NO122020B - - Google Patents
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- Publication number
- NO122020B NO122020B NO3878/68A NO387868A NO122020B NO 122020 B NO122020 B NO 122020B NO 3878/68 A NO3878/68 A NO 3878/68A NO 387868 A NO387868 A NO 387868A NO 122020 B NO122020 B NO 122020B
- Authority
- NO
- Norway
- Prior art keywords
- quinoxaline
- carboxylic acid
- oxide
- chloromethyl
- formula
- Prior art date
Links
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 208000015181 infectious disease Diseases 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 206010028470 Mycoplasma infections Diseases 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0053669 | 1967-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122020B true NO122020B (es) | 1971-05-10 |
Family
ID=7106506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3878/68A NO122020B (es) | 1967-10-04 | 1968-10-01 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US3598820A (es) |
| AT (1) | AT281838B (es) |
| BE (1) | BE721728A (es) |
| BR (1) | BR6802856D0 (es) |
| CH (1) | CH506537A (es) |
| DE (1) | DE1670939A1 (es) |
| DK (1) | DK118246B (es) |
| ES (1) | ES358798A1 (es) |
| FI (1) | FI49721C (es) |
| FR (2) | FR1601325A (es) |
| GB (1) | GB1188248A (es) |
| IL (1) | IL30713A (es) |
| NL (1) | NL6814259A (es) |
| NO (1) | NO122020B (es) |
| SE (1) | SE344202B (es) |
| YU (1) | YU32938B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728345A (en) * | 1971-03-19 | 1973-04-17 | Pfizer | Preparation of quinoxaline-2-carboxamide derivatives |
| DE2122572A1 (de) * | 1971-05-07 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von neuen Derivaten von 2-Formyl-3-carbonatnido-chinoxalin-di-N-oxiden sowie ihre Verwendung als Arzneimittel und Futtermittelzusatz |
| US3896222A (en) * | 1971-05-07 | 1975-07-22 | Bayer Ag | Compositions containing a carbonamidoquinoxaline-di-n-oxide and method of using same |
| US3957987A (en) * | 1971-05-07 | 1976-05-18 | Bayer Aktiengesellschaft | Compositions containing a carbonamidoquinoxaline-di-N-oxide and method of using same |
| US4039540A (en) * | 1974-05-07 | 1977-08-02 | Pfizer Inc. | 3-Substituted quinoxaline-2-carboxamide-1,4-dioxides |
| FR2640245B1 (fr) * | 1988-12-08 | 1992-06-12 | Garonne Ets Auriol & Cie | Procede de distribution de pieces et dispositifs de mise en oeuvre |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL260335A (es) * | 1960-01-22 |
-
1967
- 1967-10-04 DE DE19671670939 patent/DE1670939A1/de active Pending
-
1968
- 1968-09-16 IL IL30713A patent/IL30713A/en unknown
- 1968-09-16 CH CH1387568A patent/CH506537A/de not_active IP Right Cessation
- 1968-10-01 NO NO3878/68A patent/NO122020B/no unknown
- 1968-10-02 BE BE721728D patent/BE721728A/xx unknown
- 1968-10-02 US US764592A patent/US3598820A/en not_active Expired - Lifetime
- 1968-10-02 YU YU2298/68A patent/YU32938B/xx unknown
- 1968-10-03 GB GB47010/68A patent/GB1188248A/en not_active Expired
- 1968-10-03 SE SE13378/68A patent/SE344202B/xx unknown
- 1968-10-03 DK DK478468AA patent/DK118246B/da unknown
- 1968-10-04 NL NL6814259A patent/NL6814259A/xx unknown
- 1968-10-04 BR BR202856/68A patent/BR6802856D0/pt unknown
- 1968-10-04 FI FI682816A patent/FI49721C/fi active
- 1968-10-04 AT AT970068A patent/AT281838B/de not_active IP Right Cessation
- 1968-10-04 FR FR1601325D patent/FR1601325A/fr not_active Expired
- 1968-10-04 ES ES358798A patent/ES358798A1/es not_active Expired
- 1968-12-30 FR FR181601A patent/FR8132M/fr not_active Expired
-
1970
- 1970-01-22 US US10685*A patent/US3686401A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR1601325A (es) | 1970-08-17 |
| FI49721B (es) | 1975-06-02 |
| US3686401A (en) | 1972-08-22 |
| NL6814259A (es) | 1969-04-09 |
| IL30713A (en) | 1972-05-30 |
| CH506537A (de) | 1971-04-30 |
| IL30713A0 (en) | 1968-12-26 |
| BE721728A (es) | 1969-04-02 |
| BR6802856D0 (pt) | 1973-02-22 |
| FR8132M (es) | 1970-08-10 |
| DK118246B (da) | 1970-07-27 |
| GB1188248A (en) | 1970-04-15 |
| YU32938B (en) | 1975-12-31 |
| US3598820A (en) | 1971-08-10 |
| SE344202B (es) | 1972-04-04 |
| ES358798A1 (es) | 1970-05-01 |
| DE1670939A1 (de) | 1971-02-25 |
| FI49721C (fi) | 1975-09-10 |
| AT281838B (de) | 1970-06-10 |
| YU229868A (en) | 1975-06-30 |
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