JP2012528877A5 - - Google Patents
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- Publication number
- JP2012528877A5 JP2012528877A5 JP2012514087A JP2012514087A JP2012528877A5 JP 2012528877 A5 JP2012528877 A5 JP 2012528877A5 JP 2012514087 A JP2012514087 A JP 2012514087A JP 2012514087 A JP2012514087 A JP 2012514087A JP 2012528877 A5 JP2012528877 A5 JP 2012528877A5
- Authority
- JP
- Japan
- Prior art keywords
- pirfenidone
- molar ratio
- less
- solution
- retention time
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 25
- 229960003073 pirfenidone Drugs 0.000 claims 25
- 238000000034 method Methods 0.000 claims 24
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 239000012535 impurity Substances 0.000 claims 6
- 230000014759 maintenance of location Effects 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 claims 2
- GUOUIGNVUQGZFK-UHFFFAOYSA-N C1=CC=CC=C1.CC=1C=CC(NC1)=O.CC=1C=CC(NC1)=O Chemical compound C1=CC=CC=C1.CC=1C=CC(NC1)=O.CC=1C=CC(NC1)=O GUOUIGNVUQGZFK-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003637 basic solution Substances 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims 2
- 229940112669 cuprous oxide Drugs 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- 238000004811 liquid chromatography Methods 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18358809P | 2009-06-03 | 2009-06-03 | |
| US61/183,588 | 2009-06-03 | ||
| PCT/US2010/037090 WO2010141600A2 (en) | 2009-06-03 | 2010-06-02 | Improved method for synthesizing pirfenidone |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015203886A Division JP2016026196A (ja) | 2009-06-03 | 2015-10-15 | ピルフェニドンを合成するための改善された方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012528877A JP2012528877A (ja) | 2012-11-15 |
| JP2012528877A5 true JP2012528877A5 (enExample) | 2013-07-18 |
| JP5848244B2 JP5848244B2 (ja) | 2016-01-27 |
Family
ID=43298478
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012514087A Active JP5848244B2 (ja) | 2009-06-03 | 2010-06-02 | ピルフェニドンを合成するための改善された方法 |
| JP2015203886A Pending JP2016026196A (ja) | 2009-06-03 | 2015-10-15 | ピルフェニドンを合成するための改善された方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015203886A Pending JP2016026196A (ja) | 2009-06-03 | 2015-10-15 | ピルフェニドンを合成するための改善された方法 |
Country Status (35)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5627574B2 (ja) * | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| CA2824432C (en) | 2011-01-31 | 2021-10-19 | Genoa Pharmaceuticals, Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| 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 |
| EP4491180A1 (en) | 2014-01-10 | 2025-01-15 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| CN106459042B (zh) | 2014-04-02 | 2019-06-28 | 英特穆恩公司 | 抗纤维化吡啶酮类 |
| US20160045439A1 (en) * | 2014-08-15 | 2016-02-18 | PixarBio Corporation | Compositions for inhibiting inflammation in a subject with a spinal cord injury and methods of using the same |
| 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 |
| US11066368B2 (en) | 2016-01-14 | 2021-07-20 | Laurus Labs Limited | Process for the preparation and particle size reduction of pirfenidone |
| WO2017122139A1 (en) * | 2016-01-14 | 2017-07-20 | Laurus Labs Limited | An improved process for the preparation 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 |
| US20180009753A1 (en) * | 2016-07-08 | 2018-01-11 | Dipharma Francis S.R.L. | Method for preparing an antifibrotic agent |
| IT201600108927A1 (it) * | 2016-10-27 | 2018-04-27 | Dipharma Francis Srl | Metodo per sintetizzare un farmaco antifibrotico |
| 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 |
| CA3108048A1 (en) | 2017-07-31 | 2019-02-07 | Washington University | Pirfenidone derivatives for modulation of b lymphocyte activity and organ protection |
