CS258108B2 - Method of rs-(2-quinoxalinyl-1,4-dioxide)-(4-oxo-2-thion-5-thiazolidinyl)methanol preparation - Google Patents
Method of rs-(2-quinoxalinyl-1,4-dioxide)-(4-oxo-2-thion-5-thiazolidinyl)methanol preparation Download PDFInfo
- Publication number
- CS258108B2 CS258108B2 CS814080A CS408081A CS258108B2 CS 258108 B2 CS258108 B2 CS 258108B2 CS 814080 A CS814080 A CS 814080A CS 408081 A CS408081 A CS 408081A CS 258108 B2 CS258108 B2 CS 258108B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- general formula
- stands
- hydrogen
- feed
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 241001465754 Metazoa Species 0.000 abstract description 19
- -1 nitro-substituted phenyl Chemical group 0.000 abstract description 10
- 239000003674 animal food additive Substances 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052757 nitrogen Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 229910052760 oxygen Chemical group 0.000 abstract 2
- 229910052717 sulfur Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000001301 oxygen Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 13
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- 230000004584 weight gain Effects 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 239000011573 trace mineral Substances 0.000 description 5
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
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- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 229940047044 vitamin b 12 5 mg Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Birds (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS855167A CS258128B2 (cs) | 1981-06-02 | 1985-07-10 | Způsob výroby Κδ-(2-ο1ιΐηοχ3ΐΐηγ1-1,4-ύίοχίΰ)-(4<-οχο-2ι4Μοη-5<- -thiazolidinyl) methanolu |
| CS855166A CS258127B2 (cs) | 1981-06-02 | 1985-07-10 | Způsob výroby RS-(2-chinoxalinyl-l,4-dioxid)-(4 ‘ -oxo-2 ‘ -thion-5 ‘ -thiazolidinyl) methanolu |
| CS855170A CS258130B2 (cs) | 1980-06-03 | 1985-07-10 | Krmná přísada |
| CS855169A CS258129B2 (cs) | 1981-06-02 | 1985-07-10 | Způsob přípravy RS-(2-chinoxalinyl-l,4-dioxid)-(4‘-oxo-2‘-thion-5‘- -thiazolidinyl) methanolu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU801386A HU184293B (en) | 1980-06-03 | 1980-06-03 | Process for preparing quinoxaline-1,4-dioxide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS258108B2 true CS258108B2 (en) | 1988-07-15 |
Family
ID=10954225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS814080A CS258108B2 (en) | 1980-06-03 | 1981-06-02 | Method of rs-(2-quinoxalinyl-1,4-dioxide)-(4-oxo-2-thion-5-thiazolidinyl)methanol preparation |
Country Status (35)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1194451B (it) * | 1983-11-07 | 1988-09-22 | Daniele Gatti | Composti utili per combattere la dissenteria dei suini e come fattori di crescita,metodo per prepararli e composizioni che li contengono |
| CN102464642B (zh) * | 2010-11-18 | 2014-04-23 | 谢联金 | 一种化合物及其制备方法及其作为饲料添加剂的应用 |
Family Cites Families (6)
| 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 |
| US3926992A (en) * | 1972-11-03 | 1975-12-16 | Pfizer | Aldol products of 2-quinoxalinecarboxaldehy-1,4-dioxides |
| CS195508B1 (en) * | 1977-08-02 | 1980-02-29 | Jaromir Hebky | Cyanacetylhydrazones of 2-formylquinoxalin-1,4-dioxide |
| US4224324A (en) * | 1979-05-21 | 1980-09-23 | International Minerals And Chemical Corporation | Nitro-olefin-substituted quinoxaline dioxides |
| US4303657A (en) * | 1979-05-21 | 1981-12-01 | International Minerals & Chemical Corp. | Nitrohydroxyalkyl-substituted quinoxaxiline dioxides and alkanoic acid esters thereof |
| HU184772B (en) * | 1980-05-23 | 1984-10-29 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing quinoxaline-1,4-dioxide derivatives |
-
1980
- 1980-06-03 HU HU801386A patent/HU184293B/hu not_active IP Right Cessation
-
1981
- 1981-05-27 IN IN564/CAL/81A patent/IN154091B/en unknown
- 1981-06-02 RO RO108876A patent/RO85819B/ro unknown
- 1981-06-02 ES ES502681A patent/ES502681A0/es active Granted
- 1981-06-02 PL PL1981242731A patent/PL132408B1/pl unknown
- 1981-06-02 ZW ZW126/81A patent/ZW12681A1/xx unknown
- 1981-06-02 CS CS814080A patent/CS258108B2/cs unknown
- 1981-06-02 SE SE8103472A patent/SE454511B/sv not_active IP Right Cessation
- 1981-06-02 PL PL1981238599A patent/PL130661B1/pl unknown
- 1981-06-02 BE BE1/010241A patent/BE889048A/fr not_active IP Right Cessation
- 1981-06-02 PT PT73121A patent/PT73121B/pt unknown
- 1981-06-02 NO NO811859A patent/NO158502C/no unknown
- 1981-06-02 NZ NZ197269A patent/NZ197269A/xx unknown
- 1981-06-02 YU YU139381A patent/YU48449B/sh unknown
- 1981-06-02 DD DD81241587A patent/DD202384A5/de unknown
- 1981-06-02 US US06/269,720 patent/US4373100A/en not_active Expired - Lifetime
- 1981-06-02 PL PL1981238597A patent/PL130659B1/pl unknown
- 1981-06-02 RO RO108878A patent/RO85821B/ro unknown
- 1981-06-02 PH PH25711A patent/PH17078A/en unknown
- 1981-06-02 GB GB8116802A patent/GB2078216B/en not_active Expired
- 1981-06-02 LU LU83409A patent/LU83409A1/de unknown
- 1981-06-02 DD DD81230505A patent/DD159333A5/de not_active IP Right Cessation
- 1981-06-02 CA CA000378885A patent/CA1177486A/en not_active Expired
- 1981-06-02 PL PL1981231451A patent/PL133906B1/pl unknown
- 1981-06-02 RO RO108877A patent/RO85820B/ro unknown
- 1981-06-02 BR BR8103477A patent/BR8103477A/pt unknown
- 1981-06-02 FI FI811704A patent/FI73419C/fi not_active IP Right Cessation
- 1981-06-02 PL PL1981238598A patent/PL130660B1/pl unknown
- 1981-06-02 IE IE1214/81A patent/IE52088B1/en unknown
- 1981-06-02 AU AU71257/81A patent/AU539507B2/en not_active Ceased
- 1981-06-02 FR FR8110868A patent/FR2483416B1/fr not_active Expired
- 1981-06-02 DK DK241481A patent/DK151258C/da not_active IP Right Cessation
- 1981-06-02 RO RO81104477A patent/RO82505A/ro unknown
- 1981-06-02 IT IT8122084A patent/IT1211055B/it active
- 1981-06-02 CH CH3587/81A patent/CH648303A5/de not_active IP Right Cessation
- 1981-06-02 IL IL63018A patent/IL63018A/xx unknown
- 1981-06-02 NL NL8102660A patent/NL8102660A/nl not_active Application Discontinuation
- 1981-06-03 SU SU813294401A patent/SU1192622A3/ru active
- 1981-06-03 DE DE19813121978 patent/DE3121978A1/de active Granted
- 1981-06-03 JP JP8555581A patent/JPS5724370A/ja active Pending
- 1981-06-03 GR GR65142A patent/GR75689B/el unknown
-
1982
- 1982-03-22 PH PH27030A patent/PH18535A/en unknown
- 1982-05-31 ES ES512695A patent/ES8304953A1/es not_active Expired
- 1982-05-31 ES ES512696A patent/ES512696A0/es active Granted
- 1982-05-31 ES ES512697A patent/ES8303363A1/es not_active Expired
- 1982-07-09 SU SU823461110A patent/SU1396957A3/ru active
- 1982-08-04 AR AR290225A patent/AR229879A1/es active
- 1982-08-04 AR AR290224A patent/AR229613A1/es active
- 1982-09-16 SU SU823491021A patent/SU1176838A3/ru active
- 1982-09-16 SU SU823490999A patent/SU1169537A3/ru active
- 1982-10-16 SU SU823491000A patent/SU1205765A3/ru active
- 1982-10-28 SU SU823506791A patent/SU1186616A1/ru active
-
1983
- 1983-04-18 YU YU874/83A patent/YU42852B/xx unknown
- 1983-04-18 YU YU875/83A patent/YU42853B/xx unknown
- 1983-04-18 YU YU873/83A patent/YU42851B/xx unknown
- 1983-06-24 SU SU833608870A patent/SU1189346A3/ru active
-
1984
- 1984-05-10 AR AR296612A patent/AR231140A1/es active
- 1984-11-22 HK HK912/84A patent/HK91284A/xx unknown
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