ES2127413T3 - Sintesis de esteroides 17-(3-piridilo). - Google Patents
Sintesis de esteroides 17-(3-piridilo).Info
- Publication number
- ES2127413T3 ES2127413T3 ES94927003T ES94927003T ES2127413T3 ES 2127413 T3 ES2127413 T3 ES 2127413T3 ES 94927003 T ES94927003 T ES 94927003T ES 94927003 T ES94927003 T ES 94927003T ES 2127413 T3 ES2127413 T3 ES 2127413T3
- Authority
- ES
- Spain
- Prior art keywords
- beta
- steroid
- hydroxy
- group
- substituted
- 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.)
- Expired - Lifetime
Links
- 150000003431 steroids Chemical class 0.000 title abstract 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 229910000085 borane Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 238000006880 cross-coupling reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000003637 steroidlike Effects 0.000 abstract 2
- -1 (3-pyridyl)-substituted borane Chemical class 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
UN METODO PARA PREPARAR UN ESTEROIDE 3 BE -HIDROXI- O 3 BE}(ACILOXI BAJO) 16,17-ENO-17-(3-PIRIDILO)-SUSTITUIDO, DONDE EL GRUPO 3{BE}-(ACILOXI BAJO) DE LOS ESTEROIDES TIENE DE 2 A 4 ATOMOS DE CARBONO, QUE COMPRENDE SOMETER UN ESTEROIDE 3{BE}HIDROXI-16,17-ENO-17-IODO O BROMO A UNA REACCION DE ENLACE CRUZADO COMPLEJO-CATALIZADA DE PALADIO CON UN BORANO (3PIRIDILO)-SUSTITUIDO EN LA QUE EL ANILLO DE PIRIDINA ES SUSTITUIDO EN LA POSICION-5 POR UN GRUPO ALQUILO DE 1 A 4 ATOMOS DE CARBONO O ES INSUSTITUIDO EN ESE PUNTO, EN UNA PROPORCION DE AL MENOS 1.0 EQUIVALENTE DE BORANO POR EQUIVALENTE DE ESTEROIDE, EN UN LIQUIDO ORGANICO QUE ES UN SOLVENTE PARA EL PRODUCTO DE REACCION ESTEROIDAL 3{BE}-HIDROXI, Y OPCIONALMENTE ESTERIFICANDO EL PRODUCTO DE REACCION ESTEROIDAL 3{BE}-HIDROXI RESULTANTE CON UN AGENTE ESTERIFICANTE EFICAZ PARA REEMPLAZAR EL GRUPO HIDROXI POR UN GRUPO DE ACILOXI BAJO MENCIONADO; EL METODO INCLUYE (A) LLEVAR A CABO LA REACCION CON NO MAS DE 1.2 EQUIVALENTES DE BORANO POR EQUIVALENTEDE ESTEROIDE O (B) CRISTALIZAR EL PRODUCTO DE LA REACCION DE ENLACE CRUZADO MEDIANTE UNA MEZCLA DE ACETONITRILO Y METANOL.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939320132A GB9320132D0 (en) | 1993-09-30 | 1993-09-30 | Synthesis of 17-(-3-pyridyl)steroids |
| GB9414192A GB9414192D0 (en) | 1994-07-14 | 1994-07-14 | Synthesis of 17-(3-pyridyl) steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2127413T3 true ES2127413T3 (es) | 1999-04-16 |
Family
ID=26303602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES94927003T Expired - Lifetime ES2127413T3 (es) | 1993-09-30 | 1994-09-22 | Sintesis de esteroides 17-(3-piridilo). |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0721461B1 (es) |
| JP (1) | JP3722835B2 (es) |
| AT (1) | ATE176481T1 (es) |
| AU (1) | AU676088B2 (es) |
| CA (1) | CA2170286C (es) |
| DE (1) | DE69416419T2 (es) |
| DK (1) | DK0721461T3 (es) |
| ES (1) | ES2127413T3 (es) |
| GB (1) | GB2282377B (es) |
| GR (1) | GR3029601T3 (es) |
| NZ (1) | NZ273367A (es) |
| SG (1) | SG49321A1 (es) |
| WO (1) | WO1995009178A1 (es) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8569275B2 (en) | 2002-08-28 | 2013-10-29 | Harbor Therapeutics, Inc. | Steroids having 7-oxgen and 17-heteroaryl substitution |
| JP5199667B2 (ja) | 2004-08-24 | 2013-05-15 | ビーティージー・インターナショナル・リミテッド | 中間体としての17−o−ビニル−トリフレートの調製のための方法 |
| GB0418900D0 (en) | 2004-08-24 | 2004-09-29 | Btg Int Ltd | Novel salt forms |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| UA105794C2 (uk) | 2009-06-26 | 2014-06-25 | Новартіс Аг | 1,3-ДИЗАМІЩЕНІ ПОХІДНІ ІМІДАЗОЛІДИН-2-ОНУ ЯК ІНГІБІТОРИ Cyp17 |
| JP2013537210A (ja) | 2010-09-16 | 2013-09-30 | ノバルティス アーゲー | 17α−ヒドロキシラーゼ/C17,20−リアーゼ阻害剤 |
| CN102558274B (zh) * | 2010-12-08 | 2014-10-15 | 深圳万乐药业有限公司 | 一种适合工业化生产醋酸阿比特龙的合成方法 |
| CN102558275A (zh) * | 2010-12-20 | 2012-07-11 | 天津药物研究院 | α型多晶型醋酸阿比特龙结晶、其制备方法、用途和药物组合物 |
| EA023064B1 (ru) | 2011-04-28 | 2016-04-29 | Новартис Аг | ИНГИБИТОРЫ 17α-ГИДРОКСИЛАЗЫ/C-ЛИАЗЫ |
| US9353145B2 (en) * | 2011-10-10 | 2016-05-31 | Zach System | Process for preparing 17-substituted steroids |
| CN103059090B (zh) * | 2011-10-20 | 2016-06-22 | 连云港润众制药有限公司 | 醋酸阿比特龙草酸盐以及醋酸阿比特龙的纯化方法 |
| CN102336801B (zh) * | 2011-10-31 | 2013-05-15 | 南京卡文迪许生物工程技术有限公司 | 醋酸阿比特龙多晶型物和药用组合物 |
| EP2607371A1 (en) | 2011-12-23 | 2013-06-26 | Crystal Pharma, S.A.U. | Processes for the preparation of abiraterone and related compouds |
| CN105461777B (zh) * | 2012-01-04 | 2017-07-18 | 连云港润众制药有限公司 | 一种醋酸阿比特龙的纯化方法 |
| CN103254265B (zh) | 2012-02-21 | 2016-07-13 | 上海希迈医药科技有限公司 | 醋酸阿比特龙三氟乙酸盐及其制备方法和应用 |
| CN102627681B (zh) * | 2012-03-23 | 2016-04-13 | 山东新时代药业有限公司 | 一种醋酸阿比特龙的制备方法 |
| WO2013159225A1 (en) * | 2012-04-23 | 2013-10-31 | Alphora Research Inc. | Process for preparation of 17-substituted steroids |
| CN102731605B (zh) * | 2012-06-19 | 2016-04-13 | 鲁南制药集团股份有限公司 | 一种醋酸阿比特龙的纯化方法 |
| WO2014009434A1 (en) | 2012-07-11 | 2014-01-16 | Sandoz Ag | Self-microemulsifying drug delivery system of abiraterone or abiraterone acetate |
| WO2014009436A1 (en) | 2012-07-11 | 2014-01-16 | Sandoz Ag | Nanosuspension of abiraterone acetate |
| WO2014009437A1 (en) | 2012-07-11 | 2014-01-16 | Sandoz Ag | Oxidation stability of abiraterone acetate |
| CN102816199B (zh) * | 2012-08-15 | 2015-04-08 | 武汉长联来福制药股份有限公司 | 醋酸阿比特龙二聚体化合物的制备及检测方法 |
