MX343774B - Metodo de preparacion de acetato de ulipristal y su intermediario. - Google Patents
Metodo de preparacion de acetato de ulipristal y su intermediario.Info
- Publication number
- MX343774B MX343774B MX2014005245A MX2014005245A MX343774B MX 343774 B MX343774 B MX 343774B MX 2014005245 A MX2014005245 A MX 2014005245A MX 2014005245 A MX2014005245 A MX 2014005245A MX 343774 B MX343774 B MX 343774B
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- compound
- ulipristal acetate
- preparation
- reaction
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Se provee un método de preparación de acetato de Ulipristal (compuesto I), un intermediario clave novedoso (compuesto de la fórmula IV) para la preparación del acetato de Ulipristal, y la preparación del intermediario clave. Se ha descubierto, sorprendentemente en la presente invención, que el intermediario novedoso de la fórmula IV facilita la reacción con metil litio o con el reactivo metílico de Grignard; que el grupo protector puede ser eliminado fácilmente después de la reacción con menos reacciones laterales y un tratamiento de intermediario simple; se puede obtener fácilmente el reactivo usado, con bajo costo y alto rendimiento. Se prepara primero un compuesto de la fórmula III a un intermediario de la fórmula IV y se prepara entonces el intermediario a un compuesto de la fórmula y; el rendimiento total de los dos pasos es hasta de 75 por ciento, con una pureza de producto de más de 98 por ciento. R, en la fórmula, tiene los valores definidos en la descripción.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110339479.8A CN102516345B (zh) | 2011-11-01 | 2011-11-01 | 醋酸乌利司他及其关键中间体的制备方法 |
| PCT/CN2012/000952 WO2013063859A1 (zh) | 2011-11-01 | 2012-07-12 | 醋酸乌利司他的制备方法及其中间体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2014005245A MX2014005245A (es) | 2014-08-22 |
| MX343774B true MX343774B (es) | 2016-11-23 |
Family
ID=46287461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2014005245A MX343774B (es) | 2011-11-01 | 2012-07-12 | Metodo de preparacion de acetato de ulipristal y su intermediario. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9163058B2 (es) |
| EP (1) | EP2774933B1 (es) |
| JP (1) | JP5913599B2 (es) |
| CN (1) | CN102516345B (es) |
| AU (1) | AU2012331996B2 (es) |
| BR (1) | BR112014010263B1 (es) |
| CA (1) | CA2851399C (es) |
| ES (1) | ES2669052T3 (es) |
| HU (1) | HUE037674T2 (es) |
| IN (1) | IN2014CN02562A (es) |
| MX (1) | MX343774B (es) |
| PL (1) | PL2774933T3 (es) |
| RU (1) | RU2624007C2 (es) |
| WO (1) | WO2013063859A1 (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516345B (zh) * | 2011-11-01 | 2014-11-26 | 上海优拓医药科技有限公司 | 醋酸乌利司他及其关键中间体的制备方法 |
| CN103073612B (zh) * | 2013-02-04 | 2015-11-04 | 山东大学 | 醋酸乌利司他关键中间体的制备方法 |
