EA021826B1 - Усовершенствованный способ синтеза пирфенидона - Google Patents
Усовершенствованный способ синтеза пирфенидона Download PDFInfo
- Publication number
- EA021826B1 EA021826B1 EA201101695A EA201101695A EA021826B1 EA 021826 B1 EA021826 B1 EA 021826B1 EA 201101695 A EA201101695 A EA 201101695A EA 201101695 A EA201101695 A EA 201101695A EA 021826 B1 EA021826 B1 EA 021826B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- pirfenidone
- solution
- bromobenzene
- organic solvent
- less
- Prior art date
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- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 229960003073 pirfenidone Drugs 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 57
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 5
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims abstract description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 35
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 24
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18358809P | 2009-06-03 | 2009-06-03 | |
| PCT/US2010/037090 WO2010141600A2 (en) | 2009-06-03 | 2010-06-02 | Improved method for synthesizing pirfenidone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201101695A1 EA201101695A1 (ru) | 2012-05-30 |
| EA021826B1 true EA021826B1 (ru) | 2015-09-30 |
Family
ID=43298478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201101695A EA021826B1 (ru) | 2009-06-03 | 2010-06-02 | Усовершенствованный способ синтеза пирфенидона |
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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2726588C (en) | 2008-06-03 | 2019-04-16 | Karl Kossen | Compounds and methods for treating inflammatory and fibrotic disorders |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| JP6021117B2 (ja) | 2011-01-31 | 2016-11-02 | ジェノア ファーマシューティカルズ，インク． | エアロゾルのピルフェニドンおよびピリドンアナログの化合物、および、その使用 |
| MX2011007675A (es) | 2011-07-19 | 2012-07-11 | Cell Therapy And Technology S A De C V | Procedimiento para la fabricacion de una composicion farmaceutica en forma de tabletas de liberacion prolongada conteniendo pirfenidona y su aplicacion en la regresion de la insuficiencia renal cronica, contractura capsular mamaria y fibrosis hepatica humanas. |
| MX356551B (es) | 2012-08-23 | 2018-06-04 | Grupo Medifarma S A De C V Star | Composición antiséptica, antiseborreica y exfoliante para eliminar o prevenir el acné. |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| NZ760541A (en) | 2014-01-10 | 2022-08-26 | Avalyn Pharma Inc | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| CN107073112A (zh) * | 2014-08-15 | 2017-08-18 | 皮克萨尔比奥公司 | 用于在患有脊髓损伤的对象中抑制炎症的组合物及其使用方法 |
| EP3307714A1 (en) | 2015-01-26 | 2018-04-18 | Ulkar Kimya Sanayii Ve Ticaret A. S. | An improved method for the synthesis and purification of pirfenidone |
| ITUB20154832A1 (it) | 2015-10-29 | 2017-04-29 | Procos Spa | Processo per la sintesi di pirfenidone |
| CN105315198A (zh) * | 2015-11-02 | 2016-02-10 | 重庆康乐制药有限公司 | 一种吡非尼酮的晶型及其制备方法 |
| CN105330598B (zh) * | 2015-12-02 | 2017-11-14 | 新发药业有限公司 | 一种吡非尼酮的制备方法 |
| WO2017122139A1 (en) * | 2016-01-14 | 2017-07-20 | Laurus Labs Limited | An improved process for the preparation of pirfenidone |
| US11066368B2 (en) | 2016-01-14 | 2021-07-20 | Laurus Labs Limited | Process for the preparation and particle size reduction of pirfenidone |
| WO2017130166A1 (en) * | 2016-01-31 | 2017-08-03 | Granules India Limited | An improved process for the preparation of highly pure anti-fibrotic drug |
| CA2937365C (en) | 2016-03-29 | 2018-09-18 | F. Hoffmann-La Roche Ag | Granulate formulation of 5-methyl-1-phenyl-2-(1h)-pyridone and method of making the same |
| IT201600071672A1 (it) * | 2016-07-08 | 2018-01-08 | Dipharma Francis Srl | Metodo per sintetizzare un farmaco immunosoppressore |
| IT201600108927A1 (it) * | 2016-10-27 | 2018-04-27 | Dipharma Francis Srl | Metodo per sintetizzare un farmaco antifibrotico |
| US20180009753A1 (en) * | 2016-07-08 | 2018-01-11 | Dipharma Francis S.R.L. | Method for preparing an antifibrotic agent |
| WO2018083709A1 (en) * | 2016-11-07 | 2018-05-11 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of pure 5-methyl-1-phenyl-2-1 (h)-pyridone |
| WO2018178996A1 (en) * | 2017-03-28 | 2018-10-04 | Natco Pharma Limited | Improved process for the preparation of pirfenidone |
| WO2019028062A1 (en) | 2017-07-31 | 2019-02-07 | Washington University | PIRFENIDONE DERIVATIVES FOR MODULATION OF B-LYMPHOCYTE ACTIVITY AND PROTECTION OF ORGANS |
| ES2886152T3 (es) | 2017-12-11 | 2021-12-16 | Laurus Labs Ltd | Un procedimiento mejorado para la preparación de pirfenidona |
| CN112409246B (zh) * | 2019-08-21 | 2023-04-07 | 北京凯因科技股份有限公司 | 一种吡非尼酮的晶型及其制备方法 |
| JP7490813B2 (ja) * | 2020-04-22 | 2024-05-27 | ユンジン ファーム．カンパニー、リミテッド | 安全性と安定性が改善されたピルフェニドンを含む腸溶性製剤およびその製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040022232A (ko) * | 2001-08-06 | 2004-03-11 | 아사히 가라스 가부시키가이샤 | 5-메틸-1-페닐-2(1ｈ)피리디논의 제조 방법 |
| CN1817862A (zh) * | 2006-03-15 | 2006-08-16 | 浙江省医学科学院 | 一种抗纤维化药物吡非尼酮的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839346A (en) * | 1972-12-18 | 1974-10-01 | Affiliated Med Res | N-substituted pyridone and general method for preparing pyridones |
| CA2099868C (en) * | 1991-01-31 | 2002-04-02 | Thomas Richard Belliotti | Substituted 4,6-di-tertiary-butyl-5-hydroxy-pyrimidines |
| WO2002085858A1 (en) * | 2001-04-20 | 2002-10-31 | Asahi Glass Company, Limited | Process for producing purified piperidine derivative |
| CN1218942C (zh) | 2002-06-11 | 2005-09-14 | 中南大学湘雅医学院 | 抗纤维化吡啶酮化合物及其生产工艺方法 |
| MX2007006349A (es) | 2007-05-29 | 2009-02-18 | Cell Therapy And Technology S | Nuevo proceso de sintesis para la obtencion de 5-metil-1-fenil-2-(ih)-piridona, composicion y uso de la misma. |
| JP5587184B2 (ja) * | 2007-06-20 | 2014-09-10 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | 繊維症阻害剤としての置換ｎ−アリールピリジノン |
| US20090131485A1 (en) * | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040022232A (ko) * | 2001-08-06 | 2004-03-11 | 아사히 가라스 가부시키가이샤 | 5-메틸-1-페닐-2(1ｈ)피리디논의 제조 방법 |
| CN1817862A (zh) * | 2006-03-15 | 2006-08-16 | 浙江省医学科学院 | 一种抗纤维化药物吡非尼酮的制备方法 |
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