| CN102816200B (zh) * | 2012-09-05 | 2015-04-15 | 中山大学 | 一种醋酸阿比特龙的制备方法 |
| CN103665085B (zh) * | 2012-09-24 | 2016-04-20 | 成都伊诺达博医药科技有限公司 | 一种改进的乙酸阿比特龙酯合成方法 |
| CN102816201A (zh) * | 2012-09-25 | 2012-12-12 | 成都伊诺达博医药科技有限公司 | 一种阿比特龙的纯化方法 |
| WO2014058785A1 (en) | 2012-10-10 | 2014-04-17 | Novartis Ag | Combination therapy |
| ITMI20121788A1 (it) | 2012-10-22 | 2014-04-23 | Olon Spa | Procedimento per la purificazione di abiraterone acetato |
| WO2014071983A1 (en) | 2012-11-09 | 2014-05-15 | Synthon Bv | Process for making the 17-triflate intermediate of abiraterone-3-acetate |
| CA2890589A1 (en) | 2012-11-09 | 2014-05-15 | Synthon Bv | Process for making abiraterone-3-acetate |
| WO2014075978A1 (en) | 2012-11-16 | 2014-05-22 | Synthon B.V. | Process for the production of abiraterone-3-acetate involving an enol trliflation reaction in the presence of an alkoxy-pyridine compound |
| CN103059091B (zh) * | 2012-11-22 | 2017-04-19 | 常州靶点医药科技有限公司 | 一种避免重金属残留的醋酸阿比特龙的制备方法 |
| WO2014083512A1 (en) * | 2012-11-28 | 2014-06-05 | Dr. Reddy's Laboratories Limited | Process for preparation of abiraterone acetate |
| PL2792682T3 (pl) | 2013-04-19 | 2017-04-28 | Zach System | Sposób wytwarzania stałej postaci octanu abirateronu |
| WO2014188445A1 (en) * | 2013-04-26 | 2014-11-27 | Srinivasan Thirumalai Rajan | PROCESS FOR THE PREPARATION OF (3β)-17-(3-PYRIDINYL)ANDROSTA-5,16-DIEN-3-YL ACETATE AND POLYMORPH THEREOF |
| CN103387597B (zh) * | 2013-08-21 | 2015-03-25 | 苏州明锐医药科技有限公司 | 阿比特龙醋酸酯的制备方法 |
| CN104558090A (zh) * | 2013-10-28 | 2015-04-29 | 重庆医药工业研究院有限责任公司 | 醋酸阿比特龙杂质及其测定方法 |
| WO2015102022A2 (en) * | 2013-12-31 | 2015-07-09 | Laurus Labs Private Limited | An improved process for the preparation of abiraterone acetate |
| US9556219B2 (en) | 2014-01-28 | 2017-01-31 | Olon S.P.A. | Procedure for the preparation of abiraterone acetate and intermediates thereof |
| CN103965282B (zh) | 2014-04-21 | 2016-01-20 | 武汉百科药物开发有限公司 | 一种醋酸阿比特龙的制备方法 |
| EP3160450A1 (en) | 2014-06-30 | 2017-05-03 | Galenicum Health S.L. | Stable pharmaceutical compositions in the form of immediate release tablets |
| CZ2014475A3 (cs) | 2014-07-09 | 2016-01-20 | Zentiva, K.S. | Způsob přípravy Abirateron acetátu o vysoké čistotě aplikovatelný v průmyslovém měřítku |
| CN105622703B (zh) * | 2014-11-05 | 2019-09-27 | 兰州大学 | 一种制备醋酸阿比特龙的方法 |
| WO2018023017A1 (en) | 2016-07-29 | 2018-02-01 | Janssen Pharmaceutica Nv | Methods of treating prostate cancer |
| CN107056871A (zh) * | 2017-06-28 | 2017-08-18 | 李建恒 | 一种阿比特龙醋酸酯的合成方法 |
