Drug Synthesis Book Set

by Li, Jie Jack; Johnson, Douglas S.

• ISBN13: 9781119185659
• ISBN10: 1119185653
• Edition: 2nd
• Format: Hardcover
• Copyright: 2015-11-23
• Publisher: Wiley

Summary

This set presents the authoritative and acclaimed Drug Synthesis books edited by Jie Jack Li and Douglas Johnson: Contemporary Drug Synthesis, The Art of Drug Synthesis, Modern Drug Synthesis, and Innovative Drug Synthesis. This book set will be enormously useful to pharmaceutical industry labs, research scientists in lead optimization and process development, and graduate students and courses in organic chemistry, synthetic organic chemistry, heterocyclic chemistry, medicinal chemistry, and drug synthesis courses.

Author Biography

Jie Jack Li is an Associate Professor of chemistry at the University of San Francisco. Previously, he was a chemist at Bristol-Myers Squibb Company. He has authored or edited several books published by Wiley, including Drug Discovery: Practices, Processes, and Perspectives, Heterocyclic Chemistry in Drug Discovery, Name Reactions in Heterocyclic Chemistry, Name Reactions for Functional Group Transformations, Contemporary Drug Synthesis, The Art of Drug Synthesis, and Modern Drug Synthesis.

Douglas Johnson is an Associate Research Fellow and head of Chemical Biology in the Neuroscience Medicinal Chemistry group at Pfizer Worldwide Research and Development. He is a co-author on more than 70 publications and patents and is a co-author of the book Contemporary Drug Synthesis and is an editor of The Art of Drug Synthesis, and Modern Drug Synthesis (all published by Wiley).

Table of Contents

Contemporary Drug Synthesis

Preface v

Trade Names and Their Corresponding USANs xi

Acronyms and Abbreviations xiii

Chapter 1. Antithrombotics: Ticlopidine (Ticlid) and Clopidogrel (Plavix) 1

Chapter 2. Anti-inflammatory Cyclooxygenase-2 Selective Inhibitors: Celecoxib (Celebrex) and Rofecoxib (Vioxx) 11

Chapter 3. H⁺/K⁺ -ATPase Inhibitors: Esomeprazole (Nexium) 21

Chapter 4. Protein-tyrosine Kinase Inhibitors: Imatnib (Gleevec) and Gefitinib (Iressa) 29

Chapter 5. Non-sedating Antihistamines 39

Chapter 6. Cosmeceuticals: Istretinoin (Accutane), Tazarotene (Tazorac), Minoxidil (Rogaine), and Finasteride (Propecia) 55

Chapter 7. Antibacterials: Ciprofloxacin (Cipro) and Linezolid (Zyvox) 75

Chapter 8. Atypical Antupsychotics 89

Chapter 9. Atovastatin Calcium (Lipitor) 113

Chapter 10. Antidepressants 125

Chapter 11. Anti-obesity: Orlistat (Xenical) 149

Chapter 12. Triptans for Migrane 161

Chapter 13. PDE 5 Inhibitors for Erectile Dysfunction: Sildenafil (Viagra), Vardenafil (Levitra), and Tadalafil (Cialis) 189

Chapter 14. Antiasthmatics 201

Index 214

The Art of Drug Synthesis

1 THE ROLE OF MEDICINAL CHEMISTRY IN DRUG DISCOVERY 1
John A. Lowe, III

2 PROCESS RESEARCH: HOW MUCH? HOW SOON? 11
Neal G. Anderson

3 AROMATASE INHIBITORS FOR BREAST CANCER: EXEMESTANE (AROMASIN), ANASTROZOLE (ARIMIDEX), AND LETROZOLE (FEMARA) 31
Jie Jack Li

4 QUINOLONE ANTIBIOTICS: LEVOFLOXACIN (LEVAQUIN), MOXIFLOXACIN (AVELOX), GEMIFLOXACIN (FACTIVE), AND GARENOXACIN (T-3811) 39
Chris Limberakis

5 TRIAZOLE ANTIFUNGALS: ITRACONAZOLE (SPORANOX), FLUCONAZOLE (DIFLUCAN), VORICONAZOLE (VFEND), AND FOSFLUCONAZOLE (PRODIF) 71
Andrew S. Bell

6 NON-NUCLEOSIDE HIV REVERSE TRANSCRIPTASE INHIBITORS 83
Arthur Harms

7 NEURAMINIDASE INHIBITORS FOR INFLUENZA: OSELTAMIVIR PHOSPHATE (TAMIFLU) AND ZANAMIVIR (RELENZA) 95
Douglas S. Johnson and Jie Jack Li

8 PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR (PPAR) AGONISTS FOR TYPE 2 DIABETES 117
Jin Li

9 ANGIOTENSIN AT1 ANTAGONISTS FOR HYPERTENSION 129
Larry Yet

10 LEADING ACE INHIBITORS FOR HYPERTENSION 143
Victor J. Cee and Edward J. Olhava

11 DIHYDROPYRIDINE CALCIUM CHANNEL BLOCKERS FOR HYPERTENSION 159
Daniel P. Christen

12 SECOND-GENERATION HMG-CoA REDUCTASE INHIBITORS 169
Jeffrey A. Pfefferkorn

13 CHOLESTEROL ABSORPTION INHIBITORS: EZETIMIBE (ZETIA) 183
Stuart B. Rosenblum

14 DUAL SELECTIVE SEROTONIN AND NOREPINEPHRINE REUPTAKE INHIBITORS (SSNRIs) FOR DEPRESSION 199
Marta Pineiro-Nunez

15 GABAA RECEPTOR AGONISTS FOR INSOMNIA: ZOLPIDEM (AMBIEN), ZALEPLON (SONATA), ESZOPICLONE (ESTORRA, LUNESTA), AND INDIPLON 215
Peter R. Guzzo

16 Alpha2Delta LIGANDS: NEURONTIN (GABAPENTIN) AND LYRICA (PREGABALIN) 225
Po-Wai Yuen

17 APPROVED TREATMENTS FOR ATTENTION DEFICIT HYPERACTIVITY DISORDER: AMPHETAMINE (ADDERALL), METHYLPHENIDATE (RITALIN), AND ATOMOXETINE (STRATERRA) 241
David L. Gray

References 257

Index 261

Modern Drug Synthesis

Preface xi

Contributors xiii

I. Infectious Diseases 1

Chapter 1. Raltegravir (Isentress), The First-in-class HIV-1 Integrase Inhibitor 3
Julianne A. Hunt

Chapter 2. Maraviroc (Selzentry), The First-in-class CCR5 Antagonist for the Treatment of HIV 17
David Price

Chapter 3. Darunavir (Prezista), A HIV-1 Protease Inhibitor for Treatment of Multidrug Resistant HIV 29
Arun K. Ghosh and Cuthbert D. Martyr

II. Cancer 45

Chapter 4. Decitabine (Dacogen), A DNA Methyltransferase Inhibitor for Cancer 47
Jennifer A. Van Camp

Chapter 5. Capecitabine (Xeloda), An Oral Chemotherapy Agent 57
R. Jason Herr

Chapter 6. Sorafenib (Nexavar), A Multi-kinase Inhibitor for Advanced Renal Cell Carcinoma and Unresectable Hepatocellular Carcinoma 73
Shuanghua Hu

Chapter 7. Sunitinib (Sutent), An Angiogenesis Inhibitor 87
Martin Pettersson

Chapter 8. Bortezomib (Velcade), A First-in-class Proteasome Inhibitor 99
Benjamin S. Greener and David S. Millan

Chapter 9. Pazopanib (Votrient), A VEGFR Tyrosine Kinase Inhibitor for Cancer 111
Ji Zhang and Jie Jack Li

III. Cardiovascular and Metabolic Diseases 123

Chapter 10. Sitagliptin (Januvia), A Treatment for Type 2 Diabetes 125
Scott D. Edmondson, Feng Xu, and Joseph D. Armstrong III

Chapter 11. Aliskiren (Tekturna), The First-in-class Renin Inhibitor for Hypertension 141
Victor J. Cee

Chapter 12. Vernakalant (Kynapid), An Investigational Drug for the Treatment of Atrial Fibrillation 159
David L. Gray

Chapter 13. Conivaptan (Vaprisol), Vasopressin V1a and V2 Antagonist for Hyponatremia 175
Brian A. Lanman

