JPS5951947B2 - １，４↓−ジオキソ↓−および４↓−オキソキノキサリン↓−２↓−カルボキサルデヒドスルホニルヒドラゾン類 - Google Patents
１，４↓−ジオキソ↓−および４↓−オキソキノキサリン↓−２↓−カルボキサルデヒドスルホニルヒドラゾン類Info
- Publication number
- JPS5951947B2 JPS5951947B2 JP53004165A JP416578A JPS5951947B2 JP S5951947 B2 JPS5951947 B2 JP S5951947B2 JP 53004165 A JP53004165 A JP 53004165A JP 416578 A JP416578 A JP 416578A JP S5951947 B2 JPS5951947 B2 JP S5951947B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- reaction
- phenyl
- compound
- carboxaldehyde
- 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
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- 238000000034 method Methods 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 23
- -1 alkyl acetal Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
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- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
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- 239000012442 inert solvent Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
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- 239000013583 drug formulation Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000012840 feeding operation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- HORFVOWTVOJVAN-UHFFFAOYSA-N isoquinoline-1-carbaldehyde Chemical class C1=CC=C2C(C=O)=NC=CC2=C1 HORFVOWTVOJVAN-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000006180 nutrition needs Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 238000010267 two-fold dilution method Methods 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US000000760271 | 1977-01-18 | ||
| US05/760,271 US4100284A (en) | 1977-01-18 | 1977-01-18 | 1,4-Dioxo- and 4-oxoquinoxaline-2-carboxaldehyde sulfonylhydrazones and certain derivatives thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5390278A JPS5390278A (en) | 1978-08-08 |
| JPS5951947B2 true JPS5951947B2 (ja) | 1984-12-17 |
Family
ID=25058592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53004165A Expired JPS5951947B2 (ja) | 1977-01-18 | 1978-01-18 | １，４↓−ジオキソ↓−および４↓−オキソキノキサリン↓−２↓−カルボキサルデヒドスルホニルヒドラゾン類 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4100284A (en]) |
| JP (1) | JPS5951947B2 (en]) |
| BE (1) | BE862927A (en]) |
| DE (1) | DE2801412A1 (en]) |
| DK (1) | DK140758B (en]) |
| FR (1) | FR2377388A1 (en]) |
| GB (1) | GB1561624A (en]) |
| IE (1) | IE46711B1 (en]) |
| IT (1) | IT1092747B (en]) |
| LU (1) | LU78874A1 (en]) |
| NL (1) | NL7800533A (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6334236U (en]) * | 1986-08-23 | 1988-03-05 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221791A (en) * | 1979-05-21 | 1980-09-09 | International Minerals & Chemical Corp. | Substituted quinoxaline dioxides |
| US4307219A (en) * | 1980-04-30 | 1981-12-22 | Minnesota Mining And Manufacturing Company | Aqueous solvent dispersible linear polyurethane resins |
| HU184772B (en) * | 1980-05-23 | 1984-10-29 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing quinoxaline-1,4-dioxide derivatives |
| HU184825B (en) * | 1980-09-12 | 1984-10-29 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives |
| CN106727576B (zh) * | 2015-12-29 | 2020-08-04 | 广州英赛特生物技术有限公司 | 喹噁啉-1，4-二氧化物衍生物作为硫酸粘杆菌素增效剂的应用 |
| CN112194631B (zh) * | 2020-09-18 | 2022-08-02 | 哈尔滨工业大学（深圳） | 席夫碱桥接的磺胺咪唑化合物及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3371090A (en) * | 1964-09-16 | 1968-02-27 | Pfizer & Co C | Novel antibacterial agents |
| US3493572A (en) * | 1968-07-05 | 1970-02-03 | Pfizer & Co C | Process for producing quinoxaline-di-n-oxides |
| DE2015676A1 (de) * | 1970-04-02 | 1971-10-21 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Neue Imine der 2-Formyl-chinoxalindi-N-oxidcarbon-säure-(3) und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als antimikrobielle Mittel |
| DE2122572A1 (de) * | 1971-05-07 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von neuen Derivaten von 2-Formyl-3-carbonatnido-chinoxalin-di-N-oxiden sowie ihre Verwendung als Arzneimittel und Futtermittelzusatz |
| US3928608A (en) * | 1972-03-14 | 1975-12-23 | Ici Ltd | Certain quinoxaline N-oxides used to combat fungi |
| US3931174A (en) * | 1974-01-23 | 1976-01-06 | Pfizer Inc. | Alkylmercaptomethylquinoxaline-1,4-dioxides and oxidized derivatives thereof |
-
1977
- 1977-01-18 US US05/760,271 patent/US4100284A/en not_active Expired - Lifetime
-
1978
- 1978-01-13 DE DE19782801412 patent/DE2801412A1/de not_active Withdrawn
- 1978-01-16 BE BE184337A patent/BE862927A/xx not_active IP Right Cessation
- 1978-01-16 LU LU78874A patent/LU78874A1/xx unknown
- 1978-01-17 IT IT19332/78A patent/IT1092747B/it active
- 1978-01-17 IE IE96/78A patent/IE46711B1/en unknown
- 1978-01-17 DK DK24378AA patent/DK140758B/da not_active IP Right Cessation
- 1978-01-17 FR FR7801197A patent/FR2377388A1/fr active Granted
- 1978-01-17 NL NL7800533A patent/NL7800533A/xx not_active Application Discontinuation
- 1978-01-18 GB GB1937/78A patent/GB1561624A/en not_active Expired
- 1978-01-18 JP JP53004165A patent/JPS5951947B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6334236U (en]) * | 1986-08-23 | 1988-03-05 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK140758C (en]) | 1980-04-28 |
| LU78874A1 (fr) | 1979-09-06 |
| IE780096L (en) | 1978-07-18 |
| IT1092747B (it) | 1985-07-12 |
| FR2377388A1 (fr) | 1978-08-11 |
| DK140758B (da) | 1979-11-12 |
| DE2801412A1 (de) | 1978-07-20 |
| FR2377388B1 (en]) | 1981-02-27 |
| NL7800533A (nl) | 1978-07-20 |
| JPS5390278A (en) | 1978-08-08 |
| GB1561624A (en) | 1980-02-27 |
| DK24378A (en]) | 1978-07-19 |
| IE46711B1 (en) | 1983-09-07 |
| IT7819332A0 (it) | 1978-01-17 |
| US4100284A (en) | 1978-07-11 |
| BE862927A (fr) | 1978-07-17 |
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