CS200218B2 - Method of producing 1,4-dioxides of quinoxalinecarbazates - Google Patents
Method of producing 1,4-dioxides of quinoxalinecarbazates Download PDFInfo
- Publication number
- CS200218B2 CS200218B2 CS773581A CS358177A CS200218B2 CS 200218 B2 CS200218 B2 CS 200218B2 CS 773581 A CS773581 A CS 773581A CS 358177 A CS358177 A CS 358177A CS 200218 B2 CS200218 B2 CS 200218B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- equivalents
- compounds
- quinoxaline
- dioxides
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012442 inert solvent Substances 0.000 claims abstract description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BORHLJZAFILINM-UHFFFAOYSA-N C(NN)(=O)O.N1=CC=NC2=CC=CC=C12 Chemical class C(NN)(=O)O.N1=CC=NC2=CC=CC=C12 BORHLJZAFILINM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- -1 sulphonyl halide Chemical class 0.000 abstract description 5
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract description 4
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract description 2
- 150000002429 hydrazines Chemical class 0.000 abstract description 2
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 125000005997 bromomethyl group Chemical group 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000606860 Pasteurella Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DBRMJCLTIHPLCZ-UHFFFAOYSA-N 2-(bromomethyl)quinoxaline Chemical class C1=CC=CC2=NC(CBr)=CN=C21 DBRMJCLTIHPLCZ-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- ALHUXMDEZNLFTA-UHFFFAOYSA-N 2-methylquinoxaline Chemical class C1=CC=CC2=NC(C)=CN=C21 ALHUXMDEZNLFTA-UHFFFAOYSA-N 0.000 description 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 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 1
- 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 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000392514 Salmonella enterica subsp. enterica serovar Dublin Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000194048 Streptococcus equi Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 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
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BBNBSVPCCCCNDP-UHFFFAOYSA-N methyl n-(methanesulfonamido)carbamate Chemical compound COC(=O)NNS(C)(=O)=O BBNBSVPCCCCNDP-UHFFFAOYSA-N 0.000 description 1
- GOBCGGVCKHZJJE-UHFFFAOYSA-N methyl n-[(4-methylphenyl)sulfonylamino]carbamate Chemical compound COC(=O)NNS(=O)(=O)C1=CC=C(C)C=C1 GOBCGGVCKHZJJE-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS792645A CS200219B2 (cs) | 1976-06-15 | 1979-04-18 | Způsob výroby nových derivátů hydrazinu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69626376A | 1976-06-15 | 1976-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200218B2 true CS200218B2 (en) | 1980-08-29 |
Family
ID=24796354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS773581A CS200218B2 (en) | 1976-06-15 | 1977-05-31 | Method of producing 1,4-dioxides of quinoxalinecarbazates |
Country Status (31)
-
1977
- 1977-05-16 SE SE7705744A patent/SE428925B/xx not_active IP Right Cessation
- 1977-05-17 CA CA278,574A patent/CA1087616A/en not_active Expired
- 1977-05-18 GB GB764/80A patent/GB1591873A/en not_active Expired
- 1977-05-18 ZA ZA00772979A patent/ZA772979B/xx unknown
- 1977-05-18 GB GB20800/77A patent/GB1591872A/en not_active Expired
- 1977-05-18 GB GB765/80A patent/GB1591874A/en not_active Expired
- 1977-05-20 NZ NZ184167A patent/NZ184167A/xx unknown
- 1977-05-20 GR GR53522A patent/GR72289B/el unknown
- 1977-05-20 IE IE1040/77A patent/IE44684B1/en not_active IP Right Cessation
- 1977-05-25 IL IL52166A patent/IL52166A0/xx unknown
- 1977-05-26 CH CH650777A patent/CH620911A5/fr not_active IP Right Cessation
- 1977-05-26 PH PH19820A patent/PH14866A/en unknown
- 1977-05-27 YU YU1327/77A patent/YU39492B/xx unknown
- 1977-05-30 JP JP6315177A patent/JPS52153986A/ja active Granted
- 1977-05-31 DE DE19772725023 patent/DE2725023A1/de active Pending
- 1977-05-31 PT PT66618A patent/PT66618B/pt unknown
- 1977-05-31 NL NL7705938.A patent/NL166685C/xx not_active IP Right Cessation
- 1977-05-31 CS CS773581A patent/CS200218B2/cs unknown
- 1977-05-31 NO NO771903A patent/NO146864C/no unknown
- 1977-05-31 IT IT49637/77A patent/IT1078874B/it active
- 1977-06-01 AT AT387077A patent/AT357562B/de not_active IP Right Cessation
- 1977-06-01 DK DK240777AA patent/DK142497B/da unknown
- 1977-06-01 FI FI771742A patent/FI771742A7/fi not_active Application Discontinuation
- 1977-06-02 DD DD7700199261A patent/DD131371A5/xx unknown
- 1977-06-02 DD DD77204377A patent/DD135080A5/xx not_active IP Right Cessation
- 1977-06-02 LU LU77474A patent/LU77474A1/xx unknown
- 1977-06-02 AR AR267928A patent/AR221207A1/es active
- 1977-06-13 BG BG036608A patent/BG35595A3/xx unknown
- 1977-06-14 ES ES459750A patent/ES459750A1/es not_active Expired
- 1977-06-14 ES ES459745A patent/ES459745A1/es not_active Expired
- 1977-06-14 SU SU772494213A patent/SU657746A3/ru active
- 1977-06-15 PL PL1977198873A patent/PL105555B1/pl unknown
- 1977-11-09 PH PH20413A patent/PH14481A/en unknown
-
1979
- 1979-11-10 JP JP14596079A patent/JPS5589256A/ja active Granted
-
1980
- 1980-05-06 SE SE8003393A patent/SE437985B/sv not_active IP Right Cessation
- 1980-12-10 NL NL8006697A patent/NL8006697A/nl not_active Application Discontinuation
-
1981
- 1981-09-22 NO NO813221A patent/NO147422C/no unknown
-
1982
- 1982-10-11 SG SG49282A patent/SG49282G/en unknown
-
1983
- 1983-01-13 HK HK18/83A patent/HK1883A/xx unknown
- 1983-01-13 HK HK19/83A patent/HK1983A/xx unknown
- 1983-01-13 HK HK20/83A patent/HK2083A/xx unknown
- 1983-12-30 MY MY229/83A patent/MY8300229A/xx unknown
- 1983-12-30 MY MY230/83A patent/MY8300230A/xx unknown
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