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US 5,698,574 AGranted
5-membered heteroaryl-oxazolidinones
AssigneeBayer Aktiengesellschaft
InventorsBernd Riedl, Dieter Habich, Andreas Stolle, Hanno Wild, Rainer Endermann, Klaus Dieter Bremm, Hein-Peter Kroll, Harald Labischinski, Klaus Schaller, Hans-Otto Werling
Life of this patent
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Abstract
The present invention relates to 5-membered heteroaryl-oxazolidinones, to processes for their preparation and to their use as medicaments, in particular as antibacterial medicaments.
Claims6
A heteroaryl-oxazolidinone of the formula ##STR157## in which R.sup.1 represents azido;
- hydroxy;
- or a group of the formula --OR.sup.2, --O--SO.sub.2 --R.sup.3 or --NR.sup.4 R.sup.5,
- wherein
- R.sup.2 denotes straight-chain or branched acyl having up to 8 carbon atoms or a hydroxyl-protective group,
- R.sup.3 denotes straight-chain or branched alkyl having up to 4 carbon atoms or optionally substituted wherein the substituent is a straight-chain or branched alkyl having up to 4 carbon atoms,
- R.sup.4 and R.sup.5 are identical or different and denote hydrogen, or an amino-protective group,
- or
- R.sup.4 and R.sup.5 denotes a group of the formula --CO--R.sup.6,
- wherein
- R.sup.6 denotes cycloalkyl having 3 to 6 carbon atoms, straight-chain or branched alkyl having up to 8 carbon atoms, phenyl or hydrogen,
- A represents a 5-membered aromatic heterocyclic radical, which has up to 3-heteroatoms selected from the group consisting of S, N or O, is directly bonded by a carbon atom and can additionally have a fused-on benzene or naphthyl ring, wherein the heterocyclic cyclic radicals are substituted in each case up to 3 times in an identical or different manner by carboxyl;
- halogen;
- cyano;
- mercapto;
- formyl;
- trifluoromethyl;
- nitro;
- straight-chain or branched C.sub.1 -C.sub.6 -alkoxy, straight-chain or branched C.sub.1 -C.sub.6 -alkoxycarbonyl;
- straight-chain or branched C.sub.1 -C.sub.6 -alkylthio;
- straight-chain or branched C.sub.1 -C.sub.6 -acyl;
- or optionally substituted straight-chain or branched alkyl having up to 6 carbon atoms, wherein the substituents are hydroxyl, straight-chain or branched C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -acyl, or a group of the formula --NR.sup.7 R.sup.8,
- wherein
- R.sup.7 and R.sup.8 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms or phenyl,
- or R.sup.7 and R.sup.8 together with the nitrogen atom form an optionally substituted 5- to 6-membered saturated heterocyclic radical which optionally has a further hetero atom selected from the group consisting of N, S or O wherein the substituents are straight-chain or branched C.sub.1 -C.sub.2 -alkyl or straight-chain or branched C.sub.1 -C.sub.3 -acyl,
- and/or
- the heterocyclic radicals as defined in A are substituted by a group of the formula --NR.sup.7' R.sup.8',
- wherein
- R.sup.7' and R.sup.8' are identical or different and have the abovementioned meaning of R.sup.7 and R.sup.8 and are identical to or different from these,
- and/or
- the heterocyclic cyclic radicals as defined in A are substituted by optionally mono or disubstituted (C.sub.2 -C.sub.8)-alkenylphenyl, optionally mono or disubstituted phenyl or by a 5- or 6-membered saturated or unsaturated mono or disubstituted heterocyclic radical having up to 3 hetero atoms selected from the group consisting of S, N or O, wherein the optional substituents are carboxyl;
- halogen;
- cyano;
- mercapto;
- formyl;
- trifluoromethyl;
- nitro;
- phenyl;
- straight-chain or branched C.sub.1 -C.sub.6 -alkoxy;
- straight-chain or branched C.sub.1 -C.sub.6 -alkoxycarbonyl;
- straight-chain or branched C.sub.1 -C.sub.6 -alkylthio, straight-chain or branched C.sub.1 -C.sub.6 -acyl;
- straight-chain or branched C.sub.1 -C.sub.6 -alkyl wherein said alkyl is optionally substituted by hydroxyl, straight-chain or branched C.sub.1 -C.sub.5 -alkoxy, straight-chain or branched C.sub.1 -C.sub.5 -acyl or a group of the formula --NR.sup.18 R.sup.19,
- R.sup.18 and R.sup.19 have the abovementioned meaning of R.sup.7 and R.sup.8 and are identical to or different from these;
- or substituted once by a group of the formula --CO--NR.sup.9 R.sup.10, --NR.sup.11 R.sup.12, --NR.sup.13 --S(O).sub.2 --R.sup.14, R.sup.15 R.sup.16 N--SO.sub.2 -- or R.sup.17 --S(O).sub.a --
- wherein
- a denotes a number 0, 1 or 2,
- R.sup.9, R.sup.10, R.sup.13, R.sup.15 and R.sup.16 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl,
- R.sup.11 and R.sup.12 are identical or different and have the abovementioned meaning of R.sup.7 and R.sup.8 and are identical or different from these,
- R.sup.14 and R.sup.17 are identical or different and have the abovementioned meaning of R.sup.3 and are identical to or different from this,
- and/or
- the heterocyclic cyclic radicals are substituted by a radical of the formula ##STR158## wherein n denotes the number 0, 1 or 2,
- or a salt or S-oxide thereof.
48 more elements
Dependencies are inferred from the claim text.