Safe Scale-Up of Pharmaceutical Manufacturing Processes with Dimethyl Sulfoxide as the Solvent and a Reactant or a Byproduct

被引:30
作者
Wang, Zhe [1 ]
Richter, Steven M. [1 ]
Bellettini, John R. [1 ]
Pu, Yu-Ming [1 ]
Hill, David R. [1 ]
机构
[1] AbbVie Inc, Proc Res & Dev, N Chicago, IL 60064 USA
关键词
DMSO;
D O I
10.1021/op500260n
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Thermal hazard analyses of two reactions, one with DMSO as the solvent and a reactant and one with DMSO as the solvent and a byproduct, identified low-probability but severe consequence process risks associated with violent decomposition of DMSO during heating control failure or external heating. Although DMSO cannot be totally eliminated from these reactions, using an alternative solvent to replace DMSO proved to be an effective measure in reducing the thermal hazards to allow safe scale-up.
引用
收藏
页码:1836 / 1842
页数:7
相关论文
共 11 条
[1]   DMSO can be more than a solvent: Thermal analysis of its chemical interactions with certain chemicals at different process stages [J].
Bollyn, Marcus .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (06) :1299-1312
[2]  
Bretherick L., 1999, HDB REACTIVE CHEM HA, P336
[3]   Domino Synthesis of Bridged Bicyclic Tetrahydro-1,2-oxazines: Access to Stereodefined 4-Aminocyclohexanois [J].
Dias, Dwayne A. ;
Kerr, Michael A. .
ORGANIC LETTERS, 2009, 11 (16) :3694-3697
[4]  
Hall J., 1993, LOSS PREVENTION B, V114
[5]   Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)cyclopropane-1,1-dicarboxylates with Cyclopentadiene [J].
Ivanova, Olga A. ;
Budynina, Ekaterina M. ;
Chagarovskiy, Alexey O. ;
Kaplun, Alexey E. ;
Trushkov, Igor V. ;
Melnikov, Mikhail Ya. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (07) :1125-1134
[6]   Thermal hazards and safe scale-up of reactions containing dimethyl sulfoxide [J].
Lam, T. T. ;
Vickery, T. ;
Tuma, Linda .
JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2006, 85 (01) :25-30
[7]   SYNTHESIS OF NUCLEOSIDE-5' ALDEHYDES [J].
PFITZNER, KE ;
MOFFATT, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (19) :3027-&
[8]  
Stoessel F., 2008, Thermal Safety of Chemical Processes: Risk Assessment and Process Design, P59
[9]   Safety Concerns in a Pharmaceutical Manufacturing Process Using Dimethyl Sulfoxide (DMSO) as a Solvent [J].
Wang, Zhe ;
Richter, Steven M. ;
Gates, Bradley D. ;
Grieme, Timothy A. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (12) :1994-2000
[10]   Effects of incompatible substances on the thermal stability of dimethyl sulfoxide [J].
Yang, Xiao-Wu ;
Zhang, Xiang-Yang ;
Guo, Zi-Chao ;
Bai, Wen-Shuai ;
Hao, Lin ;
Wei, Hong-Yuan .
THERMOCHIMICA ACTA, 2013, 559 :76-81