CH509345A - Verfahren zur Herstellung von neuen Chinolinderivaten - Google Patents
Verfahren zur Herstellung von neuen ChinolinderivatenInfo
- Publication number
- CH509345A CH509345A CH312570A CH312570A CH509345A CH 509345 A CH509345 A CH 509345A CH 312570 A CH312570 A CH 312570A CH 312570 A CH312570 A CH 312570A CH 509345 A CH509345 A CH 509345A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- formula
- compounds
- salt
- quinoline
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 4
- 230000002192 coccidiostatic effect Effects 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- -1 trimethylenedioxy Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- MHIFATZXRQSTSN-UHFFFAOYSA-N 9-oxo-3,6-dihydro-2h-[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid Chemical compound O1CCOC2=C1C=C1NC=C(C(=O)O)C(=O)C1=C2 MHIFATZXRQSTSN-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000004659 sterilization and disinfection Methods 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 125000004997 halocarbonyl group Chemical group 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 5
- ROBKVGDBQLURAF-UHFFFAOYSA-N 1,4-dihydroquinoline Chemical compound C1=CC=C2CC=CNC2=C1 ROBKVGDBQLURAF-UHFFFAOYSA-N 0.000 claims 1
- QXXUKURODOUKTR-UHFFFAOYSA-N 6-ethyl-9-oxo-2,3-dihydro-[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid Chemical compound O1CCOC2=C1C=C1C(=O)C(C(O)=O)=CN(CC)C1=C2 QXXUKURODOUKTR-UHFFFAOYSA-N 0.000 claims 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 6
- 241000894006 Bacteria Species 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000645 desinfectant Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 244000144977 poultry Species 0.000 abstract description 3
- 208000003495 Coccidiosis Diseases 0.000 abstract description 2
- 206010023076 Isosporiasis Diseases 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000003674 animal food additive Substances 0.000 abstract description 2
- 239000003224 coccidiostatic agent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 244000045947 parasite Species 0.000 abstract description 2
- 239000003755 preservative agent Substances 0.000 abstract description 2
- 208000019206 urinary tract infection Diseases 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000004584 weight gain Effects 0.000 abstract 1
- 235000019786 weight gain Nutrition 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 239000000243 solution Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000013078 crystal Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- AXEDXMIMJGBMIP-UHFFFAOYSA-N ethyl 9-oxo-3,6-dihydro-2h-[1,4]dioxino[2,3-g]quinoline-8-carboxylate Chemical compound O1CCOC2=C1C=C1NC=C(C(=O)OCC)C(=O)C1=C2 AXEDXMIMJGBMIP-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000588767 Proteus vulgaris Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229940007042 proteus vulgaris Drugs 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- BTKVXNUPTFDVLG-UHFFFAOYSA-N 3,6-dihydro-2h-[1,4]dioxino[2,3-g]quinolin-9-one Chemical compound O1CCOC2=C1C=C1NC=CC(=O)C1=C2 BTKVXNUPTFDVLG-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 241000588770 Proteus mirabilis Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- 241000605059 Bacteroidetes Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XRCLOLVLEHDQCD-UHFFFAOYSA-N CN(C=C(C(O)=O)C(C1=C2)=O)C1=CC1=C2OCCO1 Chemical compound CN(C=C(C(O)=O)C(C1=C2)=O)C1=CC1=C2OCCO1 XRCLOLVLEHDQCD-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- 241000223924 Eimeria Species 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- GHMMSZWJXVTRRQ-UHFFFAOYSA-N ethyl 6-ethyl-9-oxo-2,3-dihydro-[1,4]dioxino[2,3-g]quinoline-8-carboxylate Chemical compound C(C)N1C=C(C(C2=CC3=C(C=C12)OCCO3)=O)C(=O)OCC GHMMSZWJXVTRRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electromechanical Clocks (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312570A CH509345A (de) | 1967-12-21 | 1967-12-21 | Verfahren zur Herstellung von neuen Chinolinderivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312570A CH509345A (de) | 1967-12-21 | 1967-12-21 | Verfahren zur Herstellung von neuen Chinolinderivaten |
| CH1797667A CH504461A (de) | 1967-12-21 | 1967-12-21 | Verfahren zur Herstellung von neuen Chinolinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH509345A true CH509345A (de) | 1971-06-30 |
Family
ID=4429491
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH312570A CH509345A (de) | 1967-12-21 | 1967-12-21 | Verfahren zur Herstellung von neuen Chinolinderivaten |
| CH1797667A CH504461A (de) | 1967-12-21 | 1967-12-21 | Verfahren zur Herstellung von neuen Chinolinderivaten |
| CH312670A CH512887A (de) | 1967-12-21 | 1967-12-21 | Neues Beifuttermittel |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1797667A CH504461A (de) | 1967-12-21 | 1967-12-21 | Verfahren zur Herstellung von neuen Chinolinderivaten |
| CH312670A CH512887A (de) | 1967-12-21 | 1967-12-21 | Neues Beifuttermittel |
Country Status (6)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1248260B (de) * | 1963-10-22 | 1967-08-24 | Baufa Werke G M B H | Heizkoerperkonsole |
| CH451450A (de) * | 1967-08-11 | 1968-05-15 | Runtal Holding Co Sa | Vorrichtung zur Befestigung von Flachheizkörpern an einer Wand |
| FR2054503A1 (en) * | 1969-07-18 | 1971-04-23 | Bellon Labor Sa Roger | 1, 4-dihydro-4-oxo quinolyl-3-carboxylic aci |
| FR2101004B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-08-05 | 1974-02-01 | Bellon Labor Sa Roger | |
| FR2100883A1 (en) * | 1971-07-09 | 1972-03-24 | Sumitomo Chemical Co | 1,4-Dihydro-1-substd-4-oxo-3-quinoline carboxylic acids and esters - having antibacterial activity |
| US3725413A (en) * | 1972-01-17 | 1973-04-03 | Warner Lambert Co | Process for the production of ethyl 8-hydroxy-1,3-dioxolo{8 4,5g{9 -quinoline-7-carboxylate |
| US3959473A (en) * | 1972-02-09 | 1976-05-25 | U.S. Philips Corporation | Quinoline derivatives having pharmacological effects |
| US4216324A (en) * | 1978-12-26 | 1980-08-05 | E. I. Du Pont De Nemours And Company | 1-Difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid |
| US4284777A (en) * | 1978-12-26 | 1981-08-18 | E. I. Du Pont De Nemours And Company | Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters |
-
1967
- 1967-12-21 CH CH312570A patent/CH509345A/de not_active IP Right Cessation
- 1967-12-21 CH CH1797667A patent/CH504461A/fr not_active IP Right Cessation
- 1967-12-21 CH CH312670A patent/CH512887A/de not_active IP Right Cessation
-
1968
- 1968-11-25 GB GB55744/68A patent/GB1240316A/en not_active Expired
- 1968-12-12 DE DE19681814187 patent/DE1814187A1/de active Pending
- 1968-12-17 FR FR1598479D patent/FR1598479A/fr not_active Expired
- 1968-12-20 BE BE725787D patent/BE725787A/xx unknown
- 1968-12-20 BR BR205056/68A patent/BR6805056D0/pt unknown
-
1969
- 1969-03-06 FR FR183272A patent/FR8404M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1598479A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-07-06 |
| CH512887A (de) | 1971-09-30 |
| DE1814187A1 (de) | 1969-07-24 |
| GB1240316A (en) | 1971-07-21 |
| BE725787A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-06-20 |
| CH504461A (de) | 1971-03-15 |
| FR8404M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-31 |
| BR6805056D0 (pt) | 1973-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |