PL132408B1 - Process for preparing novel derivative of quinoxaline - Google Patents
Process for preparing novel derivative of quinoxaline Download PDFInfo
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- PL132408B1 PL132408B1 PL1981242731A PL24273181A PL132408B1 PL 132408 B1 PL132408 B1 PL 132408B1 PL 1981242731 A PL1981242731 A PL 1981242731A PL 24273181 A PL24273181 A PL 24273181A PL 132408 B1 PL132408 B1 PL 132408B1
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- Prior art keywords
- quinoxaline
- compound
- feed
- dioxide
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 16
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000000879 imine group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 239000003674 animal food additive Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000019786 weight gain Nutrition 0.000 description 4
- -1 Alkylene glycols Chemical class 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 239000000080 wetting agent Substances 0.000 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 description 2
- HYMJHROUVPWYNQ-UHFFFAOYSA-N 2-amino-1,3-thiazol-4-one Chemical compound NC1=NC(=O)CS1 HYMJHROUVPWYNQ-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000003975 animal breeding Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000021051 daily weight gain Nutrition 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940036811 bone meal Drugs 0.000 description 1
- 239000002374 bone meal Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 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
- 230000000694 effects Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 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
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- 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
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- 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)
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- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowej pochodnej chinoksaliny o wzorze 1, a mianowicie 1,4-dwutlenku RS-/2-chinoksalinylo/-/4-keto-2-tiono-5tiazolidynylo/-metanolu. Zwiazek ten podwyzsza przyrost wagi ciala zwierzat hodowlanych. Wiadomo, ze pewne pochodne 1,4-dwutlenku chinoksaliny maja wlasciwosci przeciwmikrobowe i zwiekszaja przyrost wagowy (porównaj opis patentowy St. Zjedn. Ameryki nr 3 371 090, belgijski opis patentowy BE-PS nr 764 088, opis patentowy Republiki Federalnej Niemiec DE-PS nr 1 670 935).Sposób wytwarzania nowej pochodnej o wzorze 1 polega wedlug wynalazku na tym, ze zwiazek o ogólnym wzorze 2, w którym X oznacza atom tlenu lub grupe iminowa, poddaje sie reakcji korzystnie z pieciosiarczkiem wegla/Mozna tez stosowac inne srodki sulfonujace. Sposobem wedlug wynalazku egzocykliczny atom tlenu lub egzocykliczna grupe iminowa w zwiazku o ogólnym wzorze 2 wymienia sie na znanej drodze na atom siarki.Reakqe prowadzi sie w warunkach ogrzewania, korzystnie w temperaturze 120— 180°C. W przypadku stosowa¬ nia dwusiarczku wegla, reakcje prowadzi sie celowo w naczyniu zamknietym w temperaturze 140 —180°C.W przypadku stosowania piecioszarczku dwufosforu reakcje prowadzi sie korzystnie w temperaturze 120-160°C.Stosowane jako substrat zwiazki o ogólnym wzorze 2 sa zwiazkami nowymi. Mozna je wytwarzac droga reakcji 1,4-dwutlenku 2-formylo-chinoksaliny lub jego acetalu z 4-keto-2-iminotiazolidyna lub z 2,4-dwu- ketotiazolidyna. Zwiazek o wzorze 1 mozna stosowac jako dodatek zwiekszajacy przyrost wagowy w hodowli zwierzat, zwlaszcza w hodowli swin. Nowy zwiazek mozna wprowadzac w celu profilaktyki lub leczenia róznych zakazen