Pharmaceutical process chemistry:
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| 245 | 1 | 0 | |a Pharmaceutical process chemistry |c ed. by Takayuki Shioiri ... |
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IMAGE 1
CONTENTS
PREFACE XVII LIST OF CONTRIBUTORS XXI
1 FROM MILLIGRAMS TO TONS: THE IMPORTANCE OF SYNTHESIS AND PROCESS
RESEARCH IN THE DEVELOPMENT OF NEW DRUGS 1 MARTIN KARPF 1.1 INTRODUCTION
I
1.2 THE SYNTHETIC DEVELOPMENT OF THE MONOAMINE OXIDASE-B INHIBITOR
LAZABEMIDE* 6 1.3 THE SYNTHETIC DEVELOPMENT OF THE LIPASE INHIBITOR
TETRAHYDROLIPSTATIN (XENICAL*) 6
1.4 THE SYNTHETIC DEVELOPMENT OF THE HIV PROTEASE INHIBITOR SAQUINAVIR
(INVIRASE*) 13 1.5 THE SYNTHETIC DEVELOPMENT OF THE INFLUENZA
NEURAMINIDASE INHIBITOR OSELTAMIVIR PHOSPHATE (TAMIFLU*) 36 1.5.1
INTRODUCTION 16
1.5.2 THE DEVELOPMENT OF THE CURRENT TECHNICAL SYNTHESIS OF OSELTAMIVIR
PHOSPHATE 18 1.5.3 THE SEARCH FOR ALTERNATIVE ROUTES TO OSELTAMIVIR
PHOSPHATE 23 1.5.3.1 THE DEVELOPMENT OF AZIDE-FREE TRANSFORMATIONS OF
THE KEY EPOXIDE
INTERMEDIATE TO OSELTAMIVIR PHOSPHATE 23 1.5.3.2 THE DEVELOPMENT OF
ALTERNATIVE SYNTHESES FOR OSELTAMIVIR PHOSPHATE 27 REFERENCES 36
2 DESIGN OF DYNAMIC SALT CATALYSTS BASED ON ACID-BASE COMBINATION
CHEMISTRY 39 KAZUAKI ISHIHARA
2.1 INTRODUCTION 39
2.2 DEHYDRATIVE CONDENSATION CATALYSTS 41
PHARMACEUTICAL PROCESS CHEMISTRY. EDITED BY TAKAYUKI SHIOIRI, KUNISUKE
IZAWA, AND TOSHIRO KONOIKE COPYRIGHT 2011 W1LEY-VCH VERLAG GMBH & CO.
