DK142872B - Analogifremgangsmåde til fremstilling af trifluormethylsubstituerede kondenserede quinoxalinderivater. - Google Patents
Analogifremgangsmåde til fremstilling af trifluormethylsubstituerede kondenserede quinoxalinderivater. Download PDFInfo
- Publication number
- DK142872B DK142872B DK320576AA DK320576A DK142872B DK 142872 B DK142872 B DK 142872B DK 320576A A DK320576A A DK 320576AA DK 320576 A DK320576 A DK 320576A DK 142872 B DK142872 B DK 142872B
- Authority
- DK
- Denmark
- Prior art keywords
- compounds
- mice
- preparation
- quinoxaline
- cells
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 12
- 230000008569 process Effects 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title description 4
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title 1
- 241000699670 Mus sp. Species 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000427 antigen Substances 0.000 description 12
- 102000036639 antigens Human genes 0.000 description 12
- 108091007433 antigens Proteins 0.000 description 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical class N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- 210000000952 spleen Anatomy 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000028993 immune response Effects 0.000 description 9
- 239000003018 immunosuppressive agent Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 150000002988 phenazines Chemical class 0.000 description 8
- VRSLSEDOBUYIMM-UHFFFAOYSA-N acenaphthyleno[1,2-b]quinoxaline Chemical compound C1=CC(C=2C3=NC4=CC=CC=C4N=2)=C2C3=CC=CC2=C1 VRSLSEDOBUYIMM-UHFFFAOYSA-N 0.000 description 7
- 210000000056 organ Anatomy 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000036039 immunity Effects 0.000 description 6
- 229940125721 immunosuppressive agent Drugs 0.000 description 6
- 150000003252 quinoxalines Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 5
- 210000003743 erythrocyte Anatomy 0.000 description 5
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 3
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- KHPYJVQRBJJYSF-UHFFFAOYSA-N phenanthro[9,10-b]quinoxaline Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CC=C3C2=C1 KHPYJVQRBJJYSF-UHFFFAOYSA-N 0.000 description 3
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- MFLJFFUIURSSKM-UHFFFAOYSA-N 2-nitro-6-(trifluoromethyl)aniline Chemical compound NC1=C([N+]([O-])=O)C=CC=C1C(F)(F)F MFLJFFUIURSSKM-UHFFFAOYSA-N 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- JJUXUJPUXCPFSX-UHFFFAOYSA-N 11-(trifluoromethyl)phenanthro[9,10-b]quinoxaline Chemical compound C1=CC=C2C3=NC4=CC(C(F)(F)F)=CC=C4N=C3C3=CC=CC=C3C2=C1 JJUXUJPUXCPFSX-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- JRQDVRIQJJPHEQ-UHFFFAOYSA-N 3970-35-2 Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JRQDVRIQJJPHEQ-UHFFFAOYSA-N 0.000 description 1
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- UDLKVLXSHAGGEQ-UHFFFAOYSA-N 9-(trifluoromethyl)acenaphthyleno[1,2-b]quinoxaline Chemical compound C1=CC(C2=NC3=CC=C(C=C3N=C22)C(F)(F)F)=C3C2=CC=CC3=C1 UDLKVLXSHAGGEQ-UHFFFAOYSA-N 0.000 description 1
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
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- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
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- 231100000283 hepatitis Toxicity 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000004727 humoral immunity Effects 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000008629 immune suppression Effects 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
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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
- C07D241/38—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Transplantation (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59654375 | 1975-07-16 | ||
| US05/596,543 US4024142A (en) | 1975-07-16 | 1975-07-16 | Quinoxaline derivatives as immune regulants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK320576A DK320576A (cs) | 1977-01-17 |
| DK142872B true DK142872B (da) | 1981-02-16 |
| DK142872C DK142872C (cs) | 1981-09-21 |
Family
