Progress in Drug Research/Fortschritte der Arzneimittelforschung/Progrès des recherches pharmaceutiques

518 Pages·1987·11.708 MB·English

by  Satyavan Sharma (auth.), Ernst Jucker, Urs Meyer (eds.)

Progress in Drug Research
Fortschritte der Arzneimittelforschung
Progres des recherches pharmaceutiques
Vol. 31
Progress in Drug Research
Fortschritte der Arzneimittelforschung
Progres des recherches pharmaceutiques
Vol. 31
Edited by / Herausgegeben von / Redige par
Ernst Jucker, Basel
Assisted by Urs Meyer, Basel
Authors / Autoren / Auteurs
Satyavan Sharma· Eric J. Lien· Anil K. Saxena and Shradha Sinha·
Michael J. Antonaccio and John J. Wright· David Wilson·
Richard W. Olsen· Pramond M. Shah·G. H. Hottendorf·M. Arnaud· .
T. Mennini, S. Caccia and S. Garattini·J. Blaser and S. H. Zinner·
Anna Wirz-Justice·J. K. Nicholson and Ian D. Wilson.
1987 Birkhauser Verlag
Basel· Boston
The publisher cannot assume any legal responsibility for given data,
especially as far as directions for the use and the handling of
chemicals are concerned. This information can be obtained from the
manufacturers of chemicals and laboratory equipment.
All rights reserved.
No part of this publication may be reproduced, stored in a retrieval
system, or transmitted in any form or by any means, electronic,
mechanical, photocopying, recording or otherwise. without the prior
pennission of the copyright owner.
It> 1987 Birkhiiuser Verlag Basel
Softcover reprint of the hardcover 1S l edition [987
ISBN·[]: 978·]-0]48-9981-9 e-ISBN·[]: 978·]-0]48-9289-6
001; 10.1007/978-]-0]48-9289-6
5
Contents . Inhalt . Sommaire
Treatment of helminth diseases - challenges and achievements. . 9
Satyavan Sharma
Ribonucleotide reductase inhibitors as anticancer and antiviral
agents. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 101
Eric J. Lien
Pyrimidinones as biodynamic agents ...................... " 127
Anil K. Saxena and Shradha Sinha
Enzyme inhibitors of the renin-angiotensin system. . . . . . . . . . .. 161
Michael J. Antonaccio and John J. Wright
Cooperative effects in drug-DNA interactions . . . . . . . . . . . . . . .. 193
W. David Wilson
GABA-drug interactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 223
Richard W. Olsen
Quinolones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 243
Pramod M. Shah
Risk assessment problems in chemical oncogenesis. . . . . . . . . . .. 257
G. H. Hottendorf
The pharmacology of caffeine ............................. 273
M.J. Arnaud
Mechanism of action of anxiolytic drugs. . . . . . . . . . . . . . . . . . . .. 315
T. Mennini, S. Caccia and S. Garattini
In vitro models for the study of antibiotic activities .. . . . . . . . . .. 349
J. Blaser and S. H. Zinner
Light and dark as a "drug" ................................ 383
Anna Wirz-Justice
High resolution nuclear magnetic resonance spectroscopy of
biological samples as an aid to drug development ............. 427
I. K. Nicholson and Ian D. Wilson
Index· Sachverzeichnis· Table des matieres, Vol. 31 ........... 481
Index of titles· Verzeichnis der Titel· Index des titres, Vol. 1-31 .. 487
Author and paper index· Autoren- und Artikelindex·
Index des auteurs et des articles, Vol. 1-31 ................... 495
6
Foreword
Volume 31 of "Progress in Drug Research" contains 13 articles, a sub
ject index, an index for all articles that have been published so far in
this series of monographs, as well as an author and subject index for all
31 volumes. The reviews in this volume are particularly concerned
with the therapy of helminth diseases, with pyramidinones as biody
namic agents, and with quinolones which are of interest in the treat
ment of infections. For a deeper understanding of the pharmacokinet
ic actions of modem drugs, the articles on cooperative binding of drug
molecules to DNA, on in vitro models for the study of antibiotic activi
ties, on inhibitors of the renin-angiotensin system, on GAB A-drug in
teractions, and on the mechanism of action of anxiolytic drugs provide
a wealth offacts and new findings. The pharmacology of caffeine is re
viewed from the viewpoint of its role in combination with other phy
siologically active substances, and the chapter on high resolution nuc
lear magnetic resonance spectroscopy demonstrates the importance of
this method in the development of new drugs. Finally, the article on
light and dark touches border problems of the therapy of psychic dis
orders.
With these contributions, the authors aim to summarize latest achieve
ments in important and actual fields of drug research. Researchers
who are actively engaged in the same or in similar fields of research are
sure to benefit from these efforts. For others, the reviews present an
opportunity to get acquainted and to keep abreast with the latest devel
opments and progress in the complex and heterogeneous domaine of
drug research. The 31 volumes of "Progress in Drug Research" contain
more than 300 reviews with innumerable references to the relevant li
terature, thus providing the reader with an almost encyclopedic source
of information.