KGAA, WEINHEIM ISBN: 978-3-527-32650-1
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1002408334
DIGITALISIERT DURCH
IMAGE 2
VI CONTENTS
2.2.1 ESTERIFICATION CATALYSTS 41
2.2.2 DEHYDRATIVE CYCLOCONDENSATION CATALYSTS 43 2.3 ASYMMETRIC
MANNICH-TYPE CATALYSTS 50 REFERENCES 56
3 ASYMMETRIC OXIDATION WITH HYDROGEN PEROXIDE, AN EFFECTIVE AND
VERSATILE OXIDANT 59 TSUTOMU KATSUKI 3.1 INTRODUCTION 59
3.2 ASYMMETRIC EPOXIDATION 60
3.2.1 ASYMMETRIC EPOXIDATION WITH SYNTHETIC ENZYMES OR ORGANOCATALYSTS
60 3.2.2 METAL-CATALYZED ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED
OLEFINS 62 3.2.3 METAL-CATALYZED ASYMMETRIC EPOXIDATION OF ALLYLIC
ALCOHOLS 67 3.3 ASYMMETRIC OXIDATION OF SULFIDES 67
3.3.1 METAL-SALEN-CATALYZED OXIDATION 68 3.3.2 METAL-SCHIFF
BASE-CATALYZED OXIDATION 68 3.3.3 METAL-ONNO-TETRADENTATE
LIGAND-CATALYZED OXIDATION (INCLUDING CIS-SS METAL-SALEN-CATALYZED
OXIDATION) 69 3.3.4 MISCELLANEOUS 72
3.4 CONCLUSION 73
REFERENCES 74
4 DEVELOPMENT OF PALLADIUM CATALYSTS FOR CHEMOSELECTIVE HYDROGENATION 77
HIRONAO SAJIKI AND YASUNARI MONGUCHI 4.1 CATALYST POISONS AND
CHEMOSELECTIVE HETEROGENEOUS CATALYSTS 77 4.1.1 BACKGROUND 77
4.1.2 CHEMOSELECTIVE INHIBITION OF THE HYDROGENOLYSIS FOR O-BENZYL
PROTECTIVE GROUPS BY THE ADDITION OF A NITROGEN-CONTAINING BASE 77 4.1.3
PD/C(EN) COMPLEX AS A HETEROGENEOUS CHEMOSELECTIVE HYDROGENATION
CATALYST 82 4.1.4 PD/C (PI12S) COMPLEX AS A HETEROGENEOUS CHEMOSELECTIVE
HYDROGENATION CATALYST 85 4.2 CATALYST SUPPORTS AND CHEMOSELECTIVE
HETEROGENEOUS CATALYSTS 90 4.2A PD/FIB AS A SILK-FIBROIN-SUPPORTED
CHEMOSELECTIVE HYDROGENATION CATALYST 90 4.2.2 PD-PEI AS A PARTIAL
HYDROGENATION CATALYST OF ALKYNES
TO ALKENES 93
4.3 SUMMARY 96
ACKNOWLEDGMENT 97 REFERENCES 97
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CONTENTS VII
5 SILICON-BASED CARBON-CARBON BOND FORMATION BY TRANSITION METAL
CATALYSIS 101 YOSHIAKI NAKAO AND TAMEJIRO HIYAMA 5.1 INTRODUCTION 101
5.2 CROSS-COUPLING REACTIONS 102 5.2.1 BRIEF ASSESSMENT OF EARLY STAGE
PROTOCOLS 102 5.2.2 CROSS-COUPLING REACTIONS USING TETRAORGANOSILANES
THROUGH INTRAMOLECULAR ACTIVATION 103
5.2.3 CROSS-COUPLING REACTIONS USING ORGANOSILANOLATES 106 5.2.4 OTHER
TETRAORGANOSILICON COMPOUNDS FOR CROSS-COUPLING CHEMISTRY 108 5.2.5 NEW
TYPES OF ELECTROPHILES FOR SILICON-BASED CROSS-COUPLING 111
5.3 CARBONYL ADDITION REACTION 114 5.3.1 RHODIUM-CATALYZED REACTIONS 114
5.3.2 NICKEL-CATALYZED REACTIONS 115 5.3.3 PALLADIUM-CATALYZED REACTIONS
117 5.3.4 COPPER-CATALYZED REACTIONS 120 5.3.5 SILVER-CATALYZED
REACTIONS 121 5.4 RECENT DEVELOPMENTS IN CATALYTIC PREPARATION OF
ORGANOSILANES 121
REFERENCES 123
6 DIRECT REDUCTIVE AMINATION WITH AMINE BORANES 127 KARL MATOS AND
ELIZABETH R. BURKHARDT 6.1 INTRODUCTION 227
6.2 TYPES OF AMINE BORANES 128
6.2.1 ALKYLAMINE BORANES 128 6.2.2 AROMATIC AMINE BORANES 129 6.2.2.1
PYRIDINE BORANE 130 6.2.2.2 2-PICOLINE BORANE 232 6.2.2.3
5-ETHYL-2-METHYLPYRIDINE BORANE 232
6.3 COMPARISON TO SODIUM TRIACETOXYBOROHYDRIDE (STAB) 134 6.4 PRIMARY
AMINE SYNTHESIS 235
6.5 STEREOSELECTIVE REDUCTIVE AMINATION 237 6.6 REACTION SOLVENTS 238
6.7 REACTION WORKUP 238
6.8 CONCLUSION 242
REFERENCES 141
7 INDUSTRIAL SYNTHESIS OF PERFLUORINATED BUILDING BLOCKS BY LIQUID-PHASE
DIRECT FLUORINATION 145 TAKASHI OKAZOE
7.1 INTRODUCTION 245
7.2 HISTORY OF DIRECT FLUORINATION 146
7.3 SYNTHETIC METHODS USING PERFLUORINATED ACYL FLUORIDES FOR
INDUSTRIALLY IMPORTANT PERFLUORINATED MONOMERS 149
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VILI CONTENTS
7.3.1 DIRECT APPLICATION OF LIQUID-PHASE FLUORINATION 149
7.3.2 THE PERFECT METHOD 250 7.4 SYNTHESIS OF PERFLUORINATED BUILDING
BLOCKS BY THE PERFECT METHOD 152 7.4.1 PERFLUORINATED ACYL FLUORIDES 252
7.4.2 SYNTHESIS OF PERFLUORINATED KETONES BY THE PERFECT METHOD 254 7.5
CONCLUSION 256
REFERENCES 257
8 CROSS-LINKED ENZYME AGGREGATES AS INDUSTRIAL BIOCATALYSTS 259 ROGER A.
SHELDON 8.1 INTRODUCTION 159
8.2 CROSS-LINKED ENZYME AGGREGATES 260 8.2.1 CROSS-LINKING AGENTS 260
8.2.2 PROTOCOLS FOR CLEA PREPARATION 161 8.2.3 ADVANTAGES OF CLEAS 263
8.2.4 MULTI-CLEAS AND COMBI-CLEAS 264 8.3 CLEAS FROM HYDROLASES 164
8.3.1 LIPASE AND ESTERASE CLEAS 265 8.3.2 PROTEASE CLEAS 168
8.3.3 AMIDASE CLEAS 270
8.3.4 NITRILASES 171
8.3.5 GLYCOSIDASES 172
8.4 OXIDOREDUCTASES 272
8.4.1 OXIDASES 172
8.4.2 PEROXIDASES 273
8.5 LYASES 174
8.5.1 NITRILE HYDRATASES 274
8.5.2 C-C BOND FORMING LYASES 174 8.6 COMBI-CLEAS AND CASCADE PROCESSES
275 8.7 REACTOR DESIGN 276
8.7.1 MEMBRANE SLURRY REACTOR 277 8.7.2 CLEAS IN MICROCHANNEL REACTORS
277 8.8 CONCLUSIONS AND PROSPECTS 178
REFERENCES 178
9 APPLICATION OF WHOLE-CELL BIOCATALYSTS IN THE MANUFACTURE OF FINE
CHEMICALS 183 MICHAEL SCHWAERM
9.1 INTRODUCTION: EARLY APPLICATIONS OF BIOCATALYSIS FOR AMINO ACID
MANUFACTURE AT EVONIK DEGUSSA 183 9.2 HYDANTOINASE BIOCATALYSTS 287
9.3 AMINO ACID DEHYDROGENASE BIOCATALYSTS 292 9.4 ALCOHOL DEHYDROGENASE
BIOCATALYSTS 295
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CONTENTS IX
9.5 SUMMARY 203
ACKNOWLEDGMENTS 204 REFERENCES 204
10 PROCESS DEVELOPMENT OF AMRUBICIN HYDROCHLORIDE, AN ANTHRACYCLINE
ANTICANCER DRUG 207 KAZUHIKO TAKAHASHI AND MITSUHARU HANADA 10.1
INTRODUCTION 207
10.2 ORIGINAL SYNTHETIC ROUTE FOR AMRUBICIN 208 10.3 AMRUBICIN BULK
PRODUCTION SYNTHETIC METHOD 210 10.3.1 SAFE SYNTHETIC METHOD OF
9-AMINOKETONE 211 10.3.2 STEREOSELECTIVE INTRODUCTION OF 7-HYDROXY GROUP
213 10.3.3 POLYMORPHISM STUDY OF AMRUBICIN HYDROCHLORIDE 215 10.3.4
STABILITY OF AMRUBICIN HYDROCHLORIDE WITH REFERENCE
TO MOISTURE 216
10.3.4.1 AMRUBICIN HYDROCHLORIDE MOISTURE ADSORPTION 227 10.3.4.2
STABILITY IN VARIOUS WATER CONTENTS 227 10.3.4.3 ESTABLISHMENT OF DRYING
METHOD 227 10.4 CONCLUSION 219
REFERENCES 219
11 PROCESS DEVELOPMENT OF HIV INTEGRASE INHIBITOR S-1360 222 TOSHIRO
KONOIKE AND SUMIO SHIMIZU 11.1 INTRODUCTION 221
11.2 DISCOVERY OF INTEGRASE INHIBITOR S-1360 221 11.2.1 DISCOVERY ROUTE
OF S-1360 222 11.3 SYNTHESIS OF TWO STARTING MATERIALS FOR S-1360 225
11.3.1 TWO ONE-STEP SYNTHESES OF BENZYLFURYL METHYL KETONE 2 225
11.3.1.1 FRIEDEL-CRAFTS ALKYLATION BY ANHYDROUS ZNCL 2 IN
DICHLOROMETHANE 226 11.3.1.2 FRIEDEL-CRAFTS ALKYLATION USING AQUEOUS
ZNCL2 226 11.3.2 TWO SYNTHETIC METHODS TO TRIAZOLE ESTER 3 228 11.3.2.1
RING CONSTRUCTION METHOD 228 11.3.2.2 RING MODIFICATION METHOD 228 11.4
PROCESS CHEMISTRY OF S-1360 AND SCALE-UP OF THP ROUTE 229 11.4.1
PROTECTION OF TRIAZOLE 3 BY THE TETRAHYDROPYRANYL (THP) GROUP AND
CLAISEN CONDENSATION 229 11.4.2 DEPROTECTION OF THE THP GROUP AND
PURIFICATION OF API DEPROTECTION OF THE THP GROUP 230 11.4.2.1
PURIFICATION OF API 232 11.4.2.2 QUALITY ASSURANCE AND PRODUCTIVITY 232
11.5 PROCESS DEVELOPMENT OF S-L 360 AND COMMERCIAL ROUTE BY
METHOXYISOPROPYL (MIP) PROTECTION 233 11.5.1 MIP ROUTE 234
11.5.2 FURTHER IMPROVEMENT OF PRODUCTIVITY 235
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X CONTENTS
11.6 SUMMARY AND OUTLOOK 235
ACKNOWLEDGMENTS 237 REFERENCES 237
12 AN EFFICIENT SYNTHESIS OF THE PROTEIN KINASE CSS INHIBITOR JTT-O1O 239
TAKASHI INABA 12.1 INTRODUCTION 239
12.2 SYNTHETIC STRATEGIES 240
12.3 KEY INTERMEDIATE SYNTHESIS 240 12.3.1 OPTICAL RESOLUTION 240 12.3.2
ENZYMATIC CHIRAL INDUCTION 242 12.3.3 C-H BOND ACTIVATION BY A CHIRAL
CATALYST 243
12.3.4 FORMAL [3 + 2] CYCLOADDITION USING CHIRAL CYCLOPROPANE 244 12.4
REPLACEMENT OF THE HYDROXYL GROUP OF 1 WITH AN AMINO GROUP 250 12.5
CONSTRUCTION OF JTT-010 251 12.5.1 STEPWISE MALEIMIDE CONSTRUCTION 251
12.5.2 CONVERGENT COUPLING REACTION TO JTT-010 252 12.6 CONCLUSION 253
REFERENCES 254
13 PROCESS DEVELOPMENT OF ORAL CARBAPENEM TEBIPENEM PIVOXIL, TBPM-PI 257
TAKAO ABE AND MASATAKA KITAMURA
13.1 INTRODUCTION 257
13.2 DISCOVERY OF TBPM-PI 257 13.3 SYNTHETIC PROCESS OF SIDE CHAIN ON
THE C2-POSITION OF TBPM, TAT 260 13.3.1 ORIGINAL SYNTHETIC PROCESS OF
TAT STARTING FROM
BENZHYDRYLAMINE 260 13.3.2 PRACTICAL SYNTHETIC PROCESS OF TAT FROM
BENZYLAMINE 261 13.3.3 INDUSTRIAL SYNTHETIC PROCESS OF TAT: BACK TO
CLASSIC
BUNTE'S SALT 263
13.4 SYNTHETIC PROCESS OF TBPM-PI FROM 4-NITROBENZYL (LI?,5I?,6S)-2-
DIPHENYLPHOSPHORYLOXY-6-[(#)-L-HYDROXYETHYL]-
L-METHYL-L-CARBAPEN-2-EM-3-CARBOXYLATE, MAP 265 13.4.1 SYNTHESIS OF PNB
ESTER OF TBPM, L-188 265 13.4.2 SYNTHESIS OF TBPM-4H 2 O 266 13.4.3
PRODRUG ESTERIFICATION: SYNTHESIS OF TBPM HEXETIL,
LJC11,143 267
13.4.4 SYNTHESIS OF TBPM-PI 269 13.5 SUMMARY AND OUTLOOK 270
ACKNOWLEDGMENTS 272 REFERENCES 271
IMAGE 7
CONTENTS XI
14 SOME PROGRESS IN ORGANIC SYNTHESIS OF PHARMACEUTICALS
IN CHINA 273 DELONG LIU AND WANBIN ZHANG 14.1 INTRODUCTION 273
14.2 INDUSTRIAL SYNTHESIS OF CHINESE HERBAL MEDICINES 274 14.2.1
INDUSTRIAL SYNTHESIS OF BERBERINE 274 14.2.2 INDUSTRIAL SYNTHESIS OF
D,L-TETRAHYDROPALMATINE (THP) 277 14.3 NEW AGENTS DERIVED FROM CHINESE
HERBAL MEDICINES 281
14.3.1 BIFENDATE AND BICYCLOL 281 14.3.1.1 BIFENDATE 281 14.3.1.2
BICYCLOL 284 14.3.2 QINGHAOSU 285
14.3.2.1 SYNTHESIS 285 14.3.2.2 FIXED-DOSE RIAMET/COARTEM 287 14.4
PROCESS CHEMISTRY FOR L-ASCORBIC ACID AND BIOTIN 291 14.4.1 TWO STEPS
FERMENTATION METHOD FOR THE PREPARATION OF L-ASCORBIC
ACID (VITAMIN C) 291 14.4.2 TOTAL SYNTHESIS OF BIOTIN (VITAMIN B7) 294
14.5 CONCLUSION AND PERSPECTIVES 298
ABBREVIATIONS 299 REFERENCES 299
15 THE USE OF CONTINUOUS PROCESSING TO MAKE AZD 4407 INTERMEDIATES 303
ANDREW S. WELLS 15.1 GREEN CHEMISTRY AND THE DRIVE FOR SUSTAINABILITY
303 15.2 ADVANTAGES OF CHEMISTRY IN CONTINUOUS-FLOW REACTORS 304 15.3
INTRODUCTION TO AZD 4407 305 15.4 COMPARISON OF THE SYNTHETIC ROUTES
USED TO PREPARE
AZD 4407 305
15.5 CONVERSION OF BATCH TO A FLOW PROCESS 308 15.5.1 PREPARATION OF
SYNTHONS USED IN THE MICROREACTOR STUDY 308 15.5.1.1 DISULFIDE SYNTHESIS
308 15.5.1.2 ( S)-2-M ETHYL TETRAHYDROPYRAN-4-ONE 309 15.5.1.3 THIOPHENE
SYNTHON 310 15.5.2 N-HEXYL LITHIUM VERSUS N-BUTYL LITHIUM 320 15.5.3
BATCH REACTIONS: LITHIATION REACTION AND DISULFIDE LINKING 312 15.5.4
MICROREACTOR DESCRIPTION 311 15.5.5 LITHIATION REACTION IN FLOW MODE 312
15.5.6 COUPLING REACTION WITH DISULFIDE IN FLOW MODE 313 15.5.7 LINKING
THE LITHIATION AND REACTION WITH DISULFIDE IN FLOW MODE 3 13 15.6
CONCLUSIONS 316
ACKNOWLEDGMENTS 327 REFERENCES 327
IMAGE 8
XII I CONTENTS
16 SUSTAINABLE PROCESSES BASED ON ENZYMES ENABLING 100% YIELD AND
100% EE CONCEPTS 321 OLIVER MAY 16.1 INTRODUCTION 322
16.2 ASYMMETRIC SYNTHESIS 322 16.2.1 C-C BOND FORMATIONS 322 16.2.2
PRODUCTION OF CHIRAL ALCOHOLS BY ENZYMATIC REDUCTION OF KETONES 325
16.2.3 REDUCTION OF ACTIVATED C=C BONDS 326 16.2.4 REDUCTIVE AMINATION
OF A-KETO-ACIDS FOR THE PRODUCTION OF A-AMINO ACIDS 328 16.2.5
TRANSAMINATION REACTIONS 330
16.3 ENZYMATIC DESYMMETRIZATION 332 16.4 ENZYMATIC DERACEMIZATION 335
16.5 DYNAMIC KINETIC RESOLUTION 337 16.6 SUMMARY AND OUTLOOK 338
REFERENCES 339
17 DEVELOPMENT OF A NOVEL SYNTHETIC METHOD FOR RNA OLIGOMERS 345 TADAAKI
OHGI AND JUNICHI YANO 17.1 INTRODUCTION 345
17.2 SYNTHESIS OF CEM AMIDITES 349 17.3 SYNTHESIS OF RNA OLIGOMERS FROM
CEM AMIDITES 350 ACKNOWLEDGMENTS 360 REFERENCES 360
18 PROCESS RESEARCH WITH EXPLOSIVE REACTIONS 363 HIROMU KAWAKUBO 18.1
INTRODUCTION 363
18.2 SAFETY EVALUATION OF AN EXPLOSIVE CHEMICAL PROCESS 363 18.3
STANDARD PROCEDURES FOR RISK ASSESSMENT 365 18.3.1 CHETAH (CHEMICAL
THERMODYNAMIC AND ENERGY RELEASE EVALUATION PROGRAM) CALCULATION 365
18.3.2 DSC (DIFFERENTIAL SCANNING CALORIMETRY) 365 18.3.3 DTA
(DIFFERENTIAL THERMAL ANALYSIS) AND TG (THERMOGRAVIMETRY) 367 18.3.4
IMPACT SENSITIVITY TEST 368 18.3.5 FRICTION SENSITIVITY TEST 368 18.3.6
PRESSURE VESSEL TEST 369 18.3.7 STEEL PIPE TEST 371
18.4 SAFETY EVALUATION OF NITROACETIC ACID ETHYL ESTER 372 18.4.1
VARIOUS SAFETY EVALUATIONS OF NITROACETIC ACID ETHYL ESTER 373 18.4.2
SYNTHESIS OF NITROACETIC ACID ETHYL ESTER AND ITS RISK ASSESSMENT 374
IMAGE 9
CONTENTS XIII
18.5 DEVELOPMENT OF AN EFFICIENT METHOD FOR THE SYNTHESIS OF
NITROBENZENE
DERIVATIVES 376 REFERENCES 380
19 SCIENTIFIC STRATEGY FOR OPTICAL RESOLUTION BY SALT CRYSTALLIZATION:
NEW METHODOLOGIES FOR CONTROLLING CRYSTAL SHAPE, CRYSTALLIZATION, AND
CHIRALITY OF DIASTEREOMERIC SALT 381 RUMIKO SAKURAI AND KENICHI SAKAI
19.1 INTRODUCTION 381
19.2 CONTROL OF CRYSTAL SHAPE: CRYSTAL HABIT MODIFICATION 382 19.2.1
SIGNIFICANCE OF CRYSTAL SHAPE IN INDUSTRIAL-SCALE PRODUCTION 382 19.2.2
EFFECTIVE ADDITIVE FOR CONTROLLING CRYSTAL SHAPE 384 19.2.3 MECHANISM OF
CRYSTAL HABIT MODIFICATION 385 19.3 CONTROL OF CRYSTALLIZATION: CONCEPT
OF SPACE FILLER 387 19.3.1 EVALUATION OF MOLECULAR SIZE 387 19.3.2
CONCEPT OF SPACE FILLER 388 19.3.3 RESOLUTION OF MMT 388 19.3.4 CRYSTAL
STRUCTURES OF THE SALTS 390 19.4 CONTROL OF CHIRALITY: DIELECTRICALLY
CONTROLLED OPTICAL RESOLUTION
(DCR) 391
19.4.1 DCR 391
19.4.1.1 DCR IN RESOLUTION OF (RS)-ACL WITH (S)-TPA 391 19.4.1.2 DCR IN
RESOLUTION OF (RS)-PTE WITH (S)-MA 394 19.5 CONCLUSION AND PROSPECT 397
REFERENCES 397
20 DEVELOPMENT OF NEW DRUG AND CRYSTAL POLYMORPHS 401 MITSUHISA YAMANO
20.1 INTRODUCTION 402
20.2 SCOPE OF CRYSTAL POLYMORPHS 402 20.3 LATE-APPEARING POLYMORPHS 402
20.4 LATE-APPEARING POLYMORPHS AS A PROCESS RESEARCH ISSUE 403 20.5 DRUG
SUBSTANCE FORM SELECTION 404 20.6 POLYMORPH SCREENING 405 20.7
THERMODYNAMICALLY STABLE POLYMORPHS 406 20.7.1 ONE-COMPONENT SYSTEM 406
20.7.2 MULTICOMPONENT SYSTEM 406 20.8 POLYMORPH CONTROL 409
20.8.1 NUCLEATION AND SEEDING 42 2 20.8.2 OSTWALD'S STAGE RULE 411
20.8.3 UNINTENTIONAL SEEDING 426 20.9 PRIMARY NUCLEATION 416
20.10 SUMMARY 417
ACKNOWLEDGMENTS 428 REFERENCES 418
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XIV CONTENTS
21 DEVELOPMENT OF LIPOZYMES BASED ON BIOMEMBRANE PROCESS
CHEMISTRY 422 HIROSHI UMAKOSHI, TOSHINORI SHIMANOUCHI, AND RYOICHI KUBOI
21.1 INTRODUCTION 422
21.2 FROM "PROCESS CHEMISTRY" TO "BIOMEMBRANE PROCESS CHEMISTRY" 422
21.3 RECOGNITION (SEPARATION) FUNCTION OF LIPOSOMES 425 21A LIPOZYME:
LIPOSOME WITH ENZYME-LIKE ACTIVITY? 428
21.4.1 BREAK-DOWN TYPE LIPOZYME 428 21.4.2 BUILD-UP TYPE LIPOZYME 431
21.5 BIOMEMBRANE INTERFERENCE 433 21.6 SUMMARY 438
ACKNOWLEDGMENTS 439 REFERENCES 439
22 MATCHING CHEMISTRY WITH CHEMICAL ENGINEERING FOR OPTIMUM DESIGN AND
PERFORMANCE OF PHARMACEUTICAL PROCESSING 443 AMIL V. MAHULKAR, PARAG R.
COGATE, AND ANIRUDDHA B. PANDIT
22.1 CONCEPT OF MOLECULE TO MONEY 443 22.2 STEPS INVOLVED IN BRINGING
MOLECULE TO MARKET 444 22.2.1 SYNTHESIS IN LAB 444 22.2.2 KILO LAB 445
22.2.3 PILOT PLANT 446
22.2.4 FULL-SCALE PLANT 447 22.3 INTERRELATION IN EACH STEP AND CONCEPT
OF UNIT OPERATIONS 448 22.4 UNIT OPERATIONS 449
22.4.1 MIXING 449
22.4.1.1 UTILITY OF MIXING 449 22.4.1.2 TYPES OF EQUIPMENTS 449 22.4.1.3
SELECTION CRITERIA 451
22.4.2 CRYSTALLIZATION 452 22.4.2.1 UTILITY OF CRYSTALLIZATION 452
22.4.2.2 TYPES OF EQUIPMENTS 452 22.4.2.3 SELECTION CRITERIA 453 22.4.3
FILTRATION AND CENTRIFUGATION 454 22.4.3.1 UTILITY OF FILTRATION 454
22.4.3.2 TYPES OF EQUIPMENTS 455 22.4.3.3 SELECTION CRITERIA FOR
FILTRATION 457 22.4.4 CENTRIFUGATION 458 22 A A.I UTILITY OF
CENTRIFUGATION 458 22.4.4.2 TYPES OF EQUIPMENTS 458 22.4.4.3 SELECTION
CRITERIA 460 22.4.5 DRYING 460
22.4.5.1 UTILITY OF DRYING 460 22.4.5.2 TYPES OF EQUIPMENTS 462
IMAGE 11
CONTENTS XV
22.4.5.3 SELECTION CRITERIA 463
22.5 SCALE-UP PROBLEMS 464
22.6 OPTIMIZATION AND INTENSIFICATION OF UNIT OPERATIONS 464 22.6.1 STEP
I: ESTABLISHING MATERIAL AND ENERGY BALANCE ACROSS ALL THE EQUIPMENTS
465
22.6.2 STEP II: PRELIMINARY EVALUATION OF ALL THE MAJOR EQUIPMENTS 465
22.6.3 STEP III: ANALYSIS OF ALL THE OPERATIONS AND EQUIPMENTS AT
RELATIVELY INTRICATE LEVELS 465 22.6A STEP IV: MATHEMATICAL MODELING OF
INDIVIDUAL EQUIPMENT AND
SUBSEQUENTLY THE ENTIRE PLANT 465 22.7 SUMMARY 466
REFERENCES 466
23 THE INTEGRATION OF SAFETY, HEALTH, AND ENVIRONMENTAL CONSIDERATIONS
INTO PROCESS DEVELOPMENT 469 WESLEY WHITE, VYV COOMBE, AND JONATHAN
MOSELEY
23.1 INTRODUCTION 469
23.1.1 THE SHE TRIGGERS MODEL 469 23.1.2 INTRODUCTION TO AZD4619 473
23.2 PROCESS SAFETY 474
23.2.1 ASSESSMENT OF CHEMICAL REACTION HAZARDS 475 23.2.2 ASSESSMENT OF
OPERATIONAL HAZARDS 475 23.2.3 BASIS OF SAFETY 475 23.2.4 PROCESS SAFETY
TRIGGERS 476 23.2.4.1 EARLY DELIVERY 476 23.2.4.2 LATER PROCESS SAFETY
TRIGGERS 476 23.2.4.3 TECHNOLOGY TRANSFER 477 23.2.5 APPLICATION OF
PROCESS SAFETY TO AZD4619 477 23.2.5.1 GENERAL HAZARDS OF AQUEOUS
DIAZOTIZATION AND THE BASIS OF
SAFETY 477
23.2.5.2 ADDITIONS OF ACETONE, WATER, HYDROCHLORIC ACID, AND ACRYLIC
ACID 478 23.2.5.3 ADDITION OF SODIUM NITRITE 478 23.3 HEALTH 479
23.3.1 INTRODUCTION 479 23.3.2 HEALTH TRIGGERS 479 23.3.2.1 EARLY
DELIVERY 479 23.3.2.2 SYNTHETIC ROUTE EVALUATION 480 23.3.2.3 PROCESS
DESIGN 480 23.3.2.4 PROCESS OPTIMIZATION AND UNDERSTANDING 482 23.3.2.5
TECHNOLOGY TRANSFER 481 23.3.3 APPLICATION OF HEALTH TRIGGERS TO AZD4619
482 23.4 ENVIRONMENT 482
23.4.1 INTRODUCTION 482 23.4.2 ENVIRONMENT TRIGGERS 482
IMAGE 12
XVI CONTENTS
23.4.2.1 EARLY DELIVERY AND SYNTHETIC ROUTE EVALUATION 482
23.4.2.2 PROCESS DESIGN 484 23.4.2.3 PROCESS OPTIMIZATION AND
UNDERSTANDING 484 23.4.2.4 TECHNOLOGY TRANSFER 485 23.4.3 APPLICATION OF
ENVIRONMENTAL TRIGGERS TO AZD4619 485
23.5 THE USE OF RISK ASSESSMENT 486 23.6 CONCLUSION 487
ACKNOWLEDGMENTS 488 REFERENCES 488
INDEX 489 |
| any_adam_object | 1 |
| author2 | Shioiri, Takayuki |
| author2_role | edt |
| author2_variant | t s ts |
| author_GND | (DE-588)142540021 |
| author_facet | Shioiri, Takayuki |
| building | Verbundindex |
| bvnumber | BV036716704 |
| classification_rvk | VN 5400 |
| classification_tum | CIT 840f |
| ctrlnum | (OCoLC)690907152 (DE-599)DNB1002408334 |
| dewey-full | 615.19 |
| dewey-hundreds | 600 - Technology (Applied sciences) |
| dewey-ones | 615 - Pharmacology and therapeutics |
| dewey-raw | 615.19 |
| dewey-search | 615.19 |
| dewey-sort | 3615.19 |
| dewey-tens | 610 - Medicine and health |
| discipline | Chemie / Pharmazie Chemie-Ingenieurwesen Medizin |
| format | Book |
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| genre_facet | Aufsatzsammlung |
| id | DE-604.BV036716704 |
| illustrated | Illustrated |
| indexdate | 2024-07-20T10:48:58Z |
| institution | BVB |
| isbn | 9783527326501 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020634695 |
| oclc_num | 690907152 |
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| owner_facet | DE-M49 DE-BY-TUM DE-11 DE-29T |
| physical | XXIV, 502 S. Ill., graph. Darst. 240 mm x 170 mm |
| publishDate | 2011 |
| publishDateSearch | 2011 |
| publishDateSort | 2011 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Pharmaceutical process chemistry ed. by Takayuki Shioiri ... Weinheim Wiley-VCH 2011 XXIV, 502 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Chemische Verfahrenstechnik (DE-588)4069941-9 gnd rswk-swf Chemischer Prozess (DE-588)4147636-0 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Pharmazeutische Chemie (DE-588)4132158-3 s Chemischer Prozess (DE-588)4147636-0 s Chemische Verfahrenstechnik (DE-588)4069941-9 s DE-604 Shioiri, Takayuki (DE-588)142540021 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3474348&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020634695&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Pharmaceutical process chemistry Pharmazeutische Chemie (DE-588)4132158-3 gnd Chemische Verfahrenstechnik (DE-588)4069941-9 gnd Chemischer Prozess (DE-588)4147636-0 gnd |
| subject_GND | (DE-588)4132158-3 (DE-588)4069941-9 (DE-588)4147636-0 (DE-588)4143413-4 |
| title | Pharmaceutical process chemistry |
| title_auth | Pharmaceutical process chemistry |
| title_exact_search | Pharmaceutical process chemistry |
| title_full | Pharmaceutical process chemistry ed. by Takayuki Shioiri ... |
| title_fullStr | Pharmaceutical process chemistry ed. by Takayuki Shioiri ... |
| title_full_unstemmed | Pharmaceutical process chemistry ed. by Takayuki Shioiri ... |
| title_short | Pharmaceutical process chemistry |
| title_sort | pharmaceutical process chemistry |
| topic | Pharmazeutische Chemie (DE-588)4132158-3 gnd Chemische Verfahrenstechnik (DE-588)4069941-9 gnd Chemischer Prozess (DE-588)4147636-0 gnd |
| topic_facet | Pharmazeutische Chemie Chemische Verfahrenstechnik Chemischer Prozess Aufsatzsammlung |
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