OA10803A - Process for preparing 2,4-dihydroxypyridine and 2,4-dihydroxy-3-nitropyridine - Google Patents
Process for preparing 2,4-dihydroxypyridine and 2,4-dihydroxy-3-nitropyridine Download PDFInfo
- Publication number
- OA10803A OA10803A OA9800099A OA9800099A OA10803A OA 10803 A OA10803 A OA 10803A OA 9800099 A OA9800099 A OA 9800099A OA 9800099 A OA9800099 A OA 9800099A OA 10803 A OA10803 A OA 10803A
- Authority
- OA
- OAPI
- Prior art keywords
- adenosine
- acid
- thienyl
- ethyl
- compounds
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- BKYGVGWYPFVKTK-UHFFFAOYSA-N 4-hydroxy-3-nitro-1h-pyridin-2-one Chemical compound OC=1NC=CC(=O)C=1[N+]([O-])=O BKYGVGWYPFVKTK-UHFFFAOYSA-N 0.000 title abstract description 13
- ZEZJPIDPVXJEME-UHFFFAOYSA-N 2,4-Dihydroxypyridine Chemical compound OC=1C=CNC(=O)C=1 ZEZJPIDPVXJEME-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 238000000034 method Methods 0.000 claims abstract description 75
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
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- 230000008569 process Effects 0.000 claims abstract description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 31
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 8
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
- TXNSZEFXCQVGFV-UHFFFAOYSA-N thiophene-3-carbaldehyde 1-thiophen-3-ylethanamine Chemical compound S1C=C(C=C1)C=O.S1C=C(C=C1)C(C)N TXNSZEFXCQVGFV-UHFFFAOYSA-N 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical group C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 238000005406 washing 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US949296P | 1996-01-02 | 1996-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA10803A true OA10803A (en) | 2003-01-28 |
Family
ID=21737998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9800099A OA10803A (en) | 1996-01-02 | 1998-07-01 | Process for preparing 2,4-dihydroxypyridine and 2,4-dihydroxy-3-nitropyridine |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6307054B1 (cs) |
| EP (1) | EP0909270B1 (cs) |
| JP (1) | JP2000502709A (cs) |
| KR (1) | KR19990076966A (cs) |
| AP (1) | AP772A (cs) |
| AT (1) | ATE219767T1 (cs) |
| AU (1) | AU722894B2 (cs) |
| BR (1) | BR9612341A (cs) |
| CA (1) | CA2241887C (cs) |
| CZ (1) | CZ203998A3 (cs) |
| DE (1) | DE69622051T2 (cs) |
| DK (1) | DK0909270T3 (cs) |
| EA (1) | EA000884B1 (cs) |
| ES (1) | ES2178725T3 (cs) |
| HU (1) | HUP9900969A3 (cs) |
| IL (1) | IL125164A (cs) |
| OA (1) | OA10803A (cs) |
| PT (1) | PT909270E (cs) |
| SI (1) | SI9620137B (cs) |
| SK (1) | SK283625B6 (cs) |
| WO (1) | WO1997024327A1 (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9917000A (pt) | 1998-12-31 | 2001-12-11 | Aventis Pharm Prod Inc | Processo para preparar derivados dedesaza-adenosina n6-substituìda |
| US7018365B2 (en) | 1999-05-21 | 2006-03-28 | Micro Therapeutics, Inc. | Threaded syringe with quick stop |
| US6784165B1 (en) * | 1999-11-23 | 2004-08-31 | Aderis Pharmaceuticals, Inc. | Treatment of heart rhythm disturbances with N6-substituted-5′-(N-substituted) carboxamidoadenosines |
| US7291603B2 (en) | 2002-07-24 | 2007-11-06 | Ptc Therapeutics, Inc. | Nucleoside compounds and their use for treating cancer and diseases associated with somatic mutations |
| US20050009776A1 (en) * | 2003-04-24 | 2005-01-13 | Aderis Pharmaceuticals, Inc. | Method of treating atrial fibrillation or atrial flutter |
| WO2005025545A2 (en) * | 2003-09-17 | 2005-03-24 | Aderis Pharmaceuticals, Inc. | Pharmaceutical formulation for controlled release of selodenoson |
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| PT2013211E (pt) * | 2006-04-21 | 2012-06-21 | Novartis Ag | Derivados de purina para utilização como agonistas de receptores a2a de adenosina |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) * | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| KR20090087054A (ko) * | 2006-11-10 | 2009-08-14 | 노파르티스 아게 | 시클로펜텐 디올 모노아세테이트 유도체 |
