US2005075332A1PendingUtilityA1
Tricyclic compounds with antiviral activity
Est. expiryJan 7, 2020(expired)· nominal 20-yr term from priority
C07D 307/91C07D 209/88C07D 407/12C07C 211/61C07D 405/12C07D 213/38C07D 327/08C07D 333/76A61P 31/12C07D 211/58C07D 279/10A61P 31/22C07D 411/12C07C 2601/14C07D 333/54C07C 2603/24C07D 223/22C07C 215/88C07C 217/94C07C 2601/02C07D 409/12C07D 319/24C07C 2603/18C07C 2601/18C07C 2601/08C07D 497/04
47
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Claims
Abstract
The present invention provides a compound of the formula (I) and pharmaceutically acceptable salts having useful antiviral activity against viruses of the herpes family. In said formula, X═O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 , or a chemical bond; Y═O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 ; Z=NH, O, NR 8 , S, SO, SO 2 . The remaining substituents are described in the specification.
Claims
exact text as granted — not AI-modified1 . A compound of Formula I or a pharmaceutically acceptable salt thereof
wherein:
X═O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 or a chemical bond;
Y═O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 ;
Z=N, NH, O, NHR 8 , NR 8 , S, SO, SO 2 ;
n=an integer of from 0 to 2;
m=an integer of 1,2, or 3;
R 1 , R 2 , R 3 , R 4 , R 5 independently are hydrogen, halogen, hydroxyl, amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxy groups (1-6 carbon atoms), CF 3 , OCF 3 , aminoalkyl (1-6 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4 hetero atoms of N, O or S;
Ar=phenyl,
substituted phenyl,
benzoheterocyclic ring,
substituted benzoheterocyclic ring,
heterocyclic ring, or
substituted heterocyclic ring, which have substitutions R 6 or R 7 ;
R 6 and R 7 are independently hydrogen, alkyl group (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), halogen, alkoxy, CF 3 , aminoalkyl (1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atoms with 1-4 heteroatoms of N, O or S;
R 6 and R 7 may also form a ring, optionally cycloalkyl or aryl or substituted aryl;
R 8 is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above.
2 . The compound of claim 1 having Formula II.
3 . The compound of claim 1 having Formula III.
4 . The compound of claim 1 having Formula IV.
5 . The compound of claim 1 having Formula V.
6 . The compound of claim 1 having Formula VI.
7 . The compound of claim 1 having Formula VII.
8 . A pharmaceutical composition for the treatment of infection or disease caused by a virus, which comprises an amount of the compound of claim 1 sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier.
9 . A pharmaceutical composition for the treatment of infection or disease caused by a virus, which comprises an amount of the compound of claim 1 in the range of about 1 to about 50 mg/kg-day or up to 3 g per day and a pharmaceutically effective carrier.
10 . A method of treatment of infection or disease caused by a virus, which comprises administering to a subject in need of such treatment a composition of claim 1 .
11 . The composition of claim 8 wherein the virus is a Herpes virus.
12 . The composition of claim 9 wherein the virus is a Herpes virus.
13 . The method of claim 10 wherein the virus is a Herpes virus.
14 .
1
(1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-yl)-
amine
2
Cyclopentyl-(9H-fluoren-2-yl)-amine
3
(1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine
4
N 3 -Cyclopentyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine
5
Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine
6
(2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran-4-
yl)-amine
7
Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine
8
(1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine
9
sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine
10
N 2 ,N 2 -Dimethyl-N 3 -piperidin-4-yl-9H-fluorene-2,3-diamine
11
N 3 -(1-Benzyl-butyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-
diamine
12
(9H-Fluoren-2-yl)-piperidin-4-yl-amine
13
(1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine
14
sec-Butyl-(9H-fluoren-2-yl)-amine
15
(1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy-
dibenzofuran-3-yl)-amine
16
Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-amine
17
(Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine
18
Adamantan-2-yl-dibenzofuran-2-yl-amine
19
Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine
20
Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine
21
(4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine
22
Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine
23
Cyclopentyl-dibenzofuran-2-yl-amine
24
Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine
25
Cyclohexyl-(9H-fluoren-2-yl)-amine
26
Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine
27
Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine
28
Dibenzofuran-2-yl-dipropyl-amine
29
N 3 -(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N 2 ,N 2 -
dimethyl-9H-fluorene-2,3-diamine
30
N 3 -Isopropyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine
31
N 2 ,N 2 -Dimethyl-N 3 -(tetrahydro-thiopyran-4-yl)-9H-
fluorene-2,3-diamine
32
N 3 -Cyclohexyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine
33
N 3 -Cycloheptyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine
34
N 3 -(1-Ethyl-propyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-
diamine
35
N 3 -(1-Cyclopropyl-ethyl)-N 2 ,N 2 -dimethyl-9H-fluorene-
2,3-diamine
36
N 3 -sec-Butyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine
37
(9H-Fluoren-2-yl)-isopropyl-amine
38
(9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine
39
Cycloheptyl-(9H-fluoren-2-yl)-amine
40
Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-
yl)-amine
41
Dibenzofuran-2-yl-piperidin-4-yl-amine
42
Dibenzofuran-2-yl-isopropyl-amine
43
Cyclohexyl-dibenzofuran-2-yl-amine
44
(1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine
45
Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-
yl)-amine
46
Dibenzofuran-3-yl-piperidin-4-yl-amine
47
Dibenzofuran-3-yl-isopropyl-amine
48
Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine
49
Cyclohexyl-dibenzofuran-3-yl-amine
50
Cycloheptyl-dibenzofuran-3-yl-amine
51
(4-Chloro-benzyl)-dibenzofuran-2-yl-amine
52
(4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine
53
Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine
54
Benzo[1,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine
55
Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6-
ylmethyl)-amine
56
Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine
57
Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine
58
Dibenzofuran-2-yl-(2-methyl-benzyl)-amine
59
Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine
60
Dibenzofuran-2-yl-(4-nitro-benzyl)-amine
61
Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine
62
Dibenzofuran-2-yl-(4-methyl-benzyl)-amine
63
Benzyl-dibenzofuran-2-yl-amine
64
(3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine
65
(1-Benzyl-butyl)-dibenzofuran-2-yl-amine
66
Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl-
ethyl]-amine
67
3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol
68
Dibenzofuran-2-yl-(1-ethyl-butyl)-amine
69
Dibenzofuran-2-yl-(1-ethyl-propyl)-amine
70
Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine
71
(1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine
72
Cyclooctyl-dibenzofuran-2-yl-amine
73
Cycloheptyl-dibenzofuran-2-yl-amine
74
Dibenzofuran-2-yl-(tetrahydro-thiopyran-4-yl)-amine
75
Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine
76
Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine
77
Dibenzofuran-2-yl-(1-methyl-butyl)-amine
78
sec-Butyl-dibenzofuran-2-yl-amine
79
Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine
80
Benzofuro[3,3-b]pyridin-8-yl-pyridin-4-ylmethyl-amine
81
Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine
82
N-(2-Fluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine
83
N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-diamine
84
N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-
2,8-diamine
85
N-(4-Methanesulfonyl-benzyl)-N′-methyl-diebnzofuran-
2,8-diamine
86
N-Methyl-N′-pyridin-4-ylmethyl-dibensofuran-2,8-diamine
87
N-Methyl-N'-(2-methyl-benzyl)-dibenzofuran-2,8-diamine
88
Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine
89
(4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine
90
(3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-
anthracen-6-yl)-amine
91
(2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-
anthracen-6-yl)-amine
92
(10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-
ylmethyl-amine
93
Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-
6-yl)-amine
94
(4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-
anthracen-6-yl)-amine
95
(10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-
ylmethyl-amine
96
(2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-
6-yl)-amine
97
Anthracen-2-yl-quinolin-4-ylmethyl-amine
98
Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine
99
Anthracen-2-yl-pyridin-4-ylmethyl-amine
100
Anthracen-2-yl-(2-methyl-benzyl)-amine
101
Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine
102
Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine
103
Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine
104
Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl-
amine
105
Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl-
benzyl)-amine
106
Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine
107
8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol
108
8-(2-Fluoro-benzylamino)-dibenzofuran2-ol
109
8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol
110
8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol
111
8-(2-Methyl-benzylamino)-dibenzofuran-2-ol
112
(8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine
113
8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine
114
8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-
amine
115
(4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H-
carbazol-3-yl)-amine
116
Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol-
3-yl)-amine
117
Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-
benzyl)-amine
118
Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine
119
Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine
120
(4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)-
amine
121
Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine
122
Diebnzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine
123
Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine
124
Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine
125
N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-
2,8-diamine
126
N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-
2,8-diamine
127
N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-
2,8-diamine
128
N-Benzyl-N′-methyl-dibenzofuran-2,8-diamine
129
2-[(8-Methylamino-dibenzofuran-2-ylamino)-
methyl]-benzonitrile
130
(4-Methoxy-benzyl)-phenoxathiin-3-yl-amine
131
(8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine
132
(3-Methoxy-benzyl)-phenoxathiin-3-yl-amine
133
(3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine
134
(3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine
135
(4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine
136
Benzyl-phenoxathiin-3-yl-amine
137
(2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine
138
(8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)-
amine
139
(8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-
benzyl)-amine
140
Benzyl-(8-chloro-dibenzofuran-2-yl)-amine
141
(9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine
142
(8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine
143
(9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine
144
(3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine
145
(9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine
146
(4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine
147
Benzyl-(9H-fluoren-2-yl)-amine
148
(9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine
149
(2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine
150
Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine
151
2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-
benzonitrile
152
Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine
153
Dibenzofuran-4-yl-(3,5-dimethoxy-benzyl)-amine
154
Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine
155
(4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine
156
Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine
157
N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
158
(8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine
159
(8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine
160
Dibenzofuran-4-yl-(2,4-dimethyl-benzyl)-amine
161
N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-
diamine
162
N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-
diamine
163
(2-Bromo-benzyl)-phenoxathiin-3-yl-amine
164
Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine
165
Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine
166
(3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine
167
Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine
168
Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine
169
(8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine
170
(2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine
171
(8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2-
ylmethyl)-amine
172
(9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine
173
(5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol-
3-yl)-amine
174
(9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine
175
(2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine
176
(8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine
177
(9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine
178
(9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine
179
(9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine
180
(9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine
181
(9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine
182
(9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine
183
(8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine
184
Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine
185
Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine
186
Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine
187
Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine
188
Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine
189
Diberizofuran-4-yl-pyridin-3-ylmethyl-amine
190
Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine
191
(2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine
192
(8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine
193
N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8-
diamine
194
N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8-
diamine
195
N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
196
N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
197
N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
198
N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
199
N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
200
N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-
diamine
201
N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-
N′-methyl-dibenzofuran-2,8-diamine
202
(3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine
203
(8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-
amine
204
Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine
205
Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine
206
(2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine
207
(2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine
208
(2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine
209
(2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine
210
(2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine
211
(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-
phenoxathiin-3-yl-amine
212
Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)-amine
213
(8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-
amine
214
(8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)-
amine
215
(8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-
amine
216
(8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)-
amine
217
(9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-
amine
218
(8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)-
amine
219
(9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-
amine
220
(9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-
amine
221
(2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine
222
(2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine
223
(2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine
224
(2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine
225
(2,5-Dimethyl-benzyI)-(9-ethyl-9H-carbazol-3-yl)-amine
226
(2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine
227
(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-
9H-carbazol-3-yl)-amine
228
(9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine
229
(8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)-
amine
230
(9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine
231
(9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine
232
(2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine
233
(2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine
234
(2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine
235
(2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine
236
(2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine
237
(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren-
2-yl)-amine
238
(8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)-
amine
239
Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine
240
Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine
241
N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran-
2,8-diamine
242
(8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-
benzyl)-amine
243
(8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro-
benzo[1,4]dioxin-6-ylmethyl)-amine
244
(2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine
245
(2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine
246
(2-Chloro-benzyl)-phenoxathiin-3-yl-amine
247
(2-Methoxy-benzyl)-phenoxathiin-3-yl-amine
248
(2-Methyl-benzyl)-phenoxathiin-3-yl-amine
249
Anthracen-2-yl-(2-chloro-benzyl)-amine
250
Anthracen-2-yl-(2-fluoro-benzyl)-amine
251
Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine
252
(2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine
253
2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol
254
Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine
255
2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol
256
(9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine
257
(9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine
258
(2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine
259
2-[(9H-Fluoren-2-ylamino)-methyl]-phenol
260
(9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine
261
(9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine
262
(9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine
263
Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine
264
Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine
265
2-(Dibenzofuran-4-ylaminomethyl)-phenol
266
Dibenzofuran-4-yl-(2-methoxy-benzyl)-amine
267
(2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-
amine
268
(2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-
amine
269
(2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine
270
Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine
271
Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine
272
(2-Bromo-benzyl)-dibenzofuran-2-yl-amine
273
(8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)-
amine
274
2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-
benzonitrile
275
(2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
276
(8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)-
amine
277
(2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
278
(8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine
279
(8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine
280
Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine
281
(8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-
amine
282
(8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-
amine
283
Dibenzoforan-2-yl-(2-nitro-benzyl)-amine
284
Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine
285
2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile
286
Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine
287
Dibenzoforan-2-yl-(3-trifluoromethyl-benzyl)-amine
288
(4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine
289
Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine
290
(2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-
amine
291
(2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-
amine
292
(4-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
293
(3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
294
(4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
295
(3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
296
(2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
297
4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol
298
3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol
299
Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine
300
(8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine
301
(8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine
302
(8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine
303
(8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-
benzyl)-amine
304
(8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-
benzyl)-amine
305
(4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-
amine
306
(4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
307
(3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
308
(2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
309
(8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine
310
(8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine
311
Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine
312
Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine
313
Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine
314
(4-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine
315
Dibenzofuran-2-yl-(3-methyl-benzyl)-amine
316
(3-Chloro-benzyl)-dibenzofuran-2-yl-amine
317
3-(Dibenzofuran-2-ylaminomethyl)-phenol
318
(2-Chloro-benzyl)-dibenzofuran-2-yl-amine
319
Dibenzoforan-2-yl-(3-methoxy-benzyl)-amine
320
Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine
321
(9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine
322
Dibenzofuran-4-yl-(2-methyl-benzyl)-amine
323
(8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine
324
(2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine
325
Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine
326
Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine
327
Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine
328
Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine
329
Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine
330
(8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine
331
Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine
332
(8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine
333
(8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine
334
(8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine
335
(8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2-
ylmethyl)-amine
336
(8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl-
benzyl)-amine
337
(8-Fluoro-dibenzofaran-2-yl)-pyridin-4-ylmethyl-amine
338
(8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine
339
(8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine
340
(8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-
benzyl)-amine
341
Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine
342
(8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-
benzyl)-amine
343
(8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-
amine
344
(8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-
amine
345
(3,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
346
(3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
347
(3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
348
(2,6-Difluoro-benzyl(2,5-Difluoro-benzyl)-(8-fluoro-
dibenzofuran-2-yl)-amine
349
(2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
350
(2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
