MX384252B - Proceso para sintesis de pirfenidona. - Google Patents
Proceso para sintesis de pirfenidona.Info
- Publication number
- MX384252B MX384252B MX2018004338A MX2018004338A MX384252B MX 384252 B MX384252 B MX 384252B MX 2018004338 A MX2018004338 A MX 2018004338A MX 2018004338 A MX2018004338 A MX 2018004338A MX 384252 B MX384252 B MX 384252B
- Authority
- MX
- Mexico
- Prior art keywords
- pirfenidone
- synthesis
- reaction
- chlorobenzene
- system consisting
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 229960003073 pirfenidone Drugs 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 abstract 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 abstract 1
- 102000005720 Glutathione transferase Human genes 0.000 abstract 1
- 108010070675 Glutathione transferase Proteins 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001879 copper Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000013110 organic ligand Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Se describe un proceso para la síntesis de pirfenidona (1) a partir de 5-metil-2 (1H) piridinona y clorobenceno en presencia de un sistema catalítico que consiste de una sal de cobre y un ligando orgánico, en presencia de una base. El proceso aprovecha la alta eficiencia del sistema catalítico que consiste de sal de cobre (I) y una ligandina orgánica en presencia de una base inorgánica en la reacción de N-amidación de clorobenceno, un reactivo barato también usable como solvente en este caso; las condiciones de reacción a altas temperaturas, a presión atmosférica o superior producen una reacción con buenos rendimientos.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITUB2015A004832A ITUB20154832A1 (it) | 2015-10-29 | 2015-10-29 | Processo per la sintesi di pirfenidone |
| PCT/EP2016/075899 WO2017072216A1 (en) | 2015-10-29 | 2016-10-27 | Process for the synthesis of pirfenidone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2018004338A MX2018004338A (es) | 2018-05-22 |
| MX384252B true MX384252B (es) | 2025-03-11 |
Family
ID=55409972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2018004338A MX384252B (es) | 2015-10-29 | 2016-10-27 | Proceso para sintesis de pirfenidona. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10472325B2 (es) |
| EP (1) | EP3368513B1 (es) |
| ES (1) | ES2875126T3 (es) |
| IT (1) | ITUB20154832A1 (es) |
| MX (1) | MX384252B (es) |
| PT (1) | PT3368513T (es) |
| WO (1) | WO2017072216A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111848503B (zh) * | 2020-09-10 | 2022-11-11 | 苏州富德兆丰生化科技有限公司 | 吡非尼酮的合成方法 |
| US12331021B2 (en) * | 2020-09-10 | 2025-06-17 | Suzhou Fude Zhaofeng Biochemical Technology Co., Ltd | Total synthesis of pirfenidone |
| CN119118913B (zh) * | 2024-08-26 | 2025-09-16 | 郑州大学 | 一种抗纤维化药物吡非尼酮的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1458049A (en) * | 1972-12-18 | 1976-12-08 | Affiliated Med Res | Process for preparing aryl-substituted pyridones |
| US3839346A (en) * | 1972-12-18 | 1974-10-01 | Affiliated Med Res | N-substituted pyridone and general method for preparing pyridones |
| WO2003014087A1 (fr) * | 2001-08-06 | 2003-02-20 | Asahi Glass Company, Limited | Procede de preparation de 5-methyl-1-phenyl-2(1h)-pyridinone |
| 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. |
| US20090131485A1 (en) * | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| TWI434833B (zh) * | 2009-06-03 | 2014-04-21 | Intermune Inc | 用於合成吡非尼酮（ｐｉｒｆｅｎｉｄｏｎｅ）的改良方法 |
| CN101891676A (zh) | 2010-08-03 | 2010-11-24 | 陕西合成药业有限公司 | 一种新的5-甲基-1-苯基-2-(1h)-吡啶酮的制备方法 |
| CN102558040A (zh) | 2011-12-28 | 2012-07-11 | 辰欣药业股份有限公司 | 一种吡非尼酮的制备方法 |
-
2015
- 2015-10-29 IT ITUB2015A004832A patent/ITUB20154832A1/it unknown
-
2016
- 2016-10-27 MX MX2018004338A patent/MX384252B/es unknown
- 2016-10-27 US US15/771,050 patent/US10472325B2/en active Active
- 2016-10-27 PT PT167974658T patent/PT3368513T/pt unknown
- 2016-10-27 WO PCT/EP2016/075899 patent/WO2017072216A1/en not_active Ceased
- 2016-10-27 EP EP16797465.8A patent/EP3368513B1/en active Active
- 2016-10-27 ES ES16797465T patent/ES2875126T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ITUB20154832A1 (it) | 2017-04-29 |
| EP3368513B1 (en) | 2021-04-14 |
| ES2875126T3 (es) | 2021-11-08 |
| US20180319747A1 (en) | 2018-11-08 |
| MX2018004338A (es) | 2018-05-22 |
| PT3368513T (pt) | 2021-06-18 |
| WO2017072216A1 (en) | 2017-05-04 |
| US10472325B2 (en) | 2019-11-12 |
| EP3368513A1 (en) | 2018-09-05 |
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