RU2015106138A - Способ получения 4-[5-(пиридин-4-ил)-1н-1,2,4-триазол-3-ил]пиридин-2-карбонитрила и его промежуточное соединение - Google Patents
Способ получения 4-[5-(пиридин-4-ил)-1н-1,2,4-триазол-3-ил]пиридин-2-карбонитрила и его промежуточное соединение Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. N'-(2-цианопиридин-4-карбонимидоил)гидразид 4-пиридин карбоновой кислоты, представленный следующей формулой (4).2. Способ получения соединения, представленного в п. 1, способ включающий реакцию соединения, представленного формулой (2):.с гидразидом изоникотиновой кислоты в присутствии алкоксида щелочного металла, с последующим образованием соединения, представленного следующей формулой (3):и введение циано-группы в соединение (3) посредством цианирующего реагента.3. Способ получения 4-[5-(пиридин-4-ил)-1H-1,2,4-триазол-3-ил]пиридин-2-карбонитрила, представленного следующей формулой (1):,включающий реакцию соединения, представленного следующей формулой (2):с гидразидом изоникотиновой кислоты в присутствии алкоксида щелочного металла с последующим образованием соединения, представленного следующей формулой (3):введение циано-группы в соединение (3) посредством цианирующего реагента с образованием соединения представленного следующей формулой (4):и введение соединения (4) в реакцию циклизации в присутствии кислотного катализатора.4. Способ получения 4-[5-(пиридин-4-ил)-1H-1,2,4-триазол-3-ил]пиридин-2-карбонитрила, представленного следующей формулой (1):,включающий введение соединения, представленного следующей формулой (4):в реакцию циклизации в присутствии кислотного катализатора.
Claims (4)
1. N'-(2-цианопиридин-4-карбонимидоил)гидразид 4-пиридин карбоновой кислоты, представленный следующей формулой (4)
2. Способ получения соединения, представленного в п. 1, способ включающий реакцию соединения, представленного формулой (2):
с гидразидом изоникотиновой кислоты в присутствии алкоксида щелочного металла, с последующим образованием соединения, представленного следующей формулой (3):
и введение циано-группы в соединение (3) посредством цианирующего реагента.
3. Способ получения 4-[5-(пиридин-4-ил)-1H-1,2,4-триазол-3-ил]пиридин-2-карбонитрила, представленного следующей формулой (1):
включающий реакцию соединения, представленного следующей формулой (2):
с гидразидом изоникотиновой кислоты в присутствии алкоксида щелочного металла с последующим образованием соединения, представленного следующей формулой (3):
введение циано-группы в соединение (3) посредством цианирующего реагента с образованием соединения представленного следующей формулой (4):
и введение соединения (4) в реакцию циклизации в присутствии кислотного катализатора.
4. Способ получения 4-[5-(пиридин-4-ил)-1H-1,2,4-триазол-3-ил]пиридин-2-карбонитрила, представленного следующей формулой (1):
включающий введение соединения, представленного следующей формулой (4):
в реакцию циклизации в присутствии кислотного катализатора.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012-177538 | 2012-07-25 | ||
| JP2012177538 | 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 |
|---|---|
| RU2015106138A true RU2015106138A (ru) | 2016-09-10 |
| RU2644766C2 RU2644766C2 (ru) | 2018-02-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015106138A RU2644766C2 (ru) | 2012-07-25 | 2013-07-24 | Способ получения 4-[5-(пиридин-4-ил)-1н-1,2,4-триазол-3-ил]пиридин-2-карбонитрила и его промежуточное соединение |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9428488B2 (ru) |
| EP (1) | EP2878595A4 (ru) |
| JP (1) | JP5827407B2 (ru) |
| KR (1) | KR101719891B1 (ru) |
| CN (1) | CN104411686B (ru) |
| AU (1) | AU2013293974B2 (ru) |
| BR (1) | BR112014032229B1 (ru) |
| CA (1) | CA2876268C (ru) |
| HK (1) | HK1204788A1 (ru) |
