SK5897A3 - 2-oxo and 2-thio-1,2-dihydroquinolinyl-oxazolidinones, method for producing them, their use and pharmaceutical composition containing same - Google Patents
2-oxo and 2-thio-1,2-dihydroquinolinyl-oxazolidinones, method for producing them, their use and pharmaceutical composition containing same Download PDFInfo
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- SK5897A3 SK5897A3 SK58-97A SK5897A SK5897A3 SK 5897 A3 SK5897 A3 SK 5897A3 SK 5897 A SK5897 A SK 5897A SK 5897 A3 SK5897 A3 SK 5897A3
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- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 67
- 125000002252 acyl group Chemical group 0.000 claims abstract description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 26
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 5
- 125000005936 piperidyl group Chemical group 0.000 claims abstract description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000006239 protecting group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
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- 238000000034 method Methods 0.000 claims description 18
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004434 sulfur atom Chemical group 0.000 claims description 12
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- 239000001257 hydrogen Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
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- 239000003814 drug Substances 0.000 claims description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005518 carboxamido group Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001408 amides Chemical group 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 125000005505 thiomorpholino group Chemical group 0.000 abstract 1
- 125000005425 toluyl group Chemical group 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical group Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 64
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
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- 239000000203 mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
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- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 229940052303 ethers for general anesthesia Drugs 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
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- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- PZUKTUYUULTSSW-UHFFFAOYSA-N benzyl n-quinolin-6-ylcarbamate Chemical compound C=1C=C2N=CC=CC2=CC=1NC(=O)OCC1=CC=CC=C1 PZUKTUYUULTSSW-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
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- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- YWOCJYAVEPBMRN-UHFFFAOYSA-N lithium silylazanide Chemical class [Li+].[SiH3][NH-] YWOCJYAVEPBMRN-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- NIPCCROWCMMUHV-ZDUSSCGKSA-N n-[[(5s)-2-oxo-3-quinolin-6-yl-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N=CC=C2)C2=C1 NIPCCROWCMMUHV-ZDUSSCGKSA-N 0.000 description 1
- AOMVSJSYSMQUOP-ZDUSSCGKSA-N n-[[(5s)-3-(1-methyl-2-oxoquinolin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C1=CC=C(N(C)C(=O)C=C2)C2=C1 AOMVSJSYSMQUOP-ZDUSSCGKSA-N 0.000 description 1
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- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19601265A DE19601265A1 (de) | 1996-01-16 | 1996-01-16 | 2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK5897A3 true SK5897A3 (en) | 1997-09-10 |
Family
ID=7782816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK58-97A SK5897A3 (en) | 1996-01-16 | 1997-01-15 | 2-oxo and 2-thio-1,2-dihydroquinolinyl-oxazolidinones, method for producing them, their use and pharmaceutical composition containing same |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5861413A (cs) |
| EP (1) | EP0785197A3 (cs) |
| JP (1) | JPH09194478A (cs) |
| KR (1) | KR970059174A (cs) |
| AR (1) | AR005458A1 (cs) |
| AU (1) | AU711924B2 (cs) |
| BG (1) | BG62257B1 (cs) |
| BR (1) | BR9700688A (cs) |
| CA (1) | CA2194945A1 (cs) |
| CO (1) | CO4520188A1 (cs) |
| CZ (1) | CZ12897A3 (cs) |
| DE (1) | DE19601265A1 (cs) |
| EE (1) | EE9700019A (cs) |