| HU231297B1 (hu) | 2018-07-31 | 2022-09-28 | Richter Gedeon Nyrt | Stabil gyógyszerkészítmények és eljárás az előállításukra |
| CN109134571B (zh) * | 2018-09-13 | 2020-10-02 | 浙江工业大学 | 一种17-碘-雄甾-5,16-二烯-3β-醇的制备方法 |
| EP3944860A1 (en) | 2020-07-30 | 2022-02-02 | Galenicum Health S.L.U. | Abiraterone for use in a method of treating cancer |
| CN112125942B (zh) * | 2020-09-28 | 2021-12-14 | 湖南新合新生物医药有限公司 | 醋酸阿比特龙及其中间体的合成方法 |
| CN112940065A (zh) * | 2021-02-03 | 2021-06-11 | 山东大学 | 三氟甲磺酸盐在制备醋酸阿比特龙中的应用及合成方法 |
| CN114709557B (zh) * | 2022-04-13 | 2023-10-27 | 南京工业大学 | 一种后修饰碳硼烷的共价有机框架材料的设计合成及其在锂硫电池隔膜中的应用 |
| WO2023213151A1 (zh) | 2022-05-06 | 2023-11-09 | 奥锐特药业股份有限公司 | 一种醋酸阿比特龙及其中间体的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69327096T2 (de) * | 1992-03-31 | 2000-06-21 | Btg International Ltd., London | 17-substituierte steroide, verwendbar bei behandlung von krebs |
-
1994
- 1994-09-22 DE DE69416419T patent/DE69416419T2/de not_active Expired - Lifetime
- 1994-09-22 AU AU76618/94A patent/AU676088B2/en not_active Expired
- 1994-09-22 AT AT94927003T patent/ATE176481T1/de active
- 1994-09-22 JP JP51016395A patent/JP3722835B2/ja not_active Expired - Lifetime
- 1994-09-22 ES ES94927003T patent/ES2127413T3/es not_active Expired - Lifetime
- 1994-09-22 GB GB9419139A patent/GB2282377B/en not_active Expired - Lifetime
- 1994-09-22 DK DK94927003T patent/DK0721461T3/da active
- 1994-09-22 EP EP94927003A patent/EP0721461B1/en not_active Expired - Lifetime
- 1994-09-22 WO PCT/GB1994/002054 patent/WO1995009178A1/en not_active Ceased
- 1994-09-22 CA CA002170286A patent/CA2170286C/en not_active Expired - Lifetime
- 1994-09-22 NZ NZ273367A patent/NZ273367A/en not_active IP Right Cessation
- 1994-09-22 SG SG1996009266A patent/SG49321A1/en unknown
-
1999
- 1999-03-08 GR GR990400688T patent/GR3029601T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7661894A (en) | 1995-04-18 |
| JPH09502994A (ja) | 1997-03-25 |
| ATE176481T1 (de) | 1999-02-15 |
| CA2170286A1 (en) | 1995-04-06 |
| CA2170286C (en) | 2005-04-05 |
| DE69416419T2 (de) | 1999-06-10 |
| GB2282377B (en) | 1997-09-03 |
| SG49321A1 (en) | 1998-05-18 |
| EP0721461A1 (en) | 1996-07-17 |
| GB2282377A (en) | 1995-04-05 |
| NZ273367A (en) | 1997-07-27 |
| EP0721461B1 (en) | 1999-02-03 |
| JP3722835B2 (ja) | 2005-11-30 |
| HK1002634A1 (en) | 1998-09-04 |
| DK0721461T3 (da) | 1999-09-20 |
| GR3029601T3 (en) | 1999-06-30 |
| AU676088B2 (en) | 1997-02-27 |
| WO1995009178A1 (en) | 1995-04-06 |
| GB9419139D0 (en) | 1994-11-09 |
| DE69416419D1 (de) | 1999-03-18 |
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| FG2A | Definitive protection |
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