US 7,572,796 B2
Substituted indoles
Oliver Schadt, Rodenbach (Germany); Henning Böttcher, Darmstadt (Germany); Joachim Leibrock, Pfungstadt (Germany); Kai Schiemann, Seeheim-Jugenheim (Germany); Timo Heinrich, Groβ-Umstadt (Germany); Günter Hölzemann, Seeheim-Jugenheim (Germany); Christoph van Amsterdam, Darmstadt (Germany); Gerd Bartoszyk, Weiterstadt (Germany); and Christoph Seyfried, Seeheim-Jugenheim (Germany)
Assigned to Merck Patent GmbH, Darmstadt (Germany)
Appl. No. 10/511,155
PCT Filed Apr. 11, 2003, PCT No. PCT/EP03/03806
§ 371(c)(1), (2), (4) Date Oct. 14, 2004,
PCT Pub. No. WO03/087086, PCT Pub. Date Oct. 23, 2003.
Claims priority of application No. 102 17 006 (DE), filed on Apr. 16, 2002.
Prior Publication US 2005/0153980 A1, Jul. 14, 2005
Int. Cl. A61K 31/497 (2006.01); C07D 405/00 (2006.01)
U.S. Cl. 514—254.09  [514/323; 544/376; 546/268.4] 7 Claims
 
1. A compound which is
a) 6-{3-[4-(4-fluorobenzyl)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
b) 6-{3-[4-(2,4-difluorobenzyl)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
c) 6-{3-[4-(4-fluorophenoxy)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
d) 4-{3-[4-(4-fluorobenzyl)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
e) 4-{3-[4-(2,4-difluorobenzyl)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
f) 4-{3-[4-(4-fluorophenoxy)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
g) 5-{3-[4-(4-fluorophenoxy)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
h) 5-{3-[4-(4-fluorobenzyl)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
i) 5-{3-[4-(2,4-difluorobenzyl)-1-piperidyl]propyl}-1H-indole-3-carbonitrile;
j) 5-{3-[4-(4-cyanophenyl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
k) 5-{4-[3-(3-cyano-1H-indol-6-yl)propyl]piperazin-1-yl}benzofuran-2-carboxamide;
l) 5-{3-[4-(2-oxo-2H-chromen-6-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
m) 5-{4-[3-(3-cyano-1H-indol-4-yl)propyl]piperazin-1-yl}-benzofuran-2-carboxamide;
n) 5-{4-[3-(3-cyano-1H-indol-5-yl)propyl]piperazin-1-yl}-benzofuran-2-carboxamide;
o) 5-{3-[4-(1H-indol-4-yl)-piperazin-1-yl]propyl}-1-methanesulfonyl-1H-indole-3-carbonitrile;
p) 5-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)propyl]-1H-indole-3-carbonitrile;
q) 5-[3-(4-benzo[1,2,5]thiadiazol-4-ylpiperazin-1-yl)propyl]-1H-indole-3-carbonitrile;
r) 3-{1-[3-(3-cyano-1H-indol-5-yl)propyl]piperidin-4-yl}-1H-indole-5-carboxamide;
s) 5-[3-(4-quinolin-8-ylpiperazin-1-yl)propyl]-1H-indole-3-carbonitrile;
t) 5-{3-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
u) 1-methanesulfonyl-5-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)propyl]-1H-indole-3-carbonitrile;
v) 5-{3-[4-(1H-indol-4-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
w) 5-{3-[4-(1H-indol-3-yl)piperidin-1-yl]propyl}-1H-indole-3-carbonitrile;
x) 5-{3-[4-(5-fluoro-1H-indol-3-yl)piperidin-1-yl]propyl}-1H-indole-3-carbonitrile;
y) 3-{1-[3-(3-cyano-1H-indol-5-yl)propyl]piperidin-4-yl}-1H-indole-5-carbonitrile;
z) 5-{3-[4-(6-fluoro-1H-indol-3-yl)piperidin-1-yl]propyl}-1H-indole-3-carbonitrile;
aa) 5-{3-[4-(4-fluoro-1H-indol-3-yl)piperidin-1-yl]propyl}-1H-indole-3-carbonitrile;
bb) 5-[3-(4-benzo[d]isothiazol-3-ylpiperazin-1-yl)propyl]-1H-indole-3-carbonitrile;
cc) 4-{1-[3-(3-cyano-1H-indol-6-yl)propyl]piperidin-4-yloxy}benzamide;
dd) 6-{3-[4-(2-cyano-3-methoxyphenyl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
ee) 6-{3-[4-(4-cyano-3-methoxyphenyl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
ff) 6-{3-[4-(4-cyano-2-methoxyphenyl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
gg) 4-[3-(4-pyrazol-1-ylmethy-1-piperidyl)propyl]-1H-indole-3-carbonitrile;
hh) N-(6-{4-[3-(3-cyano-1H-indol-5-yl)propyl]piperazin-1-yl}-2-oxo-2H-chromen-3-yl)acetamide;
ii) 5-{3-[(pyridin-3-ylmethyl)amino]propyl}-1H-indole-3-carbonitrile;
jj) 5-{3-[4-(2,3-dihydrobenzo[1,4]dioxin-6-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
kk) 5-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]-1H-indole-3-carbonitrile;
ll) 5-{3-[(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amino]propyl}-1H-indole-3-carbonitrile;
mm) 5-{3-[4-(3-methoxyphenyl)-3-methylpiperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
nn) 5-{3-[4-(1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
oo) N-(4-{1-[3-(3-cyano-1H-indol-5-yl)propyl]piperidin-4-ylmethyl}-phenyl)acetamide;
pp) 5-{3-[4-(4-pyridin-3-ylthiazol-2-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
qq) ethyl 2-{4-[3-(3-cyano-1H-indol-5-yl)propyl]piperazin-1-yl}-thiazole-4-carboxylate;
rr) 5-{3-[3-(2-oxopyrrolidin-1-yl)propylamino]propyl}-1H-indole-3-carbonitrile;
ss) ethyl (6-{4-[3-(3-cyano-1H-indol-5-yl)propyl]piperazin-1-yl}-2-oxo-2H-chromen-3-yl)carbamate;
tt) 5-{3-[4-(3-amino-2-oxo-2H-chromen-6-yl)piperazin-1-yl]propyl}-1H-indole-3-carbonitrile;
uu) methyl (6-{4-[3-(3-cyano-1H-indol-5-yl)propyl]piperazin-1-yl}-2-oxo-2H-chromen-3-yl)carbamate;
vv) 2-{4-[3-(3-cyano-1H-indol-5-yl)propyl]-piperazin-1-yl}thiazole-4-carboxamide; or
ww) 4-[3-(3-cyano-1H-indol-5-yl)propyl]piperazine-1-thiocarboxamide;
or a pharmaceutically acceptable salt, stereoisomer or mixture thereof.