacyclododec-1-yl)ethyl]benzo[g]pteridine-2,4-dione and 10-[2-(2-methoxyethoxy)ethyl]-7,8-dimethyl-3-[2-oxo-2-(1,4,7,10-tetrazacyclododec-1-yl)ethyl]benzo[g]ptendine-2,4-dione, or
• where II) only 1 R1, R2, R3, R4, R5 or R6 radical is an organic radical having:
• a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and
• b) at least one positively charged, preferably quaternary, nitrogen atom not bonded directly to the isoalloxazine ring,
• and where each of the R1, R2, R3 and R4 radicals which is not an organic radical having a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, or b) at least one positively charged, preferably quaternary, nitrogen atom not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, or
• where each of the R5 and R6 radicals which is not an organic radical having a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, or b) at least one positively charged, preferably quaternary, nitrogen atom not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, or
• where III) at least 2 R1, R2, R3, R4, R5 or R6 radicals are an organic radical having:
• a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and/or
• b) at least one positively charged, preferably quaternary, nitrogen atom not bonded directly to the isoalloxazine ring, and
• where each of the R1, R2, R3 and R4 radicals which is not an organic radical having a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, or b) at least one positively charged, preferably quaternary, nitrogen atom not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, and
• where each of the R5 and R6 radicals which is not an organic radical having a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, or b) at least one positively charged, preferably quaternary, nitrogen atom not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms,
• and excluding the compound having the formula (20):