CA1154017A - 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process for preparing same and compositions containing same - Google Patents
2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process for preparing same and compositions containing sameInfo
- Publication number
- CA1154017A CA1154017A CA000385646A CA385646A CA1154017A CA 1154017 A CA1154017 A CA 1154017A CA 000385646 A CA000385646 A CA 000385646A CA 385646 A CA385646 A CA 385646A CA 1154017 A CA1154017 A CA 1154017A
- Authority
- CA
- Canada
- Prior art keywords
- group
- general formula
- alkyl
- quinoxaline
- phenyl
- 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
Links
- 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 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- -1 nitro, hydroxyl Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000005936 piperidyl group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 4
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 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 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 8
- 239000012141 concentrate Substances 0.000 abstract description 6
- 208000021017 Weight Gain Diseases 0.000 abstract description 4
- 230000000845 anti-microbial effect Effects 0.000 abstract description 4
- 230000001965 increasing effect Effects 0.000 abstract description 4
- 230000004584 weight gain Effects 0.000 abstract description 4
- 235000019786 weight gain Nutrition 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- FXKCXGBBUBCRPU-GBOPCIDUSA-N 2-[(2r,4ar,8s,8ar)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid Chemical compound C1C[C@@H](C(=C)C(O)=O)C[C@H]2[C@@](C)(O)CCC[C@@]21C FXKCXGBBUBCRPU-GBOPCIDUSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- QNVBIDULDLPCDQ-UHFFFAOYSA-N Ilicic acid Natural products CC1(O)CCC2(C)CCC(CC2C1)C(=C)C(=O)O QNVBIDULDLPCDQ-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241000192017 Micrococcaceae Species 0.000 description 1
- 101100000209 Mus musculus Orm3 gene Proteins 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000000359 Triticum dicoccon Species 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc 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
-
- 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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU2239/80 | 1980-09-12 | ||
| 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 |
|---|---|
| CA1154017A true CA1154017A (en) | 1983-09-20 |
Family
ID=10958450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000385646A Expired CA1154017A (en) | 1980-09-12 | 1981-09-11 | 2-hydroxymethyl-quinoxaline-1,4-dioxide derivatives, a process for preparing same and compositions containing same |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4511717A (enEXAMPLES) |
| JP (1) | JPS57501627A (enEXAMPLES) |
| AR (1) | AR227793A1 (enEXAMPLES) |
| BE (1) | BE890301A (enEXAMPLES) |
| CA (1) | CA1154017A (enEXAMPLES) |
| CH (1) | CH650777A5 (enEXAMPLES) |
| CS (1) | CS226038B2 (enEXAMPLES) |
| DE (1) | DE3152331A1 (enEXAMPLES) |
| DK (1) | DK211282A (enEXAMPLES) |
| ES (1) | ES8302670A1 (enEXAMPLES) |
| FI (1) | FI64802C (enEXAMPLES) |
| FR (1) | FR2490227A1 (enEXAMPLES) |
| GB (1) | GB2099422B (enEXAMPLES) |
| GR (2) | GR75080B (enEXAMPLES) |
| HU (1) | HU184825B (enEXAMPLES) |
| IT (1) | IT1168171B (enEXAMPLES) |
| NL (1) | NL8120329A (enEXAMPLES) |
| PL (1) | PL133452B1 (enEXAMPLES) |
| PT (1) | PT73656B (enEXAMPLES) |
| SE (1) | SE8202931L (enEXAMPLES) |
| SU (1) | SU1189339A3 (enEXAMPLES) |
| WO (1) | WO1982001001A1 (enEXAMPLES) |
| YU (1) | YU218681A (enEXAMPLES) |
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 |
| USD576015S1 (en) * | 2005-05-26 | 2008-09-02 | Hoffman Enclosures, Inc. | Hinge for flush mount enclosure |
| US7690616B2 (en) | 2005-05-26 | 2010-04-06 | Hoffman Enclosures, Inc. | Mounting system for 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 (enEXAMPLES) * | 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 PL PL1981232992A patent/PL133452B1/pl unknown
- 1981-09-11 NL NL8120329A patent/NL8120329A/nl unknown
- 1981-09-11 IT IT23897/81A patent/IT1168171B/it active
- 1981-09-11 DE DE813152331T patent/DE3152331A1/de not_active Withdrawn
- 1981-09-11 GR GR66023A patent/GR75332B/el unknown
- 1981-09-11 PT PT73656A patent/PT73656B/pt unknown
- 1981-09-11 CS CS816729A patent/CS226038B2/cs unknown
- 1981-09-11 US US06/593,204 patent/US4511717A/en not_active Expired - Fee Related
- 1981-09-11 GB GB8213432A patent/GB2099422B/en not_active Expired
- 1981-09-11 WO PCT/HU1981/000038 patent/WO1982001001A1/en active IP Right Grant
- 1981-09-11 JP JP56502947A patent/JPS57501627A/ja active Pending
- 1981-09-11 CA CA000385646A patent/CA1154017A/en not_active Expired
- 1981-09-11 AR AR286742A patent/AR227793A1/es active
- 1981-09-11 FR FR8117210A patent/FR2490227A1/fr active Granted
- 1981-09-11 CH CH2938/82A patent/CH650777A5/de not_active IP Right Cessation
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| CS226038B2 (en) | 1984-03-19 |
| FI821191L (fi) | 1982-04-05 |
| CH650777A5 (de) | 1985-08-15 |
| IT1168171B (it) | 1987-05-20 |
| AR227793A1 (es) | 1982-12-15 |
| DK211282A (da) | 1982-05-11 |
| FR2490227B1 (enEXAMPLES) | 1984-12-07 |
| GB2099422B (en) | 1984-05-31 |
| US4511717A (en) | 1985-04-16 |
| FI821191A0 (fi) | 1982-04-05 |
| NL8120329A (enEXAMPLES) | 1982-08-02 |
| PL232992A1 (enEXAMPLES) | 1982-10-11 |
| BE890301A (fr) | 1982-03-10 |
| ES505441A0 (es) | 1982-12-01 |
| YU218681A (en) | 1983-10-31 |
| SU1189339A3 (ru) | 1985-10-30 |
| PT73656A (en) | 1981-10-01 |
| GR75332B (enEXAMPLES) | 1984-07-13 |
| FR2490227A1 (fr) | 1982-03-19 |
| HU184825B (en) | 1984-10-29 |
| GR75080B (enEXAMPLES) | 1984-07-13 |
| GB2099422A (en) | 1982-12-08 |
| JPS57501627A (enEXAMPLES) | 1982-09-09 |
| FI64802B (fi) | 1983-09-30 |
| PT73656B (en) | 1983-02-01 |
| FI64802C (fi) | 1984-01-10 |
| WO1982001001A1 (en) | 1982-04-01 |
| PL133452B1 (en) | 1985-06-29 |
| ES8302670A1 (es) | 1982-12-01 |
| DE3152331A1 (de) | 1982-10-07 |
| IT8123897A0 (it) | 1981-09-11 |
| SE8202931L (sv) | 1982-05-10 |
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