NO123895B - - Google Patents
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- Publication number
- NO123895B NO123895B NO3047/69A NO304769A NO123895B NO 123895 B NO123895 B NO 123895B NO 3047/69 A NO3047/69 A NO 3047/69A NO 304769 A NO304769 A NO 304769A NO 123895 B NO123895 B NO 123895B
- Authority
- NO
- Norway
- Prior art keywords
- quinoxaline
- dioxide
- hydrazinocarbonyl
- methyl
- ethanol
- Prior art date
Links
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- -1 2-formyl-quinoxaline-1,4-dioxide-semicarbazone Chemical compound 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- 210000002700 urine Anatomy 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SAAFAQUUYXAZII-UHFFFAOYSA-N chembl2104307 Chemical compound C1=CC=CC2=[N+]([O-])C(C)=C(C(=O)NN)[N+]([O-])=C21 SAAFAQUUYXAZII-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 125000000815 N-oxide group Chemical group 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 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
- ATQSBOKETLMQFA-UHFFFAOYSA-N 3-methylquinoxaline-2-carbohydrazide Chemical compound C1=CC=C2N=C(C(=O)NN)C(C)=NC2=C1 ATQSBOKETLMQFA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FTHZVKHYFZBBCF-UHFFFAOYSA-N N(N)C(=O)C1=[N+](C2=CC=CC=C2[N+](=C1)[O-])[O-] Chemical compound N(N)C(=O)C1=[N+](C2=CC=CC=C2[N+](=C1)[O-])[O-] FTHZVKHYFZBBCF-UHFFFAOYSA-N 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- GMGXWZSYCXQDEF-UHFFFAOYSA-N ethyl 3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=CC=C2[N+](=O)C(C(=O)OCC)=C(C)N([O-])C2=C1 GMGXWZSYCXQDEF-UHFFFAOYSA-N 0.000 description 1
- WVRYZIXOSJVVRR-UHFFFAOYSA-N ethyl 7-methoxy-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate Chemical compound C1=C(OC)C=C2[N+](=O)C(C(=O)OCC)=C(C)N([O-])C2=C1 WVRYZIXOSJVVRR-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229940026778 other chemotherapeutics in atc Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002562 urinalysis Methods 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000005406 washing 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770975 DE1770975A1 (de) | 1968-07-25 | 1968-07-25 | Bakteriostatisch wirksame Chinoxalin-1,4-dioxyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123895B true NO123895B (es) | 1972-01-31 |
Family
ID=5700713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3047/69A NO123895B (es) | 1968-07-25 | 1969-07-23 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3600388A (es) |
| AT (1) | AT290541B (es) |
| BE (1) | BE736578A (es) |
| BR (1) | BR6911028D0 (es) |
| CH (1) | CH491936A (es) |
| DE (1) | DE1770975A1 (es) |
| DK (1) | DK120705B (es) |
| ES (1) | ES369889A1 (es) |
| FR (1) | FR2013704A1 (es) |
| GB (1) | GB1248848A (es) |
| IE (1) | IE33192B1 (es) |
| IL (1) | IL32579A (es) |
| LU (1) | LU59099A1 (es) |
| NL (1) | NL6911155A (es) |
| NO (1) | NO123895B (es) |
| SE (1) | SE350758B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980648A (en) * | 1973-04-10 | 1976-09-14 | Pfizer Inc. | Process for producing quinoxaline-di-N-oxides |
| IT7869686A0 (it) * | 1978-11-24 | 1978-11-24 | Loranze Torino A | Procedimento di preparazione di 2metil 3 bidrossietilcarbamollchinossalina i.4 di n ossido puroed altri composti ad esso simili |
-
1968
- 1968-07-25 DE DE19681770975 patent/DE1770975A1/de active Pending
-
1969
- 1969-07-04 IE IE917/69A patent/IE33192B1/xx unknown
- 1969-07-07 US US839646A patent/US3600388A/en not_active Expired - Lifetime
- 1969-07-09 IL IL32579A patent/IL32579A/xx unknown
- 1969-07-14 LU LU59099D patent/LU59099A1/xx unknown
- 1969-07-21 NL NL6911155A patent/NL6911155A/xx unknown
- 1969-07-22 SE SE10294/69A patent/SE350758B/xx unknown
- 1969-07-23 NO NO3047/69A patent/NO123895B/no unknown
- 1969-07-23 CH CH1127269A patent/CH491936A/de not_active IP Right Cessation
- 1969-07-24 ES ES369889A patent/ES369889A1/es not_active Expired
- 1969-07-24 DK DK402169AA patent/DK120705B/da unknown
- 1969-07-25 BE BE736578D patent/BE736578A/xx unknown
- 1969-07-25 FR FR6925478A patent/FR2013704A1/fr not_active Withdrawn
- 1969-07-25 AT AT722569A patent/AT290541B/de not_active IP Right Cessation
- 1969-07-25 GB GB37465/69A patent/GB1248848A/en not_active Expired
- 1969-07-25 BR BR211028/69A patent/BR6911028D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2013704A1 (es) | 1970-04-03 |
| ES369889A1 (es) | 1971-07-16 |
| DE1770975A1 (de) | 1972-01-13 |
| CH491936A (de) | 1970-06-15 |
| AT290541B (de) | 1971-06-11 |
| IL32579A0 (en) | 1969-09-25 |
| SE350758B (es) | 1972-11-06 |
| IE33192B1 (en) | 1974-04-17 |
| US3600388A (en) | 1971-08-17 |
| NL6911155A (es) | 1970-01-27 |
| GB1248848A (en) | 1971-10-06 |
| IL32579A (en) | 1972-05-30 |
| BE736578A (es) | 1970-01-26 |
| BR6911028D0 (pt) | 1973-04-26 |
| IE33192L (en) | 1970-01-25 |
| DK120705B (da) | 1971-07-05 |
| LU59099A1 (es) | 1971-06-21 |
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