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Green Chemistry in the Pharmaceutical Industry

Peter J. Dunn (Editor), Andrew Wells (Editor), Michael T. Williams (Editor)
ISBN: 978-3-527-32418-7
388 pages
April 2010
Green Chemistry in the Pharmaceutical Industry (3527324186) cover image
Edited by three of the world's leading pharmaceutical scientists, this is the first book on this important and hot topic, containing much previously unpublished information. As such, it covers all aspects of green chemistry in the pharmaceutical industry, from simple molecules to complex proteins, and from drug discovery to the fate of pharmaceuticals in the environment. Furthermore, this ready reference contains several convincing case studies from industry, such as Taxol, Pregabalin and Crestor, illustrating how this multidisciplinary approach has yielded efficient and environmentally-friendly processes. Finally, a section on technology and tools highlights the advantages of green chemistry.
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INTRODUCTION TO GREEN CHEMISTRY, ORGANIC SYNTHESIS AND PHARMACEUTICALS
The Development of Organic Synthesis
The Environmental Factor
The Role of Catalysis
Green Chemistry: Benign by Design
Ibuprofen Manufacture
The Question of Solvents: Alternative Reaction Media
Biocatalysis: Green Chemistry Meets White Biotechnology
Conclusions and Prospects
GREEN CHEMISTRY METRICS
Introduction
Measuring Resource Usage
Life Cycle Assessment (LCA)
Measuring Chemistry and Process Efficiency
Measuring Process Parameters and Emissions
Real Time Analysis
Operational Efficiency
Measuring Energy
Measuring the Toxicity of All the Substrates
Measuring Degradation Potential
Measuring the Inherent Safety of Lack of Inherent Safety
Conclusions
SOLVENT USE AND WASTE ISSUES
Introduction to Solvent Use and Waste Issues
Solvent and Process Greenness Scoring and Selection Tools
Waste Minimization and Solvent Recovery
ENVIRONMENTAL AND REGULATORY ASPECTS
Historical Perspective
Pharmaceuticals in the Environment
Environmental Regulations
A Look to the Future
SYNTHESIS OF SITAGLIPTIN, THE ACTIVE INGREDIENT IN JANUVIA AND JANUMET
Introduction
First-Generation Route
Sitagliptin through Diastereoselective Hydrogenation of an Enamine. The PGA Enamine-Ester Route
The Triazole Fragment
Direct Preparation of Beta-Keto Amides
Second-Generation Chiral Auxiliary Route. The PGA Enamine-Amide Route
Prufication and Isolation of Sitagliptin (Pharmaceutical Form)
The Final Manufacturing Route
THE DEVELOPMENT OF SHORT, EFFICIENT, ECONOMIC, AND SUSTAINABLE CHEMOENZYMATIC PROCESSES FOR STATIN SIDE CHAINS
Introduction: Biocatalysis
The Relevance of Statins
Biocatalytic Routes to Statin Side Chains
2-Deoxy-D-Ribose 5-Phosphate Aldolase (DERA)-Based Routes to Statin Intermediates
Conclusions
THE TAXOL STORY-DEVELOPMENT OF A GREEN SYNTHESIS VIA PLANT CELL FERMENTATION
Introduction
Discovery and Early Development
From Extraction of Taxol from Pacific Yew Tree Bark to Semi-Synthetic Taxol
Taxol from Plant Cell Fermentation
Comparison of Semi-Synthetic versus PCF Taxol Processes: The Environmental Impact
Comparison of Semi-Synthetic versus PCF Taxol: Green Chemistry Principles
Final Words
THE DEVELOPMENT OF A GREEN, ENERGY EFFICIENT, CHEMOENZYMATIC MANUFACTURING PROCESS OF PREGABALIN
Introduction
Process Routes to Pregabalin
Biocatalytic Route to Pregabalin
Green Chemistry Considerations
Conclusions
GREEN PROCESSES FOR PEPTIDE MIMETIC DIABETIC DRUGS
Introduction
Green Chemistry Considerations in Peptide-like API manufacture
Purification Process to Manufacture Amorphous API
Preparation of Unnatural Amino Acids
Summary
THE DEVELOPMENT OF AN ENVIRONMENTALLY SUSTAINABLE PROCESS FOR RADAFAXINE
Introduction
Chemistry Process and the Dynamic Kinetic Resolution (DKR)
Multicolumn Chromatography ? Development of Route 4
Environmental Assessment
Summary
CONTINUOUS PROCESSING IN THE PHARMACEUTICAL INDUSTRY
Introduction
Continuous Production of a Key Intermediate for Atorvastatin
Continuous Process to Prepare Celecoxib
Continuous Oxidation of Alcohols to Aldehydes
Continuous Production of Bromonitromethane
Continuous Production and Use of Diazomehtane
A Snapshot of Some Further Continuous Processes Used in the Preparation of Pharmaceutical Agents
Conclusions
PREPARATIVE AND INDUSTRIAL SCALE CHROMATOGRAPHY: GREEN AND INTEGRATED PROCESSES
Introduction
Basic Principles of Chromatography
Process Optimization to Reduce Eluent Consumption
Use of a Green Solvent: Supercritical Carbon Dioxide
Solvent Recycling Technologies
Application Examples
Conclusion: An Environmentally Friendly Solution for Each Separation
DYNAMIC RESOLUTION OF CHIRAL AMINE PHARMACEUTICALS: TURNING WASTE ISOMERS INTO USEFUL PRODUCT
Background
Integration of Chiral Amine Resolution and Racemization
Case Studies
Conclusions
GREEN TECHNOLOGIES IN THE GENERIC PHARMACEUTICAL INDUSTRY
Introduction
'Waste': Definition and Remedy
Amidation
Synthesis of Galanthamine
Synthesis of Solefinacin
Synthesis of Levetiracetam
Synthesis of a Finasteride Intermediate
Bromination
Sulfoxidation in the Synthesis of Rabeprazole
Conclusions
ENVIRONMENTAL CONSIDERATIONS IN BIOLOGICS MANUFACTURE
Introduction
Therapeutic Biologics
Environmental Impact Considerations
Overall Comparison
Environmental Indices for Therapeutic Protein Manufacture
Technologies with Potential Environmental Impact
Single-Use Biologics Manufacture
Summary
FUTURE TRENDS FOR GREEN CHEMISTRY IN THE PHARMACEUTICAL INDUSTRY
Introduction
Waste Minimization in Drug Discovery
Greener Synthetic Methods in Primary Manufacturing
Alternative Solvents in the Pharmaceutical Industry
Green Chemistry in Secondary Pharmaceutical Operations
Global Cooperation in Green Chemistry
Conclusions
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Peter Dunn received his PhD from Imperial College London in 1987 working under the supervision of Professor Charles Rees. Postdoctoral work followed with Prof. Albert Eschenmoser at the ETH, Zurich and with Prof. Henry Rapaport at the University of California, Berkeley. In 1989 he joined Pfizer and was involved with the invention of the commercial processes to make several medicines including "Viagra", Emselex, Revation and Sampatrilat. In 2000 he became Director of Chemical R & D at Pfizer and was responsible for the filing and transfer to manufacturing of human and animal medicines such as Voriconazole, Darifenacin, Fosfluconazole and Dirlotapide. In 2006 he took up his current role as Global Green Chemistry lead for Pfizer. He is currently co-chair of the Green Chemistry Institute Pharmaceutical Roundtable and a member of the editorial board for the journal of Green Chemistry.