I should like to thank all the authors who willingly shared their vast
knowledge and experience with the readers of these monographs.
Thanks are also due to Professor Urs Meyer who contributed to this
volume by inviting some of the authors to provide interesting articles.
The work of the editor was, as usually, greatly facilitated by the help
and expertise of Mr. H.-P. Thiir and A. Gomm from Birkhauser Pub
lishers; I extend my sincere thanks to both of them.
Basel, October 1987 Dr. E. JUCKER
7
Vorwort
Der 31. Band der Reihe »Fortschritte der Arzneimittelforschung« ent
halt 13 Beitrage mit einem Stichwortverzeichnis des Bandes sowie je
ein Verzeichnis aller bisher publizierten Artikel und aller Autoren mit
ihren Beitragen der 31 Bande.
Die Referate des vorliegenden Bandes decken wiederum ein weites
Gebiet der Arzneimittelforschung ab: Therapie der Wurmkrankhei
ten, Pyrimidinone mit biodynamischen Wirkungen und Chinolone mit
bakteriziden Eigenschaften sind in den drei spezifisch auf Wirkungen
und Substanzgruppen ausgerichteten Artikeln behandelt. Die Beitrage
iiber die kooperative Bindung von Wirkstoffmolekiilen an DNA, die
in vitro Modelle zum Studium der antibiotischen Wirkung, Inhibito
ren des Renin-Angiotensin-Systems, GABA-Wirkstoff-Wechselwir
kung und Wirkungs-Mechanismus von anxiolytischen Wirkstoffen
vermitteln eine Fiille von Tatsachen und neuen Befunden, die fUr das
bessere Verstandnis der pharmakokinetischen Eigenschaften moder
ner Arzneistoffe unerlaBlich sind. Die Pharmakologie des Coffeins
wird vom Standpunkt seiner Verwendung in Kombination mit ande
ren Wirkstoffen dargestellt, und der Artikel iiber die Spektroskopie be
leuchtet die Bedeutung dieser modernen physikalischen Methode bei
der Entwicklung neuer Arzneimittel. Der Beitrag iiber Licht und Dun
kel als Arznei vertieft unser Wissen in einem interessanten Randgebiet
der Therapie psychischer Erkrankungen.
Mit diesen Beitragen haben die Autoren einige der neuesten Entwick
lungen im Gebiet der Arzneimittelforschung dargestellt, und die ver
mittel ten Erkenntnisse und Befunde konnen den in dies en Gebieten
tatigen Forschern eine wertvolle Unterstiitzung ihrer Untersuchungen
bedeuten. Der nicht unmittelbar involvierte Forscher erhalt dank der
knappen und iibersichtlichen Darstellung der Materie ein Hilfsmittel
zur Aufrechterhaltung des Kontaktes mit verschiedenen Gebieten der
komplexen und heterogenen Arzneimittelforschung. Die 31 Bande der
Reihe mit den mehr als 300 Ubersichtsreferaten und den unzahligen
Literaturhinweisen stell en auch ein Nachschlagewerk von enzyklopa
dischem Charakter dar.
Das Erscheinen dieses 31. Bandes der «Arzneimittelforschung» moch
te ich zum AnlaB nehmen, den Autoren dafUr zu danken, daB sie ihr
8 Vorwort
Wissen und ihre Erfahrung uneigenniitzig dem Leserkreis dieser Rei
he zur Verfiigung gestellt haben. Auch sei Professor Urs Meyer der
Dank fiir seine Mitarbeit an dies em Band ausgesprochen; er hat mit
seiner Einladung einzelner Autoren dazu beigetragen, daB der Um
fang dieses Bandes durch verschiedene interessante Beitrage erweitert
wurde. Ganz besonders mochte ich aber dem Birkhauser Verlag, und
insbesondere den Herren H.-P. Thiir und A. Gomm, fiir ihre stete Un
terstiitzung der herausgeberischen Tatigkeit danken.
