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Patent Searching and Data


Title:
NOVEL PROCESS FOR PREPARING RAC-BICALUTAMIDE AND ITS INTERMEDIATES
Document Type and Number:
WIPO Patent Application WO2002100339
Kind Code:
A3
Abstract:
The present invention relates to a new process for the synthesis of racemic and optically active bicalutamide starting from ethyl pyruvate and methyl methacrylate. The present invention discloses processes of preparing bicalutamide intermediates including ethyl-[2-{4-fluorophenyl sulfone}]-2-hydroxy propionate, 1,2-epoxy-2-methyl propionate and 2-hydrox-2-methyl-3-(4-fluorophenylthio) propionic acid. The present invention further discloses micronized rac-bicalutamide and the preparation thereof.

Inventors:
DOLITZKY BEN-ZION (IL)
REANY OFER (IL)
SHAMMAI JENNY (IL)
Application Number:
US0218329W
Publication Date:
October 16, 2003
Filing Date:
June 13, 2002
Export Citation:
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Assignee:
BIOGAL GYOGYSZERGYAR RT.
TEVA PHARMACEUTICALS USA, INC.
DOLITZKY, BEN-ZION
REANY, OFER
SHAMMAI, JENNY
International Classes:
C07C69/675; C07C231/02; C07C231/08; C07C255/49; C07C255/50; C07C255/58; C07C315/04; C07C317/14; C07C317/44; C07C317/46; C07C317/48; C07C317/50; C07C319/14; C07F1/02; C07C323/52; (IPC1-7): C07C69/675; C07C255/49; C07C255/50; C07C317/14
Foreign References:
US4554381A1985-11-19
US5723485A1998-03-03
US3254094A1966-05-31
US4636505A1987-01-13
Other References:
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DATABASE CAPLUS [Online] TAKAHASHI ET AL.: 'Preparation and formulation of aryl sulfides, sulfoxides and sulfones as matrix metalloproteinases inhibitors', XP002966180 Retrieved from STN Database accession no. 1998-42377 & WO 97 49679 A1
DATABASE CAPLUS [Online] SLUSAREK ET AL.: 'Color photographic thermally processable film comprising blocked developer compound', XP002965454 Retrieved from STN Database accession no. 2001-867994 & EP 1 158 359 A2 28 November 2001
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DATABASE CAPLUS [Online] TUCKER ET AL.: 'Resolution of the non-sterodial antiandrogen 4'-(cyano-3-(4-fluorophenylsulfonyl)-2-hydr oxy-2-methyl-3'-trifluoromethyl)propionanil ide and the determination of the absolute configuration of the active enantiomer', XP002966182 Retrieved from STN Database accession no. 1988-150026 & J. MED. CHEM. vol. 31, no. 4, 1988, pages 885 - 887
DATABASE CAPLUS [Online] JAMES ET AL.: 'A two step synthesis of the anti-cancer drug (R,S)-bicalutamide', XP002966183 Retrieved from STN Database accession no. 2002:414656 & SYNTHESIS no. 7, 2002, pages 850 - 852
DATABASE CAPLUS [Online] VON LOCQUENGHIEN HORCHLER ET AL.: 'Preparation of oxiranecarboxylates and analogs', XP002966184 Retrieved from STN Database accession no. 1994-191513 & DE 42 18 765 A1 09 December 1993
DATABASE CAPLUS [Online] RASTETTER ET AL.: '3,5-Dinitroperoxybenzoic acid. A crystalline storable substitute for peroxytrifluoroacetic acid', XP002966185 Retrieved from STN Database accession no. 1978-490113 & J. ORG. CHEM. vol. 43, no. 16, 1978, pages 3163 - 3166
DATABASE CAPLUS [Online] EKWURIBE N.: 'Asymmetric synthesis and antiandrogenic use of enantiomers of casodex (bicalutamide) and derivatives from enantiomers of citramalic acid or proline', XP002966186 Retrieved from STN Database accession no. 2001-300671 & WO 01 28990 A2 26 April 2001
See also references of EP 1406855A2
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