NO750196L - - Google Patents
Info
- Publication number
- NO750196L NO750196L NO750196A NO750196A NO750196L NO 750196 L NO750196 L NO 750196L NO 750196 A NO750196 A NO 750196A NO 750196 A NO750196 A NO 750196A NO 750196 L NO750196 L NO 750196L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- compounds
- compound
- dioxide
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 22
- -1 sulfinylmethyl Chemical group 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000006114 decarboxylation reaction Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000003866 tertiary ammonium salts Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000012141 concentrate Substances 0.000 description 15
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000012054 meals Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000013589 supplement Substances 0.000 description 6
- 235000013343 vitamin Nutrition 0.000 description 6
- 239000011782 vitamin Substances 0.000 description 6
- 229930003231 vitamin Natural products 0.000 description 6
- 229940088594 vitamin Drugs 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- 241000282849 Ruminantia Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QWBDXWHVPNEJRT-UHFFFAOYSA-N 3-(methylsulfanylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical class C1=CC=CC2=[N+]([O-])C(CSC)=C[N+]([O-])=C21 QWBDXWHVPNEJRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000019738 Limestone Nutrition 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
- 238000007792 addition Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007952 growth promoter Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000006028 limestone Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 125000000475 sulfinyl group Chemical class [*:2]S([*:1])=O 0.000 description 3
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- SRDQSYZOPRMHHM-UHFFFAOYSA-N 2,3-dimethyl-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=C2N([O-])C(C)=C(C)[N+](=O)C2=C1 SRDQSYZOPRMHHM-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
- OKZFOCTVBXTQLM-UHFFFAOYSA-N 3-methyl-2-(methylsulfanylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CSC)=C(C)[N+]([O-])=C21 OKZFOCTVBXTQLM-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000021120 animal protein Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- NOGOPLHDYPCGCZ-UHFFFAOYSA-N methyl 3-(methylsulfanylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(C(=O)OC)=C(CSC)[N+]([O-])=C21 NOGOPLHDYPCGCZ-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- RPWAGPHVYIUHNM-UHFFFAOYSA-N 3-(ethylsulfanylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CSCC)=C[N+]([O-])=C21 RPWAGPHVYIUHNM-UHFFFAOYSA-N 0.000 description 1
- QPESHPDYMKAGOZ-UHFFFAOYSA-N 3-(ethylsulfinylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CS(=O)CC)=C[N+]([O-])=C21 QPESHPDYMKAGOZ-UHFFFAOYSA-N 0.000 description 1
- VWMHOYDAMGHJNP-UHFFFAOYSA-N 3-(ethylsulfonylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CS(=O)(=O)CC)=C[N+]([O-])=C21 VWMHOYDAMGHJNP-UHFFFAOYSA-N 0.000 description 1
- ZTYLCTYYGVSOGH-UHFFFAOYSA-N 3-(methylsulfinylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CS(=O)C)=C[N+]([O-])=C21 ZTYLCTYYGVSOGH-UHFFFAOYSA-N 0.000 description 1
