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 PDF

Info

Publication number: SK5897A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; straight; different; formula
Prior art date: 1996-01-16

Application number

SK58-97A

Other languages

English (en)

Slovak (sk)

Inventor

Dieter Habich

Andreas Stolle

Bernd Riedl

Martin Ruppelt

Stephan Bartel

Walter Guarnieri

Rainer Endermann

Hein-Peter Kroll

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-01-16

Filing date

1997-01-15

Publication date

1997-09-10

1997-01-15 Application filed by Bayer Ag filed Critical Bayer Ag

1997-09-10 Publication of SK5897A3 publication Critical patent/SK5897A3/sk

Links

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
125000004001 thioalkyl group Chemical group 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
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
-1 azido, hydroxyl Chemical group 0.000 claims description 22
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238000000034 method Methods 0.000 claims description 18
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238000006243 chemical reaction Methods 0.000 claims description 16
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 12
125000004434 sulfur atom Chemical group 0.000 claims description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 11
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
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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
150000001412 amines Chemical class 0.000 claims description 7
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
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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
150000001204 N-oxides Chemical class 0.000 claims description 4
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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
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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
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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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239000012074 organic phase Substances 0.000 description 6
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
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000008272 agar Substances 0.000 description 3
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
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
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
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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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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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YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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
238000002512 chemotherapy Methods 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
239000012043 crude product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
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UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
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239000006260 foam Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
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150000002576 ketones Chemical class 0.000 description 1
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
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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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XZDUFMCXMOWCOV-AWEZNQCLSA-N n-acetyl-n-[[(5s)-2-oxo-3-(2-oxo-1h-quinolin-6-yl)-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CN(C(=O)C)C(C)=O)CN1C1=CC=C(NC(=O)C=C2)C2=C1 XZDUFMCXMOWCOV-AWEZNQCLSA-N 0.000 description 1
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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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK58-97A 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 SK5897A3 (en)

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 (fr)
EP (1)	EP0785197A3 (fr)
JP (1)	JPH09194478A (fr)
KR (1)	KR970059174A (fr)
AR (1)	AR005458A1 (fr)
AU (1)	AU711924B2 (fr)
BG (1)	BG62257B1 (fr)
BR (1)	BR9700688A (fr)
CA (1)	CA2194945A1 (fr)
CO (1)	CO4520188A1 (fr)
CZ (1)	CZ12897A3 (fr)
DE (1)	DE19601265A1 (fr)
EE (1)	EE9700019A (fr)
HN (1)	HN1996000124A (fr)
HR (1)	HRP960614A2 (fr)
HU (1)	HUP9700126A3 (fr)
IL (1)	IL119994A0 (fr)
NO (1)	NO970174L (fr)
NZ (1)	NZ314057A (fr)
PE (1)	PE35398A1 (fr)
PL (1)	PL317930A1 (fr)
SG (1)	SG46764A1 (fr)
SK (1)	SK5897A3 (fr)
SV (1)	SV1997000002A (fr)
TN (1)	TNSN97009A1 (fr)
TR (1)	TR199601002A1 (fr)
YU (1)	YU1097A (fr)
ZA (1)	ZA97302B (fr)

