CO-NH2 CO-NH2 â€žâ€žCO-NH2 CO-NH2

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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. r 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
C o n t e n t s 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-Diphenylpropylamines (I : R = H) 13 IV Tertiary alcohols (I : R = OH) 110 V Secondary alcohols (I : R = CHOH alk) 115 VI Primary alcohols [I : R - (CH2)n—OH; n = 1, 2, 3] . . . .120 Vll Nitriles (I : R - CN) 122 VIII Diamines and derivatives (I :R contains amino group or derivative) . 129 IX Primary amides (I : R = CONH2) 132 X Acids and acid chlorides (I : R = COOH or COC1) . . . .136 XI Secondary amides (I : R = CONHRO 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 (I : R = CNHR', CNCOR'-R', COR') 155 XVII Aldehydes (I : R = COH) 160 XVIII Sulphones (I : R = SO2R') 161 XIX Other compounds of structure (I) . . . • . . .164 XX Dissociation constants . • • . . • . . .166 XXT Conflgurational studies . . . • . • • . .168 References . . . . . . . . . . . 171
Page 1: S Y N T H E T I C A N A L G E S I C
Page 7 and 8: I n t r o d u c t i o n THE main pu
Page 9 and 10: 15. 16. 17. 18. 19. 20. 21. CONH2 C
Page 11 and 12: CHAPTER I A n a l g e s i c " Activ
Page 13 and 14: CHAPTER II T h e " A n a l g e s i
Page 15 and 16: METHADONE, MORPHINE, PETHIDINE AND
Page 17 and 18: Symbol ED50 ED50 ED50 ED50 ED50 ED5
Page 19 and 20: CHAPTER III 3 : 3 - D i p h e n y l
Page 21 and 22: o .s HI S T oo HJ * 3 :3-DIPHENYLPR
Page 23 and 24: 2.1 2.2 2.3 2.4 2.5 2.6 OH „ OH O
Page 25 and 26: 2.15 2.16 2.17 2.18 2.19 2.20 2.21
Page 27 and 28: 3.15 4.1 4.2 4.3 4.4 4.5 4.6 4-7 5.
Page 29 and 30: 5.4 5.5 „ 55 » „ CN CN „ „
Page 31 and 32: 5.14 5.15 5.16 5.17 5.18 5.19 5.20
Page 33 and 34: 5.35 5.36 5.37 5.38 5.39 5.40 5.41
Page 35 and 36: 6.9 6.10 6.11 6.12 6.13 6.14 6.15 6
Page 37 and 38: 6.46 6.47 6.48 6.49 6.50 6.51 6.52
Page 39 and 40: 7.4 7.5 7.6 7.7 7.8 7.9 7.10 7.11 C
Page 41 and 42: 7.26 7.27 7.28 7.29 7.30 7.31 7.32
Page 43 and 44: 8,15 8.16 8.17 9.1 9.2 9.3 9.4 9.5
Page 45 and 46: 10.4 1 _ CONi,CH3j, 2 H" HH N CK- N
Page 47 and 48: 10.47 10.48 10.49 10.50 10.51 10.52
Page 49 and 50: 11.15 COOC-H5 11.14 COOCHg 11.15 11
Page 51 and 52: 13.9 13.10 13.11 CH-C.H5OOC- CH3
Page 53 and 54:
13.13 13.24 13.25 13.26 13.27 13.28
Page 55 and 56:
1-*»1Z c c.:-:f XH 14.13 14.14 14.
Page 57 and 58:
14.56 14.37 14.38 14.39 COCH; COCH3
Page 59 and 60:
•> 5 5? 5 5 55 M » I n 5 w 5? )?
Page 61 and 62:
14.49 14.50 14.51 14.52 14.53 14.54
Page 63 and 64:
14.66 14.67 14.68 14.69 14.70 14.71
Page 65 and 66:
14.9" CO-C£H£ 14.98 14.99 14.100
Page 67 and 68:
16.13 16.14 17.1 17.2 17.3 17.4 17.
Page 69 and 70:
ti 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8
Page 71 and 72:
2.4 2.5 2.6 2.7 2.8 2.9 2.13 2.14 2
Page 73 and 74:
3.5 3.7 4.1 4.3 4.4 4.5 4.7 5.1 5.2
Page 75 and 76:
5.53 5.59 6.1 6.4 6.8 6.9 6.14 6.18
Page 77 and 78:
3:3-DIPHENYLPROPYLAMINES 71 flo****
Page 79 and 80:
9.19 9.20 9.21 9.22 9.23 9.26 9.27
Page 81 and 82:
10.22 10.23 10.24 10.25 10.26 10.30
Page 83 and 84:
10.42 10.43 10.59 10.60 10.61 10.62
Page 85 and 86:
11.7 11.8 11.9 11.10 11.11 11.12 11
Page 87 and 88:
„ — R- 13.10 — CF RT R- CF CF
Page 89 and 90:
13.24 13.25 13.27 13.31 13.33 13,35
Page 91 and 92:
14.36 14.37 14.38 14.39 „ RT RT R
Page 93 and 94:
CF RT CF RT ET RB •>•> PRT ET R
Page 95 and 96:
14.41 14.42 14.43 14.44 RB — CF ,
Page 97 and 98:
14.54 14.55 14.56 14.57 14.58 14.59
Page 99 and 100:
14.76 14.77 14.78 14.82 14.83 14.84
Page 101 and 102:
If o ^ 1.1 1.4 1.5 1.6 1.8 1.9 1.10
Page 103 and 104:
3.3 3.4 5.1 5.2 5.3 — — — —
Page 105 and 106:
5.6 5.9 5.12 5.13 5.17 5.27 5.32 5.
Page 107 and 108:
8.8 10.2 10.41 10.43 11.4 11.6 11.9
Page 109 and 110:
14.40 8-99 10-12 d-nci /-base /-bas
Page 111 and 112:
X 14.57 14.64 14.65 14.66 14.69 14.
Page 113 and 114:
Continued from p. 13 3 :3-DIPHENYLP
Page 115 and 116:
3:3-DIPHENYLPROPYLAMINES 109 antisp
Page 117 and 118:
TERTIARY ALCOHOLS 111 halide with a
Page 119 and 120:
TERTIARY ALCOHOLS 113 Tertiary alco
Page 121 and 122:
CHAPTER V S e c o n d a r y A l c o
Page 123 and 124:
5-3 SECONDARY ALCOHOLS 117 C2H5 r n
Page 125 and 126:
SECONDARY ALCOHOLS 119 In the wo-se
Page 127 and 128:
PRIMARY ALCOHOLS reduced (PtO-CH3OH
Page 129 and 130:
NITRILES 123 Basic propyl- and wopr
Page 131 and 132:
NITRILES 125 The following elegant
Page 133 and 134:
NITRILES 127 Nitriles of type [7.1]
Page 135 and 136:
CHAPTER VIII D i a m i n e s a n d
Page 137 and 138:
DIAMINES AND DERIVATIVES 131 Only o
Page 139 and 140:
PRIMARY AMIDES ^ ^NH—CH—CH—N'
Page 141 and 142:
PRIMARY AMIDES 135 Quaternization b
Page 143 and 144:
ACIDS AND ACID CHLORIDES 137 When h
Page 145 and 146:
CHAPTER XI S e c o n d a r y A m i
Page 147 and 148:
CHAPTER XII R 8 7 5 a n d R e l a t
Page 149 and 150:
TERTIARY AMIDES 143 The relation be
Page 151 and 152:
TERTIARY AMIDES 145 (1) In man R 87
Page 153 and 154:
ESTERS DERIVED FROM AMINO ACIDS 147
Page 155 and 156:
ESTERS DERIVED FROM AMINO ACIDS 149
Page 157 and 158:
CHAPTER XV Esters derived f r o m S
Page 159 and 160:
Nomenclature of derived isomers Mel
Page 161 and 162:
CHAPTER XVI K e t i m i n e s , A c
Page 163 and 164:
NAA'* N(CH3)2 „ 55 ?? ?5 *s 5 N(C
Page 165 and 166:
KETIMINES, ACYL KETIMINES AND KETON
Page 167 and 168:
CHAPTER XVIII S u l p h o n e s (I:
Page 169 and 170:
SULPHONES 163 According to KLENK et
Page 171 and 172:
OTHER COMPOUNDS OF STRUCTURE (I) 16
Page 173 and 174:
DISSOCIATION CONSTANTS Steric facto
Page 175 and 176:
R CONFIGURATIONAL STUDIES TABLE XVI
Page 177 and 178:
REFERENCES 1 ADAMI E. and MARAZZI E
Page 179 and 180:
REFERENCES 173 89 CHEN K. K. (1948)
Page 181 and 182:
REFERENCES 175 163 FRIEBEL H. and R
Page 183 and 184:
REFERENCES 177 249 KEATS A. S. and
Page 185 and 186:
REFERENCES 179 339 MOFFETT R. B. (1
Page 187 and 188:
REFERENCES 181 411 SCHULTZ E. M., R
Page 189:
REFERENCES 183 499 WHEATLEY W. B.,
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CO-NH2 CO-NH2 â€žâ€žCO-NH2 CO-NH2

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