bakteryjnych. Zwiazek ten jest skuteczny przeciwko róznym gatunkom bakterii Gram-dodatnich i Gram-ujemnych, takich jak Escherichia coli, Salmonella cholerasuis, Staphylococcus aureus, Streptococcus pyogenes i Pasteurella multocida. Zaleznie od danego szczepu bakterii minimalne stezenie hamujace wynosi 0,5-120-y/ml.Odzywcze dzialanie nowego zwiazku stwierdzono za pomoca nizej omówionej próby. Swinie, jako zwie¬ rzeta doswiadczalne, karmiono pasza, która zawierala nowy zwiazek w ilosci 50 mg/kg paszy. Grupa zwierzat sprawdzianowych otrzymywala dokladnie taka sama ilosc paszy, lecz bez dodatku nowego zwiazku. Kazda z badanych grup skladala sie z 10 zwierzat. Gdy dzienne przyrosty wagowe grupy sprawdzianowej przyjeto za 100%, to dzienne przyrosty wagowe grupy zwierzat traktowanych zwiazkiem o wzorze 1 wynosily 150,2%.2 132 408 Obliczajac naklad wlasciwy paszy (kg paszy via 1 kg uzyskanego miesa) okazalo sie, ze naklad wlasciwy paszy w grupie zwierzat doswiadczalnych byl mniejszy i wynosil tylko 72,0% nakladu wlasciwego paszy w grupie sprawdzianowej.Zwiazek o wzorze 1 mozna zatem stosowac w hodowli zwierzat w postaci dodatku paszowego w celu podwyzszenia przyrostu wagowego. Jako nosniki odpowiednie sa substancje pochodzenia roslinnego lub zwierze¬ cego, przeznaczone na karme dla zwierzat, takie jak kasza pszeniczna, maka jeczmienna, zytnia, owsiana, otreby ryzowe, otreby pszeniczne, maka sojowa, maka z kielków kukurydzianych, maczka kostna, maka z lucerny, kasza sojowa, maczka miesna, maczka rybna lub ich mieszaniny. Szczególnie korzystnie jako nosnik stosuje sie bezwlóknisty koncentrat paszowy z roslin zielonych o podwyzszonej zawartosci bialka, taki jak koncentrat o nazwie handlowej VEPEX.® Jako substancje pomocnicze mozna stosowac np. krzemionke, zwilzacze, przeciwutleniacze, skrobie, fosfo¬ ran dwuwapniowy, weglan wapniowy, kwas sorbowy itp. Jako zwilzacze wchodza w rachube nietoksyczne oleje, takie jak olej sojowy, olej kukurydziany i oleje mineralne. Jako zwilzacze korzystnymi sa glikole alkilenowe. Jako skrobie odpowiednie sa skrobie kukurydziana, pszeniczna lub ziemniaczana. Dodatki paszowe, zawierajace zwiazek wytworzony sposobem wedlug wynalazku, na ogól zawieraja 5 — 80% wagowych, korzystnie okolo 10 — 80% wagowych, a zwlaszcza 20 — 50% wagowych substancji Czynnej o wzorze 1. Pasza zmieszana z dodat¬ kiem paszowym zawiera wówczas substancje czynna w stezeniu 1 —400 ppm, korzystnie 10— 100 ppm. Do¬ datki paszowe lub pasze moga zawierac tez znane witaminy, np. witamine A, Bi, B2, B3, B6, B12, E i K oraz mikroelementy, np. Mn, Fe, Zn, Cu i J.Podane nizej przyklady objasniaja blizej sposób wedlug wynalazku. Temperatury topnienia podane w przykladach oznaczono za pomoca przyrzadu KoffJera.Przyklad I. 6,1 g (0,02 mola) 1,4-dwutlenku RS-/2-chinoksalinylo/- /4-keto-2-imino-5-tia- zolidynylo/—metanolu, 1,9 g (0,025 mola) dwusiarczku wegla i 50 ml etanolu ogrzewa sie w zamknietym naczy¬ niu w ciagu 2 godzin w temperaturze 160°C. Mieszanine reakcyjna chlodzi sie, a produkt odsacza sie, otrzymu¬ jac 5,5 g (85% wydajnosci teoretycznej) 1,4dwutlenku RS-/2-chinoksalinylo/ -/4-keto—2-tiono— 5-tiazoli- dynylo/—metanolu o temperaturze topnienia 293- 294°C. Substrat wytwarzac mozna w sposób omówiony ni¬ zej. Mieszanine 19,0 g (0,1 mola) 1,4-dwutlenku 2—formylo—chinoksaliny, 11,6 g (0,1 mola) 4—keto—2-imino- tiazolidyny, 200 ml izopropanolu i 4 ml 10%—owego wodnego lugu sodowego miesza sie w temperaturze pokojo¬ wej wciagu 3godzin. Mieszanine reakcyjna chlodzi sie, a produkt odsacza sie, otrzymujac 25,1 g (82% wydaj¬ nosci teoretycznej) 1,4-dwutlenku RS-/2-chinoksalinylo/ —/4—keto—2—imino —5-tiazolidynylo/—metanolu