NO309766B1 - Fremgangsmåte for fremstilling av 2-aryloksy-4-klorpyridiner - Google Patents
Fremgangsmåte for fremstilling av 2-aryloksy-4-klorpyridiner Download PDFInfo
- Publication number
- NO309766B1 NO309766B1 NO975712A NO975712A NO309766B1 NO 309766 B1 NO309766 B1 NO 309766B1 NO 975712 A NO975712 A NO 975712A NO 975712 A NO975712 A NO 975712A NO 309766 B1 NO309766 B1 NO 309766B1
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- Norway
- Prior art keywords
- compound
- formula
- alkyl
- potassium
- base
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 claims description 3
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- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- 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 claims description 2
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- 230000000302 ischemic effect Effects 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001314 paroxysmal effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 208000019899 phobic disease Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000008733 trauma 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
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO975712A NO309766B1 (no) | 1995-06-06 | 1997-12-05 | Fremgangsmåte for fremstilling av 2-aryloksy-4-klorpyridiner |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IB1995/000437 WO1996039388A1 (en) | 1995-06-06 | 1995-06-06 | Process for converting 2,4-dichloropyridines into 2-aryloxy-4-chloropyridines |
| NO975712A NO309766B1 (no) | 1995-06-06 | 1997-12-05 | Fremgangsmåte for fremstilling av 2-aryloksy-4-klorpyridiner |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975712L NO975712L (no) | 1997-12-05 |
| NO975712D0 NO975712D0 (no) | 1997-12-05 |
| NO309766B1 true NO309766B1 (no) | 2001-03-26 |
Family
ID=11004337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO975712A NO309766B1 (no) | 1995-06-06 | 1997-12-05 | Fremgangsmåte for fremstilling av 2-aryloksy-4-klorpyridiner |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6316631B1 (fi) |
| EP (1) | EP0832067B1 (fi) |
| JP (1) | JP2989015B2 (fi) |
| KR (1) | KR100271513B1 (fi) |
| AT (1) | ATE244224T1 (fi) |
| CA (1) | CA2222204C (fi) |
| CZ (1) | CZ288855B6 (fi) |
| DE (1) | DE69531219T2 (fi) |
| DK (1) | DK0832067T3 (fi) |
| ES (1) | ES2199991T3 (fi) |
| FI (1) | FI974435A (fi) |
| HU (1) | HU224495B1 (fi) |
| IL (1) | IL118482A (fi) |
| NO (1) | NO309766B1 (fi) |
| NZ (1) | NZ285441A (fi) |
| PL (1) | PL177940B1 (fi) |
| PT (1) | PT832067E (fi) |
| TW (1) | TW371300B (fi) |
| WO (1) | WO1996039388A1 (fi) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
| US6191131B1 (en) | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| US7094782B1 (en) | 1996-07-24 | 2006-08-22 | Bristol-Myers Squibb Company | Azolo triazines and pyrimidines |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| US6060478A (en) * | 1996-07-24 | 2000-05-09 | Dupont Pharmaceuticals | Azolo triazines and pyrimidines |
| US20050171095A1 (en) * | 2004-01-06 | 2005-08-04 | Pfizer Inc | Combination of CRF antagonists and 5-HT1B receptor antagonists |
| CA2614529C (en) | 2005-07-21 | 2011-06-28 | F. Hoffmann-La Roche Ag | Pyridazinone derivatives as thyroid hormone receptor agonists |
| JP6564394B2 (ja) | 2014-04-28 | 2019-08-21 | ファイザー・インク | 複素環式化合物およびそのドーパミンｄ１リガンドとしての使用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6808378A (fi) * | 1967-06-15 | 1968-12-16 | ||
