The art of drug synthesis:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Hoboken, N.J.
Wiley
2007
|
| Schlagworte: | |
| Online-Zugang: | Table of contents only Inhaltsverzeichnis |
| Beschreibung: | Includes bibliographical references and index |
| Beschreibung: | XV, 276 S. graph. Darst. |
| ISBN: | 9780471752158 |
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| 264 | 1 | |a Hoboken, N.J. |b Wiley |c 2007 | |
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| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Includes bibliographical references and index | ||
| 650 | 4 | |a Drugs |x Design | |
| 650 | 4 | |a Pharmaceutical chemistry | |
| 650 | 4 | |a Drug Design | |
| 650 | 4 | |a Chemistry, Pharmaceutical |x methods | |
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Datensatz im Suchindex
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| adam_text | Foreword xi
Preface xiii
Contributors xv
1 THE ROLE OF MEDICINAL CHEMISTRY IN DRUG DISCOVERY 1
John A. Löwe, III
1.1 Introduction 1
1.2 Hurdles in the Drug Discovery Process 2
1.3 The Tools of Medicinal Chemistry 3
1.3.1 In Silico Modeling 3
1.3.2 Structure Based Drug Design (SBDD) 4
1.4 The Role of Synthetic Chemistry in Drug Discovery 6
References 7
2 PROCESS RESEARCH: HOW MUCH? HOW SOON? 11
Neal G. Anderson
2.1 Introduction 11
2.2 Considerations for Successful Scale up to Tox Batches
and Phase I Material 15
2.3 Considerations for Phase 2 Material and Beyond 16
2.3.1 Reagent Selection 16
2.3.2 Solvent Selection 18
2.3.3 Unit Operations 19
2.3.4 Developing Simple, Effective, Efficient Work ups and Isolations 22
2.3.5 The Importance of Physical States 23
2.3.6 Route Design and Process Optimization to Minimize COG 24
2.4 Summary 26
References 26
I CANCER AND INFECTIOUS DISEASES
3 AROMATASE INHIBITORS FOR BREAST CANCER: EXEMESTANE
(AROMASIN®), ANASTROZOLE (ARIMIDEX®), AND LETROZOLE
(FEMARA®) 31
Jie Jack Li
3.1 Introduction 32
3.2 Synthesis of Exemestane 35
3.3 Synthesis of Anastrozole 36
3.4 Synthesis of Letrozole 37
References 38
4 QUINOLONE ANTIBIOTICS: LEVOFLOXACIN (LEVAQUIN®),
MOXIFLOXACIN (AVELOX®), GEMIFLOXACIN (FACTIVE®),
AND GARENOXACIN (T 3811) 39
Chris Limberakis
4.1 Introduction 40
4.1.1 Mechanism of Action 43
4.1.2 Modes of Resistance 44
4.1.3 Structure Activity Relationship (SAR) and Structure Toxicity
Relationship (STR) 44
4.1.4 Pharmacokinetics 45
4.1.5 Synthetic Approaches 46
4.2 Levofloxacin 47
4.3 Moxifloxacin 57
4.4 Gemifloxacin 60
4.5 Garenoxacin (T 3811): A Promising Clinical Candidate 64
References 66
5 TRIAZOLE ANTIFUNGALS: ITRACONAZOLE (SPORANOX®),
FLUCONAZOLE (DIFLUCAN®), VORICONAZOLE (VFEND®),
AND FOSFLUCONAZOLE (PRODIF®) 71
Andrew S. Bell
5.1 Introduction 72
5.2 Synthesis of Itraconazole 74
5.3 Synthesis of Fluconazole 76
5.4 Synthesis of Voriconazole 77
5.5 Synthesis of Fosfluconazole 80
References 81
6 NON NUCLEOSIDE HIV REVERSE TRANSCRIPTASE
INHIBITORS 83
Arthur Harms
6.1 Introduction 84
6.2 Synthesis of Nevirapine 85
6.3 Synthesis of Efavirenz 87
6.4 Synthesis of Delavirdine Mesylate 90
References 92
7 NEURAMINIDASE INHIBITORS FOR INFLUENZA: OSELTAMIVIR
PHOSPHATE (TAMIFLU®) AND ZANAMIVIR (RELENZA®) 95
Douglas S. Johnson and Jie Jack Li
7.1 Introduction 95