| IL (1) | IL236081A (ru) |
| IN (1) | IN2014DN10530A (ru) |
| MX (1) | MX362102B (ru) |
| MY (1) | MY185203A (ru) |
| NZ (1) | NZ702797A (ru) |
| PH (1) | PH12015500160B1 (ru) |
| RU (1) | RU2644766C2 (ru) |
| TW (1) | TWI580675B (ru) |
| WO (1) | WO2014017516A1 (ru) |
| ZA (1) | ZA201500462B (ru) |
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 |
| CN113666909A (zh) * | 2020-05-14 | 2021-11-19 | 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| AR241530A1 (es) | 1984-12-21 | 1992-08-31 | Ciba Geigy A G Cesionaria De F | 1,2,4-triazoles, composicion para el control de pestes y procedimiento para la preparacion de 1,2,4-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 |
| DE60225341T2 (de) * | 2002-01-28 | 2009-04-09 | Fuji Yakuhin Co. Ltd., Saitama | Neue 1,2,4-triazolverbindung |
| 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 |
| TW200521122A (en) | 2003-07-24 | 2005-07-01 | Fujiyakuhin Co Ltd | Method of preparing 1,2,4-triazole compounds and intermediates thereof |
| 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 |
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2013
- 2013-07-24 CA CA2876268A patent/CA2876268C/en not_active Expired - Fee Related
- 2013-07-24 EP EP13822690.7A patent/EP2878595A4/en not_active Withdrawn
- 2013-07-24 IN IN10530DEN2014 patent/IN2014DN10530A/en unknown
- 2013-07-24 RU RU2015106138A patent/RU2644766C2/ru active
- 2013-07-24 NZ NZ702797A patent/NZ702797A/en not_active IP Right Cessation
- 2013-07-24 AU AU2013293974A patent/AU2013293974B2/en not_active Ceased
- 2013-07-24 TW TW102126521A patent/TWI580675B/zh not_active IP Right Cessation
- 2013-07-24 US US14/406,637 patent/US9428488B2/en active Active
- 2013-07-24 BR BR112014032229-5A patent/BR112014032229B1/pt not_active IP Right Cessation
- 2013-07-24 JP JP2014526957A patent/JP5827407B2/ja active Active
- 2013-07-24 CN CN201380035703.1A patent/CN104411686B/zh active Active
- 2013-07-24 WO PCT/JP2013/070005 patent/WO2014017516A1/ja active Application Filing
- 2013-07-24 MX MX2015001114A patent/MX362102B/es active IP Right Grant
- 2013-07-24 MY MYPI2014703681A patent/MY185203A/en unknown
- 2013-07-24 KR KR1020147034604A patent/KR101719891B1/ko active IP Right Grant
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2014
- 2014-12-04 IL IL236081A patent/IL236081A/en active IP Right Grant
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- 2015-01-22 ZA ZA2015/00462A patent/ZA201500462B/en unknown
- 2015-01-23 PH PH12015500160A patent/PH12015500160B1/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| PH12015500160A1 (en) | 2015-03-16 |
| HK1204788A1 (en) | 2015-12-04 |
| WO2014017516A1 (ja) | 2014-01-30 |
| MY185203A (en) | 2021-04-30 |
| RU2644766C2 (ru) | 2018-02-14 |
| TWI580675B (zh) | 2017-05-01 |
| BR112014032229B1 (pt) | 2021-02-09 |
| KR101719891B1 (ko) | 2017-03-24 |
| NZ702797A (en) | 2017-03-31 |
| US9428488B2 (en) | 2016-08-30 |
| IN2014DN10530A (ru) | 2015-08-21 |
| EP2878595A4 (en) | 2015-12-09 |
| ZA201500462B (en) | 2016-10-26 |
| CA2876268A1 (en) | 2014-01-30 |
| KR20150035586A (ko) | 2015-04-06 |
| AU2013293974A1 (en) | 2015-01-22 |
| US20150166510A1 (en) | 2015-06-18 |
| CA2876268C (en) | 2016-12-20 |
| BR112014032229A2 (pt) | 2017-06-27 |
| CN104411686B (zh) | 2016-08-31 |
| IL236081A (en) | 2017-11-30 |
| IL236081A0 (en) | 2015-02-01 |
| MX2015001114A (es) | 2015-04-08 |
| TW201408642A (zh) | 2014-03-01 |
| PH12015500160B1 (en) | 2015-03-16 |
| AU2013293974B2 (en) | 2017-06-01 |
| JP5827407B2 (ja) | 2015-12-02 |
| JPWO2014017516A1 (ja) | 2016-07-11 |
| EP2878595A1 (en) | 2015-06-03 |
| MX362102B (es) | 2019-01-04 |
| CN104411686A (zh) | 2015-03-11 |
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