| JP2012516843A (ja) | 2009-02-02 | 2012-07-26 | インドコ レメディーズ リミテッド | ニトロピリジン誘導体の調製方法 |
| CN114349873B (zh) * | 2021-04-12 | 2023-03-17 | 杭州安誉科技有限公司 | 用于多孔模块辅助控制装置的高强度风扇支架 |
| CN115716802A (zh) * | 2022-10-20 | 2023-02-28 | 山西永津集团有限公司 | 一种4-溴-2-氯烟腈的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547935A (en) * | 1967-08-07 | 1970-12-15 | American Cyanamid Co | Certain nitro-4-pyridinols,n-oxides thereof and derivatives thereof |
| GB1199699A (en) * | 1968-01-08 | 1970-07-22 | Glanzstoff Ag | Process for the Production of Condensed Aromatic Bis-(2,4-Dihydroxypyridine) Derivatives |
| DE3308449A1 (de) * | 1982-08-19 | 1984-03-15 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur reindarstellung von 2-chlor-6-alkoxy-3-nitropyridinen |
| JP3261190B2 (ja) * | 1993-01-27 | 2002-02-25 | 広栄化学工業株式会社 | 2−ヒドロキシ−3,5−ジニトロピリジン類の製造法 |
-
1996
- 1996-12-23 SK SK906-98A patent/SK283625B6/sk unknown
- 1996-12-23 EP EP96945096A patent/EP0909270B1/en not_active Expired - Lifetime
- 1996-12-23 EA EA199800621A patent/EA000884B1/ru not_active IP Right Cessation
- 1996-12-23 PT PT96945096T patent/PT909270E/pt unknown
- 1996-12-23 AT AT96945096T patent/ATE219767T1/de not_active IP Right Cessation
- 1996-12-23 IL IL12516496A patent/IL125164A/xx not_active IP Right Cessation
- 1996-12-23 BR BR9612341-9A patent/BR9612341A/pt not_active Application Discontinuation
- 1996-12-23 CA CA002241887A patent/CA2241887C/en not_active Expired - Fee Related
- 1996-12-23 WO PCT/US1996/020768 patent/WO1997024327A1/en not_active Application Discontinuation
- 1996-12-23 JP JP9524559A patent/JP2000502709A/ja not_active Ceased
- 1996-12-23 SI SI9620137A patent/SI9620137B/sl not_active IP Right Cessation
- 1996-12-23 DE DE69622051T patent/DE69622051T2/de not_active Expired - Fee Related
- 1996-12-23 ES ES96945096T patent/ES2178725T3/es not_active Expired - Lifetime
- 1996-12-23 DK DK96945096T patent/DK0909270T3/da active
- 1996-12-23 AP APAP/P/1998/001289A patent/AP772A/en active
- 1996-12-23 HU HU9900969A patent/HUP9900969A3/hu not_active Application Discontinuation
- 1996-12-23 CZ CZ982039A patent/CZ203998A3/cs unknown
- 1996-12-23 KR KR1019980705094A patent/KR19990076966A/ko not_active Ceased
- 1996-12-23 AU AU13546/97A patent/AU722894B2/en not_active Ceased
-
1998
- 1998-07-01 OA OA9800099A patent/OA10803A/en unknown
- 1998-07-01 US US09/108,622 patent/US6307054B1/en not_active Expired - Fee Related
-
2001
- 2001-05-18 US US09/861,023 patent/US6392049B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2241887C (en) | 2004-02-24 |
| JP2000502709A (ja) | 2000-03-07 |
| ATE219767T1 (de) | 2002-07-15 |
| AU722894B2 (en) | 2000-08-10 |
| SI9620137A (sl) | 1999-02-28 |
| BR9612341A (pt) | 1999-12-28 |
| IL125164A (en) | 2003-03-12 |
| AP772A (en) | 1999-10-15 |
| IL125164A0 (en) | 1999-01-26 |
| US6307054B1 (en) | 2001-10-23 |
| ES2178725T3 (es) | 2003-01-01 |
| DE69622051T2 (de) | 2003-01-23 |
| AU1354697A (en) | 1997-07-28 |
| DE69622051D1 (de) | 2002-08-01 |
| SI9620137B (sl) | 2006-02-28 |
| HUP9900969A2 (hu) | 1999-07-28 |
| CZ203998A3 (cs) | 1999-11-17 |
| WO1997024327A1 (en) | 1997-07-10 |
| SK283625B6 (sk) | 2003-10-07 |
| EP0909270A1 (en) | 1999-04-21 |
| HUP9900969A3 (en) | 2001-11-28 |
| PT909270E (pt) | 2002-11-29 |
| HK1019590A1 (en) | 2000-02-18 |
| AP9801289A0 (en) | 1998-09-30 |
| DK0909270T3 (da) | 2002-10-07 |
| EP0909270B1 (en) | 2002-06-26 |
| KR19990076966A (ko) | 1999-10-25 |
| SK90698A3 (en) | 2000-12-11 |
| EA000884B1 (ru) | 2000-06-26 |
| EP0909270A4 (cs) | 1999-04-21 |
| US6392049B1 (en) | 2002-05-21 |
| EA199800621A1 (ru) | 1999-02-25 |
| CA2241887A1 (en) | 1997-07-10 |
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