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BRPI0407252A (pt) *	2003-02-07	2006-01-31	Warner Lambert Co	Agentes antibacterianos.
CA2515269A1 (fr) *	2003-02-07	2004-08-19	Warner-Lambert Company Llc	Derives d'oxazolidinone n-substitues par un noyau bicyclique, utilises comme agents antibacteriens
US20040204463A1 (en) *	2003-04-01	2004-10-14	Harris Christina Renee	N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
JP4805139B2 (ja)	2003-04-30	2011-11-02	モルホケムアクツィエンゲゼルシャフトフューアコンビナートリッシュヒェミー	炭疽および他の感染を治療するためのオキサゾリジノン‐キノリンハイブリッド抗生物質の使用
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
US8158797B2 (en)	2003-12-18	2012-04-17	Morphochem Aktiengesellschaft Fur Kombinatorische Chemie	Oxazolidinone-quinolone hybrid antibiotics
BRPI0417193B8 (pt)	2003-12-18	2021-05-25	Morphochem Ag Fuer Komb Chemie	antibióticos híbridos de oxazolidinona-quinolona, seus sais monossódicos, dissódicos ou trissódicos e seus pró-fármacos, composições farmacêuticas, e seu uso
US7494578B2 (en) *	2004-03-01	2009-02-24	Atotech Deutschland Gmbh	Iron-phosphorus electroplating bath and method
EP1781642A1 (fr) *	2004-08-06	2007-05-09	Pharmacia & Upjohn Company LLC	Oxazolidinones contenant des oxindoles en tant qu'agents antibacteriens
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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/fr not_active Withdrawn
- 1997-01-09 AU AU10097/97A patent/AU711924B2/en not_active Ceased
- 1997-01-09 US US08/781,002 patent/US5861413A/en not_active Expired - Fee Related
- 1997-01-13 CA CA002194945A patent/CA2194945A1/fr not_active Abandoned
- 1997-01-13 NZ NZ314057A patent/NZ314057A/en unknown
- 1997-01-13 IL IL11999497A patent/IL119994A0/xx unknown
- 1997-01-13 JP JP9015889A patent/JPH09194478A/ja active Pending
- 1997-01-14 PE PE1997000019A patent/PE35398A1/es not_active Application Discontinuation
- 1997-01-14 YU YU1097A patent/YU1097A/sh unknown
- 1997-01-14 AR ARP970100134A patent/AR005458A1/es unknown
- 1997-01-14 BG BG101131A patent/BG62257B1/bg unknown
- 1997-01-14 PL PL97317930A patent/PL317930A1/xx 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 CO CO97001471A patent/CO4520188A1/es unknown
- 1997-01-15 ZA ZA97302A patent/ZA97302B/xx unknown
- 1997-01-15 CZ CZ97128A patent/CZ12897A3/cs unknown
- 1997-01-15 KR KR1019970001029A patent/KR970059174A/ko not_active Withdrawn
- 1997-01-15 NO NO970174A patent/NO970174L/no unknown
- 1997-01-15 HU HU9700126A patent/HUP9700126A3/hu unknown
- 1997-01-15 SK SK58-97A patent/SK5897A3/sk unknown
- 1997-01-15 SG SG1997000088A patent/SG46764A1/en 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
AU1009797A (en)	1997-07-24
NO970174D0 (no)	1997-01-15
MX9700419A (es)	1997-07-31
HRP960614A2 (en)	1998-02-28
BR9700688A (pt)	1998-09-01
IL119994A0 (en)	1997-04-15
HN1996000124A (es)	1997-06-18
CA2194945A1 (fr)	1997-07-17
YU1097A (sh)	1999-12-27
BG62257B1 (bg)	1999-06-30
TNSN97009A1 (fr)	2005-03-15
PL317930A1 (en)	1997-07-21
HU9700126D0 (en)	1997-02-28
SG46764A1 (en)	1998-02-20
AU711924B2 (en)	1999-10-21
TR199601002A1 (tr)	1997-08-21
EP0785197A2 (fr)	1997-07-23
CZ12897A3 (en)	1997-08-13
JPH09194478A (ja)	1997-07-29
HUP9700126A3 (en)	1999-05-28
NZ314057A (en)	1998-11-25
KR970059174A (ko)	1997-08-12
AR005458A1 (es)	1999-06-23
BG101131A (en)	1998-04-30
EE9700019A (et)	1997-08-15
HUP9700126A2 (hu)	1998-12-28
CO4520188A1 (es)	1997-10-15
NO970174L (no)	1997-07-17
SV1997000002A (es)	1997-08-29
DE19601265A1 (de)	1997-07-17
EP0785197A3 (fr)	1999-02-10
US5861413A (en)	1999-01-19
PE35398A1 (es)	1998-08-29
ZA97302B (en)	1997-07-17

Publication	Publication Date	Title
SK5897A3 (en)	1997-09-10	2-oxo and 2-thio-1,2-dihydroquinolinyl-oxazolidinones, method for producing them, their use and pharmaceutical composition containing same
CZ15897A3 (en)	1997-08-13	Hetero atom containing cyclopentanepyridyl-oxazolidinones, process of their preparation, their use and pharmaceutical composition containing thereof
EP0789025B1 (fr)	2001-04-04	Oxazolidinones substituées et leur utilisation comme médicaments antibactériens
CZ187295A3 (en)	1996-02-14	Six-membered nitrogen-containing heteroaryl-oxazolidinones, their use and medicaments in which said compounds are comprised
US5827857A (en)	1998-10-27	Pyrido-fused thienyl- and furanyl-oxazolidinones
MXPA97000886A (en)	1998-04-01	New oxazolidinones sustitui
JPH101480A (ja)	1998-01-06	新規なヘテロアリール−オキサゾリジノン類
CZ187395A3 (en)	1996-02-14	Five-membered heteroaryl-oxazolidinones, their use and medicaments in which said compounds are comprised
CZ114296A3 (en)	1997-07-16	Hetero atom containing benzocyclopentanoxazolidinones, process of their preparation, their use and pharmaceutical composition containing thereof
BG99833A (bg)	1996-02-28	Бензоксазолилови и бензотиазолилови оксазолидинони,метод за тяхното получаване и приложението им като лекарствени средства
MXPA97000885A (es)	1998-04-01	Nuevas heteroariloxazolidinonas
JPH0841057A (ja)	1996-02-13	ベンゾフラニル−およびベンゾチエニルオキサゾリジノン類
DE19649095A1 (de)	1997-08-07	Neue Heteroaryl-Oxazolidinone
MXPA97000419A (en)	1997-12-01	2-oxo and -tio-1, 2-dihydroquinolinyl-oxazolidine
MXPA97000388A (en)	1997-12-01	Ciclopentanopiridil-oxazolidinones that containheteroate