ZA200603289B - Process for producing bicalutamide and method of purifying intermediate therefor - Google Patents
Process for producing bicalutamide and method of purifying intermediate therefor Download PDFInfo
- Publication number
- ZA200603289B ZA200603289B ZA200603289A ZA200603289A ZA200603289B ZA 200603289 B ZA200603289 B ZA 200603289B ZA 200603289 A ZA200603289 A ZA 200603289A ZA 200603289 A ZA200603289 A ZA 200603289A ZA 200603289 B ZA200603289 B ZA 200603289B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- crystals
- formula
- process according
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 title claims description 7
- 229960000997 bicalutamide Drugs 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000013078 crystal Substances 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 6
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 claims description 4
- RGCBQVJAMPFHBA-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfanyl-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(C)CSC1=CC=C(F)C=C1 RGCBQVJAMPFHBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012535 impurity Substances 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- ATOLBBJUAQAWAC-UHFFFAOYSA-N n-(4-cyanophenyl)-4,4,4-trifluoro-3-(4-fluorophenyl)sulfanyl-2-hydroxy-2-methylbutanamide Chemical compound C=1C=C(C#N)C=CC=1NC(=O)C(O)(C)C(C(F)(F)F)SC1=CC=C(F)C=C1 ATOLBBJUAQAWAC-UHFFFAOYSA-N 0.000 description 1
- UQUQTWDUTIAAAY-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C1(C)CO1 UQUQTWDUTIAAAY-UHFFFAOYSA-N 0.000 description 1
- HHWDZLSGDDXUSM-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=C(C#N)C(C(F)(F)F)=C1 HHWDZLSGDDXUSM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003357038A JP4322621B2 (ja) | 2003-10-16 | 2003-10-16 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603289B true ZA200603289B (en) | 2007-07-25 |
Family
ID=34463235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603289A ZA200603289B (en) | 2003-10-16 | 2004-10-15 | Process for producing bicalutamide and method of purifying intermediate therefor |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20060183934A1 (fr) |
| EP (1) | EP1679306B1 (fr) |
| JP (1) | JP4322621B2 (fr) |
| KR (1) | KR101126948B1 (fr) |
| AT (1) | ATE461170T1 (fr) |
| AU (1) | AU2004282077A1 (fr) |
| BR (1) | BRPI0415347A (fr) |
| CA (1) | CA2542788C (fr) |
| DE (1) | DE602004026088D1 (fr) |
| ES (1) | ES2341008T3 (fr) |
| IL (1) | IL174781A (fr) |
| IS (1) | IS2757B (fr) |
| NZ (1) | NZ546466A (fr) |
| WO (1) | WO2005037777A1 (fr) |
| ZA (1) | ZA200603289B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200700938B (en) * | 2004-07-14 | 2008-09-25 | Sumitomo Chemical Co | Method of crystallizing bicalutamide |
| EP1863759A1 (fr) * | 2005-03-29 | 2007-12-12 | Usv Limited | Procede de fabrication de bicalutamide |
| CA2513356A1 (fr) * | 2005-07-26 | 2007-01-26 | Apotex Pharmachem Inc. | Procede de production de bicalutamide |
| CZ299577B6 (cs) * | 2005-12-20 | 2008-09-03 | Interpharma Praha, A. S. | Zpusob výroby vysoce cistého 4-kyano-3-trifluoromethyl-N-(3-p-fluorfenylsulfonyl-2-hydroxy-2-methylpropionyl) anilinu |
| CA2635461A1 (fr) | 2005-12-27 | 2007-07-05 | Dabur Pharma Limited | Procede ameliore de fabrication de bicalutamide |
| CN105541680B (zh) * | 2016-02-16 | 2017-12-22 | 重庆硕奥科技有限公司 | 一种比卡鲁胺的合成方法 |
| CN106748884B (zh) * | 2016-12-13 | 2021-08-20 | 山西振东制药股份有限公司 | 一种比卡鲁胺中间体的制备方法 |
| CN106831509B (zh) * | 2017-02-07 | 2018-05-18 | 西北师范大学 | 一种比卡鲁胺的合成方法 |
| CN106905265A (zh) * | 2017-03-09 | 2017-06-30 | 常州沃腾化工科技有限公司 | N‑[4‑氰基‑3‑（三氟甲基）苯基]‑2,3‑环氧‑2‑甲基丙酰胺的制备方法 |
| CN109456227B (zh) * | 2018-11-19 | 2021-11-16 | 常州新星联生物科技有限公司 | 一种比卡鲁胺环氧中间体的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU223950B1 (hu) | 1999-06-10 | 2005-03-29 | Richter Gedeon Vegyészeti Gyár Rt. | 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 |
| US6583306B1 (en) | 1999-10-19 | 2003-06-24 | Nobex Corporation | Methods of asymmetrically synthesizing enantiomers of Casodex, its derivatives and intermediates thereof |
| US6562994B2 (en) | 2000-09-21 | 2003-05-13 | Bristol-Myers Squibb Co. | Process for the preparation of N-(substituted phenyl)-3-alkyl-,aryl- and heteroarylsulfonyl-2-hydroxy-2-alkyl- and haloalkylpropanamide compounds |
| KR100938188B1 (ko) * | 2001-12-13 | 2010-01-21 | 스미또모 가가꾸 가부시키가이샤 | 비칼루타미드의 결정 및 그 제조 방법 |
-
2003
- 2003-10-16 JP JP2003357038A patent/JP4322621B2/ja not_active Expired - Fee Related
-
2004
- 2004-10-15 NZ NZ546466A patent/NZ546466A/en not_active IP Right Cessation
- 2004-10-15 EP EP04792811A patent/EP1679306B1/fr not_active Expired - Lifetime
- 2004-10-15 WO PCT/JP2004/015669 patent/WO2005037777A1/fr not_active Ceased
- 2004-10-15 AT AT04792811T patent/ATE461170T1/de not_active IP Right Cessation
- 2004-10-15 ES ES04792811T patent/ES2341008T3/es not_active Expired - Lifetime
- 2004-10-15 AU AU2004282077A patent/AU2004282077A1/en not_active Abandoned
- 2004-10-15 ZA ZA200603289A patent/ZA200603289B/en unknown
- 2004-10-15 BR BRPI0415347-2A patent/BRPI0415347A/pt not_active IP Right Cessation
- 2004-10-15 KR KR1020067009306A patent/KR101126948B1/ko not_active Expired - Fee Related
- 2004-10-15 DE DE602004026088T patent/DE602004026088D1/de not_active Expired - Lifetime
- 2004-10-15 CA CA2542788A patent/CA2542788C/fr not_active Expired - Fee Related
-
2006
- 2006-04-04 IL IL174781A patent/IL174781A/en not_active IP Right Cessation
- 2006-04-11 US US11/401,262 patent/US20060183934A1/en not_active Abandoned
- 2006-05-11 IS IS8459A patent/IS2757B/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2341008T3 (es) | 2010-06-14 |
| BRPI0415347A (pt) | 2006-12-05 |
| ATE461170T1 (de) | 2010-04-15 |
| CA2542788A1 (fr) | 2005-04-28 |
| EP1679306A1 (fr) | 2006-07-12 |
| JP2005120024A (ja) | 2005-05-12 |
| AU2004282077A2 (en) | 2005-04-28 |
| IL174781A (en) | 2011-05-31 |
| WO2005037777A1 (fr) | 2005-04-28 |
| NZ546466A (en) | 2009-08-28 |
| AU2004282077A1 (en) | 2005-04-28 |
| EP1679306A4 (fr) | 2006-10-11 |
| EP1679306B1 (fr) | 2010-03-17 |
| IL174781A0 (en) | 2006-08-20 |
| KR101126948B1 (ko) | 2012-03-20 |
| KR20060117948A (ko) | 2006-11-17 |
| IS2757B (is) | 2011-10-15 |
| JP4322621B2 (ja) | 2009-09-02 |
| IS8459A (is) | 2006-05-11 |
| US20060183934A1 (en) | 2006-08-17 |
| CA2542788C (fr) | 2012-01-03 |
| DE602004026088D1 (de) | 2010-04-29 |
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