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US 2006/0179585 A1Published application
Sulfonamide derviatives of polycyclic dyes used for analytical applications
AssigneeATTO-TEC GmbH
InventorsAlexander Zilles, Jutta Arden-Jacob, Karl-Heinz Drexhage, Norbert Kemnitzer, Monika Hamers-Schneider
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Abstract
The invention concerns the production of quinoline compounds containing sulfonic acid groups, the said quinoline compounds and their conversion into dyes containing sulfonic acid groups. The dyes according to the invention are used especially to label analytes, for example to label biomolecules.
Claims29
A process for the production of dihydroquinoline compounds of the general formula Ia or of tetrahydroquinoline compounds of the general formula Ib
- in which R1 denotes hydrogen or a hydrocarbon group with 1-20 C atoms where the hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents,
- R2, R3, R4, R5, R6, R7 and R8 on each occurrence and independently of one another denote hydrogen, halogen, a hydroxy, amino, sulfo, carboxy or aldehyde group or a hydrocarbon group with 1-20 C atoms where the hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents, or the residues R1 and R8 together form a ring system and
- X denotes OH, halogen, —O—R9, —S—R10 or —NR11R12 where R9, R10, R11 and R12 independently of one another denote hydrogen or a C1 to C20 hydrocarbon residue which can optionally contain one or more heteroatoms or/and one or more substituents, wherein
- the corresponding compounds I′a
- are sulfonated to form Ia (X=OH) and optionally converted by hydrogenation into Ib (X=OH).
2 more elements
A dihydroquinoline compound of the general formula Ia or a tetrahydroquinoline compound of the general formula Ib
- in which R1 denotes hydrogen or a hydrocarbon group with 1-20 C atoms where the hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents,
- R2, R3, R4, R5, R6, R7 and R8 on each occurrence and independently of one another denote hydrogen, halogen, a hydroxy, amino, sulfo, carboxy or aldehyde group or a hydrocarbon group with 1-20 C atoms where the hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents, or the residues R1 and R8 together form a ring system and
- X denotes OH, halogen, —O—R9, —S—R10 or —NR11R12 where R9, R10, R11 and R12 each independently of one another denote hydrogen or a C1 to C20 hydrocarbon residue which can optionally contain one or more heteroatoms or/and one or more substituents, in particular —SO3H, —PO3H2 and —COOH.
A process for the production of polycyclic dyes, wherein
- compounds which have a dihydroquinoline end group with a 4-methyl group are sulfonated and optionally hydrogenated to form a tetrahydroquinoline with the proviso that the polycyclic dye is not a compound of formula III in which Y=O and X=OH or of formula IV in which X=OH.
A polycyclic dye of the general formulae II to VII
- in which
- R′ denotes hydrogen or a hydrocarbon group with 1-20 C atoms where the hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents,
- R on each occurrence and independently of one another denotes hydrogen, halogen, a hydroxy, amino, sulfo, carboxy or aldehyde group or a hydrocarbon group with 1-20 C atoms where the hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents, or the residues R′ and R together form a ring system which can contain one or more multiple bonds,
- R13 on each occurrence and independently of one another denotes hydrogen or a hydrocarbon group with 1-20 C atoms where the
- hydrocarbon group can optionally contain one or more heteroatoms or/and one or more substituents, where R13 in particular represents hydrogen, aryl, carboxyphenyl, alkyl, perfluoroalkyl, cycloalkyl, pyridyl or carboxypyridyl, X denotes OH, halogen, —O—R9, —S—R10 or —NR11R12 where R9, R10, R11 and R12 each independently of one another denote hydrogen or a C1 to C20 hydrocarbon residue which can optionally contain one or more heteroatoms or one or more substituents, and
- Y in formula III denotes O, S or Se and Y in formula VI denotes O, S or C(R)2,
- with the proviso that the dye is not a compound of the general formula III in which Y=O and X=OH or of the general formula IV in which X=OH.
4 more elements
Dependencies are inferred from the claim text.