6-membered nitrogen-containing heteroaryl-oxazolidinones

Heteroaryl-oxazolidinones of the general formula (I) ##STR193## in which R.sup.1 represents azido or hydroxyl, or represents 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 phenyl, which is optionally substituted by straight-chain or branched alkyl having up to 4 carbon atoms,
• R.sup.4 and R.sup.5 are identical or different and cycloalkyl having 3 to 6 carbon atoms, hydrogen, phenyl or straight-chain or branched alkyl having up to 8 carbon atoms or an amino-protective group, or
• R.sup.4 or 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,
• D represents a 6-membered aromatic heterocyclic radical which has at least one nitrogen atom and is bonded directly via a carbon atom, or represents a bi- or tricyclic aromatic radical which has at least one nitrogen-containing ring, is bonded directly via a carbon atom and is in each case 6-membered,
• or represents .beta.-carbolin-3-yl, or represents indolizinyl bonded directly via the 6-membered ring, wherein the cyclic radicals are optionally 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 alkoxy, alkoxycarbonyl, alkylthio or acyl having in each case up to 6 carbon atoms or by straight-chain or branched alkyl having up to 6 carbon atoms, which can in turn be substituted by hydroxyl, by straight-chain or branched alkoxy or acyl having up to 5 carbon atoms or 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 denote hydrogen, formyl, straight-chain or branched alkyl or acyl having in each case up to 4 carbon atoms, phenyl or cycloalkyl having 3 to 6 carbon atoms, or together with the nitrogen atom form a 5- to 6-membered saturated heterocylic radical which optionally has a further hetero atom from the series consisting of N, S and/or O and can in turn be optionally substituted, including on a further nitrogen atom, by phenyl, pyrimidyl or straight-chain or branched alkyl or acyl having in each case up to 3 carbon atoms,
• and/or
• the cyclic radicals are optionally 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 cyclic radicals are optionally substituted by (C.sub.2 -C.sub.8)-alkenylphenyl, phenyl or by a 5- or 6-membered saturated or unsaturated heterocylic radical having up to 3 hetero atoms from the series consisting of S, N and/or O, which are in turn optionally substituted by a group of the formula --CO--NR.sup.9 R.sup.10, --NR.sup.11 R.sup.12, --NR.sup.13 --SO.sub.2 --R.sup.14, R.sup.15 R.sup.16 N--SO.sub.2 --, R.sup.17 --S(O).sub.a --, R.sup.18 --N.dbd.CH-- or by the radical --CH(OH)--SO.sub.3 R.sup.20,
• 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, tolyl 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 to 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,
• R.sup.18 denotes hydroxyl, benzyloxy or a radical of the formula --NH--CO--NH.sub.2, ##STR194## wherein R.sup.21 and R.sup.22 are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, which can in turn be substituted by phenyl or pyridyl,
• R.sup.20 denotes hydrogen or a sodium ion,
• and/or in turn are optionally substituted up to twice in an identical or different manner by carboxyl, halogen, cyano, mercapto, formyl, trifluoromethyl, nitro, phenyl, straight-chain or branched alkoxy, alkoxycarbonyl, alkylthio or acyl having in each case up to 6 carbon atoms or by straight-chain or branched alkyl having up to 6 carbon atoms, which can in turn be substituted by hydroxyl, azido, by straight-chain or branched alkoxy or acyl having up to 5 carbon atoms or by a group of the formula --NR.sup.23 R.sup.24, R.sup.25 --S--, R.sup.26 --SO.sub.2 O-- or ##STR195## wherein R.sup.23 and R.sup.24 have the abovementioned meaning of R.sup.7 and R.sup.8 and are identical to or different from these, or denote a radical of the formula --P(O) (OR.sup.28) (OR.sup.29) or R.sup.30 --SO.sub.2 --
• wherein
• R.sup.28 and R.sup.29 are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms and
• R.sup.30 denotes methyl, phenyl or tolyl,
• R.sup.25 denotes a radical of the formula ##STR196## R.sup.26 denotes straight-chain or branched alkyl having up to 3 carbon atoms,
• R.sup.27 denotes straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms or carboxyl
• and/or
• the cyclic radicals are optionally substituted by a radical of the formula ##STR197## wherein n denotes a number 0, 1 or 2,
• and salts and N-oxides thereof.