| 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 |
Family Cites Families (9)
| 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 |
| WO1992013844A1 (en) * | 1991-01-31 | 1992-08-20 | Warner-Lambert Company | Substituted 4,6-di-tertiary-butyl-5-hydroxy-pyrimidines |
| JPWO2002085858A1 (ja) * | 2001-04-20 | 2004-08-12 | 旭硝子株式会社 | 精製されたピペリジン誘導体の製造方法 |
| KR100898888B1 (ko) * | 2001-08-06 | 2009-05-21 | 시오노기세이야쿠가부시키가이샤 | 5-메틸-1-페닐-2(1ｈ)피리디논의 제조 방법 |
| 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 |
| CN100396669C (zh) * | 2006-03-15 | 2008-06-25 | 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 |
| 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. |
| EP2170828B1 (en) | 2007-06-20 | 2012-11-21 | Auspex Pharmaceuticals, Inc. | Substituted n-aryl pyridinones as fibrotic inhibitors |
| US20090131485A1 (en) * | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
-
2010
- 2010-06-01 TW TW099117538A patent/TWI434833B/zh active
- 2010-06-02 AP AP2012006052A patent/AP3630A/xx active
- 2010-06-02 AU AU2010256693A patent/AU2010256693B2/en not_active Revoked
- 2010-06-02 HR HRP20150696TT patent/HRP20150696T1/hr unknown
- 2010-06-02 GE GEAP201012512A patent/GEP20156223B/en unknown
- 2010-06-02 EP EP10784021.7A patent/EP2440543B1/en active Active
- 2010-06-02 BR BRPI1011015A patent/BRPI1011015B8/pt not_active IP Right Cessation
- 2010-06-02 KR KR1020117029855A patent/KR101734858B1/ko active Active
- 2010-06-02 SG SG2011089455A patent/SG176648A1/en unknown
- 2010-06-02 UA UAA201115405A patent/UA106759C2/uk unknown
- 2010-06-02 PT PT107840217T patent/PT2440543E/pt unknown
- 2010-06-02 US US12/792,387 patent/US20110003863A1/en not_active Abandoned
- 2010-06-02 MA MA34508A patent/MA33489B1/fr unknown
- 2010-06-02 CA CA2764043A patent/CA2764043C/en active Active
- 2010-06-02 RS RS20150376A patent/RS54031B1/sr unknown
- 2010-06-02 SI SI201030938T patent/SI2440543T1/sl unknown
- 2010-06-02 PL PL10784021T patent/PL2440543T3/pl unknown
- 2010-06-02 MY MYPI2011005818A patent/MY162443A/en unknown
- 2010-06-02 PE PE2011002044A patent/PE20120398A1/es not_active Application Discontinuation
- 2010-06-02 EA EA201101695A patent/EA021826B1/ru not_active IP Right Cessation
- 2010-06-02 DK DK10784021.7T patent/DK2440543T3/en active
- 2010-06-02 ES ES10784021.7T patent/ES2538103T3/es active Active
- 2010-06-02 MX MX2011012654A patent/MX2011012654A/es active IP Right Grant
- 2010-06-02 JP JP2012514087A patent/JP5848244B2/ja active Active
- 2010-06-02 HU HUE10784021A patent/HUE026014T2/en unknown
- 2010-06-02 WO PCT/US2010/037090 patent/WO2010141600A2/en not_active Ceased
- 2010-06-02 CN CN2010800245047A patent/CN102482255A/zh active Pending
- 2010-06-02 NZ NZ596872A patent/NZ596872A/en not_active IP Right Cessation
- 2010-06-03 AR ARP100101971A patent/AR076974A1/es active IP Right Grant
-
2011
- 2011-09-26 US US13/244,786 patent/US8519140B2/en active Active
- 2011-11-23 IL IL216565A patent/IL216565A/en active IP Right Grant
- 2011-11-30 ZA ZA2011/08794A patent/ZA201108794B/en unknown
- 2011-12-01 TN TNP2011000615A patent/TN2011000615A1/en unknown
- 2011-12-02 CL CL2011003069A patent/CL2011003069A1/es unknown
- 2011-12-05 NI NI201100211A patent/NI201100211A/es unknown
- 2011-12-05 HN HN2011003187A patent/HN2011003187A/es unknown
-
2013
- 2013-07-22 US US13/947,643 patent/US20130345430A1/en not_active Abandoned
-
2014
- 2014-04-08 US US14/247,357 patent/US20140221660A1/en not_active Abandoned
- 2014-11-11 US US14/538,426 patent/US20150065720A1/en not_active Abandoned
-
2015
- 2015-08-20 US US14/830,999 patent/US20150368200A1/en not_active Abandoned
- 2015-10-15 JP JP2015203886A patent/JP2016026196A/ja active Pending
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