| HN (1) | HN1996000124A (cs) |
| HR (1) | HRP960614A2 (cs) |
| HU (1) | HUP9700126A3 (cs) |
| IL (1) | IL119994A0 (cs) |
| NO (1) | NO970174L (cs) |
| NZ (1) | NZ314057A (cs) |
| PE (1) | PE35398A1 (cs) |
| PL (1) | PL317930A1 (cs) |
| SG (1) | SG46764A1 (cs) |
| SK (1) | SK5897A3 (cs) |
| SV (1) | SV1997000002A (cs) |
| TN (1) | TNSN97009A1 (cs) |
| TR (1) | TR199601002A1 (cs) |
| YU (1) | YU1097A (cs) |
| ZA (1) | ZA97302B (cs) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| DE19802239A1 (de) * | 1998-01-22 | 1999-07-29 | Bayer Ag | Neue mit Bicyclen substituierte Oxazolidinone |
| WO1999037630A1 (en) | 1998-01-23 | 1999-07-29 | Versicor, Inc. | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| WO1999064417A2 (en) * | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| US6514529B2 (en) | 2000-03-22 | 2003-02-04 | Pharmacia & Upjohn Company | Oxazolidinone tablet formulation |
| MY127336A (en) * | 2000-03-22 | 2006-11-30 | Upjohn Co | Container for linezolid iv solution |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| DE60112581T2 (de) | 2000-06-30 | 2006-06-01 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Zusammensetzungen zur Behandlung bakterieller Infektionen, welche ein Oxazolidinonderivat, Sulbactam und Ampicillin enthalten |
| CA2424402A1 (en) * | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| WO2003031441A1 (en) * | 2001-10-04 | 2003-04-17 | Morphochen Aktiengesellschaft Für Kombinatorische Chemie | Multiple action compounds |
| WO2003031443A1 (en) | 2001-10-04 | 2003-04-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Dual actions antibiotics comprising a oxazoldinone and a quinolone or naphthyridinone moiety |
| AR038536A1 (es) * | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7141588B2 (en) * | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| ES2258234T3 (es) * | 2002-08-12 | 2006-08-16 | PHARMACIA & UPJOHN COMPANY LLC | N-aril-2-oxazolidinonas y sus derivados. |
| AU2002339721A1 (en) * | 2002-09-20 | 2004-04-08 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
| US7141570B2 (en) * | 2002-11-21 | 2006-11-28 | Pharmacia & Upjohn Company | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| US7491714B2 (en) | 2002-12-04 | 2009-02-17 | Glaxo Group Limited | Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents |
| CA2515311A1 (en) * | 2003-02-07 | 2004-08-19 | Warner-Lambert Company Llc | Antibacterial agents |
| JP2006516989A (ja) * | 2003-02-07 | 2006-07-13 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 抗菌剤として使用するための二環式環によりｎ−置換されたオキサゾリジノン誘導体 |
| US20040204463A1 (en) * | 2003-04-01 | 2004-10-14 | Harris Christina Renee | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| EP1620098B1 (en) | 2003-04-30 | 2008-06-11 | Morphochem Aktiengesellschaft Für Kombinatorische Chemie | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| DE10340485B4 (de) | 2003-09-03 | 2015-05-13 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Verfahren zur Herstellung von Oxazolidinon-Chinolon Hybriden |
| US7304050B2 (en) * | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| NZ547382A (en) | 2003-12-18 | 2009-11-27 | Morphochem Ag Komb Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| US8158797B2 (en) | 2003-12-18 | 2012-04-17 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| US7494578B2 (en) * | 2004-03-01 | 2009-02-24 | Atotech Deutschland Gmbh | Iron-phosphorus electroplating bath and method |
| MX2007001568A (es) * | 2004-08-06 | 2007-04-16 | Pharmacia & Upjohn Co Llc | Oxindol oxazolidinonas como agentes antibacterianos. |
| MY150958A (en) | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
| TW200831517A (en) * | 2006-12-15 | 2008-08-01 | Astrazeneca Ab | Chemical compounds |
| US20100144717A1 (en) * | 2006-12-15 | 2010-06-10 | Janelle Comita-Prevoir | 2-quinolinone and 2-quinoxalinone-derivatives and their use as antibacterial agents |
| CA2713187C (en) * | 2008-02-22 | 2016-06-07 | Actelion Pharmaceuticals Ltd | Oxazolidinone derivatives |
| JP2017523213A (ja) * | 2014-08-06 | 2017-08-17 | ノバルティス アーゲー | 抗菌薬としてのキノロン誘導体 |