Chapter 14. Rivaroxaban (Xarelto), A Factor Xa Inhibitor for the Treatment of Thrombotic Events 191
Ji Zhang and Jason Crawford

Chapter 15. Endothelin Antagonists for the Treatment of Pulmonary Arterial Hypertension 207
David Edmonds

IV. Central Nervous System Diseases 225

Chapter 16. Varenicline (Chantix), An α4β2 Nicotinic Receptor Partial Agonist for Smoking Cessation 227
Jotham W. Coe, Frank R. Busch and Robert A. Singer

Chapter 17. Donepezil, Rivastigmine, Galantamine: Cholinesterase Inhibitors for Alzheimer's Disease 249
Subas Sakya and Kapil Karki

Chapter 18. Aprepitant (Emend), A NK1 Receptor Antagonist for the Treatment of Post-chemotherapy Emesis 275
John A. Lowe, III

Chapter 19. Armodafinil (Nuvigil), A Psychostimulant for the Treatment of Narcolepsy 291
Ji Zhang and Jason Crawford

V. Miscellaneous 307

Chapter 20. Raloxifene (Evista), A Selective Estrogen Receptor Modulator (SERM) 309
Marta Piñeiro-Núñez

Chapter 21. Latanoprost (Xalatan), A Prostanoid FP Agonist for Glaucoma 329
Sajiv K. Nair and Kevin E. Henegar

Index 339

Innovative Drug Synthesis

Preface xi

Contributors xiii

PART I. INFECTIOUS DISEASES 1

Chapter 1. Entecavir (Baraclude): A Carbocyclic Nucleoside for the Treatment of Chronic Hepatitis B 3

Chapter 2. Telaprevir (Incivek) and Boceprevir (Victrelis): NS3/4A Inhibitors for Treatment for Hepatitis C Virus (HCV) 15

Chapter 3. Daclatasvir (Daklinza): The First-in-Class HCV NS5A Replication Complex Inhibitor 43

Chapter 4. Sofosbuvir (Sovaldi): The First-in-Class HCV NS5B Nucleotide Polymerase Inhibitor 61

Chapter 5. Bedaquiline (Sirturo): A Diarylquinoline that Blocks Tuberculosis ATP Synthase for the Treatment of Multi-Drug Resistant Tuberculosis 81

PART II. CANCER 99

Chapter 6. Enzalutamide (Xtandi): An Androgen Receptor Antagonist for Late-Stage Prostate Cancer 101

Chapter 7. Crizotinib (Xalkori): The First-in-Class ALK/ROS Inhibitor for Non-small Cell Lung Cancer 119

Chapter 8. Ibrutinib (Imbruvica): The First-in-Class Btk Inhibitor for Mantle Cell Lymphoma, Chronic Lymphocytic Leukemia, and Waldenstrom's Macroglobulinemia 157

Chapter 9. Palbociclib (Ibrance): The First-in-Class CDK4/6 Inhibitor for Breast Cancer 167

PART III. CARDIOVASCULAR DISEASES 197

Chapter 10. Ticagrelor (Brilinta) and Dabigatran Etexilate (Pradaxa): P2Y12 Platelet Inhibitors as Anti-coagulants 199

PART IV. CNS DRUGS 223

Chapter 11. Suvorexant (BELSOMRA): The First-in-Class Orexin Antagonist for Insomnia 225

Chapter 12. Lorcaserin (Belviq): Serotonin 2C Receptor Agonist for the Treatment of Obesity 243

Chapter 13. Fingolimod (Gilenya): The First Oral Treatment for Multiple Sclerosis 255

Chapter 14. Perampanel (Fycompa): AMPA Receptor Antagonist for the Treatment of Seizure 271

PART V. ANTI-INFLAMMATORY DRUGS 283

Chapter 15. Tofacitinib (Xeljanz): The First-in-Class JAK Inhibitor for the Treatment of Rheumatoid Arthritis 285

PART VI. MISCELLANEOUS DRUGS 303

Chapter 16. Ivacaftor (Kalydeco): A CFTR Potentiator for the Treatment of Cystic Fibrosis 305

Chapter 17. Febuxostat (Uloric): A Xanthine Oxidase Inhibitor for the Treatment of Gout 317

Index 331