DE2624923A1 - Derivate des chinoxalin-1,4- dioxids - Google Patents
Derivate des chinoxalin-1,4- dioxidsInfo
- Publication number
- DE2624923A1 DE2624923A1 DE19762624923 DE2624923A DE2624923A1 DE 2624923 A1 DE2624923 A1 DE 2624923A1 DE 19762624923 DE19762624923 DE 19762624923 DE 2624923 A DE2624923 A DE 2624923A DE 2624923 A1 DE2624923 A1 DE 2624923A1
- Authority
- DE
- Germany
- Prior art keywords
- dioxide
- group
- benzoyl
- carbon atoms
- compounds
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 acetylthio group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- VCUDWVRYYZJTIU-UHFFFAOYSA-N [3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-phenylmethanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CO)=C1C(=O)C1=CC=CC=C1 VCUDWVRYYZJTIU-UHFFFAOYSA-N 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- REYBMQMZSZPBSW-UHFFFAOYSA-N [3-(bromomethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-phenylmethanone Chemical compound [O-][N+]=1C2=CC=CC=C2[N+]([O-])=C(CBr)C=1C(=O)C1=CC=CC=C1 REYBMQMZSZPBSW-UHFFFAOYSA-N 0.000 description 6
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical class CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VULNKVWEHILKIA-UHFFFAOYSA-N (3-benzoyl-1-oxido-4-oxoquinoxalin-4-ium-2-yl)methyl acetate Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(COC(=O)C)=C1C(=O)C1=CC=CC=C1 VULNKVWEHILKIA-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LTQXTLMHSFMWCX-UHFFFAOYSA-N [3-(methylsulfinylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-phenylmethanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CS(=O)C)=C1C(=O)C1=CC=CC=C1 LTQXTLMHSFMWCX-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
- XFBLYNKNXQDAOQ-UHFFFAOYSA-N (3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-phenylmethanone Chemical compound O=[N+]1C2=CC=CC=C2N([O-])C(C)=C1C(=O)C1=CC=CC=C1 XFBLYNKNXQDAOQ-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 241001138501 Salmonella enterica Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- MLCNGZJAUMBEAI-UHFFFAOYSA-N [3-(hydroxymethyl)-1,4-dioxidoquinoxaline-1,4-diium-2-yl]-(3-hydroxyphenyl)methanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CO)=C1C(=O)C1=CC=CC(O)=C1 MLCNGZJAUMBEAI-UHFFFAOYSA-N 0.000 description 2
- CFXBOXIKBQYSOU-UHFFFAOYSA-N [3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=C(CO)[N+]([O-])=C(C=CC=C2)C2=[N+]1[O-] CFXBOXIKBQYSOU-UHFFFAOYSA-N 0.000 description 2
- BFPQKZZDPNAHOK-UHFFFAOYSA-N [3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=C(CO)[N+]([O-])=C(C=CC=C2)C2=[N+]1[O-] BFPQKZZDPNAHOK-UHFFFAOYSA-N 0.000 description 2
- KCAVBRMRBXRHCQ-UHFFFAOYSA-N [3-(methylsulfanylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-phenylmethanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CSC)=C1C(=O)C1=CC=CC=C1 KCAVBRMRBXRHCQ-UHFFFAOYSA-N 0.000 description 2
- QFKLMEJZRNZBPH-UHFFFAOYSA-N [3-(methylsulfonylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-phenylmethanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CS(=O)(=O)C)=C1C(=O)C1=CC=CC=C1 QFKLMEJZRNZBPH-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- NYOWXLYJAOYBGF-UHFFFAOYSA-N (2-ethylphenyl)-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone Chemical compound CCC1=CC=CC=C1C(=O)C1=C(C)[N+]([O-])=C(C=CC=C2)C2=[N+]1[O-] NYOWXLYJAOYBGF-UHFFFAOYSA-N 0.000 description 1
- BITSNHXAYRRUCV-UHFFFAOYSA-N (2-fluorophenyl)-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(C)=C1C(=O)C1=CC=CC=C1F BITSNHXAYRRUCV-UHFFFAOYSA-N 0.000 description 1
- LLMJMHGTIVCWLQ-UHFFFAOYSA-N (2-fluorophenyl)-[3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]methanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CO)=C1C(=O)C1=CC=CC=C1F LLMJMHGTIVCWLQ-UHFFFAOYSA-N 0.000 description 1
- GGSCTEZPXZDERA-UHFFFAOYSA-N (2-methoxyphenyl)-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=C(C)[N+]([O-])=C(C=CC=C2)C2=[N+]1[O-] GGSCTEZPXZDERA-UHFFFAOYSA-N 0.000 description 1
- GKXYTPSWWKWOCQ-UHFFFAOYSA-N (3-chlorophenyl)-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(C)=C1C(=O)C1=CC=CC(Cl)=C1 GKXYTPSWWKWOCQ-UHFFFAOYSA-N 0.000 description 1
- UQONMYNEPBRUCO-UHFFFAOYSA-N (3-fluorophenyl)-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(C)=C1C(=O)C1=CC=CC(F)=C1 UQONMYNEPBRUCO-UHFFFAOYSA-N 0.000 description 1
- NXFOHYUZQVWLLW-UHFFFAOYSA-N (3-methoxyphenyl)-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone Chemical compound COC1=CC=CC(C(=O)C=2[N+](=C3C=CC=CC3=[N+]([O-])C=2C)[O-])=C1 NXFOHYUZQVWLLW-UHFFFAOYSA-N 0.000 description 1
- GSTVZNBFOFJSMZ-UHFFFAOYSA-N (3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=C(C)[N+]([O-])=C(C=CC=C2)C2=[N+]1[O-] GSTVZNBFOFJSMZ-UHFFFAOYSA-N 0.000 description 1