7.1.1 Relenza 97
7.1.2 Tamiflu 97
7.2 Synthesis of Oseltamivir Phosphate (Tamiflu®) 99
7.3 Synthesis of Zanamivir (Relenza®) 110
References 113
II CARDIOVASCULAR AND METABOLIC DISEASES
8 PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR
(PPAR) AGONISTS FOR TYPE 2 DIABETES 117
Jin Li
8.1 Introduction 117
8.1.1 Insulin 118
8.1.2 Sulfonylurea Drugs 119
8.1.3 Meglitinides 119
8.1.4 Biguanides 119
8.1.5 Alpha Glucosidase Inhibitors 120
8.1.6 Thiazolidinediones 120
8.2 Synthesis of Rosiglitazone 121
8.3 Synthesis of Pioglitazone 122
8.4 Synthesis of Muraglitazar 124
References 125
9 ANGIOTENSIN AT] ANTAGONISTS FOR
HYPERTENSION 129
Larry Yet
9.1 Introduction 130
9.2 Losartan Potassium 132
9.2.1 Introduction to Losartan Potassium 132
9.2.2 Synthesis of Losartan Potassium 133
9.3 Valsartan 134
9.3.1 Introduction to Valsartan 134
9.3.2 Synthesis of Valsartan 134
9.4 Irbesartan 135
9.4.1 Introduction to Irbesartan 135
9.4.2 Synthesis of Irbesartan 135
9.5 Candesartan Cilexetil 136
9.5.1 Introduction to Candesartan Cilexetil 136
9.5.2 Synthesis of Candesartan Cilexetil 136
9.6 Olmesartan Medoxomil 137
9.6.1 Introduction to Olmesartan Medoxomil 137
9.6.2 Synthesis of Olmesartan Medoxomil 137
9.7 Eprosartan Mesylate 138
9.7.1 Introduction to Eprosartan Mesylate 138
9.7.2 Synthesis of Eprosartan Mesylate 138
9.8 Telmisartan 139
9.8.1 Introduction to Telmisartan 139
9.8.2 Synthesis of Telmisartan 139
References 140
10 LEADING ACE INHIBITORS FOR HYPERTENSION 143
Victor J. Cee and Edward J. Olhava
10.1 Introduction 144
10.2 Synthesis of Enalapril Maleate 146
10.3 Synthesis of Lisinopril 147
10.4 Synthesis of Quinapril 148
10.5 Synthesis of Benazepril 150
10.6 Synthesis of Ramipril 151
10.7 Synthesis of Fosinopril Sodium 154
References 156
11 DIHYDROPYRIDINE CALCIUM CHANNEL BLOCKERS FOR
HYPERTENSION 159
Daniel P. Christen
11.1 Introduction 160
11.2 Synthesis of Nifedipine (Adalat®) 162
11.3 Synthesis of Felodepine (Plendil®) 163
11.4 Synthesis of Amlodipine Besylate (Norvasc®) 164
11.5 Synthesis of Azelnidipine (Calblock®) 165
References 166
12 SECOND GENERATION HMG CoA REDUCTASE
INHIBITORS 169
Jeffrey A. Pfefferkorn
12.1 Introduction 170
12.2 Synthesis of Fluvastatin (Lescol®) 171
12.3 Synthesis of Rosuvastatin (Crestor®) 174
12.4 Synthesis of Pitavastatin (Livalo®) 177
References 181
13 CHOLESTEROL ABSORPTION INHIBITORS: EZETIMIBE
(ZETIA®) 183
Stuart B. Rosenblum
13.1 Introduction 183
13.2 Discovery Path to Ezetimibe 184
13.3 Synthesis of Ezetimibe (Zetia®) 187
References 195
III CENTRAL NERVOUS SYSTEM DISEASES
14 DUAL SELECTIVE SEROTONIN AND NOREPINEPHRINE
REUPTAKE INHIBITORS (SSNRIs) FOR DEPRESSION 199
Marta Pineiro Nünez
14.1 Introduction 200
14.2 Synthesis of Venlafaxine 203
14.3 Synthesis of Milnacipran 205
14.4 Synthesis of Duloxetine 207
References 212
15 GABAA RECEPTOR AGONISTS FOR INSOMNIA: ZOLPIDEM
(AMBIEN®), ZALEPLON (SONATA®), ESZOPICLONE
(ESTORRA®, LUNESTA®), AND INDIPLON 215
Peter R. Guzzo
15.1 Introduction 216
15.2 Synthesis of Zolpidem 217
15.3 Synthesis of Zaleplon 219
15.4 Synthesis ofEszopiclone 220
15.5 Synthesis of Indiplon 221
References 223
16 a28 LIGANDS: NEURONTIN® (GABAPENTIN) AND LYRICA®
(PREGABALIN) 225
Po Wai Yuen
16.1 Introduction 225
16.2 Synthesis of Gabapentin 227
16.3 Synthesis of Pregabalin 234
References 239
17 APPROVED TREATMENTS FOR ATTENTION DEFICIT
HYPERACTIVITY DISORDER: AMPHETAMINE (ADDERALL®),
METHYLPHENIDATE (RITALIN®), AND ATOMOXETINE
(STRATERRA®) 241
David L Gray
17.1 Introduction 242
17.1.1 Stimulant versus Nonstimulants 242
17.2 Synthesis of Amphetamine 244
17.2.1 Pharmacokinetic Properties of d and Z Amphetamine 246
17.2.2 Chiral Synthesis of Amphetamine 246
17.3 Synthesis of Methylphenidate 247
17.3.1 Methylphenidate Formulations 249
17.3.2 Chiral Synthesis of Methylphenidate 250
17.4 Synthesis ofAtomoxetine 253
References 257
Index 261
|
| adam_txt |
Foreword xi
Preface xiii
Contributors xv
1 THE ROLE OF MEDICINAL CHEMISTRY IN DRUG DISCOVERY 1
John A. Löwe, III
1.1 Introduction 1
1.2 Hurdles in the Drug Discovery Process 2
1.3 The Tools of Medicinal Chemistry 3
1.3.1 In Silico Modeling 3
1.3.2 Structure Based Drug Design (SBDD) 4
1.4 The Role of Synthetic Chemistry in Drug Discovery 6
References 7
2 PROCESS RESEARCH: HOW MUCH? HOW SOON? 11
Neal G. Anderson
2.1 Introduction 11
2.2 Considerations for Successful Scale up to Tox Batches
and Phase I Material 15
2.3 Considerations for Phase 2 Material and Beyond 16
2.3.1 Reagent Selection 16
2.3.2 Solvent Selection 18
2.3.3 Unit Operations 19
2.3.4 Developing Simple, Effective, Efficient Work ups and Isolations 22
2.3.5 The Importance of Physical States 23
2.3.6 Route Design and Process Optimization to Minimize COG 24
2.4 Summary 26
References 26
I CANCER AND INFECTIOUS DISEASES
3 AROMATASE INHIBITORS FOR BREAST CANCER: EXEMESTANE
(AROMASIN®), ANASTROZOLE (ARIMIDEX®), AND LETROZOLE
(FEMARA®) 31
Jie Jack Li
3.1 Introduction 32
3.2 Synthesis of Exemestane 35
3.3 Synthesis of Anastrozole 36
3.4 Synthesis of Letrozole 37
References 38
4 QUINOLONE ANTIBIOTICS: LEVOFLOXACIN (LEVAQUIN®),
MOXIFLOXACIN (AVELOX®), GEMIFLOXACIN (FACTIVE®),
AND GARENOXACIN (T 3811) 39
Chris Limberakis
4.1 Introduction 40
4.1.1 Mechanism of Action 43
4.1.2 Modes of Resistance 44
4.1.3 Structure Activity Relationship (SAR) and Structure Toxicity
Relationship (STR) 44
4.1.4 Pharmacokinetics 45
4.1.5 Synthetic Approaches 46
4.2 Levofloxacin 47
4.3 Moxifloxacin 57
4.4 Gemifloxacin 60
4.5 Garenoxacin (T 3811): A Promising Clinical Candidate 64
References 66
5 TRIAZOLE ANTIFUNGALS: ITRACONAZOLE (SPORANOX®),
FLUCONAZOLE (DIFLUCAN®), VORICONAZOLE (VFEND®),
AND FOSFLUCONAZOLE (PRODIF®) 71
Andrew S. Bell
5.1 Introduction 72
5.2 Synthesis of Itraconazole 74
5.3 Synthesis of Fluconazole 76
5.4 Synthesis of Voriconazole 77
5.5 Synthesis of Fosfluconazole 80
References 81
6 NON NUCLEOSIDE HIV REVERSE TRANSCRIPTASE
INHIBITORS 83
Arthur Harms
6.1 Introduction 84
6.2 Synthesis of Nevirapine 85
6.3 Synthesis of Efavirenz 87
6.4 Synthesis of Delavirdine Mesylate 90
References 92
7 NEURAMINIDASE INHIBITORS FOR INFLUENZA: OSELTAMIVIR
PHOSPHATE (TAMIFLU®) AND ZANAMIVIR (RELENZA®) 95
Douglas S. Johnson and Jie Jack Li
7.1 Introduction 95
7.1.1 Relenza 97
7.1.2 Tamiflu 97
7.2 Synthesis of Oseltamivir Phosphate (Tamiflu®) 99
7.3 Synthesis of Zanamivir (Relenza®) 110
References 113
II CARDIOVASCULAR AND METABOLIC DISEASES
8 PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR
(PPAR) AGONISTS FOR TYPE 2 DIABETES 117
Jin Li
8.1 Introduction 117
8.1.1 Insulin 118
8.1.2 Sulfonylurea Drugs 119
8.1.3 Meglitinides 119
8.1.4 Biguanides 119
8.1.5 Alpha Glucosidase Inhibitors 120
8.1.6 Thiazolidinediones 120
8.2 Synthesis of Rosiglitazone 121
8.3 Synthesis of Pioglitazone 122
8.4 Synthesis of Muraglitazar 124
References 125
9 ANGIOTENSIN AT] ANTAGONISTS FOR
HYPERTENSION 129
Larry Yet
9.1 Introduction 130
9.2 Losartan Potassium 132
9.2.1 Introduction to Losartan Potassium 132
9.2.2 Synthesis of Losartan Potassium 133
9.3 Valsartan 134
9.3.1 Introduction to Valsartan 134
9.3.2 Synthesis of Valsartan 134
9.4 Irbesartan 135
9.4.1 Introduction to Irbesartan 135
9.4.2 Synthesis of Irbesartan 135
9.5 Candesartan Cilexetil 136
9.5.1 Introduction to Candesartan Cilexetil 136
9.5.2 Synthesis of Candesartan Cilexetil 136
9.6 Olmesartan Medoxomil 137
9.6.1 Introduction to Olmesartan Medoxomil 137
9.6.2 Synthesis of Olmesartan Medoxomil 137
9.7 Eprosartan Mesylate 138
9.7.1 Introduction to Eprosartan Mesylate 138
9.7.2 Synthesis of Eprosartan Mesylate 138
9.8 Telmisartan 139
9.8.1 Introduction to Telmisartan 139
9.8.2 Synthesis of Telmisartan 139
References 140
10 LEADING ACE INHIBITORS FOR HYPERTENSION 143
Victor J. Cee and Edward J. Olhava
10.1 Introduction 144
10.2 Synthesis of Enalapril Maleate 146
10.3 Synthesis of Lisinopril 147
10.4 Synthesis of Quinapril 148
10.5 Synthesis of Benazepril 150
10.6 Synthesis of Ramipril 151
10.7 Synthesis of Fosinopril Sodium 154
References 156
11 DIHYDROPYRIDINE CALCIUM CHANNEL BLOCKERS FOR
HYPERTENSION 159
Daniel P. Christen
11.1 Introduction 160
11.2 Synthesis of Nifedipine (Adalat®) 162
11.3 Synthesis of Felodepine (Plendil®) 163
11.4 Synthesis of Amlodipine Besylate (Norvasc®) 164
11.5 Synthesis of Azelnidipine (Calblock®) 165
References 166
12 SECOND GENERATION HMG CoA REDUCTASE
INHIBITORS 169
Jeffrey A. Pfefferkorn
12.1 Introduction 170
12.2 Synthesis of Fluvastatin (Lescol®) 171
12.3 Synthesis of Rosuvastatin (Crestor®) 174
12.4 Synthesis of Pitavastatin (Livalo®) 177
References 181
13 CHOLESTEROL ABSORPTION INHIBITORS: EZETIMIBE
(ZETIA®) 183
Stuart B. Rosenblum
13.1 Introduction 183
13.2 Discovery Path to Ezetimibe 184
13.3 Synthesis of Ezetimibe (Zetia®) 187
References 195
III CENTRAL NERVOUS SYSTEM DISEASES
14 DUAL SELECTIVE SEROTONIN AND NOREPINEPHRINE
REUPTAKE INHIBITORS (SSNRIs) FOR DEPRESSION 199
Marta Pineiro Nünez
14.1 Introduction 200
14.2 Synthesis of Venlafaxine 203
14.3 Synthesis of Milnacipran 205
14.4 Synthesis of Duloxetine 207
References 212
15 GABAA RECEPTOR AGONISTS FOR INSOMNIA: ZOLPIDEM
(AMBIEN®), ZALEPLON (SONATA®), ESZOPICLONE
(ESTORRA®, LUNESTA®), AND INDIPLON 215
Peter R. Guzzo
15.1 Introduction 216
15.2 Synthesis of Zolpidem 217
15.3 Synthesis of Zaleplon 219
15.4 Synthesis ofEszopiclone 220
15.5 Synthesis of Indiplon 221
References 223
16 a28 LIGANDS: NEURONTIN® (GABAPENTIN) AND LYRICA®
(PREGABALIN) 225
Po Wai Yuen
16.1 Introduction 225
16.2 Synthesis of Gabapentin 227
16.3 Synthesis of Pregabalin 234
References 239
17 APPROVED TREATMENTS FOR ATTENTION DEFICIT
HYPERACTIVITY DISORDER: AMPHETAMINE (ADDERALL®),
METHYLPHENIDATE (RITALIN®), AND ATOMOXETINE
(STRATERRA®) 241
David L Gray
17.1 Introduction 242
17.1.1 Stimulant versus Nonstimulants 242
17.2 Synthesis of Amphetamine 244
17.2.1 Pharmacokinetic Properties of d and Z Amphetamine 246
17.2.2 Chiral Synthesis of Amphetamine 246
17.3 Synthesis of Methylphenidate 247
17.3.1 Methylphenidate Formulations 249
17.3.2 Chiral Synthesis of Methylphenidate 250
17.4 Synthesis ofAtomoxetine 253
References 257
Index 261 |
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| id | DE-604.BV022617778 |
| illustrated | Illustrated |
| index_date | 2024-07-02T18:18:55Z |
| indexdate | 2024-07-09T21:01:46Z |
| institution | BVB |
| isbn | 9780471752158 |
| language | English |
| lccn | 2007017891 |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-015823886 |
| oclc_num | 123962939 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-19 DE-BY-UBM |
| owner_facet | DE-91G DE-BY-TUM DE-19 DE-BY-UBM |
| physical | XV, 276 S. graph. Darst. |
| publishDate | 2007 |
| publishDateSearch | 2007 |
| publishDateSort | 2007 |
| publisher | Wiley |
| record_format | marc |
| spelling | The art of drug synthesis ed. by Douglas S. Johnson ... Hoboken, N.J. Wiley 2007 XV, 276 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Drugs Design Pharmaceutical chemistry Drug Design Chemistry, Pharmaceutical methods Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Arzneimittel (DE-588)4003115-9 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Arzneimittel (DE-588)4003115-9 s Chemische Synthese (DE-588)4133806-6 s DE-604 Pharmazeutische Chemie (DE-588)4132158-3 s Johnson, Douglas S. Sonstige oth http://www.loc.gov/catdir/toc/ecip0717/2007017891.html Table of contents only HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015823886&sequence=000006&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | The art of drug synthesis Drugs Design Pharmaceutical chemistry Drug Design Chemistry, Pharmaceutical methods Pharmazeutische Chemie (DE-588)4132158-3 gnd Arzneimittel (DE-588)4003115-9 gnd Chemische Synthese (DE-588)4133806-6 gnd |
| subject_GND | (DE-588)4132158-3 (DE-588)4003115-9 (DE-588)4133806-6 |
| title | The art of drug synthesis |
| title_auth | The art of drug synthesis |
| title_exact_search | The art of drug synthesis |
| title_exact_search_txtP | The art of drug synthesis |
| title_full | The art of drug synthesis ed. by Douglas S. Johnson ... |
| title_fullStr | The art of drug synthesis ed. by Douglas S. Johnson ... |
| title_full_unstemmed | The art of drug synthesis ed. by Douglas S. Johnson ... |
| title_short | The art of drug synthesis |
| title_sort | the art of drug synthesis |
| topic | Drugs Design Pharmaceutical chemistry Drug Design Chemistry, Pharmaceutical methods Pharmazeutische Chemie (DE-588)4132158-3 gnd Arzneimittel (DE-588)4003115-9 gnd Chemische Synthese (DE-588)4133806-6 gnd |
| topic_facet | Drugs Design Pharmaceutical chemistry Drug Design Chemistry, Pharmaceutical methods Pharmazeutische Chemie Arzneimittel Chemische Synthese |
| url | http://www.loc.gov/catdir/toc/ecip0717/2007017891.html http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015823886&sequence=000006&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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