HU184825B - Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives - Google Patents
Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives Download PDFInfo
- Publication number
- HU184825B HU184825B HU802239A HU223980A HU184825B HU 184825 B HU184825 B HU 184825B HU 802239 A HU802239 A HU 802239A HU 223980 A HU223980 A HU 223980A HU 184825 B HU184825 B HU 184825B
- Authority
- HU
- Hungary
- Prior art keywords
- group
- formula
- general formula
- alkyl
- hydroxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- HJJQBNPBMPQJEY-UHFFFAOYSA-N OC1=[N+](C2=CC=CC=C2[N+](=C1C)[O-])[O-] Chemical class OC1=[N+](C2=CC=CC=C2[N+](=C1C)[O-])[O-] HJJQBNPBMPQJEY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- -1 nitro, hydroxyl Chemical group 0.000 claims abstract description 15
- FLWOWDJSGNGQFU-UHFFFAOYSA-N (1-oxido-4-oxoquinoxalin-4-ium-2-yl)methanol Chemical class C1=CC=CC2=[N+]([O-])C(CO)=C[N+]([O-])=C21 FLWOWDJSGNGQFU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000012141 concentrate Substances 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 235000019786 weight gain Nutrition 0.000 claims abstract description 4
- 230000004584 weight gain Effects 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 241001465754 Metazoa Species 0.000 claims description 7
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 208000021017 Weight Gain Diseases 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 230000001965 increasing effect Effects 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- JZJFIUXMPBVEFS-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbaldehyde Chemical compound C1=CC=C2N([O-])C(C=O)=C[N+](=O)C2=C1 JZJFIUXMPBVEFS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 239000002253 acid Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
- PKBGHORNUFQAAW-UHFFFAOYSA-N 4-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Cl)C=C1 PKBGHORNUFQAAW-UHFFFAOYSA-N 0.000 description 1
- ZMZGIVVRBMFZSG-UHFFFAOYSA-N 4-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C=C1 ZMZGIVVRBMFZSG-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- 241000192017 Micrococcaceae Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ABUFLIQKCSBKME-UHFFFAOYSA-N N-(2-hydroxypropan-2-yl)pyridine-4-carboxamide Chemical compound CC(C)(O)NC(=O)c1ccncc1 ABUFLIQKCSBKME-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000947836 Pseudomonadaceae Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 235000021052 average daily weight gain Nutrition 0.000 description 1
- 235000021053 average weight gain Nutrition 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960000427 carbadox Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940023064 escherichia coli Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- BPMVRAQIQQEBLN-OBPBNMOMSA-N methyl n-[(e)-(1-hydroxy-4-oxidoquinoxalin-4-ium-2-ylidene)methyl]iminocarbamate Chemical compound C1=CC=C2N(O)C(=C/N=NC(=O)OC)/C=[N+]([O-])C2=C1 BPMVRAQIQQEBLN-OBPBNMOMSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- NQSJOBCWGOKIMH-UHFFFAOYSA-N n-(cyanomethyl)pyridine-4-carboxamide Chemical compound N#CCNC(=O)C1=CC=NC=C1 NQSJOBCWGOKIMH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009885 systemic effect Effects 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Furan Compounds (AREA)
- Feed For Specific Animals (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802239A HU184825B (en) | 1980-09-12 | 1980-09-12 | Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives |
| GR66022A GR75080B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-12 | 1981-09-08 | |