| CN103145788B (zh) * | 2013-03-25 | 2015-08-19 | 浙江仙琚制药股份有限公司 | 醋酸优力司特关键中间体的制备方法 |
| HU230319B1 (hu) | 2013-10-01 | 2016-01-28 | Richter Gedeon Nyrt. | Ipari eljárás szteroid hatóanyagok előállítására |
| CN104558089A (zh) * | 2013-10-25 | 2015-04-29 | 上海医药工业研究院 | 一种3-(亚乙二氧基)-17β-氰基-17α-羟基-雌-5(10)，9(11)-二烯的制备方法 |
| CN103641881A (zh) * | 2013-11-22 | 2014-03-19 | 湖南新合新生物医药有限公司 | 乌利司他中间体的制备方法 |
| CN103601785A (zh) * | 2013-11-25 | 2014-02-26 | 四川大学 | 一种醋酸优力斯特新的合成方法 |
| CN104774231A (zh) * | 2014-01-13 | 2015-07-15 | 上海医药工业研究院 | 17α-羟基-19-去甲孕甾-4,9-二烯-3,20-二酮的制备工艺 |
| CN105294808B (zh) * | 2015-09-28 | 2017-08-25 | 国家卫生计生委科学技术研究所 | 醋酸乌利司他晶g型物质及制备方法和其组合物与用途 |
| CN105237607B (zh) * | 2015-10-29 | 2018-10-02 | 国家卫生计生委科学技术研究所 | 醋酸乌利司他晶k型物质及制备方法和其组合物与用途 |
| CN105669810B (zh) * | 2016-02-19 | 2017-05-10 | 常州市第四制药厂有限公司 | 一种醋酸乌利司他的杂质及其制备和检测方法 |
| CN105566432B (zh) * | 2016-02-19 | 2017-11-03 | 常州四药制药有限公司 | 一种醋酸乌利司他的杂质及其制备和检测方法 |
| CN105566431B (zh) * | 2016-02-19 | 2017-11-24 | 常州市第四制药厂有限公司 | 一种醋酸乌利司他的杂质及其制备和检测方法 |
| CN105669819B (zh) * | 2016-03-23 | 2017-06-23 | 浙江仙琚制药股份有限公司 | 制备醋酸优力司特双缩酮异构体的方法 |
| CN106866778A (zh) * | 2017-04-25 | 2017-06-20 | 广西万德药业有限公司 | 一种5(10)位α环氧甾族化合物的合成方法 |
| CN108070016B (zh) * | 2017-12-29 | 2020-07-07 | 广西万德药业有限公司 | 甾体环氧异构体的循环利用方法 |
| CN108558981B (zh) * | 2018-05-08 | 2020-05-08 | 浙江仙琚制药股份有限公司 | 制备双缩酮的方法 |
| JP7303618B2 (ja) * | 2018-10-05 | 2023-07-05 | 日本精化株式会社 | スフィンゴリン脂質前駆体及びその製造方法、並びに、スフィンゴリン脂質の製造方法 |
| CN110256519B (zh) * | 2019-05-23 | 2021-06-08 | 江苏联环药业股份有限公司 | 一锅法制备醋酸乌利司他的方法 |
| CN111018935A (zh) * | 2019-12-31 | 2020-04-17 | 浙江仙居君业药业有限公司 | 一种醋酸乌利斯他中间体的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0263569B1 (en) * | 1986-10-10 | 1992-12-09 | Roussel-Uclaf | 9-alpha-hydroxysteroids, process for their preparation and process for the preparation of the corresponding 9(11)-dehydro-derivatives. |
| US4954490A (en) * | 1988-06-23 | 1990-09-04 | Research Triangle Institute | 11 β-substituted progesterone analogs |
| US5929262A (en) * | 1995-03-30 | 1999-07-27 | The United States Of America As Represented By The Department Of Health And Human Services | Method for preparing 17α-acetoxy-11β-(4-N, N-dimethylaminophyl)-19-Norpregna-4,9-diene-3, 20-dione, intermediates useful in the method, and methods for the preparation of such intermediates |
| US6020328A (en) * | 1998-03-06 | 2000-02-01 | Research Triangle Institute | 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| DE60134126D1 (de) * | 2000-03-17 | 2008-07-03 | Us Gov Health & Human Serv | 17-alpha-substituierte-11-beta-substituierte-4-aryl und 21-substituierte 19-norpregnadienedione mit antigestagener aktivität |
| EP1613640A4 (en) * | 2003-02-28 | 2010-05-19 | Us Gov Health & Human Serv | PROCESS FOR PREPARING 17 ALPHA-ACETOXY-11 BETA- (4-N, N-DIMETHYLAMINOPHENYL) -19-NORPREGNA-4,9-DIENE-3,20-DION, INTERMEDIATE PRODUCTS AND METHOD OF MANUFACTURING THESE INTERMEDIATE PRODUCTS |