- DLFALBRFNNCFAW-UHFFFAOYSA-N 3-methyl-2-(methylsulfinylmethyl)-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(C)=C(CS(C)=O)[N+]([O-])=C21 DLFALBRFNNCFAW-UHFFFAOYSA-N 0.000 description 1
- PZUHHXFIMAEXGO-UHFFFAOYSA-N 3-methyl-4-oxidoquinoxalin-1-ium 1-oxide Chemical compound C1=CC=C2N([O-])C(C)=C[N+](=O)C2=C1 PZUHHXFIMAEXGO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KOZNYRFGBSQKMW-UHFFFAOYSA-N 4-oxido-3-(propylsulfinylmethyl)quinoxalin-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CS(=O)CCC)=C[N+]([O-])=C21 KOZNYRFGBSQKMW-UHFFFAOYSA-N 0.000 description 1
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
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- 241000283707 Capra Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
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- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- RPBRHCAAJOPFEC-UHFFFAOYSA-N methyl 3-(bromomethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(C(=O)OC)=C(CBr)[N+]([O-])=C21 RPBRHCAAJOPFEC-UHFFFAOYSA-N 0.000 description 1
- FMNNTLNCACHITB-UHFFFAOYSA-N methyl 3-(ethylsulfanylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(CSCC)=C(C(=O)OC)[N+]([O-])=C21 FMNNTLNCACHITB-UHFFFAOYSA-N 0.000 description 1
- OVOBHWOOPREFSN-UHFFFAOYSA-N methyl 3-(ethylsulfonylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(CS(=O)(=O)CC)=C(C(=O)OC)[N+]([O-])=C21 OVOBHWOOPREFSN-UHFFFAOYSA-N 0.000 description 1
- QIFUWTDWJDNGLK-UHFFFAOYSA-N methyl 3-(methylsulfinylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(C(=O)OC)=C(CS(C)=O)[N+]([O-])=C21 QIFUWTDWJDNGLK-UHFFFAOYSA-N 0.000 description 1
- RMVIJFANAGITNY-UHFFFAOYSA-N methyl 3-(methylsulfonylmethyl)-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(C(=O)OC)=C(CS(C)(=O)=O)[N+]([O-])=C21 RMVIJFANAGITNY-UHFFFAOYSA-N 0.000 description 1
- SSXXUNNLZOOPGP-UHFFFAOYSA-N methyl 3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=C2[N+](=O)C(C(=O)OC)=C(C)N([O-])C2=C1 SSXXUNNLZOOPGP-UHFFFAOYSA-N 0.000 description 1
- DCNKQUMCYHRLSO-UHFFFAOYSA-N methyl 4-oxido-1-oxo-3-(propylsulfanylmethyl)quinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(CSCCC)=C(C(=O)OC)[N+]([O-])=C21 DCNKQUMCYHRLSO-UHFFFAOYSA-N 0.000 description 1
- DBBNIZQCPBNOSM-UHFFFAOYSA-N methyl 4-oxido-1-oxo-3-(propylsulfonylmethyl)quinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=CC2=[N+]([O-])C(CS(=O)(=O)CCC)=C(C(=O)OC)[N+]([O-])=C21 DBBNIZQCPBNOSM-UHFFFAOYSA-N 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DGJWOGSPXZKBSO-UHFFFAOYSA-M trimethyl-[(3-methylquinoxalin-2-yl)methyl]azanium;bromide Chemical compound [Br-].C1=CC=C2N=C(C[N+](C)(C)C)C(C)=NC2=C1 DGJWOGSPXZKBSO-UHFFFAOYSA-M 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/435,874 US3931174A (en) | 1974-01-23 | 1974-01-23 | Alkylmercaptomethylquinoxaline-1,4-dioxides and oxidized derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO750196L true NO750196L (nl) | 1975-07-24 |
Family
ID=23730175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO750196A NO750196L (nl) | 1974-01-23 | 1975-01-22 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3931174A (nl) |
| JP (1) | JPS50101371A (nl) |
| AU (1) | AU7708675A (nl) |
| BE (1) | BE824583A (nl) |
| DD (1) | DD116233A5 (nl) |
| DE (1) | DE2501875A1 (nl) |