Basel, im Oktober 1987 Dr. E. JUCKER
9
Treatment of helminth diseases -
challenges and achievements
l
By Satyavan Sharma
Medicinal Chemistry Division, Central Drug Research
Institute, Lucknow 226 001, India
1 Introduction .............................................. . 11
2 Helminthiasis of the gastrointestinal tract ...................... . 13
2.1 Treatment of ascariasis ...................................... . 15
2.1.1 Natural products .......................................... . 15
2.1.2 Piperazines ............................................... . 16
2.1.3 Quaternary ammonium salts ................................. . 16
2.1.4 Tetrahydropyrimidines ..................................... . 17
2.1.5 Imidazothiazolines ......................................... . 17
2.1.6 Benzimidazoles ............................................ . 18
2.2 Treatment of hookworm infections ............................ . 19
2.2.1 Natural products .......................................... . 19
2.2.2 Halogenated hydrocarbons .................................. . 19
2.2.3 Substituted phenols ........................................ . 20
2.2.4 Quaternary ammonium salts ................................. . 21
2.2.5 Imidazothiazolines ......................................... . 22
2.2.6 Tetrahydropyrimidines ..................................... . 22
2.2.7 Arylisothiocyanates ........................................ . 22
2.2.8 Benzimidazoles ............................................ . 23
2.2.9 Miscellaneous compounds .................................. . 24
2.3 Treatment oftrichuriasis .................................... . 26
2.3.1 Phenols and piperazines .................................... . 26
2.3.2 Quaternary ammonium salts ................................. . 27
2.3.3 Older drugs ............................................... . 27
2.3.4 Newer drugs .............................................. . 28
2.4 Treatment of enterobiasis (oxyuriasis) ......................... . 28
2.4.1 Older drugs ............................................... . 28
2.4.2 Antibiotics and sulpha drugs ................................. . 29
2.4.3 Piperazines ............................................... . 30
2.4.4 Quaternary ammonium salts ................................. . 30
2.4.5 Newer drugs .............................................. . 30
2.5 Treatment of strongyloidiasis ................................ . 31
2.5.1 Quaternary ammonium salts ................................. . 31
2.5.2 Benrimidazoles ............................................ . 31
2.6 Treatment oftrichostrongyliasis .............................. . 32
2.7 Treatment of capillariasis ................................... . 32
2.8 Treatment of tapeworm infections ............................ . 33
2.8.1 Natural products .......................................... . 33
2.8.2 Metallic compounds ........................................ . 35
Communication No. 3816 from Central Drug Research Institute,
1
Lucknow 226001, India
10 Satyavan Sharma
2.8.3 Organometallic compounds ................................. . 35
2.8.4 Alkylamines .............................................. . 35
2.8.5 Acridine derivatives ........................................ . 36
2.8.6 Substituted phenols ........................................ . 36
2.8.7 Halogenated diphenyl methanes .............................. . 37
2.8.8 Diphenyl sulphides, sulphoxides and sulphones ................ . 37
2.8.9 Substituted salicylanilides and naphthanilides .................. . 38
2.8.10 Isothiocyanates ............................................ . 40
2.8.11 Quaternary ammonium salts ................................. . 41
2.8.12 Substituted ami dines ....................................... . 41
2.8.13 Benzimidazoles ............................................ . 42
2.8.14 Quinolines and isoquinolines ................................ . 42
2.9 Treatment offasciolopsiasis ................................. . 43
3 Helminthiasis of blood, liver and lungs ........................ . 44
3.1 Schistosomiasis ............................................ . 44
3.1.1 Treatment of schistosomiasis ................................. . 48
3.1.1.1 Organometallic compounds ................................. . 48
3.1.1.2 Miracils .................................................. . 51
3.1.1.3 Mirasanes ................................................ . 53
3.1.1.4 Tetrahydroquinolines ...................................... . 54
3.1.1.5 Phenoxyalkanes ........................................... . 55
3.1.1.6 Tris (4-aminophenyl)carbonium salts (TA C salts) ................ . 56
3.1.1. 7 Substituted naphthylamines ................................. . 56
3.1.1.8 Nitroheterocycles .......................................... . 57
3.1.1.9 Substituted quinolines ...................................... . 60
3.1.1.10 Substituted sulfanilamides and salicylamides ................... . 61
3.1.1.11 Substituted nitroanilines .................................... . 61
3.1.1.12 Praziquantel .............................................. . 62
3.1.1.13 Natural products .......................................... . 63
3.1.1.14 Miscellaneous compounds .................................. . 63
3.2 Liver fluke infections ....................................... . 64
3.2.1 Treatment of fascioliasis (the liver rot disease) .................. . 64
3.2.1.1 Halogenated compounds .................................... . 64
3.2.1.2 Substituted phenols ........................................ . 66
3.2.1.3 Salicylanilides ............................................. . 67
3.2.1.4 Phenoxyalkanes ........................................... . 69
3.2.1.5 Sulfonamides ............................................. . 70
3.2.1.6 Benzimidazoles ............................................ . 71
3.2.1.7 Natural products .......................................... . 71
3.2.1.8 Miscellaneous compounds .................................. . 72
3.2.2 Treatment of clonorchiasis (Chinese liver fluke disease) .......... . 72
3.2.3 Treatment of dicrocoeliasis (lancet fluke infection) .............. . 73
3.3 Lung fluke infections ....................................... . 74
3.3.1 Treatment oflung fluke infections ............................ . 75
4 Helminthiasis of musculature ................................ . 76
5 Future prospects ........................................... . 78
6 Conclusion ............................................... . 81
Addendum ............................................... . 82
References ................................................ . 83