US2001031758A1PendingUtilityA1
Substituted 9H-pyridino[2,3-b] indole and 9H-pyrimidino[4,5-b] indole derivatives: selective neuropeptide Y receptor ligands
Est. expiryApr 2, 2018(expired)· nominal 20-yr term from priority
C07D 487/04C07D 471/04A61P 9/12
44
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Claims
Abstract
Disclosed are compounds of the formula: wherein Ar, R 1 , W and X are substituents as defined herein, which compounds are effective neuropeptide Y1 receptor antagonists, and are therefore useful in the treatment of a wide variety of clinical conditions which are characterized by the presence of an excess of neuropeptide Y.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of the formula:
or pharmaceutically acceptable salts thereof wherein:
Ar is phenyl, 1- or 2-naphthyl, 2-, 3-, or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, each of which is optionally mono-, di-, or trisubstituted with halogen, trifluoromethyl, hydroxy, amino, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 3 -C 7 cycloalkylamino, carboxamido, C 1 -C 6 alkylcarboxamido, C 3 -C 7 cycloalkylcarboxamido, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkoxy, C 3 -C 7 cycloalkoxy, with the proviso that at least one of the positions ortho or para to the point of attachment of Ar to the tricyclic ring system is substituted;
R 1 is hydrogen, halogen, trifluoromethyl, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, or (C 1 -C 6 alkylene)-G 1 —R 2 wherein G 1 is oxygen or sulfur and R 2 is hydrogen, C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl;
W is N or C—R 3 , wherein R 3 is hydrogen or C 1 -C 6 alkyl;
X is
wherein A 1 is NR 4 R 5 wherein R 4 and R 5 are independently hydrogen, a C 1 -C 6 alkyl group which optionally forms a heterocycloalkyl group with Y, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl; C 1 -C 6 alkanoyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkanoyl, C 3 -C 7 cycloalkanoyl, C 1 -C 6 alkylsulfonyl, or C 3 -C 7 cycloalkylsulfonyl with the proviso that R 4 and R 5 may not both be alkanoyl or alkylsulfonyl; C 1 -C 6 heterocycloalkyl, wherein heterocycloalkyl is morpholinyl, piperazinyl, piperidinyl, or pyrrolidinyl; C 1 -C 6 arylalkyl or C 1 -C 6 heteroarylalkyl, where aryl is phenyl, and heteroaryl is 2-,3-, or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, 1-, 2- or 4-imidazolyl, 2-, 4-, or 5-oxazolyl, 2-, 4-, or 5-thiazolyl, 1-, 3- or 4-pyrazolyl, 1-, 3- or 4-triazolyl, 2-pyrazinyl, or 1-, 2- or 5-tetrazolyl, each of which is optionally mono-, di-, or tri-substituted with halogen, trifluoromethyl, hydroxy, amino, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 3 -C 7 cycloalkylamino, C 1 -C 6 alkylcarboxamido, C 3 -C 7 cycloalkylcarboxamido, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkoxy, or C 3 -C 7 cycloalkoxy, where any 2 adjacent substituents may together form a 5-7 fused cycloalkyl or heterocycloalkyl ring; NR 4 R 5 taken together form a C 3 -C 6 heterocycloalkyl, or a group of the formula: wherein e and f are independently 1, 2, or 3 and the sum of e and f is at least 3; and
G 2 is
(i) NR 6 wherein R 6 is hydrogen, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl; or
(ii) CH(C 0 -C 6 alkyl)-G 3 —R 7 wherein G 3 is —CONH—, —CONH(C 1 -C 6 alkyl)-, —NH—, —NH(C 1 -C 6 alkyl)-, —NH(C 3 -C 7 cycloalkyl)-, and R 7 is hydrogen, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl; or
(iii) —CONH 2 —, or —CO[N(C 1 -C 6 alkylene)R 8 ]— wherein R 8 is hydrogen, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl;
A 2 is NH, SO 2 , oxygen or sulfur; V is CH 2 , CO, CS, SO 2 , CH(C 1 -C 6 alkyl), CH(C 3 -C 7 cycloalkyl), with the proviso that V may not be CO, CS or SO 2 when A 2 is SO 2 , oxygen or sulfur; and Y is a bond or C 1 -C 6 alkylene; or
X is
wherein
heteroaryl is 2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, 1-, 2- or 4-imidazolyl, 2-, 4-, or 5-oxazolyl, 1-, 3- , or 5-thiazolyl, 1-, 3- or 4-pyrazolyl, 1-, 3- or 4-triazolyl, 2-pyrazinyl, or 1-, 2- or 5-tetrazolyl, each of which is optionally mono- or di-substituted with halogen, trifluoromethyl, amino, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 3 -C 7 cycloalkylamino, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, or C 3 -C 7 cycloalkoxy, with the proviso that tetrazolyl may have at most one substituent;
Z is C 1 -C 6 alkylene; and
A 2 is NH, SO 2 , oxygen or sulfur.
2 . A compound according to claim 1 wherein W is CH or N, A 2 is NH or O, and R 1 is C 1 -C 6 alkyl.
3 . A compound according to claim 1 wherein W is CH or N, and wherein R 4 and R 5 are independently hydrogen, a C 1 -C 6 alkyl group which optionally forms a heterocycloalkyl group with Y, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl.
4 . A compound according to claim 4 wherein Ar is 2,4,6-trimethylphenyl, A 2 is NH or O, Y is CH 2 , V is CH 2 or (CH 2 ) 2 , R 4 ls hydrogen, and R 5 is hydrogen, methyl, ethyl, propyl, isopropyl, 2-methylpropyl, 2-ethylpropyl, 1,1-dimethyl propyl, butyl, tert-butyl, 2-methylbutyl, 3-methylbutyl, 1,3-dimethyl butyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclopropylmethyl.
5 . A compound according to claim 1 wherein W is CH or N, Ar is 2,4,6-trimethylphenyl, A 2 is NH or O, Y is CH 2 , V is CH 2 or (CH 2 ) 2 , R 4 is hydrogen, and R 5 is C 1 -C 6 heterocycloalkyl, wherein heterocycloalkyl is morpholin-4-yl, piperazin-4-yl, piperidin-4-yl, or pyrrolidin-2-yl.
6 . A compound according to claim 1 wherein W is CH or N, Ar is 2,4,6-trimethylphenyl, A 2 is NH or O, Y is CH 2 , V is CH 2 or (CH 2 ) 2 , and NR 4 R 5 taken together form a C 3 -C 6 heterocycloalkyl, or a group of the formula:
wherein e and f are independently 1, 2, or 3 and the sum of e and f is at least 3; and
G 2 is
(i) NR 6 wherein R 6 is hydrogen, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl; or
(ii) CH(C 0 -C 6 alkyl)-G 3 —R 7 wherein G 3 is —CONH—, CONH(C 1 -C 6 alkyl)-, —NH—, —NH(C 1 -C 6 alkyl)-, —NH(C 3 -C 7 cycloalkyl)-, and R 7 is hydrogen, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl; or
(iii) —CONH 2 —, or —CO[N(C 1 -C 6 alkylene)R 8 ]— wherein R 8 is hydrogen, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, or C 3 -C 7 cycloalkyl.
7 . A compound according to claim 6 wherein NR 4 R 5 is pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl, N-methylpiperazinyl.
8 . A compound according to claim 1 wherein W is CH or N, and wherein R 4 and R 5 are independently hydrogen, C 1 -C 6 arylalkyl or C 1 -C 6 heteroarylalkyl, where aryl is phenyl, and heteroaryl is 2-,3-, or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, 1-, 2- or 4-imidazolyl, 2-, 4-, or 5-oxazolyl, 2-, 4-, or 5-thiazolyl, 1-, 3- or 4-pyrazolyl, 1-, 3- or 4-triazolyl, 2-pyrazinyl, or 1-, 2- or 5-tetrazolyl, each of which is optionally mono-, di-, or tri-substituted with halogen, trifluoromethyl, hydroxy, amino, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 3 -C 7 cycloalkylamino, C 1 -C 6 alkylcarboxamido, C 3 -C 7 cycloalkylcarboxamido, C 1 -C 6 alkyl, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, (C 3 -C 7 cycloalkyl) C 1 -C 6 alkoxy, or C 3 -C 7 cycloalkoxy, where any 2 adjacent substituents may together form a 5-7 fused cycloalkyl or heterocycloalkyl ring.
9 . A compound according to claim 8 wherein Ar is 2,4,6-trimethylphenyl, A 2 is NH or O, Y is CH 2 , V is CH 2 or (CH 2 ) 2 , R 4 is hydrogen, and R 5 is (CH 2 ) 2 -phenyl, (CH 2 ) 3 -phenyl, (CH 2 ) 4 -phenyl, (CH 2 ) 2 -(2-methoxy) phenyl, (CH 2 ) 2 -(3-methoxy) phenyl, (CH 2 ) 2 -(4-hydroxy) phenyl, (CH 2 ) 2 -(4-methoxy) phenyl, (CH 2 ) 2 -(4-ethoxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-ethoxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-isopropoxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-isobutyloxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-cyclopropylmethyloxy) phenyl, (CH 2 ) 2 -(2,4-dimethoxy) phenyl, (CH 2 ) 2 -(3,4-dimethoxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-hydroxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-propoxy)phenyl, (CH 2 ) 2 -(3-methoxy-4-propoxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-butoxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-pentoxy)phenyl, (CH 2 ) 2 -(3-methoxy-4-cyclopentyloxy) phenyl, (CH 2 ) 2 -(3-methoxy-4-cyclohexyloxy) phenyl, (CH 2 ) 2 -(2H-benzo[3,4-d]1,3-dioxolan-5-yl), (CH 2 ) 2 -(2H,3H-benzo[e]1,4-dioxin-6-yl), (CH 2 ) 2 -(4-trifluoromethyl) phenyl, (CH 2 ) 2 -(4-amino) phenyl, or (CH 2 )2-(4-dimethylamino) phenyl.
10 . A compound according to claim 8 wherein Ar is 2,4,6-trimethylphenyl, A 2 is NH or O, Y is CH 2 , V is CH 2 or (CH 2 ) 2 , R 4 is hydrogen, and R 5 is (CH 2 ) 2 -pyridin-2-yl, (CH 2 ) 2 -pyridin-3-yl, (CH 2 ) 2 -pyridin-4-yl, (CH 2 ) 2 -(2-methyl-imidazol-4-yl), CH 2 -imidazol-5-yl, or (CH 2 ) 2 -(imidazol-5-yl).
11 . A compound according to claim 1 , which is [2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl](2-(4-piperidyl) ethyl) amine.
12 . A compound of the formula:
where R x and R y are methyl; or NR x R y represents pyrrolidinyl.
13 . A compound according to claim 1 , which is [2-(1-ethylimidazol-5-yl)ethyl][2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino [4,5-b] indol-4-yl] amine.
14 . A compound of the formula:
where R x is selected from 3,4-dimethoxybenzylcarbonyl; 4-methoxybenzylcarbonyl; imidazol-5-ylcarbonyl; pyrazin-2-ylcarbonyl; 2-(4-ethoxy-3-methoxyphenyl)ethyl; 2-(4-trifluoromethylphenyl)ethyl; 2-(4-ethoxyphenyl)ethyl; 2-(4-methoxyphenyl)ethyl; 2-(imidazol-5-yl)ethyl; 2-phenylethyl; imidazol-5-ylmethylcarbonyl; cyclopropylcarbonyl; cyclobutyl; 2-methylimidazol-4-ylmethyl; imidazol-5-ylmethyl; cyclohexyl; cyclopentyl; cyclopropyl; ethyl; isopropyl; methyl; propyl; 2-(morpholin-4-yl)ethyl; cycloheptyl; (2-methyl-(1,3-thiazol-4-yl)methyl; (5-bromo-2-methyl-(1,3-thiazol-4-yl)methyl; and (2H,3H-benzo[e]1,4-dioxin-6-yl).
15 . A compound of the formula:
where
f is 3 and NR x R y represents piperidin-4-yl;
f is 3, R x is hydrogen, and R y is 2-(morpholin-4-yl)ethyl;
f is 3 and R x and R y are hydrogen;
f is 3 and NR x R y represents pyrrolidinyl; or
f is 4 and R x and R y are hydrogen.
