ES2188550T3 - Procedimiento para la sintesis de n-(4-ciano-3-trifluorometil-fenil)-3-(4-fluorofenil-sulfonil)-2-hidroxi-2-metil-propionamida. - Google Patents
Procedimiento para la sintesis de n-(4-ciano-3-trifluorometil-fenil)-3-(4-fluorofenil-sulfonil)-2-hidroxi-2-metil-propionamida.Info
- Publication number
- ES2188550T3 ES2188550T3 ES00937111T ES00937111T ES2188550T3 ES 2188550 T3 ES2188550 T3 ES 2188550T3 ES 00937111 T ES00937111 T ES 00937111T ES 00937111 T ES00937111 T ES 00937111T ES 2188550 T3 ES2188550 T3 ES 2188550T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- formula
- racemic
- optically pure
- solvent
- 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
- -1 4-FLUOROPHENYL-SULPHONYL Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000008282 halocarbons Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 2
- 239000003444 phase transfer catalyst Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- DGADNPLBVRLJGD-UHFFFAOYSA-N 2,3-dihydroxy-2-methylpropanoic acid Chemical compound OCC(O)(C)C(O)=O DGADNPLBVRLJGD-UHFFFAOYSA-N 0.000 abstract 1
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 abstract 1
- PMDYLCUKSLBUHO-UHFFFAOYSA-N 4-amino-2-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C#N)C(C(F)(F)F)=C1 PMDYLCUKSLBUHO-UHFFFAOYSA-N 0.000 abstract 1
- RLYHGDXBALNOJK-UHFFFAOYSA-N 4-methyl-2-oxo-1,3,2-dioxathiolane-4-carbonyl chloride Chemical compound ClC(=O)C1(C)COS(=O)O1 RLYHGDXBALNOJK-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- IIBBSRFFFOOJBY-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2,3-dihydroxy-2-methylpropanamide Chemical compound OCC(O)(C)C(=O)NC1=CC=C(C#N)C(C(F)(F)F)=C1 IIBBSRFFFOOJBY-UHFFFAOYSA-N 0.000 abstract 1
- AUQOJOMQBSXVBP-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3,2-dioxathiolane-4-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C1(C)COS(=O)O1 AUQOJOMQBSXVBP-UHFFFAOYSA-N 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940080818 propionamide Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Un nuevo procedimiento para la síntesis de R-(-)- y S-(+)-N-[4-ciano-3-trifluorometil-fenil]-3-[4fluorofenil-sulfonil]-2-hidroxi-2-metil-propionamida racémica u ópticamente pura de fórmula (I), (Ia) y (Ib), respectivamente, caracterizado por: hacer reaccionar el ácido 2, 3-dihidroxi-2-metil-propiónico racémico u ópticamente puro de fórmula (VII) con cloruro de tionilo en un hidrocarburo halogenado o en un disolvente aromático, en presencia de una amina aromática como base, hacer reaccionar la 4-cloro-carbonil-4-metil-1, 3, 2-dioxatiolan-2-ona racémica u ópticamente pura de fórmula (VI), con 4-ciano-3-trifluorometil-anilina en un disolvente inerte, en presencia de una amina terciaria como base, entre -40 y 0°C, hidrolizar la 4-{[4-ciano-3-(trifluorometil)-anilino]-carbonil}-4-metil-1, 3, 2-dioxatiolan-2-ona de fórmula (V), bajo condiciones acuosas básicas, sulfonilar la N-[4-ciano-3-(trifluorometil)-fenil]-2, 3-dihidroxi-2-metil-propionamida de fórmula (IV) con un haluro de sulfonilo de fórmula R-SO2-X - en la que el significado de R era un grupo metilo, p-tolilo o p-bromo-fenilo y