Drug Synthesis Book Set

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).

• Contemporary Drug Synthesis Preface vTrade Names and Their Corresponding USANs xiAcronyms and Abbreviations xiiiChapter 1. Antithrombotics: Ticlopidine (Ticlid) and Clopidogrel (Plavix) 1Chapter 2. Anti-inflammatory Cyclooxygenase-2 Selective Inhibitors: Celecoxib (Celebrex) and Rofecoxib (Vioxx) 11Chapter 3. H+/K+ -ATPase Inhibitors: Esomeprazole (Nexium) 21Chapter 4. Protein-tyrosine Kinase Inhibitors: Imatnib (Gleevec) and Gefitinib (Iressa) 29Chapter 5. Non-sedating Antihistamines 39Chapter 6. Cosmeceuticals: Istretinoin (Accutane), Tazarotene (Tazorac), Minoxidil (Rogaine), and Finasteride (Propecia) 55Chapter 7. Antibacterials: Ciprofloxacin (Cipro) and Linezolid (Zyvox) 75Chapter 8. Atypical Antupsychotics 89Chapter 9. Atovastatin Calcium (Lipitor) 113Chapter 10. Antidepressants 125Chapter 11. Anti-obesity: Orlistat (Xenical) 149Chapter 12. Triptans for Migrane 161Chapter 13. PDE 5 Inhibitors for Erectile Dysfunction: Sildenafil (Viagra), Vardenafil (Levitra), and Tadalafil (Cialis) 189Chapter 14. Antiasthmatics 201Index 214The Art of Drug Synthesis1 THE ROLE OF MEDICINAL CHEMISTRY IN DRUG DISCOVERY 1John A. Lowe, III2 PROCESS RESEARCH: HOW MUCH? HOW SOON? 11Neal G. Anderson3 AROMATASE INHIBITORS FOR BREAST CANCER: EXEMESTANE (AROMASIN), ANASTROZOLE (ARIMIDEX), AND LETROZOLE (FEMARA) 31Jie Jack Li4 QUINOLONE ANTIBIOTICS: LEVOFLOXACIN (LEVAQUIN), MOXIFLOXACIN (AVELOX), GEMIFLOXACIN (FACTIVE), AND GARENOXACIN (T-3811) 39Chris Limberakis5 TRIAZOLE ANTIFUNGALS: ITRACONAZOLE (SPORANOX), FLUCONAZOLE (DIFLUCAN), VORICONAZOLE (VFEND), AND FOSFLUCONAZOLE (PRODIF) 71Andrew S. Bell6 NON-NUCLEOSIDE HIV REVERSE TRANSCRIPTASE INHIBITORS 83Arthur Harms7 NEURAMINIDASE INHIBITORS FOR INFLUENZA: OSELTAMIVIR PHOSPHATE (TAMIFLU) AND ZANAMIVIR (RELENZA) 95Douglas S. Johnson and Jie Jack Li8 PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR (PPAR) AGONISTS FOR TYPE 2 DIABETES 117Jin Li9 ANGIOTENSIN AT1 ANTAGONISTS FOR HYPERTENSION 129Larry Yet10 LEADING ACE INHIBITORS FOR HYPERTENSION 143Victor J. Cee and Edward J. Olhava11 DIHYDROPYRIDINE CALCIUM CHANNEL BLOCKERS FOR HYPERTENSION 159Daniel P. Christen12 SECOND-GENERATION HMG-CoA REDUCTASE INHIBITORS 169Jeffrey A. Pfefferkorn13 CHOLESTEROL ABSORPTION INHIBITORS: EZETIMIBE (ZETIA) 183Stuart B. Rosenblum14 DUAL SELECTIVE SEROTONIN AND NOREPINEPHRINE REUPTAKE INHIBITORS (SSNRIs) FOR DEPRESSION 199Marta Pineiro-Nunez15 GABAA RECEPTOR AGONISTS FOR INSOMNIA: ZOLPIDEM (AMBIEN), ZALEPLON (SONATA), ESZOPICLONE (ESTORRA, LUNESTA), AND INDIPLON 215Peter R. Guzzo16 Alpha2Delta LIGANDS: NEURONTIN (GABAPENTIN) AND LYRICA (PREGABALIN) 225Po-Wai Yuen17 APPROVED TREATMENTS FOR ATTENTION DEFICIT HYPERACTIVITY DISORDER: AMPHETAMINE (ADDERALL), METHYLPHENIDATE (RITALIN), AND ATOMOXETINE (STRATERRA) 241David L. GrayReferences 257Index 261Modern Drug SynthesisPreface xi Contributors xiiiI. Infectious Diseases 1Chapter 1. Raltegravir (Isentress), The First-in-class HIV-1 Integrase Inhibitor 3Julianne A. HuntChapter 2. Maraviroc (Selzentry), The First-in-class CCR5 Antagonist for the Treatment of HIV 17David PriceChapter 3. Darunavir (Prezista), A HIV-1 Protease Inhibitor for Treatment of Multidrug Resistant HIV 29Arun K. Ghosh and Cuthbert D. MartyrII. Cancer 45Chapter 4. Decitabine (Dacogen), A DNA Methyltransferase Inhibitor for Cancer 47Jennifer A. Van CampChapter 5. Capecitabine (Xeloda), An Oral Chemotherapy Agent 57R. Jason HerrChapter 6. Sorafenib (Nexavar), A Multi-kinase Inhibitor for Advanced Renal Cell Carcinoma and Unresectable Hepatocellular Carcinoma 73Shuanghua HuChapter 7. Sunitinib (Sutent), An Angiogenesis Inhibitor 87Martin PetterssonChapter 8. Bortezomib (Velcade), A First-in-class Proteasome Inhibitor 99Benjamin S. Greener and David S. MillanChapter 9. Pazopanib (Votrient), A VEGFR Tyrosine Kinase Inhibitor for Cancer 111Ji Zhang and Jie Jack LiIII. Cardiovascular and Metabolic Diseases 123Chapter 10. Sitagliptin (Januvia), A Treatment for Type 2 Diabetes 125Scott D. Edmondson, Feng Xu, and Joseph D. Armstrong IIIChapter 11. Aliskiren (Tekturna), The First-in-class Renin Inhibitor for Hypertension 141Victor J. CeeChapter 12. Vernakalant (Kynapid), An Investigational Drug for the Treatment of Atrial Fibrillation 159David L. GrayChapter 13. Conivaptan (Vaprisol), Vasopressin V1a and V2 Antagonist for Hyponatremia 175Brian A. LanmanChapter 14. Rivaroxaban (Xarelto), A Factor Xa Inhibitor for the Treatment of Thrombotic Events 191Ji Zhang and Jason CrawfordChapter 15. Endothelin Antagonists for the Treatment of Pulmonary Arterial Hypertension 207David EdmondsIV. Central Nervous System Diseases 225Chapter 16. Varenicline (Chantix), An α4β2 Nicotinic Receptor Partial Agonist for Smoking Cessation 227Jotham W. Coe, Frank R. Busch and Robert A. SingerChapter 17. Donepezil, Rivastigmine, Galantamine: Cholinesterase Inhibitors for Alzheimer's Disease 249Subas Sakya and Kapil KarkiChapter 18. Aprepitant (Emend), A NK1 Receptor Antagonist for the Treatment of Post-chemotherapy Emesis 275John A. Lowe, IIIChapter 19. Armodafinil (Nuvigil), A Psychostimulant for the Treatment of Narcolepsy 291Ji Zhang and Jason CrawfordV. Miscellaneous 307Chapter 20. Raloxifene (Evista), A Selective Estrogen Receptor Modulator (SERM) 309Marta Piñeiro-NúñezChapter 21. Latanoprost (Xalatan), A Prostanoid FP Agonist for Glaucoma 329Sajiv K. Nair and Kevin E. HenegarIndex 339Innovative Drug SynthesisPreface xiContributors xiiiPART I. INFECTIOUS DISEASES 1Chapter 1. Entecavir (Baraclude): A Carbocyclic Nucleoside for the Treatment of Chronic Hepatitis B 3Chapter 2. Telaprevir (Incivek) and Boceprevir (Victrelis): NS3/4A Inhibitors for Treatment for Hepatitis C Virus (HCV) 15Chapter 3. Daclatasvir (Daklinza): The First-in-Class HCV NS5A Replication Complex Inhibitor 43Chapter 4. Sofosbuvir (Sovaldi): The First-in-Class HCV NS5B Nucleotide Polymerase Inhibitor 61Chapter 5. Bedaquiline (Sirturo): A Diarylquinoline that Blocks Tuberculosis ATP Synthase for the Treatment of Multi-Drug Resistant Tuberculosis 81PART II. CANCER 99Chapter 6. Enzalutamide (Xtandi): An Androgen Receptor Antagonist for Late-Stage Prostate Cancer 101Chapter 7. Crizotinib (Xalkori): The First-in-Class ALK/ROS Inhibitor for Non-small Cell Lung Cancer 119Chapter 8. Ibrutinib (Imbruvica): The First-in-Class Btk Inhibitor for Mantle Cell Lymphoma, Chronic Lymphocytic Leukemia, and Waldenstrom's Macroglobulinemia 157Chapter 9. Palbociclib (Ibrance): The First-in-Class CDK4/6 Inhibitor for Breast Cancer 167PART III. CARDIOVASCULAR DISEASES 197Chapter 10. Ticagrelor (Brilinta) and Dabigatran Etexilate (Pradaxa): P2Y12 Platelet Inhibitors as Anti-coagulants 199PART IV. CNS DRUGS 223Chapter 11. Suvorexant (BELSOMRA): The First-in-Class Orexin Antagonist for Insomnia 225Chapter 12. Lorcaserin (Belviq): Serotonin 2C Receptor Agonist for the Treatment of Obesity 243Chapter 13. Fingolimod (Gilenya): The First Oral Treatment for Multiple Sclerosis 255Chapter 14. Perampanel (Fycompa): AMPA Receptor Antagonist for the Treatment of Seizure 271PART V. ANTI-INFLAMMATORY DRUGS 283Chapter 15. Tofacitinib (Xeljanz): The First-in-Class JAK Inhibitor for the Treatment of Rheumatoid Arthritis 285PART VI. MISCELLANEOUS DRUGS 303Chapter 16. Ivacaftor (Kalydeco): A CFTR Potentiator for the Treatment of Cystic Fibrosis 305Chapter 17. Febuxostat (Uloric): A Xanthine Oxidase Inhibitor for the Treatment of Gout 317Index 331