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US 6,610,687 B1Granted
Benzofuranylsulfonates
AssigneeBayer Aktiengesellschaft
InventorsGabriele Bräunlich, Mazen Es-Sayed, Rüdiger Fischer, Burkhard Fugmann, Rolf Henning, Stephan Schneider, Michael Sperzel, Karl-Heinz Schlemmer, Graham Sturton, Mary F. Fitzgerald, Barbara Briggs, Arnel Concepcion, William Bullock
Life of this patent
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Abstract
The invention relates to benzofuranylsulfonates of the general formula (I), their preparation and their use for the treatment of inflammation.
Claims9
Benzofuranylsulfonates of the general formula (I)
- in which
- A represents hydrogen, straight-chain or branched acyl or alkoxycarbonyl, each having up to 6 carbon atoms, halogen, carboxyl, cyano, nitro, hydroxyl, trifuoromethyl or trifuoromethoxy, or straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by carboxyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, phenoxy or benzoyl,
- R1 represents hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms, an amino protecting group or a group of the formula —CO—R5
- in which
- R5 denotes straight chain or branched alkoxy having up to 4 carbon atoms,
- R2 and R3 are identical or different and represent hydrogen, cycloalkyl having up to 6 carbon atoms, straight chain or branched alkyl, alkoxycarbonyl or alkenyl each having up to 8 carbon atoms,
- or
- R2 and R3 together with the nitrogen atom form a 5- to 7-membered saturated heterocycle optionally having a further O atom,
- R4 represents aryl having 6 to 10 carbon atoms or represents a 5 to 7 membered, aromatic, saturated or unsaturated heterocycle, which can contain up to 3 heteroatoms selected from oxygen, sulphur and nitrogen atoms, or a residue of a formula —NR6,
- wherein
- R6 denotes hydrogen or straight-chain or branched alkyl or alkoxycarbonyl each having up to 6 carbon atoms,
- and to which further a benzene ring can be fused and wherein aryl and the heterocycle are optionally monosubstituted to trisubstituted by identical or different substituents from the series hydroxyl, halogen, nitro, 1H-tetrazolyl, pyridyl, trifluoromethyl, trifluromethoxy, difluoromethyl, difluoromethoxy, cyano, carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms or by straight-chain or branched alkyl having up to 5 carbon atoms, which is optionally substituted by carboxyl or straight-chain or branched alkoxycarbonyl having up to 4 carbon atoms or by a group of formula —NR7R8, —SR9, —(NH)a—SO2R10 or —O—SO2R11,
- in which
- R7 and R8 are identical or different and denote hydrogen or a straight-chain or branched alkyl having up to 4 carbon atoms,
- or
- R7 denotes hydrogen
- and
- R8 denotes straight-chain or branched acyl having up to 6 carbon atoms
- R9 denotes hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms,
- a denotes a number 0 or 1,
- R10 and R11 are identical or different and represent straight-chain or branched alkyl having up to 6 carbon atoms, benzyl or phenyl, which are optionally substituted by trifluoromethyl, halogen or straight-chain or branched alkyl having up to 4 carbon atoms,
- L represents an oxygen or sulfur atom,
- D represents a residue of a formula
- or aryl having 6 to 10 carbon atoms or a 5 to 7-membered aromatic, saturated or unsaturated heterocycle having up to 3 heteroatoms from the series N, S and O and to which a phenyl ring can be fused, wherein all abovementioned residues and ring systems are optionally monosubstituted to trisubstituted by at least one substituent selected from halogen, carboxyl, straight-chain or branched alkyl or alkoxycarbonyl each having up to 6 carbon atoms, pyridyl, and groups having the formulae —NR12—E—R13, —NR14—CO—NR15R16, —NR17—SO2—NR18R19, —SO2R20 and —(SO2)b—NR21R22,
- wherein
- b denotes a number 0 or 1,
- E denotes a residue of formula SO2 or CO,
- R12, R14, R15, R16, R17, R18, R19, R21 and R22 are identical or different and denote hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms,
- R13 denotes straight-chain or branched alkyl or alkoxy each having up to 6 carbon atoms,
- R20 denotes benzyl, phenyl, pyridyl or straight-chain or branched alkyl having up to 6 carbon atoms,
- or
- D represents straight-chain or branched alkyl or alkenyl having up to 8 carbon atoms, which are monosubstituted to trisubstituted by at least one substituent selected from halogen, aryl having 6 to 10 carbon atoms, a 5 to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the series N, S and O and to which a phenyl ring can be fused, a group of formula —NR23R24,
- and
- wherein
- R23 and R24 have the abovementioned meaning of R15 and R16 and are identical or different.
- wherein the abovementioned ring systems are optionally substituted by halogen,
- and in the case that
- R4 does not represent phenyl or substituted phenyl,
- D in addition can represent benzyl or straight-chain or branched alkyl having up to 5 carbon atoms,
- or
- D optionally represents a residue of a formula —NR25R26
- wherein
- R25 and R26 have the abovementioned meaning of R21 and R22 and are identical or different,
- and salts thereof.
41 more elements
Dependencies are inferred from the claim text.