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Pharmaceutical Substances, 5th Edition, 2009 - Axel Kleemann - E-Book

Pharmaceutical Substances, 5th Edition, 2009 E-Book

Axel Kleemann

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Beschreibung

"Pharmaceutical Substances" is a compendium of 1,300 of the most significant pharmaceutical compounds that are of interest to the chemical and pharmaceutical industries. It is the ideal companion to the "Pharmaceutical Substances Online Edition" and an authoritative resource for everyone involved in design, discovery, development, evaluation, and marketing of drugs. Profs. Axel Kleemann, Jürgen Engel, Bernhard Kutscher, and Dr. Dietmar Reichert present in a clear and concise manner highly evaluated information collected from all the relevant literature, and commercial patent data. This includes synthetic routes and all intermediates for approved drugs from the six most important markets. All compounds are organized alphabetically according to their International Non-proprietary Name (INN). The book features four indexes: Trade Names / Intermediates / Enzymes, Microorganisms, Plants, and Animal Tissues / Substance Classes. // The content of this e-book was originally published in 2009.

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Veröffentlichungsjahr: 2014

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Table of Contents

Preface to the fifth edition

Introduction

Sample Entry

Alphabetical List of Drug Monographs

Drug Monographs

Indexes

a) Trade Names

b) Intermediates

c) Enzymes, Microorganisms, Plants, Animal Tissues

d) Substance Classes

Preface to the fifth printed edition

Over the last few years many users of Pharmaceutical Substances asked the authors and the publisher for an updated print edition, as under some circumstances, a print edition would come in handier than a solely electronic version; this electronic version, which was launched in 2003, has since been - and will continue to be - constantly updated. Knowing that a new print edition would require much effort, we last year finally agreed to take on this challenge. Prof. Bernhard Kutscher and Dr. Dietmar Reichert continued to work especially hard on Pharmaceutical Substances. They therefore more than deserve to be promoted from “co-authors” to “authors” of both this fifth printed edition and the electronic version.

The fourth edition of this book was published seven years ago and is in many aspects outdated. Since 2001, many changes have taken place on the pharmaceutical market. Many new NCEs were launched. Well-known companies and vendors disappeared or changed their names, and new companies or company names have appeared on the scene. A vast number of brand names disappeared or changed, drugs were withdrawn or sold to another vendor, and last but not least, many drugs became generic after their patents expired.

A few random examples may illustrate these changes. Vendor names that disappeared from the pharmaceutical market include ASTA Medica, Altana, Beecham, Boehringer Mannheim, Byk Gulden, Carter Wallace, Ciba-Geigy, Fujisawa, Hoechst, ICI, Knoll, Searle, Upjohn. New vendor names include Actelion, Astellas, Celgene, Cephalon, Daiichi Sankyo, Gilead, Intendis, MEDA Pharma, Medpointe Pharmaceuticals, mibe, RIEMSER, et al.

As a consequence of the aforementioned changes, 165 new monograph entries were added, the existing monographs, were completely revised (syntheses schemes, patents, literature, etc.), the medical use information was harmonized wherever possible, and countless changes to trade names and vendor names were made. For the convenience of our users, it was our aim to return to a printed edition in one volume. The focus of this fifth edition is on the most important drugs in terms of volume and sales, excluding biopharmaceuticals. Due to the continued availability and updates of the electronic version, we decided not to describe in the print edition drugs that were withdrawn from all of the six markets we are referring to, as well as those drugs, which have become much less commercially important or are quite trivial (such as salicylamide, salicylic acid, phenol, etc.) and to highlight key intermediates in the electronic version only. The alphabetical list of monographs at the beginning of this book lists all active pharmaceutical ingredients (“APIs”) covered in the electronic version, while those that made it into this book are printed in bold. We are convinced that these measures will greatly increase the utility of the book, used as a standalone resource as well as in combination with the electronic version.

This fifth printed edition contains about 1300 APIs. When it comes to the information provided about a given drug, no fundamental changes were made in comparison to the previous printed editions.

We hope that this standard reference book will continue to serve the needs of specialists in drug synthesis and manufacturing, as well as a broad user group in the chemical, intermediates and pharmaceutical industry, pharmacists, universities, and other research institutes. We sincerely believe that this current issue will greatly assist readers in teaching as well as in solving problems at work.

We are very grateful to the many readers who kindly provided us with proposals for corrections and improvements. The authors are deeply indebted to Ingo Adamczyk, Ulrich Quandt, and Martin Holberg from the FIZ CHEMIE BERLIN, for their invaluable contributions to the preparation process of this book. We also would like to thank Dr. Thomas Krimmer from Georg Thieme Verlag for the always excellent and fruitful cooperation. A special thank you goes to our Japanese friend and colleague Nobuo Kumagai, who provided us with the trade name information for the Japanese market.

Frankfurt a.M., July 2008

Axel KleemannJürgen EngelBernhard KutscherDietmar Reichert

Prefaces to previous editions can be viewed at www.thieme-chemistry.com

Introduction

This reference work describes the production/isolation processes of about 1300 active pharmaceutical substances (including the syntheses of the corresponding intermediates) that are currently marketed. In order to illustrate what particular information can be drawn from the book an excerpt of a typical monograph is depicted and labelled on the next two pages. The content shown has been shortened for demonstration purposes. A larger version of this sample entry is also available at www.thieme-chemistry.com.

Frequently used abbreviations are explained in a separate list, q.v. front and back endpapers.

With respect to the names of reagents and intermediates in the course of the syntheses the authors tried to use the names found in the catalogues of commercial providers of fine chemicals, e.g. Sigma-Aldrich, otherwise the Chemical Abstracts Names are given.

In addition to the respective patents and publications in journals several standard reference books for Pharmaceuticals and Fine Chemicals were used and sometimes also cited. The most important sources are named here:

The Merck Index, 14.ed., Merck & Co., Inc.; NJ 2006

Index Nominum, 18./19. ed., medpharm GmbH, Stuttgart 2004/2008

D. Lednicer, The Organic Chemistry of Drug Synthesis, vols. 1-7,1977-2008, Wiley-Interscience, New York

Ullmann’s Encyclopedia of Industrial Chemistry, 5.ed., vols. A1-A28, B1-B8, Wiley-VCH, Weinheim 1985-1997

Ullmann’s Encyclopedia of Industrial Chemistry, 6.ed., online version with regular updates, Wiley-VCH, Weinheim

USP Dictionary of USAN and International Drug Names, US Pharmacopeia, Rockville, MD, 2008

The acute toxicity data were in most cases taken from different data banks or other secondary sources, so no guarantee can be given for validity.

Sample Entry Pharmaceutical Substances 5th edition

The International Nonproprietary Names (INN) of pharmaceutical substances form the title of each monograph. All the synonyms in use for the compounds are shown in the second line. Factual data listed here include chemical name (written according IUPAC), Anatomical Therapeutic Chemical (ATC) Code, major uses, CAS numbers (RN), molecular formula (Hill System) and weight.

Atorvastatin calcium

(CI-981’ YM-548)

ATC:

C10AA05

Use:

hypolipidemic, HMG-CoA-reductase inhibitor

RN:

134523-03-8 MF: C

66

H

68

CaF

2

N

4

O

10

MW: 1155.36

CN: [

R

-(

R*,R*

)]-2-(4-fluorophenyl)-

β,δ

-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylammo)carbonyl]-1

H

-pyrrole-1-heptanoic acid calcium salt (2:1)

free acid

RN: 134523-00-5 MF: C

33

H

35

FN

2

O

5

MW: 558.65

Great care is taken by the authors to ascertain the synthetic route(s) used for industrial large-scale production of the drugs listed in Pharmaceutical Substances. A detailed description of the preparation of each substance is provided, including the synthesis of intermediates.

In many cases, different synthetic routes are described, especially for the most economically important drugs. All substances referenced in the synthetic pathways are listed in the substance index at the end of the book.

Excerpt*

*The content shown has been shortened for demonstration purposes.

The references in Pharmaceutical Substances give an overview of the patents that apply to the synthetic route, the dates of issue of the US patents, as well as application and priority dates. When applicable, patent references for alternative syntheses are listed as well as references to nonpatent literature.

Experpt*

Reference(s)

US 4 681 893 (Warner-Lambert; 21.7.1987; appl. 30.5.1986).

US 5 273 995 (Warner-Lambert; 28.12.1993; appl. 26.2.1991; USA-prior. 21.7.1989).

EP 409 281 (Warner-Lambert; appl. 23.1.1991; USA-prior. 21.7.1989, 26.2.1991).

DE 1 061 073 (Warner-Lambert; appl. 20.7.1990; USA-prior. 21.7.1989).

improved process:

WO 2 005 087 723 (Apotex Pharmachem; appl. 11.3.2005; CA-prior. 15.3.2004).

CA 2 460 935 (Apotex Pharmachem; appl. 15.3.2004).

a4 US 4 681 893 (Warner-Lambert; appl. 21.7.1987; USA-prior. 30.5.1986).

bc1 US 5 155 251 (Warner-Lambert; 13.10.1992; appl. 11.10.1991).

c1 US 5 103 024 (Warner-Lambert; 7.4.1992; appl. 17.10.1990).US 6 433 213 (Warner-Lambert; 13.8.2002; appl. 2.12.1998, 16.6.2000; USA-prior. 19.12.1997).US 6 596 879 (Warner-Lambert; 22.7.2003; appl. 11.6.2002; USA-prior. 19.12.1997, 2.12.1998).US 6 962 994 (Warner-Lambert; 8.11.2005; appl. 11.4.2003; USA-prior. 19.12.1997, 11.6.2002).

c2 US 5 248 793 (Warner-Lambert; 28.9.1993; appl. 21.12.1992; USA-prior. 17.10.1990, 27.12.1991).

(S)-3,4-dihydroxybutanoic acid and (S)-3-hydroxybutyrolactone from carbohydrates (e.g. maltose, lactose):

d1 US 5 292 939 (Hollingsworth, R.I., Michigan State University; 8.3.1994; appl. 26.10.1992; USA-prior. 13.5.1991).

US 5 319 110 (Hollingsworth, R.I., Michigan State University; 7.6.1994; appl. 26.10.1992; USA-prior. 13.5.1991).

US 5 374 773 (Hollingsworth, R.I., Michigan State University; 20.12.1994; appl. 27.10.1993; USA-prior. 13.5.1991, 26.10.1992).

US 6 239 311 (Hollingsworth, R.I., Michigan State University; 29.5.2001; appl. 24.4.2000).

*The content shown has been shortened for demonstration purposes.

The most important pharmaceutical dosage forms are provided to enable the user to assess the order of magnitude a compound is needed in and thus helping to estimate its commercial value.

Formulation(s):

tabl. 5 mg, 10 mg, 20 mg, 40 mg, 80 mg

For the six most important markets trade names and the names of companies that produce and market the product are given. Years of introduction are added in those cases where they differ from the date the original patent was granted.

Trade Name(s):

D:

Sortis (Parke Davis; Gödecke; Pfizer; Mack, Illert.)

F :

Caduet (Pfizer)-comb.Tahor (Pfizer)

GB:

Lipitor (Pfizer)

I:

Lipitor (Warner-Lambert)Torvast (Pfizer)Totalip (Guidotti)

J:

Lipitor (Astellas)

USA:

Lipitor (Parke Davis; Pfizer)

Alphabetical List of Drug Monographs

A

547785

149097 (as free base) online

151235 (as hydrochloride) online

A 50 online

A 4166949

A-56268307

A-640771497

A-730011250

A-845381221

A-157378.0814

AA-673 online

AA-24141250

Abacavir1

Abarelix5

Abbott 41070649

Abbott-43818775

ABC-12/3 online

Abciximab online

ABT-0011250

ABT-0771497

ABT-378814

ABT-5381221

ABT-5691369

AC-2993537

AC 44641409

Acamprosate calcium6

Acamylophenin online

Acarbose7

ACC 9653 online

Acebutolol7

Acecarbromal online

Aceclidine online

Aceclofenac9

Acediasulfone online

Acefylline online

Acefylline heptaminol online

Aceglutamide aluminum online

Acemetacin9

Acenocoumarol online

Acenocumarin online

Acepifylline online

Aceprolinum1022

Acepromazine11

Aceprometazine online

Acetaminophenol1057

Acetarsol online

Acetarsone online

Acetazolamide11

Acetazoleamide11

Acetcarbromal online

Acethydrocodone online

Acetiamine online

Acetohexamide online

Acetomenadione online

Acetomenaftone online

Acetophenazine online

Acetophenetidin online

Acetorphan online

Acetphenolisatin online

Acetrizoic acid online

Acetsalicylamide online

Acetylcarbromal online

Acetylcholine chloride12

Acetylcysteine13

Acetyldigitoxin online

α-Acetyldigoxin online

β-Acetyldigoxin14

Acetylhomocysteine

thiolactone online

N-Acetyl-4-hydroxy-Lproline1022

Acetylsalicylic acid16

Acetylsulfafurazole online

N′-acetylsulfanilamide1290

Acetylsulfisoxazole online

Acexamic acid online

Aciclovir17

Acide acexamique online

Acide aminocaproique59

Acide ascorbique88

Acide aspartique90

Acide bucloxique online

Acide chenodéoxycholique266

Acide cicrotoique online

Acide déhydrocholique online

Acide edetique online

Acide étacrynique online

Acide flufenamique online

Acide gadobénique620

Acide Gadopentétique624

Acide gadotérique625

Acide gentisique online

Acide hyaluronique665

Acide iobenzamique online

Acide iocétamique online

Acide ioglycamique online

Acide iotalamique online

Acide ioxaglique723

Acide ioxitalamique724

Acide métiazinique online

Acide nicotinique966

Acide orotique1016

Acide oxolinique online

Acide pipemidique1096

Acide protizinique online

Acide tiludronique1379

Acide tranexamique1415

Acido bendazolico127

Acidum acetylsalicylicum16

Acidum azolinicum online

Acidum cromoglicicum344

Acidum edeticum online

Acidum iopanoicum online

Acidum iophenoicum online

Acidum nicotinicum966

Acidum salicylicum online

Acipimox online

Aclacinomycin A online

Aclarubicin online

Aclatonium napadisilate20

ACNU975

Acriflavine hydrochloride online

Acriflavinium chloride online

Acrinol519

Acrivastine21

Acrosoxacin online

ACRT105739

Actarit online

Actinomycin D358

Actinoquinol online

Actinospectacin online

Acycloguanosine17

Acyclovir17

AD-6 online

AD 32 online

AD-8101506

AD-48331093

ADD-03055545

Adefovir dipivoxil23

Ademetionine24

Adenosylcobalamin online

Adenosylmethionine24

Adiphenine online

Adipiodone online

Adrafinil25

Adrenaline482

Adrenalone online

Adriamycin444

4′-epi-Adriamycin483

Aescin506

Aethacridin519

Äthacrynsäure online

Aethiazidum online

Aethinylöstradiol522

Aethotoin online

Äthylestrenol online

Äthylisobutrazin online

Äthyloestrenol online

Äthynodioldiacetat online

AF-2139 online

AF-102B265

Afloqualone online

AG-629 online

AG-1343954

AG-EE-3881196

AG-EE-623ZW1196

AGN-1901681322

AGN-190342LF (tartrate)169

AGN 19201339

AGN-192024156

AHR-10282 online

AICA-Orotate online

Ajmaline26

AL-4862170

AL-66211417

ALA59

Alacepril26

L-Alanine online

Alatrofloxacin mesilate online

Albendazole27

Albuterol1239

(R)-Albuterol800

Alclofenac online

Alclometasone dipropionate28

Alcloxa41

Alcoholum benzylicum online

Alcuronium chloride29

Aldesulfon Natrium online

Aldioxa42

Aldosterone online

Alendronate sodium30

Alfacalcidol32

Alfadolone acetate online

Alfaprodina online

Alfasone acetophenide online

Alfaxalone online

Alfentanil33

Alfuzosin35

Algestone acetophenide online

Alibendol online

Alimemazine online

Alindapril370

Aliskiren36

Alitretinoin39

Alizapride41

Allantoin41

Allobarbital online

Allobarbitone online

Allopurinol43

Allylbarbituric acid195

Allylestrenol online

Allyloestrenol online

Alminoprofen44

Almitrine online

Almotriptan45

ALO 4943A999

Alosetron hydrochloride46

Aloxiprin online

Alphachymotrypsin online

Alphadolone acetate online

Alphaprodine online

Alphasone acetophenide online

Alphaxalone online

Alpidem online

Alprazolam48

Alprenolol online

Althiazide online

Altizide online

Altretamine online

Alufibrate online

Aluminium clofibrate online

Aluminum nicotinate online

Alverine online

AM 833 online

AM 1155634

AMA-1080 online

Amantadine49

Ambazone online

Ambenonium chloride online

Ambrisentan50

Ambroxol51

Ambuside online

Amcinonide52

Ametazole online

Amethocaine1355

Amethopterin866

Amezinium metilsulfate53

Amfebutamone191

Amfenac sodium online

Amfepramone online

Amfetaminil online

AMG-073 HCl293

Amidefrine mesilate online

Amidephrine mesilate online

Amidophenazon online

Amidopyrin online

Amidotrizoic acid54

Amifostine55

Amikacin56

Amiloride58

Amineptine online

Aminocaproic acid59

Aminoglutethimide online

5-Aminolevulinic acid59

δ-Aminolevulinic acid59

Aminophenazone online

Aminophylline1361

Aminoprofen online

Aminopromazine online

Aminopyrine online

p-Aminosalicylic acid60

Aminosalylum60

Aminosidine1060

L-2-Aminosuccinic acid90

Aminosulfopride62

Amiodarone61

Amiphenazole online

Amisulpride62

Amitriptyline63

Amitriptylinoxide65

Amixetrine online

Amlexanox online

Amlodipine65

Ammoidin869

AMN-107970

Amobarbital online

Amodiaquine online

Amorolfine67

Amosulalol online

Amoxapine67

Amoxicillin68

Amoxycillin68

Amphetaminil online

Amphotericin B71

Ampicillin72

Ampiroxicam online

Amprenavir75

Amrinone online

Amrubicin online

m-AMSA online

Amsacrine online

Amviran814

Amylobarbitone online

Anagestone acetate online

Anagrelide hydrochloride77

Anastrozole79

Ancitabine online

Ancrod online

Androstanolone online

Anethole online

Anethole trithione online

Aneurine1362

Angiotensinamide online

Anileridine online

Aniracetam online

Anisindione online

Anisotropine

methylbromide online

Antazoline80

Anthralin421

Antocin II101

Antrafenine online

Apalcillin online

Apazone online

APD1052

Aplonidine81

Apomorphine80

Apraclonidine81

Aprepitant82

Aprindine online

Aprobarbital online

Aprotinine online

Aquocobalamin674

ara C353

Aranidipine online

Argatroban85

Arginine aspartate online

Arginine pidolate online

Arginine pyroglutamate online

Argipidine85

Aripiprazole87

Aritromicina112

Arotinolol online

Arsenic trioxide online

Arsenous acid online

Arteether online

Artemotil online

Articaine88

AS-4370 online

5-ASA856

Ascorbic acid88

Aseptamide online

ASM 9811091

L-Asparaginase90

Asparaginase90

Aspartame online

L-Aspartic acid90

Aspirin16

Aspoxicillin online

ASS16

Astemizole online

Astromicin online

AT-877 online

AT-4140 online

Atazanavir sulfate91

Atebrin online

Atenolol93

Atomoxetine hydrochloride1406

Atorvastatin calcium94

Atosiban101

Atovaquone103

Atracurium besilate104

Atropine105

Atropine methonitrate online

Atropinmethylnitrat online

15 AU81 online

AU-7801 online

Auranofin106

Avastatin online

Axerophthol1202

Ay 416949

AY-229891265

AY-24031649

AY-256501437

Azacitidine107

Azacort369

Azacortid online

Azacosterol online

Azacyclonol online

5-Azacytidine107

6-Azamianserin904

Azapetine online

Azapropazone online

Azatadine108

Azathioprine109

Azelaic acid110

Azelastine111

Azelnidipine online

Azidamfenicol online

Azidoamphenicol online

Azidocillin online

Azidothymidine1495

Azimilide hydrochloride online

Azintamide online

Azithromycin112

Azlocillin online

Azolinic acid online

Azosemide online

AZT1495

Azthreonam114

Aztreonam114

B

B 8510-291055

B-16880719

BA-168 online

BA 6791387

BA-598 BR online

Bacampicillin online

Bacitracin117

Baclofen118

Balsalazide sodium119

Bambuterol120

Bamethan online

Bamifylline online

Bamipine online

Barbexaclone online

Barbital online

Barnidipine120

Batroxobin online

Bay-12-8039922

Bay-38-94561462

Bay 43-90061273

Bay 59-79391224

Bay-g-54217

Bay-K 5552975

Bay-m-1099895

Bay-o-9867297

Bay u 3405 online

Bay-W-6228 online

BBP online

BCH-790755

BCNU225

BDF-5895925

Beclamide online

Beclobrate online

Beclometasone122

Beclomethasone122

Befunolol123

Bekanamycin124

Bemegride online

Bemetizide online

Benactyzine online

Benaprizine online

Benapryzine online

Benazepril125

Benciclano online

Bencyclane online

Bendacort online

Bendacortone online

Bendamustine hydrochloride126

Bendazac127

Bendrofluazide128

Bendroflumethiazide128

Benethamine Penicilline134

Benexate online

Benfluorex online

Benfotiamine129

Benfurodil hemisuccinate online

Benidipine129

Benmoxin online

Benorilate online

Benorilato online

Benorylate online

Benoxaprofen online

Benoxinate1036

Benperidol130

Benproperine131

Benserazide132

Bentiamine online

Bentiromide online

Benzalkonium chloride133

Benzapril125

Benzarone online Benzathine benzylpenicillin134

Benzatropine online

Benzbromarone online

Benzethonium chloride online

Benzhexol1430

Benzilonium bromide online

Benzilpenicillin134

Benziodarone online

Benzocaine134

Benzoctamine online

Benzoesäurebenzylester137

Benzonatate135

Benzothiazide online

Benzoyl peroxide135

Benzoylsulfanilamide online

Benzoylthiamine disulfide online

Benzperidol130

Benzphetamine online

Benzquinamide online

Benzthiazide online

Benztiazide online

Benztropine online

Benzydamine136

Benzyl alcohol online

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