SE427751B - Pyridinderivat och sett for framstellning derav - Google Patents
Pyridinderivat och sett for framstellning deravInfo
- Publication number
- SE427751B SE427751B SE7812081A SE7812081A SE427751B SE 427751 B SE427751 B SE 427751B SE 7812081 A SE7812081 A SE 7812081A SE 7812081 A SE7812081 A SE 7812081A SE 427751 B SE427751 B SE 427751B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- compound
- treated
- pyridine
- preparing
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- -1 ketone compound Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000036325 urinary excretion Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 206010018910 Haemolysis Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 2
- 229960001650 glafenine Drugs 0.000 description 2
- 230000008588 hemolysis Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 235000008160 pyridoxine Nutrition 0.000 description 2
- 239000011677 pyridoxine Substances 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229960002180 tetracycline Drugs 0.000 description 2
- 229930101283 tetracycline Natural products 0.000 description 2
- 235000019364 tetracycline Nutrition 0.000 description 2
- 150000003522 tetracyclines Chemical class 0.000 description 2
- 229940011671 vitamin b6 Drugs 0.000 description 2
- UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 1
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101150060239 MOM1 gene Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BUIQRTDBPCHRIR-UHFFFAOYSA-L O[Cr](Cl)(=O)=O Chemical compound O[Cr](Cl)(=O)=O BUIQRTDBPCHRIR-UHFFFAOYSA-L 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005534 hematocrit Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4919977 | 1977-11-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7812081L SE7812081L (sv) | 1979-05-26 |
| SE427751B true SE427751B (sv) | 1983-05-02 |
Family
ID=10451529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7812081A SE427751B (sv) | 1977-11-25 | 1978-11-23 | Pyridinderivat och sett for framstellning derav |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4221795A (de) |
| JP (1) | JPS54109996A (de) |
| AR (1) | AR216558A1 (de) |
| AT (1) | AT366687B (de) |
| AU (1) | AU520800B2 (de) |
| BE (1) | BE872004A (de) |
| CA (1) | CA1096869A (de) |
| CH (1) | CH635345A5 (de) |
| DE (1) | DE2850948C2 (de) |
| DK (1) | DK148234C (de) |
| EG (1) | EG13732A (de) |
| ES (1) | ES475361A1 (de) |
| FI (1) | FI63941C (de) |
| FR (2) | FR2409998A1 (de) |
| HK (1) | HK18883A (de) |
| IE (1) | IE47417B1 (de) |
| IN (1) | IN150337B (de) |
| IT (1) | IT1101293B (de) |
| LU (1) | LU80523A1 (de) |
| MX (1) | MX5442E (de) |
| MY (1) | MY8500030A (de) |
| NL (1) | NL176265C (de) |
| NO (1) | NO150160C (de) |
| NZ (1) | NZ188973A (de) |
| OA (1) | OA06122A (de) |
| PT (1) | PT68824A (de) |
| SE (1) | SE427751B (de) |
| ZA (1) | ZA786269B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN156817B (de) * | 1981-02-10 | 1985-11-09 | Scras | |
| IN160104B (de) * | 1983-04-05 | 1987-06-27 | Scras | |
| ZA842029B (en) * | 1983-04-05 | 1984-10-31 | Scras | Furo-(3,4-c)-pyridine derivatives preparation thereof and therapeutic compositions containing the same |
| GB8327817D0 (en) * | 1983-10-18 | 1983-11-16 | Scras | 4-halo-furo-(3 4-c)-pyridine derivatives |
| GB8330517D0 (en) * | 1983-11-16 | 1983-12-21 | Scras | 6-vinyl-furo-(3,4-c)pyridine derivatives |
| GB8330658D0 (en) * | 1983-11-17 | 1983-12-29 | Scras | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| GB8422029D0 (en) * | 1984-08-31 | 1984-10-03 | Scras | 6-substituted-furo-(3 4-c)-pyridine derivatives |
| GB8422379D0 (en) * | 1984-09-05 | 1984-10-10 | Scras | Derivatives |
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
| CN108203439B (zh) * | 2016-12-20 | 2020-04-14 | 四川大学 | 苯乙烯吡啶类化合物、其制备方法和用途 |
-
1978
- 1978-11-07 ZA ZA00786269A patent/ZA786269B/xx unknown
- 1978-11-09 IN IN807/DEL/78A patent/IN150337B/en unknown
- 1978-11-13 FI FI783452A patent/FI63941C/fi not_active IP Right Cessation
- 1978-11-14 BE BE191724A patent/BE872004A/xx not_active IP Right Cessation
- 1978-11-15 LU LU80523A patent/LU80523A1/xx unknown
- 1978-11-15 CH CH1171678A patent/CH635345A5/fr not_active IP Right Cessation
- 1978-11-15 NL NLAANVRAGE7811292,A patent/NL176265C/xx not_active IP Right Cessation
- 1978-11-16 AT AT0818078A patent/AT366687B/de not_active IP Right Cessation
- 1978-11-22 JP JP14347078A patent/JPS54109996A/ja active Granted
- 1978-11-22 MX MX787553U patent/MX5442E/es unknown
- 1978-11-22 NZ NZ188973A patent/NZ188973A/xx unknown
- 1978-11-22 IT IT30054/78A patent/IT1101293B/it active
- 1978-11-23 PT PT68824A patent/PT68824A/pt unknown
- 1978-11-23 SE SE7812081A patent/SE427751B/sv not_active IP Right Cessation
- 1978-11-23 AU AU41873/78A patent/AU520800B2/en not_active Expired
- 1978-11-23 AR AR274551A patent/AR216558A1/es active
- 1978-11-24 OA OA56668A patent/OA06122A/xx unknown
- 1978-11-24 DE DE2850948A patent/DE2850948C2/de not_active Expired
- 1978-11-24 US US05/963,383 patent/US4221795A/en not_active Expired - Lifetime
- 1978-11-24 ES ES475361A patent/ES475361A1/es not_active Expired
- 1978-11-24 FR FR7833172A patent/FR2409998A1/fr active Granted
- 1978-11-24 IE IE2327/78A patent/IE47417B1/en unknown
- 1978-11-24 NO NO783970A patent/NO150160C/no unknown
- 1978-11-24 DK DK524878A patent/DK148234C/da not_active IP Right Cessation
- 1978-11-24 FR FR7833173A patent/FR2409753A1/fr active Granted
- 1978-11-24 CA CA316,808A patent/CA1096869A/en not_active Expired
- 1978-11-25 EG EG668/78A patent/EG13732A/xx active
-
1983
- 1983-06-02 HK HK188/83A patent/HK18883A/xx unknown
-
1985
- 1985-12-30 MY MY30/85A patent/MY8500030A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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