351
(2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
352
(2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine
353
(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro-
dibenzofuran-2-yl)-amine
354
(3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-
amine
355
Dibenzofuran-2-yl-furan-2-ylmethyl-amine
356
Dibenzofuran-2-yl-furan-3-ylmethyl-amine
357
Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine
358
Dibenzofuran-2-yl-(4-methanesulfonyl-benzyl)-amine
359
Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine
360
Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine
361
Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine
362
Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine
363
Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine
364
Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine
365
Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine
366
Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine
367
Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine
368
Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine
369
Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine
370
Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine
371
(4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine
372
(2-Chloro-benzyl)-dibenzothiohen-2-yl-amine
373
Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine
374
Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine
375
Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine
376
Benzyl-dibenzothiohen-2-yl-amine
377
Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine
378
Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine
379
Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine
380
Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine
381
Dibenzothiohen-2-yl-(2,3,4-trifluoro-benzyl)-amine
382
(-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine
383
Dibenzothiohen-2-yl-(2,3-dihydro-1,4-benzodioxin-6-
ylmethyl)-amine
384
Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-
amine
385
Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine
386
Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine
387
Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine
388
Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine
389
Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine
390
Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine
391
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-
2-methyl-benzyl)-amine
392
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl-
benzyl)-amine
393
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4-
dimethyl-benzyl)-amine
394
(4-tert-Butyl-benzyl)-(10,11-dihydro-5H-
dibenz[b,f]azepin-2-yl)-amine
395
(2-Chloro-benzyl)-(10,11-dihydro-5H-
dibenz[b,f]azepin-2-yl)-amine
396
(2,6-Difluoro-benzyl)-(10,11-dihydro-5H-
dibenz[b,f]azepin-2-yl)-amine
397
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-
(2,3,6-trifluoro-benzyl)-amine
398
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-
fluoro-benzyl)-amine
399
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-
(3,5-dimethoxy-benzyl)-amine
400
Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-
yl)-amine
401
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4-
methoxy-benzyl)-amine
402
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3-
dimethoxy-benzyl)-amine
403
(2,5-difluoro-benzyl)-(10,11-dihydro-5H-
dibenz[b,f]azepin-2-yl)-amine
404
(10,11-Dihydro-5H-dibenz[b,f)azepin-2-yl)-(3-
methoxy-benzyl)-amine
405
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-
(2,3,4-trifluoro-benzyl)-amine
406
(2-Bromo-benzyl)-(10,11-dihydro-5H-
dibenz[b,f]azepin-2-yl)-amine
407
(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11-dihydro-5H-
dibenz[b,f]azepin-2-yl)-amine
408
(10,11-Dihydro-5H-dibenz[b,f)azepin-2-yl)-(3-
fluoro-4-methoxy-benzyl)-amine
409
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,5-
dimethyl-benzyl)-amine
410
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-thiophen-
3-ylmethyl-amine
411
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-
naphthalen-1-ylmethyl-amine
412
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-
(2-trifluoromethyl-benzyl)-amine
413
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-
naphthalen-2-ylmethyl-amine
414
(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-
ethoxy-benzyl)-amine
415
(3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine
416
(2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine
417
(4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine
418
(2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine
419
(2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine
420
(10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine
421
(2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine
422
(3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine
423
Benzyl-(10H-phenothiazin-2-yl)-amine
424
(4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine
425
(2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine
426
(10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine
427
(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H-
phenothiazin-2-yl)-amine
428
(3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)-
amine
429
(2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine
430
(10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine
431
(10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-amine
432
(9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine
433
(9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine
434
(9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine
435
(4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine
436
(9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine
437
(9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine
438
(9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine
439
(9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine
440
(9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine
441
(9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine
442
(9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine
443
(9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin-6-
ylmethyl)-amine
444
(9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine
445
(9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine
446
(9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine
447
Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-
6-ylmethyl)-amine
448
Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine
449
Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine
450
2-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole
451
2-Dibenzofuran-2-yl--1H-isoindole-1,3-dione
452
Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine
453
Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine
454
Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine
455
Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine
456
Dibenzofuran-2-yl-(1-phenyl-butyl)-amine
457
Dibenzofuran-2-yl-phenethyl-amine
458
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