Synthetic analgesics, Leki
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SYNTHETIC
ANALGESICS
PART I
Diphenylpropylamines
By
Paul A. J. Janssen
Research Laboratoria
Dr. C. Janssen n.v, Beerse
Belgium
PERGAMON PRESS
NEW YORK • OXFORD • LONDON • PARIS
1960
PERGAMON PRESS INC.
122 East 55th Street, New York 22, N. Y.
P.O. Box 47715, Los Angeles, California
PERGAMON PRESS LTD.
Headington Hill Hall, Oxford
4 and 5 Fitzroy Square, London WJ
PERGAMON PRESS S.A.R.L.
24 Rue des Ecoles, Paris V
e
PERGAMON PRESS G.m.b.H.
Kaiserstrasse 75, Frankfurt am Main
Copyright
©
1960
Pergamon Press Ltd.
Library of Congress Card No. 59-13814
Printed in Great Britain by
CHORLEY & PICKERSGILL LTD
Leeds and London
Contents
Page
Preface
.
vii
Introduction
.
.
.
1
I
"Analgesic" activity in man and in animals
.
5
LI
The "analgesic" activity of methadone, morphine, pethidine and codeine
in animals
.
7
III
3:3-Dipheny!propylamines (I : R = H)
.
.
.
.
.
.13
IV
Tertiary alcohols (I : R = OH)
110
V
Secondary alcohols (I : R - CHOH alk)
115
Vl
Primary alcohols [I : R - (CH
2
)
n
—OH;
n =
1, 2, 3] .
.
.
.120
ViI
Nitriles (I : R - CN)
122
VIII
Diamines and derivatives (I :R contains amino group or derivative) . 129
IX
Primary amides (I : R - CONH
2
)
132
X
Acids and acid chlorides (I : R = COOH or COCl)
.
.
.
.136
Xl
Secondary amides (I : R = CONHR')
139
XII
R875 and related basic tertiary amides (I : R = CONR'R") .
.
.141
XIII
Esters derived from amino acids of type I (R = COOR')
.
.
.146
XIV
Esters derived from tertiary alcohols (I : R = OCOR')
.
.
.150
XV
Esters derived from secondary alcohols (I : R = CHOCOR"-R') .
.151
XVI
Ketimines, acyl ketimines and ketones (IrR = CNHR', CNCOR"-R',
COR')
155
XVII
Aldehydes (I : R = COH)
160
XVIII
Sulphones (I : R = SO
2
R')
161
XIX
Other compounds of structure (I)
.
.
.
•
.
.
.164
XX
Dissociation constants .
•
•
.
.
.
.
.
.166
XXT
Conflgurational studies .
.
.
.
.
•
•
.
.168
References .
.
171
v
Preface
THE task of producing this book would have been impossible without help
from my friends and collaborators of the departments of Organic Chemistry,
Analytical Chemistry and Pharmacology.
I would like to thank especially Miss J.
DE CANNI^RE
for her careful analysis
o
r the literature and Mr.
ANDRE JANSSENS
for his indefatigable efforts in
preparing the final manuscript and correcting the galley proofs.
VIl
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