X representa un átomo de halógeno - en un hidrocarburo halogenado como disolvente, en presencia de una amina terciaria como base, hacer reaccionar el derivado de éster sulfónico racémico u ópticamente puro obtenido de fórmula (III) - en la que R representa un grupo metilo, p-tolilo o p-bromo-fenilo - con 4-fluorotiofenol, en presencia de una base, y finalmente oxidar el derivado de tioéter racémico u ópticamente puro obtenido de fórmula (II) i) con una sal peróxido inorgánico en una mezcla de agua y un disolvente miscible o no miscible con agua, en el último caso en presencia de un catalizador de transferencia de fase, o ii) con peróxido de hidrógeno acuoso alpha) en un ácido carboxílico alifático C1-C4, o beta) bajo condiciones acuosas básicas, en su caso en presencia de un disolvente orgánico miscible con agua, o gamma) en un disolvente orgánico no miscible con agua, en presencia de un catalizadorde transferencia de fase y una sal de un metal perteneciente al grupo del vanadio o del cromo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9901937A HU223950B1 (hu) | 1999-06-10 | 1999-06-10 | Eljárás a racém, valamint az R-(-)- és S-(+)-N-[4-ciano-3-(trifluor-metil)-fenil]-3-[(4-fluor-fenil)-szulfonil]-2-hidroxi-2-metil-propánsavamid előállítására |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2188550T3 true ES2188550T3 (es) | 2003-07-01 |
Family
ID=89998474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00937111T Expired - Lifetime ES2188550T3 (es) | 1999-06-10 | 2000-05-26 | Procedimiento para la sintesis de n-(4-ciano-3-trifluorometil-fenil)-3-(4-fluorofenil-sulfonil)-2-hidroxi-2-metil-propionamida. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7199257B1 (es) |
| EP (1) | EP1189898B1 (es) |
| AT (1) | ATE234294T1 (es) |
| AU (1) | AU5239700A (es) |
| DE (1) | DE60001657T2 (es) |
| ES (1) | ES2188550T3 (es) |
| HU (1) | HU223950B1 (es) |
| WO (1) | WO2001000608A1 (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7102026B2 (en) | 2001-06-13 | 2006-09-05 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Process for preparing and isolating rac-bicalutamide and its intermediates |
| EP1406855A4 (en) | 2001-06-13 | 2006-04-19 | Teva Gyogyszergyar Reszvenytar | NOVEL PROCESS FOR THE PREPARATION OF RAC-BICALUTAMIDE AND INTERMEDIATE PRODUCTS THEREOF |
| NZ533943A (en) | 2001-12-13 | 2006-06-30 | Sumitomo Chemical Co | Crystal of bicalutamide and production method thereof |
| DE10222104A1 (de) * | 2002-05-17 | 2003-12-04 | Helm Ag | Verfahren zur Herstellung von N-(4'-Cyano-3'-trifluormethyl)-3-(4"-fluorphenylsulfonyl)-2-hydroxy-2-methylpropionamid |
| US20040063782A1 (en) * | 2002-09-27 | 2004-04-01 | Westheim Raymond J.H. | Bicalutamide forms |
| US6818766B2 (en) | 2002-10-02 | 2004-11-16 | Synthon Bv | Process for making bicalutamide and intermediates thereof |
| AU2003209667A1 (en) * | 2003-02-21 | 2004-09-09 | Hetero Drugs Limited | Bicalutamide polymorphs |
| US20050008691A1 (en) | 2003-05-14 | 2005-01-13 | Arturo Siles Ortega | Bicalutamide compositions |
| WO2005009946A1 (en) * | 2003-06-25 | 2005-02-03 | TEVA Gyógyszergyár Részvénytársaság | Process for purifying and isolating rac-bicalutamide |
