NO750196L - - Google Patents

Info

Publication number: NO750196L
Authority: NO; Norway
Prior art keywords: methyl; compounds; compound; dioxide; formula
Prior art date: 1974-01-23

Application number

NO750196A

Other languages

English (en)

Norwegian (no)

Inventor

J W Mcfarland

Original Assignee

Pfizer

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

1974-01-23

Filing date

1975-01-22

Publication date

1975-07-24

1975-01-22 Application filed by Pfizer filed Critical Pfizer

1975-07-24 Publication of NO750196L publication Critical patent/NO750196L/no

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
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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
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125000001309 chloro group Chemical group Cl* 0.000 description 4
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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
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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
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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
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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
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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)
Fodder In General (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NO750196A 1974-01-23 1975-01-22 NO750196L (fr)

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 (fr)	1975-07-24

Family

ID=23730175

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO750196A NO750196L (fr)	1974-01-23	1975-01-22

Country Status (20)

Country	Link
US (1)	US3931174A (fr)
JP (1)	JPS50101371A (fr)
AU (1)	AU7708675A (fr)
BE (1)	BE824583A (fr)
DD (1)	DD116233A5 (fr)
DE (1)	DE2501875A1 (fr)
DK (1)	DK19375A (fr)
ES (1)	ES434045A1 (fr)
FI (1)	FI750144A7 (fr)
FR (1)	FR2311546A1 (fr)
GB (1)	GB1462496A (fr)
IE (1)	IE40561B1 (fr)
IL (1)	IL46385A0 (fr)
IT (1)	IT1056097B (fr)
LU (1)	LU71696A1 (fr)
NL (1)	NL7500627A (fr)
NO (1)	NO750196L (fr)
RO (1)	RO72516A (fr)
SE (1)	SE7416332L (fr)
ZA (1)	ZA7599B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3803145A (en) *	1970-02-05	1974-04-09	Pfizer	Quinoxaline-di-n-oxides
US3752812A (en) *	1970-02-05	1973-08-14	Pfizer	2-trifluoromethylquinoxalinedi 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 IL IL46385A patent/IL46385A0/xx unknown
- 1975-01-02 IE IE4/75A patent/IE40561B1/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/fr unknown
- 1975-01-16 DE DE19752501875 patent/DE2501875A1/de not_active Withdrawn
- 1975-01-20 NL NL7500627A patent/NL7500627A/xx not_active Application Discontinuation
- 1975-01-21 FI FI750144A patent/FI750144A7/fi not_active Application Discontinuation
- 1975-01-21 LU LU71696*A patent/LU71696A1/xx unknown
- 1975-01-21 FR FR7501774A patent/FR2311546A1/fr active Granted
- 1975-01-21 BE BE1006413A patent/BE824583A/fr unknown
- 1975-01-22 IT IT47791/75A patent/IT1056097B/it active
- 1975-01-22 NO NO750196A patent/NO750196L/no unknown
- 1975-01-22 DD DD183750A patent/DD116233A5/xx unknown
- 1975-01-22 DK DK19375*BA patent/DK19375A/da unknown
- 1975-01-22 ES ES434045A patent/ES434045A1/es not_active Expired
- 1975-01-23 JP JP50010108A patent/JPS50101371A/ja active Pending

Also Published As

Publication number	Publication date
JPS50101371A (fr)	1975-08-11
NL7500627A (nl)	1975-07-25
SE7416332L (fr)	1975-07-24
FI750144A7 (fr)	1975-07-24
GB1462496A (en)	1977-01-26
IE40561L (en)	1975-07-23
BE824583A (fr)	1975-07-22
LU71696A1 (fr)	1975-12-09
DK19375A (fr)	1975-09-15
FR2311546A1 (fr)	1976-12-17
DE2501875A1 (de)	1975-07-24
US3931174A (en)	1976-01-06
RO72516A (fr)	1982-02-26
FR2311546B1 (fr)	1979-02-23
DD116233A5 (fr)	1975-11-12
IE40561B1 (en)	1979-07-04
IT1056097B (it)	1982-01-30
ES434045A1 (es)	1976-12-01
IL46385A0 (en)	1975-04-25
ZA7599B (en)	1976-01-28
AU7708675A (en)	1976-07-08

Publication	Publication Date	Title
JPS62263155A (ja)	1987-11-16	動物の生産促進用ヘテロアリ−ルエチルアミンの使用、ヘテロアリ−ルエチルアミンおよびその製造方法
WO1999054301A1 (fr)	1999-10-28	Acide alcane-2-oxo-[2-(indol-3-yl)-ethyl]amides substitues
US4373101A (en)	1983-02-08	Quinoxaline-2-yl ethenyl ketones
NO750196L (fr)	1975-07-24
HU202841B (en)	1991-04-29	Process for producing compositions for enhancing productivity of animals containing pyridyl-ethanol-amine as active component and process for producing the active components
EP0209025B1 (fr)	1988-09-28	Aryléthanolhydroxylamines, procédé pour leur préparation et leur utilisation pour améliorer la productivité
CS9589A2 (en)	1991-08-13	Agent for animals' yield increase and method of active substances production
US4100284A (en)	1978-07-11	1,4-Dioxo- and 4-oxoquinoxaline-2-carboxaldehyde sulfonylhydrazones and certain derivatives thereof
JPS63295536A (ja)	1988-12-01	新規なアミノフエニルエチルアミン誘導体類、それらの製造方法および生産量増進剤としてのそれらの使用
US3728345A (en)	1973-04-17	Preparation of quinoxaline-2-carboxamide derivatives
US4039540A (en)	1977-08-02	3-Substituted quinoxaline-2-carboxamide-1,4-dioxides
EP0093949B1 (fr)	1986-03-12	Azacycloheptan-2-ones sulfinyliques et sulfonyliques, procédé pour leur préparation et leur application comme suppléments pour la pâture
US3644360A (en)	1972-02-22	3-substituted methylquinoxaline-2-carboxamide-1 4-dioxides
CA1049518A (fr)	1979-02-27	Oxydes d'imino-3 benzotriazine-1,2,4
US4154835A (en)	1979-05-15	Anthelmintic imidazo [1,2-a] pyridines
JPH01313463A (ja)	1989-12-18	４‐ブロム‐６‐クロル‐５‐アミノ‐２‐ピリジル‐エタノールアミン類、その製造法及びその使用
EP0012725B1 (fr)	1984-02-29	Dérivés de Di-N-oxydes de quinoxaline, procédé pour leur préparation, compositions les contenant et leur application
US2945062A (en)	1960-07-12	N-lower-alkyl-n-nitroso-3, 5-dinitro-o-toluamides
EP0207358A2 (fr)	1987-01-07	Agent de croissance
JPS6377851A (ja)	1988-04-08	アリールエタノールアミン、それらの製造方法、及び成長を促進するためのそれらの使用
EP0456067A1 (fr)	1991-11-13	Quinoxalines 2,3-disubstituées comme stimulateurs de croissance animale
EP0018837A1 (fr)	1980-11-12	Imidazo (1,2-a) pyridines substituées en position 3, leur préparation, compositions les contenant et leur application comme anthelmintiques
GB2080306A (en)	1982-02-03	Pyridszino[4,5-b]quinoxaline- 5,10-dioxide Derivatives, a Process for Preparing Same and Compositions Containing Same
DE2243015A1 (de)	1973-03-08	4-nitro-5-cyanimidazole und verfahren zur herstellung derselben
JPS597158A (ja)	1984-01-14	シスタミン誘導体