Andrew Wells obtained his PhD in organophosphorous and organometallic chemistry from Essex University, before joining the Chemical Development Group of SmithKline & French in 1986, which later became SmithKline Beecham. In 1999 he received a SKB corporate award for green chemistry/technology. In 2000, he joined AstraZeneca in Global Process R & D where he is currently a Senior Principal Scientist and heads the AZ GPRD Green Chemistry group. He is an active member of the ACS Green Chemistry Institute Pharmaceutical Roundtable and has acted as an advisor to the UK Chemical Innovation Knowledge Transfer Network and the UK Technology Strategy Board. A keen supporter of the industry-academia interface, having been involved closely with several major collaborations such as the Centre for Biocatalysis at Manchester and the Institute of Process R & D at Leeds University, he has also been an industrial supervisor to around 20 PhD and MSc students.

Michael Williams obtained his chemistry BSc from King's College, London, and spent time as a medicinal chemist at ICI Pharmaceuticals (Alderley Park), before obtaining his PhD working with Professor Charles Rees at the University of Liverpool. He joined the Chemical R & D department at Pfizer at Sandwich in 1972, where his career responsibilities included the Medicinal Chemistry/Development interface, and technology adoption. In addition to his experience with approximately 50 early drug candidates, he played a significant role in the late development, filing and commercializing of many agents including Zoloft, Viagra and Relpax. He became Executive Director and Departmental Head of UK Chemical R & D in 2003, leading a significant growth to 117 laboratory staff, and helping to build a 40 strong Material Sciences group. Since retiring from Pfizer in 2007, he has been an independent consultant, in addition to his work in editing and scientific writing.
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“At last! A book which looks at Green Chemistry from an industrial viewpoint!  This is the best book I have read on   Green Chemistry and should be on the bookshelf of every process chemist and engineer. Outstanding!” (Organic Process Research & Development, March 2010)
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