16 . A compound of the formula:
where R x is 1,1-dimethylpropyl; 1,3-dimethylbutyl; 2-ethylpropyl; 2-methylbutyl; 2-methylpropyl; 3-methylbutyl; 2-(2-methoxyphenyl)ethyl; 2-(2,4-dimethoxyphenyl)ethyl; 2-(3-methoxy-4-(cyclopropylmethoxy)phenyl)ethyl; 2-(3-methoxy-4-cyclohexyloxyphenyl)ethyl; 2-(3-methoxy-4-ethoxyphenyl)ethyl; 2-(3-methoxy-4-isopropoxyphenyl)ethyl; 2-(3-methoxy-4-butoxyphenyl)ethyl; 2-(3-methoxy-4-(2-methylpropoxy)phenyl)ethyl; 2-(3-methoxy-4-hydroxyphenyl)ethyl; 2-(3-methoxy-4-pentoxyphenyl)ethyl; 2-(3,4-dimethoxyphenyl)ethyl; 2-(4-ethoxyphenyl)ethyl; 2-(4-methoxyphenyl)ethyl; 2-(4-aminophenyl)ethyl; 2-(4-hydroxyphenyl)ethyl; 2-(imidazol-5-yl)ethyl; 2-(morpholin-4-yl)ethyl; 2-phenylethyl; 2-(2-pyridyl)ethyl; 2-(3-pyridyl)ethyl; 2-(4-pyridyl)ethyl; 3-phenylpropyl; 4-phenylbutyl; butyl; cyclobutyl; 3-methoxybenzyl; 4-ethoxybenzyl; 4-methoxybenzyl; cyclopropylmethyl; cyclohexyl; cyclopentyl; ethyl; hexyl; isopropyl; methyl; propyl; tert-butyl; 4-(dimethylamino)phenylmethyl; (2H,3H-benzo[e]1,4-dioxin-6-yl)carbonylmethyl; 2-((2H,3H-benzo[e]1,4-dioxin-6-yl)carbonyl)ethyl; or 2-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)ethyl; cycloheptyl; 2-(3,4-dimethoxyphenyl)ethyl.
17 . A compound according to claim 1 , which is 4-(2-(2-(4-Methoxyphenyl)ethylamino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
18 . A compound according to claim 1 , which is 4-(2-Amino-2-methylethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
19 . A compound according to claim 1 , which is 4-(2-Aminoethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
20 . A compound according to claim 1 , which is 4-(2-Dimethylamino-1-oxoethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
21 . A compound according to claim 1 , which is 4-(2-(1-Methyl-2-pyrrolidino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
22 . A compound according to claim 1 , which is 4-(2-Aminoethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyrimidino[4,5-b]indole.
23 . A compound according to claim 1 , which is 4-(2-(Cyclohexylamino)ethyl)oxy-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyrimidino[4,5-b]indole.
24 . A compound according to claim 1 , which is A compound according to claim 1 , which is 4-(2-(Cyclohexylamino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyrimidino[4,5-b]indole.
25 . A compound according to claim 1 , which is 4-(2-(2-Phenethylamino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyrimidino[4,5-b]indole.
26 . A compound according to claim 1 , which is 2-(3,4-dimethoxyphenyl)-N-(2-{[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amino}ethyl)acetamide.
27 . A compound according to claim 1 , which is (2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}ethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
28 . A compound according to claim 1 , which is 4-(N-(2-hydroxyethyl)-N-cyclopropylmethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyrimidino[4,5-b]indole.
29 . A compound according to claim 1 , which is 4-(2-(Cyclopropylmethylamino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyrimidino[4,5-b]indole.
30 . A compound according to claim 1 , which is 4-(2-(1-Oxo-2-(3-methoxy-4-hydroxyphenyl)ethylamino) ethyl) amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
31 . A compound according to claim 1 , which is 4-(2-(1-Oxo-2-(3-methoxy-4-propoxyphenyl)ethylamino) ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
32 . A compound according to claim 1 , which is 4-(2-(2-(3-Methoxy-4-propoxyphenyl) ethylamino) ethyl) amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
33 . A compound according to claim 1 , which is 4-(2-(1-Oxo-2-(3-methoxy-4-cyclopentyloxyphenyl) ethylamino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
34 . A compound according to claim 1 , which is 4-(2-(2-(3-Methoxy-4-cyclopentyloxyphenyl)ethylamino)ethyl)amino-2-methyl-9-(2,4,6-trimethylphenyl)-9H-pyridino[2,3-b]indole.