| EP0021453B1 (en) * | 1977-08-12 | 1985-04-10 | Imperial Chemical Industries Plc | 2-chloro-5-trichloromethylpyridine |
| DD154538A1 (de) | 1979-07-30 | 1982-03-31 | Eberhard Schroetter | Verfahren zur herstellung substituierter 2,4-und 2,6-dihalogen-pyridine |
| DE3205150A1 (de) * | 1982-02-13 | 1983-08-18 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Pyridinderivate, ihre herstellung und verwendung |
| US5032168A (en) * | 1987-03-18 | 1991-07-16 | Dowelanco | 4-((aryloxy)phenoxy)fluoroalkanoic acid derivatives and their herbicidal uses |
| MY103631A (en) * | 1987-11-07 | 1993-08-28 | Sumitomo Chemical Co | Certain insecticidal 6-(phenoxy-2-pyridyl)-methyl-neo-phental ethers |
| US5068336A (en) * | 1989-02-27 | 1991-11-26 | Tosoh Corporation | Process for producing 2-(4'-hydroxphenoxy)-3-chloro-5-trifluoromethylpyridine |
-
1995
- 1995-06-06 HU HU9900626A patent/HU224495B1/hu not_active IP Right Cessation
- 1995-06-06 PT PT95918714T patent/PT832067E/pt unknown
- 1995-06-06 CZ CZ19973934A patent/CZ288855B6/cs not_active IP Right Cessation
- 1995-06-06 DK DK95918714T patent/DK0832067T3/da active
- 1995-06-06 PL PL95323817A patent/PL177940B1/pl not_active IP Right Cessation
- 1995-06-06 US US09/254,387 patent/US6316631B1/en not_active Expired - Fee Related
- 1995-06-06 NZ NZ285441A patent/NZ285441A/en unknown
- 1995-06-06 ES ES95918714T patent/ES2199991T3/es not_active Expired - Lifetime
- 1995-06-06 DE DE69531219T patent/DE69531219T2/de not_active Expired - Fee Related
- 1995-06-06 WO PCT/IB1995/000437 patent/WO1996039388A1/en active IP Right Grant
- 1995-06-06 KR KR1019970708904A patent/KR100271513B1/ko not_active IP Right Cessation
- 1995-06-06 AT AT95918714T patent/ATE244224T1/de not_active IP Right Cessation
- 1995-06-06 EP EP95918714A patent/EP0832067B1/en not_active Expired - Lifetime
- 1995-06-06 CA CA002222204A patent/CA2222204C/en not_active Expired - Fee Related
- 1995-06-06 JP JP52977096A patent/JP2989015B2/ja not_active Expired - Fee Related
-
1996
- 1996-03-26 TW TW085103626A patent/TW371300B/zh active
- 1996-05-30 IL IL11848296A patent/IL118482A/xx not_active IP Right Cessation
-
1997
- 1997-12-05 NO NO975712A patent/NO309766B1/no not_active IP Right Cessation
- 1997-12-05 FI FI974435A patent/FI974435A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2452995A (en) | 1996-12-24 |
| CA2222204A1 (en) | 1996-12-12 |
| JP2989015B2 (ja) | 1999-12-13 |
| KR100271513B1 (ko) | 2000-12-01 |
| CA2222204C (en) | 2002-02-19 |
| EP0832067B1 (en) | 2003-07-02 |
| DK0832067T3 (da) | 2003-09-29 |
| ES2199991T3 (es) | 2004-03-01 |
| FI974435A0 (fi) | 1997-12-05 |
| FI974435A (fi) | 1997-12-05 |
| ATE244224T1 (de) | 2003-07-15 |
| IL118482A (en) | 2000-08-13 |
| KR19990022424A (ko) | 1999-03-25 |
| CZ393497A3 (cs) | 1999-01-13 |
| CZ288855B6 (cs) | 2001-09-12 |
| US6316631B1 (en) | 2001-11-13 |
| EP0832067A1 (en) | 1998-04-01 |
| JPH10506634A (ja) | 1998-06-30 |
| DE69531219D1 (de) | 2003-08-07 |
| NO975712L (no) | 1997-12-05 |
| AU700924B2 (en) | 1999-01-14 |
| NZ285441A (en) | 1999-07-29 |
| PL323817A1 (en) | 1998-04-27 |
| PT832067E (pt) | 2003-10-31 |
| TW371300B (en) | 1999-10-01 |
| HU224495B1 (hu) | 2005-10-28 |
| WO1996039388A1 (en) | 1996-12-12 |
| IL118482A0 (en) | 1996-09-12 |
| PL177940B1 (pl) | 2000-02-29 |
| HUT78061A (hu) | 1999-07-28 |
| DE69531219T2 (de) | 2004-02-12 |
| NO975712D0 (no) | 1997-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |