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US 6,069,160 AGranted
Heteroatom-containing benzocyclopentane-oxazolidinones
AssigneeBayer Aktiengesellschaft
InventorsAndreas Stolle, Dieter Habich, Stephan Bartel, Bernd Riedl, Martin Ruppelt, Hanno Wild, Rainer Endermann, Klaus-Dieter Bremm, Hein-Peter Kroll, Harald Labischinski, Klaus Schaller, Hans-Otto Werling
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Abstract
The invention relates to heteroatom-containing benzocyclopentaneoxazolidinones, to processes for their preparation and their use as medicaments, especially as antibacterial medicaments.
Claims8
Compounds of the formula (I):
- ##STR372## in which R.sup.1 represents azido, 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, in which
- R.sup.2 denotes straight-chain or branched acyl having up to 8 carbon atoms, or a hydroxy-protecting group,
- R.sup.3 denotes straight-chain or branched alkyl having up to 4 carbon atoms or phenyl or tolyl,
- R.sup.4 and R.sup.5 are identical or different and denote cycloalkyl having 3 to 6 carbon atoms, hydrogen, phenyl or straight-chain or branched alkyl or alkoxy having in each case up to 8 carbon atoms, or an amino-protecting group, or
- R.sup.4 and R.sup.5 denotes a group of the formula --CO--R.sup.6, P(O)(OR.sup.7)(OR.sup.8) or --SO.sub.2 --R.sup.9, in which
- R.sup.6 denotes cycloalkyl or halogen substituted cycloalkyl each having 3 to 6 carbon atoms, straight-chain or branched alkoxy having up to 8 carbon atoms, phenyl, benzyloxy or hydrogen, or
- R.sup.6 denotes straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms which are optionally substituted by cyano or halogen, or
- R.sup.6 denotes straight-chain or branched thioalkyl or acyl having in each case up to 6 carbon atoms, or
- R.sup.6 denotes a group of the formula --NR.sup.10 R.sup.11, in which
- R.sup.10 and R.sup.11 are identical or different and denote hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms, or
- R.sup.6 denotes isoxazolyl, furyl, thienyl, pyrroyl, oxazolyl or imidazolyl, each of which is optionally substituted by straight-chain or branched alkyl having up to 3 carbon atoms,
- R.sup.7 and R.sup.8 are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms,
- R.sup.9 denotes straight-chain or branched alkyl having up to 4 carbon atoms, or phenyl,
- A represents a radical of the formula:
- ##STR373## in which G, L and M are identical or different and represent hydrogen, carboxyl, fluorine, chlorine, cyano, formyl, trifluromethyl, straight-chain or branched alkyl having up to 3 carbon atoms, or a group of the formula --CO--NR.sup.17 R.sup.18, in which
- R.sup.17 and R.sup.18 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms, or phenyl,
- R.sup.12 denotes cycloalkylcarbonyl or cycloalkyl having in each case 3 to 6 carbon atoms, or denotes straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms, or denotes straight-chain or branched alkyl or alkenyl having in each case up to 10 carbon atoms, which are optionally substituted by cyano, azido, halogen, hydroxyl, carboxyl, straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms, benzloxycarbonyl, aryl having 6 to 10 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or by a group of the formula --(CO).sub.c --NR.sup.19 R.sup.20, --N(R.sup.21)--SO.sub.2 --R.sup.22, R.sup.23 R.sup.24 --N--SO.sub.2 --, R.sup.25 --S(O).sub.d -- or ##STR374## in which c is a number 0 or 1,
- R.sup.19, R.sup.20 and R.sup.21 have the meaning given above of R.sup.17 and R.sup.18 and are identical to or different from it, or together with the nitrogen atom form a 5-membered saturated heterocycle having optionally a further heteroatom selected from the group consisting of N, S or O, which can in turn optionally be substituted, even on a further nitrogen atom, by straight-chain or branched alkyl or acyl having up to 3 carbon atoms,
- R.sup.23 and R.sup.24 have the meaning given above of R.sup.17 and R.sup.18 and are identical to or different from it,
- d denotes a number 0, 1 or 2,
- R.sup.22 and R.sup.25 are identical or different and denote straight-chain or branched alkyl having up to 4 carbon atoms, benzyl, phenyl or tolyl, or
- R.sup.12 denotes a residue of a formula:
- ##STR375## R.sup.12 denotes a group of the formula --COCCl.sub.3 or straight-chain or branched acyl having up to 6 carbon atoms which is optionally substituted by trifluoromethyl, trichloromethyl or by a group of the formula --OR.sup.26, in which
- R.sup.26 denotes hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by aryl having up to 10 carbon atoms,
- R.sup.12 denotes a group of the formula --(CO).sub.e --NR.sup.27 R.sup.28, --NR.sup.29 --SO.sub.2 R.sup.30, R.sup.31 R.sup.32 --N--SO.sub.2 -- or R.sup.33 --S(O).sub.f, in which
- e has the meaning given above of c and is identical to or different from it,
- R.sup.27 and R.sup.28 and R.sup.29 each have the meaning given above of R.sup.19, R.sup.20 and R.sup.21 and are identical to or different from it,
- R.sup.31 and R.sup.32 have the meaning given above of R.sup.17 and R.sup.18 and are identical to or different from it,
- f has the meaning given above of d and is identical to or different from it,
- R.sup.30 and R.sup.33 have the meanings in each case given above of R.sup.22 and R.sup.25 and are identical to or different from these,
- D denotes a sulphur atom or an oxygen atom,
- E denotes an oxygen or sulphur atom,
- and the tautomeric forms, isomers and salts thereof.
30 more elements
Dependencies are inferred from the claim text.