ID=24387731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK320576AA DK142872B (da) | 1975-07-16 | 1976-07-15 | Analogifremgangsmåde til fremstilling af trifluormethylsubstituerede kondenserede quinoxalinderivater. |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US4024142A (cs) |
| JP (1) | JPS5212181A (cs) |
| AR (1) | AR213409A1 (cs) |
| AT (1) | AT351032B (cs) |
| AU (1) | AU498254B2 (cs) |
| BE (1) | BE844084A (cs) |
| BG (2) | BG25646A3 (cs) |
| CA (1) | CA1057289A (cs) |
| CH (1) | CH621779A5 (cs) |
| CS (1) | CS189016B2 (cs) |
| DD (1) | DD126751A5 (cs) |
| DE (1) | DE2631888A1 (cs) |
| DK (1) | DK142872B (cs) |
| FR (1) | FR2317931A1 (cs) |
| GB (1) | GB1550467A (cs) |
| GR (1) | GR62257B (cs) |
| HU (1) | HU172133B (cs) |
| IE (1) | IE43242B1 (cs) |
| IL (1) | IL49880A (cs) |
| MX (1) | MX3387E (cs) |
| NL (1) | NL7607882A (cs) |
| NZ (1) | NZ181248A (cs) |
| PH (1) | PH12095A (cs) |
| PL (1) | PL100501B1 (cs) |
| PT (1) | PT65343B (cs) |
| RO (1) | RO72510A (cs) |
| SE (1) | SE423814B (cs) |
| SU (1) | SU674673A3 (cs) |
| YU (1) | YU160576A (cs) |
| ZA (1) | ZA763764B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60130541A (ja) * | 1983-12-15 | 1985-07-12 | Sumitomo Chem Co Ltd | メチルフエノ−ルの製造方法 |
| JPS62240637A (ja) * | 1986-04-11 | 1987-10-21 | Maruzen Petrochem Co Ltd | フエノ−ル類のアルキル化方法 |
| EP2125756A4 (en) * | 2007-01-16 | 2011-06-15 | Jj Pharma Inc | PHENAZINE COMPOUNDS AND THEIR USE FOR THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISEASES |
| US8336289B2 (en) * | 2007-08-30 | 2012-12-25 | United Technologies Corporation | Gas turbine engine systems and related methods involving multiple gas turbine cores |
| WO2012054739A2 (en) * | 2010-10-21 | 2012-04-26 | New York University | Structure-guided identification of binding interactions of human laminin receptor precursor with laminin and identification of compounds that affect binding |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2046254A (en) * | 1932-06-14 | 1936-06-30 | Gen Aniline Works Inc | Vat dyestuffs derived from aceanthrenequinone and process of preparing them |
| US3005789A (en) * | 1955-10-11 | 1961-10-24 | Gen Aniline & Film Corp | Drier composition |
| US3481931A (en) * | 1965-06-01 | 1969-12-02 | Donald L Vivian | Acenaphtho(1,2-b)quinoxaline,7,12-dioxide |
-
1975
- 1975-07-16 US US05/596,543 patent/US4024142A/en not_active Expired - Lifetime
-
1976
- 1976-06-19 GR GR51044A patent/GR62257B/el unknown
- 1976-06-21 IE IE1334/76A patent/IE43242B1/en unknown
- 1976-06-21 CA CA255,318A patent/CA1057289A/en not_active Expired
- 1976-06-22 NZ NZ181248A patent/NZ181248A/xx unknown
- 1976-06-23 IL IL49880A patent/IL49880A/xx unknown
- 1976-06-23 ZA ZA00763764A patent/ZA763764B/xx unknown
- 1976-06-24 AU AU15256/76A patent/AU498254B2/en not_active Expired
- 1976-06-25 PH PH18612A patent/PH12095A/en unknown
- 1976-06-30 YU YU01605/76A patent/YU160576A/xx unknown
- 1976-07-05 JP JP51080326A patent/JPS5212181A/ja active Pending
- 1976-07-08 PT PT65343A patent/PT65343B/pt unknown
- 1976-07-12 GB GB28834/76A patent/GB1550467A/en not_active Expired
- 1976-07-13 MX MX001305U patent/MX3387E/es unknown
- 1976-07-14 AT AT517476A patent/AT351032B/de not_active IP Right Cessation
- 1976-07-14 BE BE1007508A patent/BE844084A/xx unknown
- 1976-07-15 CH CH909576A patent/CH621779A5/de not_active IP Right Cessation
- 1976-07-15 BG BG033757A patent/BG25646A3/xx unknown
- 1976-07-15 DK DK320576AA patent/DK142872B/da unknown
- 1976-07-15 NL NL7607882A patent/NL7607882A/xx not_active Application Discontinuation
- 1976-07-15 FR FR7621655A patent/FR2317931A1/fr active Granted
- 1976-07-15 SU SU762381008A patent/SU674673A3/ru active
- 1976-07-15 DD DD193904A patent/DD126751A5/xx unknown
- 1976-07-15 DE DE19762631888 patent/DE2631888A1/de not_active Withdrawn
- 1976-07-15 BG BG034558A patent/BG26668A4/xx unknown
- 1976-07-15 SE SE7608115A patent/SE423814B/xx unknown
- 1976-07-15 HU HU76EI00000688A patent/HU172133B/hu unknown
- 1976-07-16 RO RO7687004A patent/RO72510A/ro unknown
- 1976-07-16 AR AR263978A patent/AR213409A1/es active
- 1976-07-16 CS CS764733A patent/CS189016B2/cs unknown
- 1976-07-16 PL PL1976191224A patent/PL100501B1/pl unknown
- 1976-12-23 US US05/754,065 patent/US4064127A/en not_active Expired - Lifetime
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