Commercial Synthesis of (S,S)-Reboxetine Succinate: A Journey To Find the Cheapest Commercial Chemistry for Manufacture

被引:18
作者
Hayes, Stewart T. [1 ]
Assaf, Georges [1 ]
Checksfield, Graham [1 ]
Cheung, Chi [1 ]
Critcher, Doug [1 ]
Harris, Laurence [1 ]
Howard, Roger [1 ]
Mathew, Suju [1 ]
Regius, Christian [1 ]
Scotney, Gemrna [1 ]
Scott, Adam [1 ]
机构
[1] Pfizer Inc, Sandwich Labs, Chem Res & Dev, Sandwich CT13 9NJ, Kent, England
关键词
D O I
10.1021/op200181f
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The development of a synthetic process for (S,S)-reboxetine succinate, a candidate for the treatment of fibromylagia, is disclosed from initial scale-up to deliver material for registrational stability testing through to commercial route evaluation and subsequent nomination. This entailed evaluation of several alternative routes to result in what would have been a commercially attractive process for launch of the compound.
引用
收藏
页码:1305 / 1314
页数:10
相关论文
共 11 条
[1]   Application of a process friendly morpholine synthesis to (S,S)-Reboxetine [J].
Assaf, Georges ;
Cansell, Gemma ;
Critcher, Doug ;
Field, Stuart ;
Hayes, Stewart ;
Mathew, Suju ;
Pettman, Alan .
TETRAHEDRON LETTERS, 2010, 51 (38) :5048-5051
[2]   Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2-(hydroxymethyl)morpholine preparation [J].
Brenner, E ;
Baldwin, RM ;
Tamagnan, G .
ORGANIC LETTERS, 2005, 7 (05) :937-939
[3]   SYNTHESIS AND RESOLUTION OF THE NOVEL APPETITE-SUPPRESSANT 2-BENZYLMORPHOLINE, A NONSTIMULANT ISOMER OF PHENMETRAZINE [J].
BROWN, GR ;
FORSTER, G ;
FOUBISTER, AJ ;
STRIBLING, D .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1990, 42 (11) :797-799
[4]   Critical assessment of pharmaceutical processess - A rationale for changing the synthetic route [J].
Butters, Mike ;
Catterick, David ;
Craig, Andrew ;
Curzons, Alan ;
Dale, David ;
Gillmore, Adam ;
Green, Stuart P. ;
Marziano, Ivan ;
Sherlock, Jon-Paul ;
White, Wesley .
CHEMICAL REVIEWS, 2006, 106 (07) :3002-3027
[5]  
Ellis A.J., Patent, Patent No. [WO/2010044016, 2010044016]
[6]   Process development for (S,S)-reboxetine succinate via a sharpless asymmetric epoxidation [J].
Henegar, Kevin E. ;
Cebula, Mateusz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :354-358
[7]   Process development and scale-up for (±)-reboxetine mesylate [J].
Henegar, Kevin E. ;
Ball, Cynthia T. ;
Horvath, Carolyn M. ;
Maisto, Keith D. ;
Mancini, Sarah E. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :346-353
[8]  
Hughes B., Patent, Patent No. [WO/2006000903, 2006000903]
[9]   CONFIGURATIONAL STUDIES ON 2-[ALPHA-(2-ETHOXYPHENOXY)BENZYL]MORPHOLINE FCE-20124 [J].
MELLONI, P ;
DELLATORRE, A ;
LAZZARI, E ;
MAZZINI, G ;
MERONI, M .
TETRAHEDRON, 1985, 41 (07) :1393-1399
[10]   Biological relevance and synthesis of C-substituted morpholine derivatives [J].
Wijtmans, R ;
Vink, MKS ;
Schoemaker, HE ;
van Delft, FL ;
Blaauw, RH ;
Rutjes, FPJT .
SYNTHESIS-STUTTGART, 2004, (05) :641-662