o temperaturze topnienia 220°C.Przyklad II. Postepuje sie analogicznie jak w przykladzie I, lecz z ta róznica, ze zamiast dwusiarczku wegla stosuje sie 0,025 mola pieciosiarczku dwufosforu. Otrzymuje sie 5,6 g (88% wydajnosci teoretycznej) 1,4-dwutlenku RS—12—chinoksalinylo/—/4 —keto—2—tiono—5 -tiazolidynyló/-metanolu o temperaturze top¬ nienia 293- 294°C.Zastrzezenia patentowe 1. Sposób wytwarzania nowej pochodnej chinoksaliny o wzorze 1, a mianowicie 1,4-dwutlenku RS—/2-chinoksalinylo/—/4#—keto—2—tiono—5 —tiazolidynylo/-metanolu, znamienny tym, ze zwiazek o ogólnym wzorze 2, w którym X oznacza atom tlenu lub grupe iminowa, poddaje sie reakcji z pieciosiarczkiem dwufosforu lub z dwusiarczkiem wegla. 2. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w temperaturze 120-180°C.Pracownia Poligraficzna UP PRL. Naklad 100 egz.Ona 100 zl PL PL PL
Claims (2)
1.Zastrzezenia patentowe 1. Sposób wytwarzania nowej pochodnej chinoksaliny o wzorze 1, a mianowicie 1,4-dwutlenku RS—/2-chinoksalinylo/—/4#—keto—2—tiono—5 —tiazolidynylo/-metanolu, znamienny tym, ze zwiazek o ogólnym wzorze 2, w którym X oznacza atom tlenu lub grupe iminowa, poddaje sie reakcji z pieciosiarczkiem dwufosforu lub z dwusiarczkiem wegla.
2. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w temperaturze 120-180°C. Pracownia Poligraficzna UP PRL. Naklad 100 egz. Ona 100 zl PL PL PL
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 |
|---|---|
| PL132408B1 true PL132408B1 (en) | 1985-02-28 |
Family
ID=10954225
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981242731A PL132408B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivative of quinoxaline |
| PL1981231451A PL133906B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing derivatives of methylquinoxaline 1,4-dioxide |
| PL1981238598A PL130660B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivatives of methylquinoxaline 1,4-dioxide |
| PL1981238599A PL130661B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivatives of methylquinoxaline 1,4-dioxide |
| PL1981238597A PL130659B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivatives of methylquinoxaline 1,4-dioxide |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981231451A PL133906B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing derivatives of methylquinoxaline 1,4-dioxide |
| PL1981238598A PL130660B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivatives of methylquinoxaline 1,4-dioxide |
| PL1981238599A PL130661B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivatives of methylquinoxaline 1,4-dioxide |
| PL1981238597A PL130659B1 (en) | 1980-06-03 | 1981-06-02 | Process for preparing novel derivatives of methylquinoxaline 1,4-dioxide |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US4373100A (pl) |
| JP (1) | JPS5724370A (pl) |
| AR (3) | AR229613A1 (pl) |
| AU (1) | AU539507B2 (pl) |
| BE (1) | BE889048A (pl) |
| BR (1) | BR8103477A (pl) |
| CA (1) | CA1177486A (pl) |
| CH (1) | CH648303A5 (pl) |
| CS (1) | CS258108B2 (pl) |
| DD (2) | DD159333A5 (pl) |
| DE (1) | DE3121978A1 (pl) |
| DK (1) | DK151258C (pl) |
| ES (4) | ES502681A0 (pl) |
| FI (1) | FI73419C (pl) |
| FR (1) | FR2483416B1 (pl) |
| GB (1) | GB2078216B (pl) |
| GR (1) | GR75689B (pl) |
| HK (1) | HK91284A (pl) |
| HU (1) | HU184293B (pl) |
| IE (1) | IE52088B1 (pl) |
| IL (1) | IL63018A (pl) |
| IN (1) | IN154091B (pl) |
| IT (1) | IT1211055B (pl) |
| LU (1) | LU83409A1 (pl) |
| NL (1) | NL8102660A (pl) |
| NO (1) | NO158502C (pl) |
| NZ (1) | NZ197269A (pl) |
| PH (2) | PH17078A (pl) |
| PL (5) | PL132408B1 (pl) |
| PT (1) | PT73121B (pl) |
| RO (4) | RO82505A (pl) |
| SE (1) | SE454511B (pl) |
| SU (7) | SU1192622A3 (pl) |
| YU (4) | YU48449B (pl) |
| ZW (1) | ZW12681A1 (pl) |
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 |
| US4303657A (en) * | 1979-05-21 | 1981-12-01 | International Minerals & Chemical Corp. | Nitrohydroxyalkyl-substituted quinoxaxiline dioxides and alkanoic acid esters thereof |
| US4224324A (en) * | 1979-05-21 | 1980-09-23 | International Minerals And Chemical Corporation | Nitro-olefin-substituted quinoxaline dioxides |
| 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 RO81104477A patent/RO82505A/ro unknown
- 1981-06-02 DK DK241481A patent/DK151258C/da not_active IP Right Cessation
- 1981-06-02 RO RO108876A patent/RO85819B/ro unknown
- 1981-06-02 CS CS814080A patent/CS258108B2/cs unknown
- 1981-06-02 PL PL1981242731A patent/PL132408B1/pl unknown
- 1981-06-02 DD DD81230505A patent/DD159333A5/de not_active IP Right Cessation
- 1981-06-02 FR FR8110868A patent/FR2483416B1/fr not_active Expired
- 1981-06-02 ES ES502681A patent/ES502681A0/es active Granted
- 1981-06-02 YU YU139381A patent/YU48449B/sh unknown
- 1981-06-02 PT PT73121A patent/PT73121B/pt unknown
- 1981-06-02 NO NO811859A patent/NO158502C/no unknown
- 1981-06-02 BR BR8103477A patent/BR8103477A/pt unknown
- 1981-06-02 GB GB8116802A patent/GB2078216B/en not_active Expired
- 1981-06-02 NZ NZ197269A patent/NZ197269A/xx unknown
- 1981-06-02 IE IE1214/81A patent/IE52088B1/en unknown
- 1981-06-02 US US06/269,720 patent/US4373100A/en not_active Expired - Lifetime
- 1981-06-02 CH CH3587/81A patent/CH648303A5/de not_active IP Right Cessation
- 1981-06-02 BE BE1/010241A patent/BE889048A/fr not_active IP Right Cessation
- 1981-06-02 IL IL63018A patent/IL63018A/xx unknown
- 1981-06-02 PL PL1981231451A patent/PL133906B1/pl unknown
- 1981-06-02 PL PL1981238598A patent/PL130660B1/pl unknown
- 1981-06-02 RO RO108877A patent/RO85820B/ro unknown
- 1981-06-02 CA CA000378885A patent/CA1177486A/en not_active Expired
- 1981-06-02 RO RO108878A patent/RO85821B/ro unknown
- 1981-06-02 FI FI811704A patent/FI73419C/fi not_active IP Right Cessation
- 1981-06-02 IT IT8122084A patent/IT1211055B/it active
- 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 PL PL1981238597A patent/PL130659B1/pl unknown
- 1981-06-02 ZW ZW126/81A patent/ZW12681A1/xx unknown
- 1981-06-02 LU LU83409A patent/LU83409A1/de unknown
- 1981-06-02 NL NL8102660A patent/NL8102660A/nl not_active Application Discontinuation
- 1981-06-02 PH PH25711A patent/PH17078A/en unknown
- 1981-06-02 DD DD81241587A patent/DD202384A5/de unknown
- 1981-06-02 AU AU71257/81A patent/AU539507B2/en not_active Ceased
- 1981-06-03 GR GR65142A patent/GR75689B/el unknown
- 1981-06-03 JP JP8555581A patent/JPS5724370A/ja active Pending
- 1981-06-03 DE DE19813121978 patent/DE3121978A1/de active Granted
- 1981-06-03 SU SU813294401A patent/SU1192622A3/ru active
-
1982
- 1982-03-22 PH PH27030A patent/PH18535A/en unknown
- 1982-05-31 ES ES512697A patent/ES512697A0/es active Granted
- 1982-05-31 ES ES512695A patent/ES8304953A1/es not_active Expired
- 1982-05-31 ES ES512696A patent/ES8303362A1/es not_active Expired
- 1982-07-09 SU SU823461110A patent/SU1396957A3/ru active
- 1982-08-04 AR AR290224A patent/AR229613A1/es active
- 1982-08-04 AR AR290225A patent/AR229879A1/es active
- 1982-09-16 SU SU823490999A patent/SU1169537A3/ru active
- 1982-09-16 SU SU823491021A patent/SU1176838A3/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 YU873/83A patent/YU42851B/xx unknown
- 1983-04-18 YU YU874/83A patent/YU42852B/xx unknown
- 1983-04-18 YU YU875/83A patent/YU42853B/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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