CN104411686B - 4-[5-(吡啶-4-基)-1h-1,2,4-三唑-3-基]吡啶-2-腈的制造方法及中间体 - Google Patents
4-[5-(吡啶-4-基)-1h-1,2,4-三唑-3-基]吡啶-2-腈的制造方法及中间体 Download PDFInfo
- Publication number
- CN104411686B CN104411686B CN201380035703.1A CN201380035703A CN104411686B CN 104411686 B CN104411686 B CN 104411686B CN 201380035703 A CN201380035703 A CN 201380035703A CN 104411686 B CN104411686 B CN 104411686B
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- China
- Prior art keywords
- compound
- pyridine
- following formula
- reaction
- triazol
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- 0 N#CC1=IC=CC(C2=N*C(C3=CC=NCC3)=N2)=C1 Chemical compound N#CC1=IC=CC(C2=N*C(C3=CC=NCC3)=N2)=C1 0.000 description 1
- UVTQPXJSXOYROI-UHFFFAOYSA-N N=C(c1cc(C#N)ncc1)NNC(c1ccncc1)=O Chemical compound N=C(c1cc(C#N)ncc1)NNC(c1ccncc1)=O UVTQPXJSXOYROI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D213/84—Nitriles
-
- 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
- C07D213/86—Hydrazides; Thio or imino analogues thereof
-
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012177538 | 2012-07-25 | ||
| JP2012-177538 | 2012-07-25 | ||
| PCT/JP2013/070005 WO2014017516A1 (ja) | 2012-07-25 | 2013-07-24 | ４－［５－（ピリジン－４－イル）－１ｈ－１，２，４－トリアゾール－３－イル］ピリジン－２－カルボニトリルの製造方法および中間体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104411686A CN104411686A (zh) | 2015-03-11 |
| CN104411686B true CN104411686B (zh) | 2016-08-31 |
Family
ID=49997325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380035703.1A Active CN104411686B (zh) | 2012-07-25 | 2013-07-24 | 4-[5-(吡啶-4-基)-1h-1,2,4-三唑-3-基]吡啶-2-腈的制造方法及中间体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9428488B2 (enExample) |
| EP (1) | EP2878595A4 (enExample) |
| JP (1) | JP5827407B2 (enExample) |
| KR (1) | KR101719891B1 (enExample) |
| CN (1) | CN104411686B (enExample) |
| AU (1) | AU2013293974B2 (enExample) |
| BR (1) | BR112014032229B1 (enExample) |
| CA (1) | CA2876268C (enExample) |
| HK (1) | HK1204788A1 (enExample) |
| IL (1) | IL236081A (enExample) |
| IN (1) | IN2014DN10530A (enExample) |
| MX (1) | MX362102B (enExample) |
| MY (1) | MY185203A (enExample) |
| NZ (1) | NZ702797A (enExample) |
| PH (1) | PH12015500160B1 (enExample) |
| RU (1) | RU2644766C2 (enExample) |
| TW (1) | TWI580675B (enExample) |
| WO (1) | WO2014017516A1 (enExample) |
| ZA (1) | ZA201500462B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367490B (zh) * | 2014-08-18 | 2019-01-04 | 上海医药工业研究院 | 合成托吡司他的新中间体及其制备方法 |
| WO2016134854A1 (en) | 2015-02-25 | 2016-09-01 | Pharmathen S.A. | Methods for the preparation of topiroxostat and intermediates thereof |
| CN105693699B (zh) * | 2015-03-30 | 2019-06-18 | 苏州晶云药物科技股份有限公司 | 托吡司他的晶型及其制备方法 |
| CN104758263B (zh) * | 2015-04-22 | 2017-08-22 | 青岛正大海尔制药有限公司 | 一种托匹司他片及其制备方法 |
| CN105294656A (zh) * | 2015-10-10 | 2016-02-03 | 大道隆达（北京）医药科技发展有限公司 | 一种托匹司他的制备工艺和方法 |
| CN106008465A (zh) * | 2016-03-16 | 2016-10-12 | 江苏悦兴药业有限公司 | 一种托匹司他杂质的合成方法 |
| CN108101840A (zh) * | 2018-01-26 | 2018-06-01 | 南京华威医药科技集团有限公司 | 托吡司他及其中间体制备方法 |
| CN113666909B (zh) * | 2020-05-14 | 2024-07-02 | 鲁南制药集团股份有限公司 | 一种托匹司他的制备方法 |
| CN115093399A (zh) * | 2022-07-29 | 2022-09-23 | 武汉工程大学 | 一种抗痛风药物托匹司他的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788210A (en) * | 1984-12-21 | 1988-11-29 | Hoffmann-La Roche Inc. | 1,2,4-Triazole compounds |
| CN1561340A (zh) * | 2002-01-28 | 2005-01-05 | 株式会社富士药品 | 新的1,2,4－三唑类化合物 |
| CN1826335A (zh) * | 2003-07-24 | 2006-08-30 | 株式会社富士药品 | 1,2,4－三唑化合物的制造方法以及其中间体 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947577A (en) * | 1973-05-21 | 1976-03-30 | Merck & Co., Inc. | Anti-hyperuricemia composition |
| US4097599A (en) * | 1973-11-13 | 1978-06-27 | Commonwealth Scientific And Industrial Research Organization | Triazoles |
| ZA859576B (en) | 1984-12-21 | 1986-08-27 | Hoffmann La Roche | Heterocyclic compounds |
| JP3217846B2 (ja) * | 1992-03-04 | 2001-10-15 | クミアイ化学工業株式会社 | トリアゾール誘導体及び殺虫剤 |
| BR9915534B1 (pt) * | 1998-10-23 | 2011-04-19 | 1-piridil substituìdo)-1,2,4-triazóis inseticidas. | |
| JP2003064410A (ja) | 2001-08-22 | 2003-03-05 | Nippon Steel Corp | 転炉吹錬方法および上吹きランス |
| JP2005009991A (ja) | 2003-06-18 | 2005-01-13 | Alpine Electronics Inc | 車載用ナビゲーション装置及び車載用ナビゲーション装置の表示方法 |
| JP2005041802A (ja) | 2003-07-25 | 2005-02-17 | Fujiyakuhin Co Ltd | １，２，４−トリアゾール化合物の製造方法 |
| US20060189811A1 (en) | 2004-07-23 | 2006-08-24 | Fujiyakuhin Co., Ltd. | Process for producing 1,2,4-triazole compound and intermediate therefor |
-
2013
- 2013-07-24 CN CN201380035703.1A patent/CN104411686B/zh active Active
- 2013-07-24 BR BR112014032229-5A patent/BR112014032229B1/pt not_active IP Right Cessation
- 2013-07-24 HK HK15105377.5A patent/HK1204788A1/en unknown
- 2013-07-24 MX MX2015001114A patent/MX362102B/es active IP Right Grant
- 2013-07-24 MY MYPI2014703681A patent/MY185203A/en unknown
- 2013-07-24 TW TW102126521A patent/TWI580675B/zh not_active IP Right Cessation
- 2013-07-24 KR KR1020147034604A patent/KR101719891B1/ko not_active Expired - Fee Related
- 2013-07-24 NZ NZ702797A patent/NZ702797A/en not_active IP Right Cessation
- 2013-07-24 JP JP2014526957A patent/JP5827407B2/ja active Active
- 2013-07-24 AU AU2013293974A patent/AU2013293974B2/en not_active Ceased
- 2013-07-24 US US14/406,637 patent/US9428488B2/en not_active Expired - Fee Related
- 2013-07-24 IN IN10530DEN2014 patent/IN2014DN10530A/en unknown
- 2013-07-24 CA CA2876268A patent/CA2876268C/en not_active Expired - Fee Related
- 2013-07-24 WO PCT/JP2013/070005 patent/WO2014017516A1/ja not_active Ceased
- 2013-07-24 RU RU2015106138A patent/RU2644766C2/ru active
- 2013-07-24 EP EP13822690.7A patent/EP2878595A4/en not_active Withdrawn
-
2014
- 2014-12-04 IL IL236081A patent/IL236081A/en active IP Right Grant
-
2015
- 2015-01-22 ZA ZA2015/00462A patent/ZA201500462B/en unknown
- 2015-01-23 PH PH12015500160A patent/PH12015500160B1/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788210A (en) * | 1984-12-21 | 1988-11-29 | Hoffmann-La Roche Inc. | 1,2,4-Triazole compounds |
| CN1561340A (zh) * | 2002-01-28 | 2005-01-05 | 株式会社富士药品 | 新的1,2,4－三唑类化合物 |
| CN1826335A (zh) * | 2003-07-24 | 2006-08-30 | 株式会社富士药品 | 1,2,4－三唑化合物的制造方法以及其中间体 |
Non-Patent Citations (3)
| Title |
|---|
| Discovery of 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051-a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia;Takahiro Sato,等;《Bioorganic & Medicinal Chemistry Letters》;20090902;第19卷(第21期);第6226页方案1，第6228页表5、表6、左栏第6-11行 * |
| Takahiro Sato,等.Discovery of 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051-a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia.《Bioorganic & Medicinal Chemistry Letters》.2009,第19卷(第21期),第6225-6229页. * |
| Zinc cyanide mediated direct a-cyanation of isonicotinic acid N-oxide.Application to the synthesis of FYX-051, a xanthine oxidoreductase inhibitor;Zhibao Huo,等;《Tetrahedron Letters》;20080510;第49卷(第28期);第4369-4371页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2878595A1 (en) | 2015-06-03 |
| MY185203A (en) | 2021-04-30 |
| EP2878595A4 (en) | 2015-12-09 |
| US9428488B2 (en) | 2016-08-30 |
| IN2014DN10530A (enExample) | 2015-08-21 |
| NZ702797A (en) | 2017-03-31 |
| MX2015001114A (es) | 2015-04-08 |
| US20150166510A1 (en) | 2015-06-18 |
| CA2876268C (en) | 2016-12-20 |
| IL236081A (en) | 2017-11-30 |
| HK1204788A1 (en) | 2015-12-04 |
| JPWO2014017516A1 (ja) | 2016-07-11 |
| AU2013293974B2 (en) | 2017-06-01 |
| WO2014017516A1 (ja) | 2014-01-30 |
| BR112014032229A2 (pt) | 2017-06-27 |
| TW201408642A (zh) | 2014-03-01 |
| KR20150035586A (ko) | 2015-04-06 |
| CA2876268A1 (en) | 2014-01-30 |
| KR101719891B1 (ko) | 2017-03-24 |
| JP5827407B2 (ja) | 2015-12-02 |
| TWI580675B (zh) | 2017-05-01 |
| MX362102B (es) | 2019-01-04 |
| RU2644766C2 (ru) | 2018-02-14 |
| IL236081A0 (en) | 2015-02-01 |
| AU2013293974A1 (en) | 2015-01-22 |
| CN104411686A (zh) | 2015-03-11 |
| ZA201500462B (en) | 2016-10-26 |
| BR112014032229B1 (pt) | 2021-02-09 |
| RU2015106138A (ru) | 2016-09-10 |
| PH12015500160A1 (en) | 2015-03-16 |
| PH12015500160B1 (en) | 2015-03-16 |
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