| BE1/10311A BE890301A (fr) | 1980-09-12 | 1981-09-10 | Derives de 2-hydroxymethyl-quinoxaline-1,4-dioxyde procede pour les preparer et compositions les renfermant |
| US06/593,204 US4511717A (en) | 1980-09-12 | 1981-09-11 | 2-Hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process for preparing same and compositions containing same |
| AR286742A AR227793A1 (es) | 1980-09-12 | 1981-09-11 | Procedimiento para la produccion de derivados de 1,4-dioxido de 2-alpha-de derivados de 1,4-dioxido de 2-(alpha-hidrazino-alpha-hidroximetil)-quinoxalina |
| IT23897/81A IT1168171B (it) | 1980-09-12 | 1981-09-11 | Derivati del 2-idrossimetil-chinossalin-1,4-biossido, procedimento per la loro preparazione e composizioni contenenti gli stessi |
| PL1981232992A PL133452B1 (en) | 1980-09-12 | 1981-09-11 | Process for preparing novel derivatives of 1,4-dioxide of 2-hydroxymethylquinoxaline |
| CS816729A CS226038B2 (en) | 1980-09-12 | 1981-09-11 | Method of preparing 2-hydromethylquinoxaline-1,4-dioxide derivatives |
| GR66023A GR75332B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-12 | 1981-09-11 | |
| CA000385646A CA1154017A (en) | 1980-09-12 | 1981-09-11 | 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process for preparing same and compositions containing same |
| DE813152331T DE3152331A1 (de) | 1980-09-12 | 1981-09-11 | 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives,a process for preparing same and compositions containing same |
| JP56502947A JPS57501627A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-12 | 1981-09-11 | |
| FR8117210A FR2490227A1 (fr) | 1980-09-12 | 1981-09-11 | Derives de 2-hydroxymethyl-quinoxaline-1,4-dioxyde, procede pour les preparer et compositions douees de proprietes antimicrobiennes les renfermant |
| CH2938/82A CH650777A5 (de) | 1980-09-12 | 1981-09-11 | 2-hydroxymethyl-chinoxalin-1,4-dioxyd-derivate, verfahren zu ihrer herstellung und solche verbindungen enthaltende kompositionen. |
| YU02186/81A YU218681A (en) | 1980-09-12 | 1981-09-11 | Process for obtaining 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives |
| PT73656A PT73656B (en) | 1980-09-12 | 1981-09-11 | Process for preparing 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives |
| NL8120329A NL8120329A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-12 | 1981-09-11 | |
| PCT/HU1981/000038 WO1982001001A1 (en) | 1980-09-12 | 1981-09-11 | 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives,a process for preparing same and compositions containing same |
| GB8213432A GB2099422B (en) | 1980-09-12 | 1981-09-11 | 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives a process for preparing same and compositions containing same |
| ES505441A ES8302670A1 (es) | 1980-09-12 | 1981-09-12 | Procedimiento de preparacion de nuevos derivados 2-hidroxi- metil-quinoxalino-1,4-dioxidos |
| FI821191A FI64802C (fi) | 1980-09-12 | 1982-04-05 | 2-hydroximetylkinoxalin-1,4-dioxidderivat foerfarande foer deras framstaellning och dessa innehaollande kompositioner |
| SU823434349A SU1189339A3 (ru) | 1980-09-12 | 1982-05-10 | Способ получени производных 2-оксиметилхиноксалин-1,4-диоксида |
| SE8202931A SE8202931L (sv) | 1980-09-12 | 1982-05-10 | 2-hydroximetyl-kinoxalin-1,4-dioxid-derivat, forfarande for framstellning derav och kompositioner innehallande dessa derivat |
| DK211282A DK211282A (da) | 1980-09-12 | 1982-05-11 | 2-hydroxymethyl-quinoxalin-1,4-dioxidderivater,fremgangsmaade til fremstilling deraf samt praeparater indeholdende disse |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802239A HU184825B (en) | 1980-09-12 | 1980-09-12 | Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184825B true HU184825B (en) | 1984-10-29 |
Family
