US3926991A - Process for producing quinoxaline-di-N-oxides - Google Patents
Process for producing quinoxaline-di-N-oxides Download PDFInfo
- Publication number
- US3926991A US3926991A US338906A US33890673A US3926991A US 3926991 A US3926991 A US 3926991A US 338906 A US338906 A US 338906A US 33890673 A US33890673 A US 33890673A US 3926991 A US3926991 A US 3926991A
- Authority
- US
- United States
- Prior art keywords
- acid
- carbazate
- reaction
- methyl
- oxidizing agent
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- SOEMFPLGOUBPJQ-NTUHNPAUSA-N methyl n-[(e)-quinoxalin-2-ylmethylideneamino]carbamate Chemical compound C1=CC=CC2=NC(/C=N/NC(=O)OC)=CN=C21 SOEMFPLGOUBPJQ-NTUHNPAUSA-N 0.000 claims abstract description 13
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012442 inert solvent Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- OVGGLBAWFMIPPY-UHFFFAOYSA-N methyl N-[(1,4-dioxidoquinoxaline-1,4-diium-2-yl)methylideneamino]carbamate Chemical compound C1=CC=CC2=[N+]([O-])C(C=NNC(=O)OC)=C[N+]([O-])=C21 OVGGLBAWFMIPPY-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 abstract description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 10
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 abstract description 3
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 abstract description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 abstract description 3
- 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 abstract description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 2
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- -1 acetic acid Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- UJEHWLFUEQHEEZ-UHFFFAOYSA-N quinoxaline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CN=C21 UJEHWLFUEQHEEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 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
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 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
-
- 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
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Definitions
- oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide.
- the present invention discloses a process for the preparation of methyl 3-( 2-quinoxalinylmethylene)carbazate N ,N -dioxide which comprises contacting methyl 3-(2-quinoxalinylmethylene)carbazate with at least about 2 equivalents of oxidizing agent in a reaction inert solvent at a temperature of from about C. up to 100C. until the reaction is substantially complete, said oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, mchloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide, and recovery of the product.
- a catalyst is usually employed.
- Suitable catalysts are tungstic acid, sodium tungstate, sodium vanadate, sodium molybdate, potassium tungstate, potassium molybdate, vanadium pentaoxide, zirconium dioxide, tungsten trioxide or molybdenum trioxide.
- a particularly preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is peracetic acid and said solvent is acetic acid, since both the reagent and solvent are inexpensive.
- a second preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is m-chloroperbenzoic acid and said solvent is chloroform.
- reaction tem perature is preferably maintained at less than 50C.
- the new reaction of the present invention is carried out in a reaction-inert solvent.
- An inert solvent for purposes of this invention contemplates any solvent which allows solubilization of the reactants and is free of ad.- verse effect on the reagents and products under the conditions employed.
- Two preferred types include organic acids, such as acetic acid, and halogenated solvents, such as chloroform and methylene chloride. In some cases water may be employed. However, any solvent possessing the qualities set forth above will be satisfactory.
- the temperature at which the reaction is performed may vary from C. to about 100C. and for the most part the optimum temperature will vary with the choice of oxidizing agent. Depending upon the particular oxidizing agent and temperature, the reaction time can vary from a few minutes to as long as 24 hours. Generally, to ensure complete reaction the relatively long time periods are preferred. Optimum reaction conditions are readily determined by experiment.
- the proportion of oxidizing agent relative to the starting carbazate may vary widely butfor efficient conversion at least about two equivalents of oxidizing agent per mole ofcarbanate are preferred.
- the product is a crystalline substance which precipitates from the reaction mixture. It is collected by suit- .able means and dried.
- the valuable product of this invention exhibits activity as urinary tract systemic anti-infective in animals, includingman, against a wide :variety of microorganisms including Gram positive and Gram-negative bacteria. It is especially valuable against Gram negative infection both invitro and in vivo.
- poultry chickens, ducks, turkeys
- the beneficial effects in growth rate and feed efficiency are over and above what is normally obtained with complete nutritious diets containing all the nutrients, vitamins, minerals and other factors known to be required for the maximum healthy growth of such animals.
- the animals thus attain market size sooner and on less feed.
- feed compositions have been found to be particularly valuable and outstanding in the case of such animals as poultry, rats, hogs, swine, lambs, cattle, and the like. In some instances the degree of response may vary with respect to the sex of the animals.
- the products may, of course, be administered in one component of the feed or they may be blended uniformly throughout a mixed feed; alternatively as noted above, they may be administered in an equivalent amount via the animalss water ration. It should be noted that a variety of feed components may be of use in the nutritionally balanced feeds.
- reaction mixture is allowed to stand for 12 hours and then diluted with water.
- the solid which precipitates is collected, washed with water and dried to give crystalline methyl 3-(2-quinoxalinylmethylene)carbazate N ,N -dioxide.
- EXAMPLE lll A mixture of methyl 3-( 2-quinoxalinylmethylene)- carbazate (23.0 g, 0.1 mole), tungstic acid (2.5 g) and 30 ml of t-butanol is heated to 6065. An aqueous solution of 30 percent hydrogen peroxide (30 ml) is solvent is acetic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US338906A US3926991A (en) | 1973-03-07 | 1973-03-07 | Process for producing quinoxaline-di-N-oxides |
| IE197/74A IE39170B1 (en) | 1973-03-07 | 1974-02-04 | Process for producing a quinoxaline -n1 n4 - dioxide derivative |
| ZA740745A ZA74745B (en) | 1973-03-07 | 1974-02-05 | Carbacox from 2-quinoxaline,carboxaldehyde methyl carbazate |
| SE7401528A SE420603B (sv) | 1973-03-07 | 1974-02-05 | Forfarande for framstellning av metyl-3-(2-kinoxolinylmetylen)-karbazat-n?721, n?724-dioxid |
| NL7401966A NL7401966A (enrdf_load_stackoverflow) | 1973-03-07 | 1974-02-13 | |
| FI490/74A FI59404C (fi) | 1973-03-07 | 1974-02-20 | Foerfarande foer framstaellning av metyl-3-(2-kinoxalinylmetylen)karbazat-n1,n4-dioxid |
| IT48504/74A IT1056054B (it) | 1973-03-07 | 1974-02-20 | Processo per la preparazione di mitil 3(2 chinossalinil metalen) catalazato ni n 4 diossido |
| YU00439/74A YU39150B (en) | 1973-03-07 | 1974-02-20 | Process for obtaining methyl-3(2-quinoxalinyl-methylene carbazate n1,n4-dioxides |
| JP49019992A JPS5024282A (enrdf_load_stackoverflow) | 1973-03-07 | 1974-02-21 | |
| DK92574AA DK138945B (da) | 1973-03-07 | 1974-02-21 | Fremgangsmåde til fremstilling af methyl-3-(2-quinoxalinylmethylen)carbazat-N1,N4-dioxid. |
| ES423464A ES423464A1 (es) | 1973-03-07 | 1974-02-21 | Un procedimiento para la preparacion de n', n'-dioxido de 3-(2-quinoxalinilmetilen) carbazato de metilo. |
| FR7406155A FR2220524B1 (enrdf_load_stackoverflow) | 1973-03-07 | 1974-02-22 | |
| AR252487A AR200516A1 (es) | 1973-03-07 | 1974-02-22 | Procedimiento para preparar el 3-(2-quinoxalinilmetileno) carbazato de metilo n1,n4-dioxido |
| LU69471A LU69471A1 (enrdf_load_stackoverflow) | 1973-03-07 | 1974-02-22 | |
| CH254874A CH580096A5 (enrdf_load_stackoverflow) | 1973-03-07 | 1974-02-22 | |
| HUPI408A HU170488B (enrdf_load_stackoverflow) | 1973-03-07 | 1974-02-28 | |
| CS7400001493A CS180003B2 (en) | 1973-03-07 | 1974-02-28 | Method for production of n1,n4-dioxide of methyl-3/2-chinoxalinylmethylene/carbazate |
| SU2002363A SU539527A3 (ru) | 1973-03-07 | 1974-03-01 | Способ получени 1- 4-двуокиси метил-3-(2-хиноксалинилметилен)карбазата |
| PL1974169209A PL94858B1 (enrdf_load_stackoverflow) | 1973-03-07 | 1974-03-01 | |
| CA194,053A CA982584A (en) | 1973-03-07 | 1974-03-05 | Carbadox from 2-quinoxaline, carboxaldehyde methyl carbazate |
| GB1014974A GB1459561A (en) | 1973-03-07 | 1974-03-06 | Process for producing a quinoxaline-di-n-oxide derivative |
| US05/597,209 US4006142A (en) | 1973-03-07 | 1975-07-18 | Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide |
| HK471/77A HK47177A (en) | 1973-03-07 | 1977-09-15 | Process for producing a quinoxaline-di-n-oxide derivative |
| MY13/78A MY7800013A (en) | 1973-03-07 | 1978-12-30 | Process for producing a quinoxaline d1-n-oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US338906A US3926991A (en) | 1973-03-07 | 1973-03-07 | Process for producing quinoxaline-di-N-oxides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/597,209 Division US4006142A (en) | 1973-03-07 | 1975-07-18 | Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3926991A true US3926991A (en) | 1975-12-16 |
Family
ID=23326639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US338906A Expired - Lifetime US3926991A (en) | 1973-03-07 | 1973-03-07 | Process for producing quinoxaline-di-N-oxides |
Country Status (23)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006142A (en) * | 1973-03-07 | 1977-02-01 | Pfizer Inc. | Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide |
| US4935575A (en) * | 1988-12-12 | 1990-06-19 | Uop | Process for the oligomerization of olefins and a catalyst thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4740652A (en) * | 1985-05-23 | 1988-04-26 | Uop Inc. | Process for the oligomerization of olefins |
| US4737479A (en) * | 1986-03-21 | 1988-04-12 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4737480A (en) * | 1986-03-25 | 1988-04-12 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4795851A (en) * | 1987-03-12 | 1989-01-03 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
| US4795852A (en) * | 1987-03-13 | 1989-01-03 | Uop Inc. | Process for the oligomerization of olefins and a catalyst thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545786A (en) * | 1951-03-20 | S-methoxyquinoxaline-l | ||
| US2626259A (en) * | 1953-01-20 | Ffiii-ce | ||
| US3479354A (en) * | 1967-03-21 | 1969-11-18 | Ici Ltd | Derivatives of 5-hydroxyquinoxaline-1,4-dioxide |
| US3720673A (en) * | 1970-06-18 | 1973-03-13 | Ici Ltd | Process for the manufacture of quinoxaline 1,4-dioxides |
| US3819616A (en) * | 1970-04-02 | 1974-06-25 | Bayer Ag | Imines/their preparation and their pharmaceutical use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA725675B (en) * | 1971-06-21 | 1973-05-30 | Ciba Geigy Ag | New heterocyclic compounds |
-
1973
- 1973-03-07 US US338906A patent/US3926991A/en not_active Expired - Lifetime
-
1974
- 1974-02-04 IE IE197/74A patent/IE39170B1/xx unknown
- 1974-02-05 SE SE7401528A patent/SE420603B/xx not_active IP Right Cessation
- 1974-02-05 ZA ZA740745A patent/ZA74745B/xx unknown
- 1974-02-13 NL NL7401966A patent/NL7401966A/xx unknown
- 1974-02-20 FI FI490/74A patent/FI59404C/fi active
- 1974-02-20 YU YU00439/74A patent/YU39150B/xx unknown
- 1974-02-20 IT IT48504/74A patent/IT1056054B/it active
- 1974-02-21 ES ES423464A patent/ES423464A1/es not_active Expired
- 1974-02-21 JP JP49019992A patent/JPS5024282A/ja active Pending
- 1974-02-21 DK DK92574AA patent/DK138945B/da not_active IP Right Cessation
- 1974-02-22 AR AR252487A patent/AR200516A1/es active
- 1974-02-22 CH CH254874A patent/CH580096A5/xx not_active IP Right Cessation
- 1974-02-22 FR FR7406155A patent/FR2220524B1/fr not_active Expired
- 1974-02-22 LU LU69471A patent/LU69471A1/xx unknown
- 1974-02-28 HU HUPI408A patent/HU170488B/hu unknown
- 1974-02-28 CS CS7400001493A patent/CS180003B2/cs unknown
- 1974-03-01 PL PL1974169209A patent/PL94858B1/pl unknown
- 1974-03-01 SU SU2002363A patent/SU539527A3/ru active
- 1974-03-05 CA CA194,053A patent/CA982584A/en not_active Expired
- 1974-03-06 GB GB1014974A patent/GB1459561A/en not_active Expired
-
1977
- 1977-09-15 HK HK471/77A patent/HK47177A/xx unknown
-
1978
- 1978-12-30 MY MY13/78A patent/MY7800013A/xx unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545786A (en) * | 1951-03-20 | S-methoxyquinoxaline-l | ||
| US2626259A (en) * | 1953-01-20 | Ffiii-ce | ||
| US3479354A (en) * | 1967-03-21 | 1969-11-18 | Ici Ltd | Derivatives of 5-hydroxyquinoxaline-1,4-dioxide |
| US3819616A (en) * | 1970-04-02 | 1974-06-25 | Bayer Ag | Imines/their preparation and their pharmaceutical use |
| US3720673A (en) * | 1970-06-18 | 1973-03-13 | Ici Ltd | Process for the manufacture of quinoxaline 1,4-dioxides |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006142A (en) * | 1973-03-07 | 1977-02-01 | Pfizer Inc. | Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide |
| US4935575A (en) * | 1988-12-12 | 1990-06-19 | Uop | Process for the oligomerization of olefins and a catalyst thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7401966A (enrdf_load_stackoverflow) | 1974-09-10 |
| AR200516A1 (es) | 1974-11-15 |
| ES423464A1 (es) | 1976-05-01 |
| YU39150B (en) | 1984-06-30 |
| IE39170L (en) | 1974-09-07 |
| FI59404B (fi) | 1981-04-30 |
| DK138945B (da) | 1978-11-20 |
| PL94858B1 (enrdf_load_stackoverflow) | 1977-09-30 |
| SU539527A3 (ru) | 1976-12-15 |
| HK47177A (en) | 1977-09-23 |
| JPS5024282A (enrdf_load_stackoverflow) | 1975-03-15 |
| CS180003B2 (en) | 1977-12-30 |
| YU43974A (en) | 1982-06-30 |
| CH580096A5 (enrdf_load_stackoverflow) | 1976-09-30 |
| GB1459561A (en) | 1976-12-22 |
| FI59404C (fi) | 1981-08-10 |
| SE420603B (sv) | 1981-10-19 |
| LU69471A1 (enrdf_load_stackoverflow) | 1974-09-25 |
| FR2220524A1 (enrdf_load_stackoverflow) | 1974-10-04 |
| HU170488B (enrdf_load_stackoverflow) | 1977-06-28 |
| DK138945C (enrdf_load_stackoverflow) | 1979-05-07 |
| CA982584A (en) | 1976-01-27 |
| ZA74745B (en) | 1974-12-24 |
| MY7800013A (en) | 1978-12-31 |
| FR2220524B1 (enrdf_load_stackoverflow) | 1977-03-04 |
| IE39170B1 (en) | 1978-08-16 |
| IT1056054B (it) | 1982-01-30 |
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