35 . A compound according to claim 1 , which is (2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}ethyl)[9-(2,6-dimethylphenyl)-2-methylpyridino[2,3-b]indol-4-yl]amine.
36 . A compound according to claim 1 , which is [9-(3,5-dimethylphenyl)-2-methylpyridino[2,3-b]indol-4-yl](2-{[2-(4-methoxyphenyl)ethyl]amino}ethyl)amine.
37 . A compound according to claim 1 , which is (cyclopropylmethyl){2-[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yloxy]ethyl}amine.
38 . A compound according to claim 1 , which is [9-(3,5-dimethylphenyl)-2-methylpyridino[2,3-b]indol-4-yl][2-(cyclohexylamino)ethyl]amine.
39 . A compound according to claim 1 , which is [9-(2,4-dimethylphenyl)-2-methylpyridino[2,3-b]indol-4-yl][2-(cyclohexylamino)ethyl]amine.
40 . A compound according to claim 1 , which is [9-(3,5-dimethylphenyl)-2-methylpyridino[2,3-b]indol-4-yl][2-(cyclopentylamino)ethyl]amine.
41 . A compound according to claim 1 , which is [2-(cyclopentylamino)ethyl][2-ethyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
42 . A compound according to claim 1 , which is [9-(2,4-dimethylphenyl)-2-methylpyridino[2,3-b]indol-4-yl][2-(cyclopentylamino)ethyl]amine.
43 . A compound according to claim 1 , which is [2-(ethylamino)ethyl][9-(4-methoxy-2-methylphenyl)-2-methylpyrimidino[4,5-b]indol-4-yl]amine.
44 . A compound according to claim 1 , which is [9-(4-chloro-2-methylphenyl)-2-methylpyrimidino[4,5-b]indol-4-yl][2-(ethylamino)ethyl]amine.
45 . A compound according to claim 1 , which is (tert-butyl){2-[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yloxy]ethyl}amine.
46 . A compound according to claim 1 , which is (2-aminoethyl)[2-ethyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
47 . A compound according to claim 1 , which is (2-aminoethyl)[2-(trifluoromethyl)-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
48 . A compound according to claim 1 , which is (2-aminoethyl) [9-(4-methoxy-2-methylphenyl)-2-methylpyrimidino[4,5-b]indol-4-yl]amine.
49 . A compound according to claim 1 , which is cyclopentylmethyl(2-{[2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]indol-4-yl]amino}ethyl)amine.
50 . A compound according to claim 1 , which is 2-methyl-4-(3-piperidylpropoxy)-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indole.
51 . A compound according to claim 1 , which is 2-{[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amino}acetamide.
52 . A compound according to claim 1 , which is [((2S)pyrrolidin-2-yl)methyl][2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
53 . A compound according to claim 1 , which is [2-(cyclopentylamino)propyl][2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
54 . A compound according to claim 1 , which is (2-aminopropyl) [2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
55 . A compound according to claim 1 , which is (2-{[2-(4-ethoxy-3-methoxyphenyl)ethyl]amino}propyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine
56 . A compound according to claim 1 , which is [2-(cyclopentylamino)-2-methylpropyl][2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
57 . A compound according to claim 1 , which is [2-(cyclopropylamino)-2-methylpropyl][2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
58 . A compound according to claim 1 , which is (2-amino-2-methylpropyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
59 . A compound according to claim 1 , which is (cis-2-aminocyclohexyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indol-4-yl]amine.
60 . The use of a compound according to claim 1 for the manufacture of a pharmaceutical composition for the prophylaxis and treatment of diseases or disorders associated with an excess of neuropeptide Y.
61 . A method of treating or preventing a physiological condition in a mammal characterized by the presence of an excess of neuropeptide Y which comprises administering to a mammal in need of such treatment a therapeutically effective amount of a compound according to claim 1 , a prodrug, or a pharmaceutically acceptable salt thereof.
62 . A pharmaceutical composition according to claim 1 for the treatment of disorders or disease states caused by &eating disorders, of obesity, bulimia nervosa, diabetes, dislipidemia, hypertension, memory loss, epileptic seizures, migraine, sleep disorders, pain, sexual/reproductive disorders, depression, anxiety, cerebral hemorrhage, shock, congestive heart failure, nasal congestion or diarrhea.Join the waitlist — get patent alerts
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