| JP4322621B2 (ja) | 2003-10-16 | 2009-09-02 | 住友化学株式会社 | ４’−シアノ−３−［（４−フルオロフェニル）スルホニル］−２−ヒドロキシ−２−メチル−３’−トリフルオロメチルプロピオンアニリドの製造方法 |
| KR20070114343A (ko) * | 2005-03-29 | 2007-12-03 | 유에스브이 리미티드 | 비칼루타미드의 제조 방법 |
| WO2007013094A2 (en) * | 2005-04-15 | 2007-02-01 | Sun Pharmaceutical Industries Limited | A process for preparation of antiandrogen compound |
| CA2513356A1 (en) * | 2005-07-26 | 2007-01-26 | Apotex Pharmachem Inc. | Process for production of bicalutamide |
| CA2635461A1 (en) * | 2005-12-27 | 2007-07-05 | Dabur Pharma Limited | An improved process for preparation of bicalutamide |
| CN101462988B (zh) * | 2007-12-21 | 2014-01-01 | 中国医学科学院药物研究所 | 一种比卡鲁胺的合成工艺 |
| WO2012042532A1 (en) * | 2010-09-29 | 2012-04-05 | Shilpa Medicare Limited | Process for preparing bicalutamide |
| CN102086167B (zh) * | 2010-12-09 | 2013-05-08 | 济南大学 | 一种乙磺酰基乙腈的制备方法 |
| CN102351762A (zh) * | 2011-07-21 | 2012-02-15 | 宁波人健药业集团有限公司 | 用n-(4-氰基-3-三氟甲基苯基)-3-(4-氟苯硫基)-2-甲基-2-羟基丙酰胺制备比卡鲁胺的方法 |
| CN102321000A (zh) * | 2011-07-21 | 2012-01-18 | 宁波人健药业集团有限公司 | 氧化制备比卡鲁胺的方法 |
| CN108069887B (zh) * | 2016-11-17 | 2021-04-20 | 山西振东制药股份有限公司 | 一种(r)-比卡鲁胺中间体的制备方法 |
| CN109336798B (zh) * | 2018-11-19 | 2021-11-16 | 常州新星联生物科技有限公司 | 一种比卡鲁胺硫醚中间体的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE28864T1 (de) * | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| AU1687395A (en) | 1994-01-21 | 1995-08-08 | Sepracor, Inc. | Methods and compositions for treating androgen-dependent diseases using optically pure r-(-)-casodex |
| WO1998055153A1 (en) | 1997-06-04 | 1998-12-10 | The University Of Tennessee Research Corporation | Non-steroidal radiolabeled agonist/antagonist compounds and their use in prostate cancer imaging |
| NZ533943A (en) * | 2001-12-13 | 2006-06-30 | Sumitomo Chemical Co | Crystal of bicalutamide and production method thereof |
| US6818766B2 (en) * | 2002-10-02 | 2004-11-16 | Synthon Bv | Process for making bicalutamide and intermediates thereof |
-
1999
- 1999-06-10 HU HU9901937A patent/HU223950B1/hu active IP Right Grant
-
2000
- 2000-05-26 EP EP00937111A patent/EP1189898B1/en not_active Expired - Lifetime
- 2000-05-26 AU AU52397/00A patent/AU5239700A/en not_active Abandoned
- 2000-05-26 AT AT00937111T patent/ATE234294T1/de active
- 2000-05-26 US US10/030,665 patent/US7199257B1/en not_active Expired - Fee Related
- 2000-05-26 WO PCT/HU2000/000049 patent/WO2001000608A1/en not_active Ceased
- 2000-05-26 DE DE60001657T patent/DE60001657T2/de not_active Expired - Lifetime
- 2000-05-26 ES ES00937111T patent/ES2188550T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1189898B1 (en) | 2003-03-12 |
| ATE234294T1 (de) | 2003-03-15 |
| WO2001000608A1 (en) | 2001-01-04 |
| US7199257B1 (en) | 2007-04-03 |
| WO2001000608A8 (en) | 2001-06-21 |
| DE60001657T2 (de) | 2003-12-04 |
| EP1189898A1 (en) | 2002-03-27 |
| DE60001657D1 (de) | 2003-04-17 |
| HU9901937D0 (en) | 1999-08-30 |
| HUP9901937A2 (hu) | 2001-04-28 |
| AU5239700A (en) | 2001-01-31 |
| HU223950B1 (hu) | 2005-03-29 |
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