ID=10958450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU802239A HU184825B (en) | 1980-09-12 | 1980-09-12 | Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives |
Country Status (23)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPR527801A0 (en) * | 2001-05-25 | 2001-06-21 | University Of Sydney, The | Animal husbandry iii |
| US7690616B2 (en) | 2005-05-26 | 2010-04-06 | Hoffman Enclosures, Inc. | Mounting system for enclosure |
| USD576015S1 (en) * | 2005-05-26 | 2008-09-02 | Hoffman Enclosures, Inc. | Hinge for flush mount enclosure |
| RU2325162C1 (ru) * | 2006-11-08 | 2008-05-27 | Тамара Семеновна Одарюк | Применение диоксидина в качестве противоопухолевого средства |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1494068A (fr) * | 1964-08-31 | 1967-09-08 | Pfizer & Co C | Procédé pour la préparation de di-nu-oxydes de quinoxalines |
| US3371090A (en) * | 1964-09-16 | 1968-02-27 | Pfizer & Co C | Novel antibacterial agents |
| US3649363A (en) * | 1970-09-02 | 1972-03-14 | Globe Union Inc | Water activatable battery |
| US3926992A (en) * | 1972-11-03 | 1975-12-16 | Pfizer | Aldol products of 2-quinoxalinecarboxaldehy-1,4-dioxides |
| US4211781A (en) * | 1974-09-23 | 1980-07-08 | Pfizer Inc. | Process for the preparation of dustless quinoxaline-1,4-dioxide animal feed supplement premixes |
| HU169299B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-11-21 | 1976-11-28 | ||
| HU171738B (hu) * | 1975-03-14 | 1978-03-28 | Egyt Gyogyszervegyeszeti Gyar | Sposob poluchenija proizvodnykh kinoksalin-1,4-dioksid-azometina |
| US4100284A (en) * | 1977-01-18 | 1978-07-11 | Pfizer Inc. | 1,4-Dioxo- and 4-oxoquinoxaline-2-carboxaldehyde sulfonylhydrazones and certain derivatives thereof |
| IT7967949A0 (it) * | 1979-05-07 | 1979-05-07 | Marxer Spa | Preparato farmacologico composto da un derivato chinossalinico miscelato a bicarbonato di sodio |
| US4221791A (en) * | 1979-05-21 | 1980-09-09 | International Minerals & Chemical Corp. | Substituted quinoxaline dioxides |
-
1980
- 1980-09-12 HU HU802239A patent/HU184825B/hu not_active IP Right Cessation
-
1981
- 1981-09-08 GR GR66022A patent/GR75080B/el unknown
- 1981-09-10 BE BE1/10311A patent/BE890301A/fr not_active IP Right Cessation
- 1981-09-11 CS CS816729A patent/CS226038B2/cs unknown
- 1981-09-11 IT IT23897/81A patent/IT1168171B/it active
- 1981-09-11 GR GR66023A patent/GR75332B/el unknown
- 1981-09-11 AR AR286742A patent/AR227793A1/es active
- 1981-09-11 NL NL8120329A patent/NL8120329A/nl unknown
- 1981-09-11 US US06/593,204 patent/US4511717A/en not_active Expired - Fee Related
- 1981-09-11 PL PL1981232992A patent/PL133452B1/pl unknown
- 1981-09-11 DE DE813152331T patent/DE3152331A1/de not_active Withdrawn
- 1981-09-11 PT PT73656A patent/PT73656B/pt unknown
- 1981-09-11 JP JP56502947A patent/JPS57501627A/ja active Pending
- 1981-09-11 CH CH2938/82A patent/CH650777A5/de not_active IP Right Cessation
- 1981-09-11 WO PCT/HU1981/000038 patent/WO1982001001A1/en active IP Right Grant
- 1981-09-11 FR FR8117210A patent/FR2490227A1/fr active Granted
- 1981-09-11 GB GB8213432A patent/GB2099422B/en not_active Expired
- 1981-09-11 CA CA000385646A patent/CA1154017A/en not_active Expired
- 1981-09-11 YU YU02186/81A patent/YU218681A/xx unknown
- 1981-09-12 ES ES505441A patent/ES8302670A1/es not_active Expired
-
1982
- 1982-04-05 FI FI821191A patent/FI64802C/fi not_active IP Right Cessation
- 1982-05-10 SU SU823434349A patent/SU1189339A3/ru active
- 1982-05-10 SE SE8202931A patent/SE8202931L/xx not_active Application Discontinuation
- 1982-05-11 DK DK211282A patent/DK211282A/da not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |