NO832810L - 1,3-dioksolo(4,5-g)-kinoliner og fremgangsmaate for deres fremstilling. - Google Patents
1,3-dioksolo(4,5-g)-kinoliner og fremgangsmaate for deres fremstilling.Info
- Publication number
- NO832810L NO832810L NO832810A NO832810A NO832810L NO 832810 L NO832810 L NO 832810L NO 832810 A NO832810 A NO 832810A NO 832810 A NO832810 A NO 832810A NO 832810 L NO832810 L NO 832810L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- compound
- formula
- dioxolo
- quinoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- -1 alkali metal salt Chemical class 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- YLACRFYIUQZNIV-UHFFFAOYSA-N o-(2,4-dinitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 claims description 4
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims description 4
- 229910000288 alkali metal carbonate Chemical group 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
- ILLFAGPCJNJIBX-UHFFFAOYSA-N ethyl 5-[(2-methoxy-2-oxoethyl)amino]-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(NCC(=O)OC)C2=CC2=C1OCO2 ILLFAGPCJNJIBX-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- SNHCYVGJJIKKNG-UHFFFAOYSA-N 8-oxo-5h-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2C(=O)C(C(=O)O)=CNC2=CC2=C1OCO2 SNHCYVGJJIKKNG-UHFFFAOYSA-N 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- GYTQBNQDCNZROL-UHFFFAOYSA-N ethyl 5-amino-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(N)C2=CC2=C1OCO2 GYTQBNQDCNZROL-UHFFFAOYSA-N 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- NXDUKMHYOOHXFX-UHFFFAOYSA-N ethyl 5-formamido-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(NC=O)C2=CC2=C1OCO2 NXDUKMHYOOHXFX-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- DKSFTXNZKIEDGT-UHFFFAOYSA-N 5-(methylamino)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2N(NC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 DKSFTXNZKIEDGT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- JXONQEGGKAHGSV-UHFFFAOYSA-N ethyl 5-[formyl(propyl)amino]-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2N(N(C=O)CCC)C=C(C(=O)OCC)C(=O)C2=CC2=C1OCO2 JXONQEGGKAHGSV-UHFFFAOYSA-N 0.000 description 3
- QTWDVCKZNCYUIT-UHFFFAOYSA-N ethyl 8-oxo-5-(2-oxoethylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(NCC=O)C2=CC2=C1OCO2 QTWDVCKZNCYUIT-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OYXUZBBUESIKEU-UHFFFAOYSA-N 8-oxo-5-(propylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2N(NCCC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 OYXUZBBUESIKEU-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- CRYZNKNYUIRABD-UHFFFAOYSA-N 1-(dimethylamino)-2-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2N(N(C)C)C(C)=C(C(O)=O)C(=O)C2=C1 CRYZNKNYUIRABD-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- YCAZALSUJDPQPP-UHFFFAOYSA-N 4-oxo-3h-quinoline-3-carboxylic acid Chemical class C1=CC=C2C(=O)C(C(=O)O)C=NC2=C1 YCAZALSUJDPQPP-UHFFFAOYSA-N 0.000 description 1
- GKWWKUWIXFQKQM-UHFFFAOYSA-N 5-(ethylamino)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2N(NCC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 GKWWKUWIXFQKQM-UHFFFAOYSA-N 0.000 description 1
- KEHTUYYHWVNAIR-UHFFFAOYSA-N 5-formamido-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2C(=O)C(C(=O)O)=CN(NC=O)C2=CC2=C1OCO2 KEHTUYYHWVNAIR-UHFFFAOYSA-N 0.000 description 1
- JAUAXTCFILIAAR-UHFFFAOYSA-N 7-butylsulfanyl-1-(dimethylamino)-2-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound CN(C)N1C(C)=C(C(O)=O)C(=O)C2=C1C=C(SCCCC)C([N+]([O-])=O)=C2 JAUAXTCFILIAAR-UHFFFAOYSA-N 0.000 description 1
- NWYFRVIGBHZYGF-UHFFFAOYSA-N 7-chloro-1-(dimethylamino)-2-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound [O-][N+](=O)C1=C(Cl)C=C2N(N(C)C)C(C)=C(C(O)=O)C(=O)C2=C1 NWYFRVIGBHZYGF-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- DWAVARUDIVSTBG-UHFFFAOYSA-N [1,3]dioxolo[4,5-g]quinoline Chemical group C1=CN=C2C=C(OCO3)C3=CC2=C1 DWAVARUDIVSTBG-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- APGIBOKVFCQIBB-UHFFFAOYSA-N ethyl 5-(methylamino)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(NC)C2=CC2=C1OCO2 APGIBOKVFCQIBB-UHFFFAOYSA-N 0.000 description 1
- BXUVVONDQSTPLE-UHFFFAOYSA-N ethyl 5-[ethyl(formyl)amino]-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(N(CC)C=O)C2=CC2=C1OCO2 BXUVVONDQSTPLE-UHFFFAOYSA-N 0.000 description 1
- VZKWWMFVWHSLHK-UHFFFAOYSA-N ethyl 8-oxo-5h-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CNC2=CC2=C1OCO2 VZKWWMFVWHSLHK-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002569 water oil cream Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (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)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/405,263 US4439436A (en) | 1982-08-04 | 1982-08-04 | 1,3-Dioxolo(4,5-G)quinoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO832810L true NO832810L (no) | 1984-02-06 |
Family
ID=23602957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO832810A NO832810L (no) | 1982-08-04 | 1983-08-03 | 1,3-dioksolo(4,5-g)-kinoliner og fremgangsmaate for deres fremstilling. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4439436A (fr) |
| EP (1) | EP0101951A1 (fr) |
| JP (1) | JPS5946283A (fr) |
| KR (1) | KR840005813A (fr) |
| AU (1) | AU1689683A (fr) |
| CA (1) | CA1218659A (fr) |
| DK (1) | DK353983A (fr) |
| FI (1) | FI832780A (fr) |
| GR (1) | GR78962B (fr) |
| IL (1) | IL69267A0 (fr) |
| NO (1) | NO832810L (fr) |
| NZ (1) | NZ204900A (fr) |
| PH (1) | PH19689A (fr) |
| PT (1) | PT77133B (fr) |
| ZA (1) | ZA835239B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
| US4774246A (en) * | 1984-01-26 | 1988-09-27 | Abbott Laboratories | Quinoline antibacterial compounds |
| US4542133A (en) * | 1984-04-26 | 1985-09-17 | Abbott Laboratories | Methylenedioxy quino-benoxazine derivatives and antibacterial use |
| US4528285A (en) * | 1984-04-26 | 1985-07-09 | Abbott Laboratories | Methylenedioxy quino-benzothiazine derivatives |
| US4607032A (en) * | 1984-04-26 | 1986-08-19 | Abbott Laboratories | Quino-benoxazine antibacterial compounds |
| US4687770A (en) * | 1985-12-23 | 1987-08-18 | Abbott Laboratories | Isoxazolo-pyrido-benzoxazine and isothiazolo-pyrido-benzoxazine derivatives |
| US4689325A (en) * | 1985-12-23 | 1987-08-25 | Abbott Laboratories | Isoxazolo-pyrido-phenoxazine and isothiazolo-pyrido-phenoxazine derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1076828A (en) * | 1963-12-12 | 1967-07-26 | Warner Lambert Pharmaceutical | Methylenedioxy quinoline derivatives |
| CA947301A (en) * | 1970-01-28 | 1974-05-14 | Sumitomo Chemical Company | Process for the preparation of compound having antibacterial action |
| CA942311A (en) * | 1970-07-09 | 1974-02-19 | Sumitomo Chemical Company | 1,4-dihydro-1-substituted-4-oxo-3-quinoline-carboxylic acid derivative |
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
-
1982
- 1982-08-04 US US06/405,263 patent/US4439436A/en not_active Expired - Fee Related
-
1983
- 1983-07-14 NZ NZ204900A patent/NZ204900A/en unknown
- 1983-07-15 AU AU16896/83A patent/AU1689683A/en not_active Abandoned
- 1983-07-18 IL IL69267A patent/IL69267A0/xx unknown
- 1983-07-19 ZA ZA835239A patent/ZA835239B/xx unknown
- 1983-07-20 PH PH29257A patent/PH19689A/en unknown
- 1983-07-28 EP EP83107464A patent/EP0101951A1/fr not_active Withdrawn
- 1983-07-28 GR GR72072A patent/GR78962B/el unknown
- 1983-07-29 PT PT77133A patent/PT77133B/fr unknown
- 1983-08-02 FI FI832780A patent/FI832780A/fi not_active Application Discontinuation
- 1983-08-03 NO NO832810A patent/NO832810L/no unknown
- 1983-08-03 DK DK353983A patent/DK353983A/da not_active Application Discontinuation
- 1983-08-03 CA CA000433752A patent/CA1218659A/fr not_active Expired
- 1983-08-03 KR KR1019830003631A patent/KR840005813A/ko not_active Application Discontinuation
- 1983-08-04 JP JP58143086A patent/JPS5946283A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK353983D0 (da) | 1983-08-03 |
| JPS5946283A (ja) | 1984-03-15 |
| AU1689683A (en) | 1984-02-09 |
| PH19689A (en) | 1986-06-13 |
| GR78962B (fr) | 1984-10-02 |
| PT77133A (fr) | 1983-08-01 |
| US4439436A (en) | 1984-03-27 |
| DK353983A (da) | 1984-02-05 |
| PT77133B (fr) | 1986-01-24 |
| NZ204900A (en) | 1986-11-12 |
| FI832780A (fi) | 1984-02-05 |
| IL69267A0 (en) | 1983-11-30 |
| ZA835239B (en) | 1984-03-28 |
| CA1218659A (fr) | 1987-03-03 |
| EP0101951A1 (fr) | 1984-03-07 |
| FI832780A0 (fi) | 1983-08-02 |
| KR840005813A (ko) | 1984-11-19 |
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