| CN116419922B (zh) * | 2020-10-26 | 2025-05-02 | 艾维斯生物株式会社 | 一种从泊马度胺选择性合成3,6′-二硫代泊马度胺的方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705799A (en) * | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| US4801600A (en) * | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4965268A (en) * | 1987-10-09 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| CA1320730C (en) * | 1987-10-16 | 1993-07-27 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US4942183A (en) * | 1987-10-16 | 1990-07-17 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US5254577A (en) * | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| US5164510A (en) * | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| DE68918792T2 (de) | 1988-09-15 | 1995-03-30 | Upjohn Co | 5-Indolinyl-5-beta-amidomethyloxazolidin-2-one, 3-(substituierte kondensierte)phenyl-5-beta amidomethyloxazolidin-2-one und 3-(Nitrogen-substituierte)phenyl-5-beta-amidomethyloxazolidin-2-one. |
| JP2669579B2 (ja) | 1991-10-23 | 1997-10-29 | エーザイ株式会社 | オキサゾリドン誘導体 |
| DE4332384A1 (de) * | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
| TW286317B (cs) * | 1993-12-13 | 1996-09-21 | Hoffmann La Roche | |
| DE4425612A1 (de) * | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
-
1996
- 1996-01-16 DE DE19601265A patent/DE19601265A1/de not_active Withdrawn
- 1996-12-12 TR TR96/01002A patent/TR199601002A1/xx unknown
- 1996-12-23 HR HR19601265.1A patent/HRP960614A2/hr not_active Application Discontinuation
- 1996-12-27 HN HN1996000124A patent/HN1996000124A/es unknown
-
1997
- 1997-01-03 EP EP97100026A patent/EP0785197A3/de not_active Withdrawn
- 1997-01-09 US US08/781,002 patent/US5861413A/en not_active Expired - Fee Related
- 1997-01-09 AU AU10097/97A patent/AU711924B2/en not_active Ceased
- 1997-01-13 CA CA002194945A patent/CA2194945A1/en not_active Abandoned
- 1997-01-13 JP JP9015889A patent/JPH09194478A/ja active Pending
- 1997-01-13 NZ NZ314057A patent/NZ314057A/en unknown
- 1997-01-13 IL IL11999497A patent/IL119994A0/xx unknown
- 1997-01-14 AR ARP970100134A patent/AR005458A1/es unknown
- 1997-01-14 PE PE1997000019A patent/PE35398A1/es not_active Application Discontinuation
- 1997-01-14 YU YU1097A patent/YU1097A/sh unknown
- 1997-01-14 BG BG101131A patent/BG62257B1/bg unknown
- 1997-01-14 PL PL97317930A patent/PL317930A1/xx unknown
- 1997-01-15 SG SG1997000088A patent/SG46764A1/en unknown
- 1997-01-15 ZA ZA97302A patent/ZA97302B/xx unknown
- 1997-01-15 HU HU9700126A patent/HUP9700126A3/hu unknown
- 1997-01-15 CZ CZ97128A patent/CZ12897A3/cs unknown
- 1997-01-15 SK SK58-97A patent/SK5897A3/sk unknown
- 1997-01-15 KR KR1019970001029A patent/KR970059174A/ko not_active Withdrawn
- 1997-01-15 NO NO970174A patent/NO970174L/no unknown
- 1997-01-15 CO CO97001471A patent/CO4520188A1/es unknown
- 1997-01-15 BR BR9700688A patent/BR9700688A/pt not_active Application Discontinuation
- 1997-01-15 EE EE9700019A patent/EE9700019A/xx unknown
- 1997-01-15 TN TNTNSN97009A patent/TNSN97009A1/fr unknown
- 1997-01-16 SV SV1997000002A patent/SV1997000002A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR970059174A (ko) | 1997-08-12 |
| EE9700019A (et) | 1997-08-15 |
| HUP9700126A2 (hu) | 1998-12-28 |
| EP0785197A3 (de) | 1999-02-10 |
| TR199601002A1 (tr) | 1997-08-21 |
| SG46764A1 (en) | 1998-02-20 |
| CO4520188A1 (es) | 1997-10-15 |
| AU1009797A (en) | 1997-07-24 |
| MX9700419A (es) | 1997-07-31 |
| HU9700126D0 (en) | 1997-02-28 |
| JPH09194478A (ja) | 1997-07-29 |
| HRP960614A2 (en) | 1998-02-28 |
| BR9700688A (pt) | 1998-09-01 |
| TNSN97009A1 (fr) | 2005-03-15 |
| HN1996000124A (es) | 1997-06-18 |
| BG62257B1 (bg) | 1999-06-30 |
| NO970174D0 (no) | 1997-01-15 |
| YU1097A (sh) | 1999-12-27 |
| IL119994A0 (en) | 1997-04-15 |
| AR005458A1 (es) | 1999-06-23 |
| NZ314057A (en) | 1998-11-25 |
| DE19601265A1 (de) | 1997-07-17 |
| PL317930A1 (en) | 1997-07-21 |
| NO970174L (no) | 1997-07-17 |
| AU711924B2 (en) | 1999-10-21 |
| HUP9700126A3 (en) | 1999-05-28 |
| ZA97302B (en) | 1997-07-17 |
| BG101131A (en) | 1998-04-30 |
| CZ12897A3 (en) | 1997-08-13 |
| SV1997000002A (es) | 1997-08-29 |
| US5861413A (en) | 1999-01-19 |
| CA2194945A1 (en) | 1997-07-17 |
| PE35398A1 (es) | 1998-08-29 |
| EP0785197A2 (de) | 1997-07-23 |
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