| US20050288521A1 (en) * | 2004-06-29 | 2005-12-29 | Phytogen Life Sciences Inc. | Semi-synthetic conversion of paclitaxel to docetaxel |
| HU227112B1 (hu) * | 2006-06-14 | 2010-07-28 | Richter Gedeon Nyrt | Ipari eljárás 17-alfa-acetoxi-11-béta-[4-(N,N-dimetil-amino)-fenil]-19-norpregna-4,9-dién-3,20-dion elõállítására és új intermedierek az eljáráshoz |
| HU228636B1 (en) * | 2007-06-27 | 2013-04-29 | Richter Gedeon Nyrt | Industrial method for the synthesis of 17-acetoxy-11betha-4[-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process |
| CN102516345B (zh) | 2011-11-01 | 2014-11-26 | 上海优拓医药科技有限公司 | 醋酸乌利司他及其关键中间体的制备方法 |
-
2011
- 2011-11-01 CN CN201110339479.8A patent/CN102516345B/zh active Active
-
2012
- 2012-07-12 US US14/233,757 patent/US9163058B2/en active Active
- 2012-07-12 AU AU2012331996A patent/AU2012331996B2/en active Active
- 2012-07-12 BR BR112014010263-5A patent/BR112014010263B1/pt active IP Right Grant
- 2012-07-12 CA CA2851399A patent/CA2851399C/en active Active
- 2012-07-12 MX MX2014005245A patent/MX343774B/es active IP Right Grant
- 2012-07-12 WO PCT/CN2012/000952 patent/WO2013063859A1/zh active Application Filing
- 2012-07-12 RU RU2014120908A patent/RU2624007C2/ru active IP Right Revival
- 2012-07-12 PL PL12845071T patent/PL2774933T3/pl unknown
- 2012-07-12 JP JP2014534915A patent/JP5913599B2/ja active Active
- 2012-07-12 ES ES12845071.5T patent/ES2669052T3/es active Active
- 2012-07-12 EP EP12845071.5A patent/EP2774933B1/en active Active
- 2012-07-12 IN IN2562CHN2014 patent/IN2014CN02562A/en unknown
- 2012-07-12 HU HUE12845071A patent/HUE037674T2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2014528459A (ja) | 2014-10-27 |
| WO2013063859A1 (zh) | 2013-05-10 |
| EP2774933A1 (en) | 2014-09-10 |
| BR112014010263B1 (pt) | 2021-11-03 |
| AU2012331996B2 (en) | 2015-04-23 |
| CN102516345B (zh) | 2014-11-26 |
| MX2014005245A (es) | 2014-08-22 |
| RU2624007C2 (ru) | 2017-06-30 |
| ES2669052T3 (es) | 2018-05-23 |
| BR112014010263A2 (pt) | 2017-04-18 |
| CN102516345A (zh) | 2012-06-27 |
| EP2774933B1 (en) | 2018-02-21 |
| IN2014CN02562A (es) | 2015-08-07 |
| RU2014120908A (ru) | 2015-12-10 |
| JP5913599B2 (ja) | 2016-04-27 |
| AU2012331996A1 (en) | 2014-05-15 |
| US9163058B2 (en) | 2015-10-20 |
| CA2851399C (en) | 2019-06-25 |
| US20140296510A1 (en) | 2014-10-02 |
| HUE037674T2 (hu) | 2018-09-28 |
| CA2851399A1 (en) | 2013-05-10 |
| PL2774933T3 (pl) | 2018-08-31 |
| EP2774933A4 (en) | 2015-07-08 |
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Legal Events
| Date | Code | Title | Description |
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| FG | Grant or registration |