DE60001657D1 - Verfahren zur herstellung von n-(4-cyan-3-trifluormethylphenyl)-3-(4-flurophenylsulfonyl)-2-hydroxy-2-methylpropionamid - Google Patents
Verfahren zur herstellung von n-(4-cyan-3-trifluormethylphenyl)-3-(4-flurophenylsulfonyl)-2-hydroxy-2-methylpropionamidInfo
- Publication number
- DE60001657D1 DE60001657D1 DE60001657T DE60001657T DE60001657D1 DE 60001657 D1 DE60001657 D1 DE 60001657D1 DE 60001657 T DE60001657 T DE 60001657T DE 60001657 T DE60001657 T DE 60001657T DE 60001657 D1 DE60001657 D1 DE 60001657D1
- Authority
- DE
- Germany
- Prior art keywords
- methylpropionamide
- hydroxy
- flurophenylsulfonyl
- trifluormethylphenyl
- cyan
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 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)
Applications Claiming Priority (2)
| 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 |
| PCT/HU2000/000049 WO2001000608A1 (en) | 1999-06-10 | 2000-05-26 | Process for the synthesis of n-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfonyl)-2-hydroxy-2-methylpropionamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60001657D1 true DE60001657D1 (de) | 2003-04-17 |
| DE60001657T2 DE60001657T2 (de) | 2003-12-04 |
Family
ID=89998474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60001657T Expired - Lifetime DE60001657T2 (de) | 1999-06-10 | 2000-05-26 | Verfahren zur herstellung von n-(4-cyan-3-trifluormethylphenyl)-3-(4-flurophenylsulfonyl)-2-hydroxy-2-methylpropionamid |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7199257B1 (de) |
| EP (1) | EP1189898B1 (de) |
| AT (1) | ATE234294T1 (de) |
| AU (1) | AU5239700A (de) |
| DE (1) | DE60001657T2 (de) |
| ES (1) | ES2188550T3 (de) |
| HU (1) | HU223950B1 (de) |
| WO (1) | WO2001000608A1 (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1406855A4 (de) * | 2001-06-13 | 2006-04-19 | Teva Gyogyszergyar Reszvenytar | Neues verfahren zur herstellung von rac-bicalutamid und dessen zwischenprodukten |
| US7102026B2 (en) | 2001-06-13 | 2006-09-05 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Process for preparing and isolating rac-bicalutamide and its intermediates |
| KR100938188B1 (ko) * | 2001-12-13 | 2010-01-21 | 스미또모 가가꾸 가부시키가이샤 | 비칼루타미드의 결정 및 그 제조 방법 |
| 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 |
| JP2007521224A (ja) * | 2003-06-25 | 2007-08-02 | テバ ジョジセルジャール ザ−トケルエン ムケド レ−スベニュタ−ルシャシャ−グ | Rac−ビカルタミドの精製及び単離方法 |
| 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 |
| EP1863759A1 (de) * | 2005-03-29 | 2007-12-12 | Usv Limited | Verfahren zur herstellung von bicalutamid |
| 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 |
| US8895772B2 (en) | 2010-09-29 | 2014-11-25 | 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 |
|---|---|---|---|---|
| LU88769I2 (fr) | 1982-07-23 | 1996-11-05 | Zeneca Ltd | Bicalutamide et ses sels et esters pharmaceutiquement acceptables (Casodex (R)) |
| JPH09508125A (ja) | 1994-01-21 | 1997-08-19 | セプラコー,インコーポレイテッド | 光学的純正r−(−)−カソデックスを使用した男性ホルモン依存疾患治療のための方法と組成 |
| AU7723198A (en) | 1997-06-04 | 1998-12-21 | University Of Tennessee Research Corporation, The | Non-steroidal radiolabeled agonist/antagonist compounds and their use in prostate cancer imaging |
| KR100938188B1 (ko) * | 2001-12-13 | 2010-01-21 | 스미또모 가가꾸 가부시키가이샤 | 비칼루타미드의 결정 및 그 제조 방법 |
| 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 DE DE60001657T patent/DE60001657T2/de not_active Expired - Lifetime
- 2000-05-26 ES ES00937111T patent/ES2188550T3/es not_active Expired - Lifetime
- 2000-05-26 AT AT00937111T patent/ATE234294T1/de active
- 2000-05-26 WO PCT/HU2000/000049 patent/WO2001000608A1/en not_active Ceased
- 2000-05-26 AU AU52397/00A patent/AU5239700A/en not_active Abandoned
- 2000-05-26 US US10/030,665 patent/US7199257B1/en not_active Expired - Fee Related
- 2000-05-26 EP EP00937111A patent/EP1189898B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU5239700A (en) | 2001-01-31 |
| HU9901937D0 (en) | 1999-08-30 |
| WO2001000608A1 (en) | 2001-01-04 |
| ES2188550T3 (es) | 2003-07-01 |
| HUP9901937A2 (hu) | 2001-04-28 |
| WO2001000608A8 (en) | 2001-06-21 |
| DE60001657T2 (de) | 2003-12-04 |
| HU223950B1 (hu) | 2005-03-29 |
| EP1189898B1 (de) | 2003-03-12 |
| US7199257B1 (en) | 2007-04-03 |
| ATE234294T1 (de) | 2003-03-15 |
| EP1189898A1 (de) | 2002-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |