The art of process chemistry:
Saved in:
| Other Authors: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim [u.a.]
Wiley-VCH
2011
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XV, 282 S. graph. Darst. |
| ISBN: | 9783527324705 |
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Record in the Search Index
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| adam_text | IMAGE 1
CONTENTS
PREFACE XI LIST OF CONTRIBUTORS XV
1 EFAVIRENZ, A NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR (NNRTI),
AND A PREVIOUS STRUCTURALLY RELATED DEVELOPMENT CANDIDATE 1 NOBUYOSHI
YASUDA AND LUSHI TAN 1.1 FIRST DRUG CANDIDATE 2 2
1.1.1 PROJECT DEVELOPMENT 2 1.1.1.1 MEDICINAL ROUTE 2 1.1.1.2 PROCESS
DEVELOPMENT 3 1.1.2 CHEMISTRY DEVELOPMENT 10 1.1.2.1 SUGASAWA REACTION
10
1.1.2.2 ASYMMETRIC ADDITION OF 2-PYRIDINYLACETYLENE ANION TO KETIMINE 5
AND 17 35
1.2 EFAVIRENZ 19
1.2.1 PROJECT DEVELOPMENT 19 1.2.1.1 MEDICINAL ROUTE 19 1.2.1.2 PROCESS
DEVELOPMENT 20 1.2.2 CHEMISTRY DEVELOPMENT 34 1.2.2.1 REACTION MECHANISM
FOR THE LITHIUM ACETYLIDE ADDITION TO PMB
PROTECTED AMINO KETONE 41 35 1.2.2.2 REACTION MECHANISM FOR THE ZINC
ACETYLIDE ADDITION TO AMINO KETONE 36 40 1.3 CONCLUSION 41
ACKNOWLEDGMENTS 41 REFERENCES 42
2 CCR5 RECEPTOR ANTAGONIST 45 NOBUYOSHI YASUDA 2.1 PROJECT DEVELOPMENT
45 2.1.1 MEDICINAL ROUTE 45
THE ART OF PROCESS CHEMISTRY. EDITED BY NOBUYOSHI YASUDA COPYRIGHT
2011 WILEY-VCH VERLAG GMBH & CO. KGAA, WEINHEIM ISBN: 978-3-527-32470-5
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/994010834
DIGITALISIERT DURCH
IMAGE 2
VI CONTENTS
2.1.2 PROCESS DEVELOPMENT 47
2.1.2.1 ROUTE SELECTION FOR CYCLOPENTENONE 2 47 2.1.2.2 PROCESS
OPTIMIZATION FOR PREPARATION OF 2 50 2.1.2.3 OPTIMIZATION OF THE
PREPARATION OF PYRAZOLE 3 57 2.1.2.4 OPTIMIZATION OF THE PREPARATION OF
OUR TARGET 1 (END GAME) 59
2.1.2.5 OVERALL PREPARATION SCHEME 61 2.2 CHEMISTRY DEVELOPMENT 62 2.2.1
KINETIC RESOLUTION 64
2.2.2 MODIFICATION OF LIGANDS 67 2.2.3 NMR STUDIES REVEALED THE REACTION
MECHANISM 68 2.2 A ADDITIONAL STUDIES FOR CONFIRMATION OF THE
RETENTION-RETENTION MECHANISM 72
2.3 CONCLUSION 74
ACKNOWLEDGMENTS 74 REFERENCES 74
3 5A-REDUCTASE INHIBITORS-THE FINASTERIDE STORY 77 J. MICHAEL WILLIAMS
3.1 PROJECT DEVELOPMENT 78 3.1.1 FINASTERIDE 78 3.1.1.1 THE MEDICINAL
CHEMISTRY ROUTE 78 3.1.1.2 PROCESS DEVELOPMENT 80
3.1.2 THE SECOND GENERATION CANDIDATES 96 3.1.2.1 THE MEDICINAL
CHEMISTRY ROUTE 96 3.1.2.2 PROCESS DEVELOPMENT 97 3.2 CHEMISTRY
DEVELOPMENT 105 3.2.1 MECHANISTIC STUDIES-THE DDQ OXIDATION 105 3.2.2 A
NEW GENERAL METHOD FOR THE PREPARATION OF WEINREB AMIDES
FROM ESTERS 112 3.3 CONCLUSION 313
ACKNOWLEDGMENTS 113 REFERENCES 113
4 RIZATRIPTAN (MAXALT): A 5-HT 1D RECEPTOR AGONIST 117 CHENG-YI CHEN
4.1 PROJECT DEVELOPMENT 118 4.1.1 MEDICINAL CHEMISTRY ROUTE 338 4.1.1.1
PROBLEMS OF THE ORIGINAL ROUTE 119 4.1.1.2 ADVANTAGES OF THE ORIGINAL
ROUTE 119 4.1.2 PROCESS DEVELOPMENT 2 29
4.1.2.1 CONVERGENT FISHER INDOLE SYNTHESIS 2 29 4.1.2.2
PALLADIUM-CATALYZED INDOLE SYNTHESIS 222 4.2 CHEMISTRY DEVELOPMENT 232
4.2.1 APPLICATION OF PD-CATALYZED ANNULATION TO THE SYNTHESIS OF THE
INDOLE
ACETIC ACID 232
IMAGE 3
CONTENTS VII
4.2.2 NEW INDOLE CHEMISTRY FROM DEVELOPMENT OF PD CHEMISTRY 234
4.2.2.1 DISCOVERY OF NEW INDOLE SYNTHESIS FROM AMINES 234 4.2.2.2 DIRECT
COUPLING OF IODOANILINE WITH KETONE 136 4.2.2.3 APPLICATION TO
LAROPIPRANT INDOLE SYNTHESIS 139 4.3 CONCLUSION 242
ACKNOWLEDGMENTS 242 REFERENCES 242
5 SERM: SELECTIVE ESTROGEN RECEPTOR MODULATOR 243 ZHIGUOJAKE SONG 5.1
PROJECT DEVELOPMENT 144 5.1.1 MEDICINAL ROUTE 244 5.1.1.1 PROBLEMS OF
THE ORIGINAL ROUTE 245 5.1.2 PROCESS DEVELOPMENT 245 5.1.2.1 PREPARATION
OF INTERMEDIATE 15 247 5.1.2.2 QUINONE KETAL ROUTE TO RIS-DIARYL
DIHYDROBENZOXATHIIN 30 247 5.1.2.3 BENZOXATHIIN REDUCTION ROUTE TO THE
CIS-DIARYL
DIHYDROBENZOXATHIIN INTERMEDIATE 12 150 5.1.2.4 INSTALLATION OF
PYRROLIDINYL ETHANOL 255 5.1.2.5 FINAL DEPROTECTION AND ISOLATION OF
COMPOUND 1 256 5.1.2.6 OVERALL SYNTHESIS SUMMARY 257 5.2 CHEMISTRY
DEVELOPMENT 257 5.2.1 MECHANISM OF THE SULFOXIDE-DIRECTED OLEFIN
REDUCTION 257 5.2.2 APPLICATION OF THE SULFOXIDE-DIRECTED BORANE
REDUCTION TO OTHER
SIMILAR COMPOUNDS 260 5.3 CONCLUSION 262
ACKNOWLEDGMENTS 262 REFERENCES 2 63
6 HIV INTEGRASE INHIBITOR: RALTEGRAVIR 265 CUY R. HUMPHREY AND YONG-LI
ZHONG 6.1 PROJECT DEVELOPMENT 266 6.1.1 MEDICINAL CHEMISTRY ROUTE 166
6.1.1.1 ADVANTAGES OF THE MEDICINAL CHEMISTRY ROUTE 267 6.1.1.2 PROBLEMS
WITH THE MEDICINAL CHEMISTRY ROUTE 167 6.1.2 PROCESS DEVELOPMENT 268
6.1.2.1 FIRST GENERATION MANUFACTURING PROCESS FOR THE SYNTHESIS OF 1
268
6.1.2.2 SECOND GENERATION MANUFACTURING PROCESS FOR THE SYNTHESIS OF 1
177 6.2 FURTHER CHEMISTRY DEVELOPMENT 283 6.2.1 DEVELOPMENT OF
MICROWAVE-ACCELERATED THERMAL REARRANGEMENT 283 6.2.2 MECHANISTIC
STUDIES ON THE THERMAL REARRANGEMENT 285
6.3 CONCLUSION 289
ACKNOWLEDGMENTS 289 REFERENCES 2 90
IMAGE 4
VILI CONTENTS
7 CYCLOPENTANE-BASED NKL RECEPTOR ANTAGONIST 192
JEFFREY T. KUETHE 7.1 PROJECT DEVELOPMENT COMPOUND L 292 7.1.1 MEDICINAL
ROUTE 292 7.1.1.1 PROBLEMS OF THE ORIGINAL ROUTE 293 7.1.2 PROCESS
DEVELOPMENT 194 7.1.2.1 PREPARATION OF CYCLOPENTANONE 27 295 7.1.2.2
CONVERSION OF CYCLOPENTENONE 27 TO CHIRAL HYDROXY ACID 26 299 7.1.2.3
ETHERIFICATION OF 10 202
7.1.2.4 PREPARATION OF (R)-NIPECOTATE 76 AND COMPLETION OF THE SYNTHESIS
OF 1 209 7.2 CHEMISTRY DEVELOPMENT 213 7.2.1 REDUCTION OF THE ALLYLIC
ALCOHOL 46 WITH RED-AL 22 2
7.2.2 OXONIUM REDUCTION CONFIGURATION ISSUE 223 7.2.3 ETHER BOND
FORMATION WITH CHIRAL IMIDATE 67 224 ACKNOWLEDGMENTS 229 REFERENCES 229
8 CLUCOKINASE ACTIVATOR 223 ARTIS KLAPARS 8.1 PROJECT DEVELOPMENT 223
8.1.1 MEDICINAL ROUTE 223
8.1.1.1 PROBLEMS OF THE ORIGINAL ROUTE 224 8.1.1.2 ADVANTAGES OF THE
ORIGINAL ROUTE 225 8.1.2 PROCESS DEVELOPMENT 225 8.1.2.1 PREPARATION OF
HYDROXYPYRIDINE FRAGMENT 9 226 8.1.2.2 ENANTIOSELECTIVE PREPARATION OF
THE OC-ARYLPYRROLIDINE 12 226
8.1.2.3 ELABORATION OF 12 TO THE FINAL PRODUCT 1 230 8.1.2.4 SUMMARY OF
PROCESS DEVELOPMENT 232 8.2 CHEMISTRY DEVELOPMENT 232 8.2.1 DEVELOPMENT
OF ENANTIOSELECTIVE OC-ARYLATION OF N-BOC PYRROLIDINES 232 8.2.2 SCOPE
OF ENANTIOSELECTIVE OC-ARYLATION OF N-BOC PYRROLIDINES 234 8.2.3
DETAILED EXAMINATION OF THE COUPLING REACTION 236
8.3 CONCLUSION 237
ACKNOWLEDGMENTS 238 REFERENCES 238
9 CB1R INVERSE AGONIST-TARANABANT 242 DEBRA WALLACE 9.1 PROJECT
DEVELOPMENT 242 9.1.1 INTRODUCTION 242 9.1.2 MEDICINAL CHEMISTRY ROUTE
242 9.1.3 INITIAL STRATEGY-AMIDE BOND FORMATION AS THE FINAL STEP 243
9.1.3.1 AMIDE BOND FORMATION AS THE FINAL STEP-CLASSICAL RESOLUTION
APPROACH 244
IMAGE 5
CONTENTS IX
9.1.3.2 AMIDE BOND FORMATION AS THE FINAL STEP-DYNAMIC KINETIC
RESOLUTION 250 9.2 FURTHER PROJECT DEVELOPMENT 253 9.2.1 INTRODUCTION
253 9.2.2 NEW SYNTHETIC APPROACH 254 9.2.2.1 ENOL TRINATE SYNTHESIS 256
9.2.2.2 SYNTHESIS OF A MODEL ENAMIDE 258 9.2.2.3 PRELIMINARY
HYDROGENATION STUDIES 260 9.2.2.4 FORMATION OF AN ENOL TOSYLATE 262
9.2.2.5 AMIDATION OF THE ENOL TOSYLATE 262
9.2.2.6 ASYMMETRIC HYDROGENATION OF ENAMIDE 22 265 9.2.2.7 USE OF A
BROMOSUBSTITUTED-ENAMIDE 267 9.2.2.8 USE OF A NITRITE PROTECTED
ENAMIDE 268 9.2.3 EVALUATION AND ROUTE SELECTION 272 9.3 CONCLUSION 273
ACKNOWLEDGMENTS 273 REFERENCES 273
INDEX 275
|
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| dewey-hundreds | 500 - Natural sciences and mathematics 600 - Technology (Applied sciences) |
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| dewey-sort | 3547.704426015727 |
| dewey-tens | 540 - Chemistry and allied sciences 610 - Medicine and health |
| discipline | Chemie / Pharmazie Chemie Chemie-Ingenieurwesen Biotechnologie Medizin |
| format | Book |
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| indexdate | 2024-07-09T22:47:37Z |
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| isbn | 9783527324705 |
| language | English |
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| spelling | The art of process chemistry ed. by Nobuyoshi Yasuda Weinheim [u.a.] Wiley-VCH 2011 XV, 282 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Wirkstoff-Rezeptor-Bindung (DE-588)4190019-4 gnd rswk-swf Chemische Verfahrenstechnik (DE-588)4069941-9 gnd rswk-swf Chemischer Prozess (DE-588)4147636-0 gnd rswk-swf Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Enzyminhibitor (DE-588)4152479-2 gnd rswk-swf Enzyminhibitor (DE-588)4152479-2 s Wirkstoff-Rezeptor-Bindung (DE-588)4190019-4 s DE-604 Pharmazeutische Chemie (DE-588)4132158-3 s Chemischer Prozess (DE-588)4147636-0 s Chemische Verfahrenstechnik (DE-588)4069941-9 s b DE-604 Yasuda, Nobuyoshi (DE-588)142712485 edt DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020683010&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | The art of process chemistry Wirkstoff-Rezeptor-Bindung (DE-588)4190019-4 gnd Chemische Verfahrenstechnik (DE-588)4069941-9 gnd Chemischer Prozess (DE-588)4147636-0 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd Enzyminhibitor (DE-588)4152479-2 gnd |
| subject_GND | (DE-588)4190019-4 (DE-588)4069941-9 (DE-588)4147636-0 (DE-588)4132158-3 (DE-588)4152479-2 |
| title | The art of process chemistry |
| title_auth | The art of process chemistry |
| title_exact_search | The art of process chemistry |
| title_full | The art of process chemistry ed. by Nobuyoshi Yasuda |
| title_fullStr | The art of process chemistry ed. by Nobuyoshi Yasuda |
| title_full_unstemmed | The art of process chemistry ed. by Nobuyoshi Yasuda |
| title_short | The art of process chemistry |
| title_sort | the art of process chemistry |
| topic | Wirkstoff-Rezeptor-Bindung (DE-588)4190019-4 gnd Chemische Verfahrenstechnik (DE-588)4069941-9 gnd Chemischer Prozess (DE-588)4147636-0 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd Enzyminhibitor (DE-588)4152479-2 gnd |
| topic_facet | Wirkstoff-Rezeptor-Bindung Chemische Verfahrenstechnik Chemischer Prozess Pharmazeutische Chemie Enzyminhibitor |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020683010&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT yasudanobuyoshi theartofprocesschemistry |