- XKAKTTUFWNIKDA-UHFFFAOYSA-N (3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-(3-nitrophenyl)methanone Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(C)=C1C(=O)C1=CC=CC([N+]([O-])=O)=C1 XKAKTTUFWNIKDA-UHFFFAOYSA-N 0.000 description 1
- KVZWLXDHMVQEKP-UHFFFAOYSA-N (3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-(3-propan-2-ylphenyl)methanone Chemical compound CC(C)C1=CC=CC(C(=O)C=2[N+](=C3C=CC=CC3=[N+]([O-])C=2C)[O-])=C1 KVZWLXDHMVQEKP-UHFFFAOYSA-N 0.000 description 1
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- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
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- NTYSMUARZGUVEM-UHFFFAOYSA-N [3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-(3-propan-2-ylphenyl)methanone Chemical compound CC(C)C1=CC=CC(C(=O)C=2[N+](=C3C=CC=CC3=[N+]([O-])C=2CO)[O-])=C1 NTYSMUARZGUVEM-UHFFFAOYSA-N 0.000 description 1
- RZMKBCRPHPNISV-UHFFFAOYSA-N [3-(hydroxymethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(CO)[N+]([O-])=C(C=CC=C2)C2=[N+]1[O-] RZMKBCRPHPNISV-UHFFFAOYSA-N 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
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- 239000002285 corn oil Substances 0.000 description 1
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- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
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- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
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- 239000003589 local anesthetic agent Substances 0.000 description 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- PPLIZCOMLGAUMU-UHFFFAOYSA-N s-[(3-benzoyl-1-oxido-4-oxoquinoxalin-4-ium-2-yl)methyl] ethanethioate Chemical compound [O-][N+]1=C2C=CC=CC2=[N+]([O-])C(CSC(=O)C)=C1C(=O)C1=CC=CC=C1 PPLIZCOMLGAUMU-UHFFFAOYSA-N 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- 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
-
- 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
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/602,480 US4012385A (en) | 1975-08-06 | 1975-08-06 | Antibacterial quinoxaline 1,4-dioxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2624923A1 true DE2624923A1 (de) | 1977-02-10 |
Family
ID=24411511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762624923 Ceased DE2624923A1 (de) | 1975-08-06 | 1976-06-03 | Derivate des chinoxalin-1,4- dioxids |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4012385A (enExample) |
| JP (2) | JPS5219687A (enExample) |
| BE (1) | BE843086A (enExample) |
| DE (1) | DE2624923A1 (enExample) |
| FR (2) | FR2361891A1 (enExample) |
| GB (2) | GB1515063A (enExample) |
| IT (1) | IT1068229B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0141354A3 (en) * | 1983-11-07 | 1986-02-19 | Daniele Gatti | Compounds useful for combatting swine dysentery and as growth promoting factors, method for the preparation thereof and compositions containing them |
| EP0192992A3 (en) * | 1985-03-01 | 1987-08-12 | Enrico Marotta | Quinoxaline derivatives useful for treatment and prophilaxis of swine dysentery and as animal growth promotants |
-
1975
- 1975-08-06 US US05/602,480 patent/US4012385A/en not_active Expired - Lifetime
-
1976
- 1976-06-03 DE DE19762624923 patent/DE2624923A1/de not_active Ceased
- 1976-06-15 JP JP51070323A patent/JPS5219687A/ja active Granted
- 1976-06-18 BE BE1007457A patent/BE843086A/xx unknown
- 1976-06-18 IT IT50002/76A patent/IT1068229B/it active
- 1976-06-21 FR FR7618834A patent/FR2361891A1/fr active Granted
- 1976-07-29 GB GB31748/76A patent/GB1515063A/en not_active Expired
- 1976-07-29 GB GB1504/78A patent/GB1515064A/en not_active Expired
-
1977
- 1977-01-06 FR FR7700242A patent/FR2359143A1/fr active Granted
-
1979
- 1979-09-28 JP JP54125211A patent/JPS5817759B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0141354A3 (en) * | 1983-11-07 | 1986-02-19 | Daniele Gatti | Compounds useful for combatting swine dysentery and as growth promoting factors, method for the preparation thereof and compositions containing them |
| EP0192992A3 (en) * | 1985-03-01 | 1987-08-12 | Enrico Marotta | Quinoxaline derivatives useful for treatment and prophilaxis of swine dysentery and as animal growth promotants |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2361891B1 (enExample) | 1980-12-05 |
| FR2359143A1 (fr) | 1978-02-17 |
| FR2359143B1 (enExample) | 1980-12-26 |
| GB1515063A (en) | 1978-06-21 |
| JPS5219687A (en) | 1977-02-15 |
| JPS5817759B2 (ja) | 1983-04-09 |
| IT1068229B (it) | 1985-03-21 |
| US4012385A (en) | 1977-03-15 |
| GB1515064A (en) | 1978-06-21 |
| JPS5555189A (en) | 1980-04-22 |
| FR2361891A1 (fr) | 1978-03-17 |
| BE843086A (fr) | 1976-12-20 |
| JPS562064B2 (enExample) | 1981-01-17 |
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| 8131 | Rejection |