US2006142321A1PendingUtilityA1
5-HT7 receptor antagonists
Est. expiryDec 28, 2024(expired)· nominal 20-yr term from priority
Inventors:Antoni Torrens JoverSusana Yenes MinguezJose Mas PrioLuz Romero AlonsoAlberto Dordal ZuerasHelmut Henrich Buschmann
A61P 9/12A61P 43/00A61P 25/20A61P 25/18A61P 25/28A61P 25/24A61P 25/00A61P 25/04A61P 25/06A61P 25/22A61P 13/02C07D 405/12A61P 1/04C07D 221/16A61P 1/00C07D 413/12C07D 413/14C07D 401/12C07D 409/12A61K 9/0053A61K 31/473C07D 221/06
42
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Claims
Abstract
The invention relates to compounds having pharmacological activity towards the 5-HT7 receptor, and more particularly to some some 2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen substituted sulfonamide compounds, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT is involved, such as CNS disorders.
Claims
exact text as granted — not AI-modified1 . A compound of the formula I:
wherein
W is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl;
R 1 , R 2 , R 3 , R 4 , R 4B , R 5 , R 5B , R 6 and R 7 are each independently selected from the group formed by hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 , —HC═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , —NO 2 , —N═CR 8 R 9 or halogen;
L is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, —COR 8 , —C(O)OR 8 , —C(O)NR 8 R 9 , —HC═NR 8 , —CN, —OR 8 , —OC(O)R 8 , —S(O) t —R 8 , —NR 8 R 9 , —NR 8 C(O)R 9 , or —N═CR 8 R 9 ; and wherein the pair R 4 and R 4B or the pair R 5 and R 5B taken together may form a carbonyl group, t is 1, 2 or 3;
R 8 and R 9 are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, halogen;
n is 2, 3, 4 or 5;
or a pharmaceutically acceptable salt, isomer, prodrug or solvate thereof.
2 . A compound according to claim 1 characterized in that n is 3 or 4.
3 . A compound according to claim 1 characterized in that W is an aromatic group selected from substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted phenyl.
4 . A compound according to claim 3 characterized in that W is selected from alkyl, alkoxy and/or halo substituted phenyl.
5 . A compound according to claim 1 characterized in that R 5 , R 5B , R 6 and R 7 are H.
6 . A compound according to claim 1 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and and R 4B taken together form a carbonyl group.
7 . A compound according to claims 5 or 6 wherein R 2 and R 3 are alkoxy, or in that R 2 is alkoxy and R 3 is H.
8 . A process for the preparation of a compound of formula (I) or a salt, isomer or solvate thereof as claimed in any of claims 1 - 7 , which comprises the coupling of a compound of Formula (II):
in which R1-R7 and n are as defined in Formula (I), with a compound of Formula (III):
in which W is as defined in Formula (I) and X is an halogen, preferably Cl.
9 . A pharmaceutical composition which comprises a compound as defined in any of claims 1 - 7 or a pharmaceutically acceptable salt, prodrug, isomer or solvate thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
10 . A pharmaceutical composition according to claim 9 for oral administration.
11 . A method of manufacturing a medicament comprising combining a compound as defined in any of claims 1 - 7 with a pharmaceutically acceptable carrier.
12 . A method of treating a 5-HT 7 mediated disease or condition comprising administering a composition according to claim 11 .
13 . A method according to claim 12 wherein the disease is sleep disorder, shift worker syndrome, jet lag, depression, seasonal affective disorder, migraine, anxiethy, psychosis, schizophrenia, pain, cognition and memory disorders, neuronal degeneration resulting from ischemic events, cardiovascular diseases, as hypertension, irritable bowel syndrome, inflammatory bowel disease, spastic colon or urinary incontinence.
14 . A method for treating or preventing a central nervous disorder comprising administering to a patient in need thereof a therapeutically effective amount of a compound as defined in any of claims 1 - 7 , or a pharmaceutically acceptable salt, isomer, prodrug or solvate thereof.
15 . A compound according to claim 2 characterized in that W is an aromatic group selected from substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted phenyl.
16 . A compound according to claim 15 characterized in that W is selected from alkyl, alkoxy and/or halo substituted phenyl.
17 . A compound according to claim 2 characterized in that R 5 , R 5B , R 6 and R 7 are H.
18 . A compound according to claim 3 characterized in that R 5 , R 5B , R 6 and R 7 are H.
19 . A compound according to claim 15 characterized in that R 5 , R 5B , R 6 and R 7 are H.
20 . A compound according to claim 14 characterized in that R 5 , R 5B , R 6 and R 7 are H.
21 . A compound according to claim 16 characterized in that R 5 , R 5B , R 6 and R 7 are H.
22 . A compound according to claim 2 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
23 . A compound according to claim 3 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
24 . A compound according to claim 4 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
25 . A compound according to claim 5 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
26 . A compound according to claim 15 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
27 . A compound according to claim 16 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
28 . A compound according to claim 17 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
29 . A compound according to claim 18 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
30 . A compound according to claim 19 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
31 . A compound according to claim 20 characterized in that R 1 , R 4 , R 4B , R 5 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
32 . A compound according to claim 21 characterized in that R 1 , R 4 , R 4B , R 1 and R 5B are H or in that R 1 , R 5 and R 5B are H and R 4 and R 4B taken together form a carbonyl group.
33 . A compound according to claim 5 wherein R 2 and R 3 are methoxy, or in that R 2 is methoxy and R 3 is H.
34 . A compound according to claim 6 wherein R 2 and R 3 are methoxy, or in that R 2 is methoxy and R 3 is H.Join the waitlist — get patent alerts
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