| DK (1) | DK19375A (nl) |
| ES (1) | ES434045A1 (nl) |
| FI (1) | FI750144A (nl) |
| FR (1) | FR2311546A1 (nl) |
| GB (1) | GB1462496A (nl) |
| IE (1) | IE40561B1 (nl) |
| IL (1) | IL46385A0 (nl) |
| IT (1) | IT1056097B (nl) |
| LU (1) | LU71696A1 (nl) |
| NL (1) | NL7500627A (nl) |
| NO (1) | NO750196L (nl) |
| RO (1) | RO72516A (nl) |
| SE (1) | SE7416332L (nl) |
| ZA (1) | ZA7599B (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4039540A (en) * | 1974-05-07 | 1977-08-02 | Pfizer Inc. | 3-Substituted quinoxaline-2-carboxamide-1,4-dioxides |
| US4038392A (en) * | 1975-10-14 | 1977-07-26 | Pfizer Inc. | 3-(heterocyclicthiomethyl) quinoxaline-1,4-dioxides |
| US4100284A (en) * | 1977-01-18 | 1978-07-11 | Pfizer Inc. | 1,4-Dioxo- and 4-oxoquinoxaline-2-carboxaldehyde sulfonylhydrazones and certain derivatives thereof |
| GB1604738A (en) | 1977-07-28 | 1981-12-16 | Yamanouchi Pharma Co Ltd | 1,3-dithietane-2-carboxylic acid derivatives and the preparation thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752812A (en) * | 1970-02-05 | 1973-08-14 | Pfizer | 2-trifluoromethylquinoxalinedi n oxides |
| US3803145A (en) * | 1970-02-05 | 1974-04-09 | Pfizer | Quinoxaline-di-n-oxides |
-
1974
- 1974-01-23 US US05/435,874 patent/US3931174A/en not_active Expired - Lifetime
- 1974-09-27 GB GB4219574A patent/GB1462496A/en not_active Expired
- 1974-12-27 SE SE7416332A patent/SE7416332L/xx unknown
-
1975
- 1975-01-02 IE IE4/75A patent/IE40561B1/xx unknown
- 1975-01-02 IL IL46385A patent/IL46385A0/xx unknown
- 1975-01-03 AU AU77086/75A patent/AU7708675A/en not_active Expired
- 1975-01-06 ZA ZA00750099A patent/ZA7599B/xx unknown
- 1975-01-14 RO RO7581106A patent/RO72516A/ro unknown
- 1975-01-16 DE DE19752501875 patent/DE2501875A1/de not_active Withdrawn
- 1975-01-20 NL NL7500627A patent/NL7500627A/nl not_active Application Discontinuation
- 1975-01-21 FR FR7501774A patent/FR2311546A1/fr active Granted
- 1975-01-21 FI FI750144A patent/FI750144A/fi not_active Application Discontinuation
- 1975-01-21 BE BE1006413A patent/BE824583A/xx unknown
- 1975-01-21 LU LU71696*A patent/LU71696A1/xx unknown
- 1975-01-22 DK DK19375*BA patent/DK19375A/da unknown
- 1975-01-22 ES ES434045A patent/ES434045A1/es not_active Expired
- 1975-01-22 DD DD183750A patent/DD116233A5/xx unknown
- 1975-01-22 IT IT47791/75A patent/IT1056097B/it active
- 1975-01-22 NO NO750196A patent/NO750196L/no unknown
- 1975-01-23 JP JP50010108A patent/JPS50101371A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50101371A (nl) | 1975-08-11 |
| IT1056097B (it) | 1982-01-30 |
| GB1462496A (en) | 1977-01-26 |
| BE824583A (fr) | 1975-07-22 |
| DK19375A (nl) | 1975-09-15 |
| AU7708675A (en) | 1976-07-08 |
| DE2501875A1 (de) | 1975-07-24 |
| NL7500627A (nl) | 1975-07-25 |
| FI750144A (nl) | 1975-07-24 |
| FR2311546A1 (fr) | 1976-12-17 |
| FR2311546B1 (nl) | 1979-02-23 |
| ZA7599B (en) | 1976-01-28 |
| IL46385A0 (en) | 1975-04-25 |
| ES434045A1 (es) | 1976-12-01 |
| US3931174A (en) | 1976-01-06 |
| IE40561L (en) | 1975-07-23 |
| DD116233A5 (nl) | 1975-11-12 |
| SE7416332L (nl) | 1975-07-24 |
| IE40561B1 (en) | 1979-07-04 |
| RO72516A (ro) | 1982-02-26 |
| LU71696A1 (nl) | 1975-12-09 |
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