Back to results
US 2007/0191342 A1Published application
Thiophenyl and pyrrolyl azepines as serotonin 5-HT2c receptor ligands and uses thereof
AssigneeAthersys, Inc.
InventorsL. Tumey, David Bom, Youssef Bennani, Michael Robarge
Life of this patent
Estimating the term…
Abstract
The present invention generally relates to a series of compounds, to pharmaceutical compositions containing the compounds, and to use of the compounds and compositions as therapeutic agents. More specifically, compounds of the present invention are thiophenyl and pyrrolyl azepine compounds. These compounds are serotonin receptor (5-HT2c) ligands and are useful for treating diseases, disorders, and conditions wherein modulation of the activity of serotonin receptors (5-HT2c) is desired (e.g. addiction, anxiety, depression, obesity, and others).
Claims15
A compound of the formula
- X is S or NR11;
- R1 and R2 are independently selected from the group consisting of H, halogen, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, perhalo alkyl, C1-8 alkylperhalo alkyl, —CN, OR8, SR8, —SO2R10, —C(═O)R10, —C(═O)NR8R9, —NR8CO2R10, —SO2NR8R9, —NR8SO2R10, aryl or heteroaryl, C1-8 alkylaryl or heteroaryl, —C1-8 alkyl-O—C1-8alkyl, and —C1-8 alkyl-O-aryl or heteroaryl;
- R1 and R2 taken together with the atoms to which they are attached can form a 5-7-member carbocycle or heterocycle optionally substituted with up to two substituents selected from alkyl, CF3, and —OR8;
- R3 is selected from the group consisting of H, C1-8 alkyl, OR8, aryl and heteroaryl;
- R3a is H or C1-8 alkyl;
- or R3 and R3a taken together are —CH2CH2—;
- R2 and R3 taken together form a 5-7-member carbocycle or heterocycle optionally substituted with up to two substituents selected from alkyl, CF3, and —OR8;
- R4 is H, C1-8 alkyl, or OR8;
- R4a is H, C1-8 alkyl;
- or R4 and R4a taken together are —CH2CH2—;
- R5 is selected from the group consisting of H, —C1-8 alkyl, —C1-8 alkyl-O—C1-8 alkyl, C1-8 alkylaryl or heteroaryl, and —C1-8 alkyl-O-aryl or heteroaryl;
- R5a is H or —C1-8 alkyl;
- R6 is selected from the group consisting of H, —C1-8 alkyl, C1-8 alkyl-O—C1-8 alkyl, C1-9 alkylaryl or heteroaryl, and —C1-8 alkyl-O-aryl or heteroaryl;
- R6a is H or —C1-8 alkyl;
- R7 is selected from the group consisting of H, —C1-8 alkyl, and —C1-8alkylaryl or heteroaryl;
- R8, R9 are independently selected from the group consisting of H, —C1-8 alkyl, —C2-8 alkenyl, —C2-8 alkynyl, aryl or heteroaryl, —C1-8 alkylaryl or heteroaryl, —C1-8 alkyl-O—C1-8 alkyl, and —C1-8 alkyl —O-aryl or heteroaryl;
- R8 and R9 taken together with the atom to which they are attached form a 5-7-member heterocycle;
- R10 is selected from the group consisting of —C1-8 alkyl, —C2-8 alkenyl, —C2-8 alkynyl, 25 aryl or heteroaryl, —C1-8 alkylaryl or heteroaryl, —C1-8 alkyl-O—C1-8 alkyl, and —C1-8 alkyl-O-aryl or heteroaryl;
- R11 is selected from the group consisting of H, —C1-8 alkyl, —C1-8 alkyl-O—C1-8 alkyl, —SO2R10, —C(═O)R10, —C(═O)OR10, aryl, and heteroaryl, or C1-8 alkylaryl or heteroaryl;
- R11 and R1 together with the atoms to which they are attached may form a 5-7-membered heterocycle optionally substituted with up to two substituents selected from —C1-8 alkyl, CF3, and —OR8;
- and
- R11 and R4 together with the atoms to which they are attached may form a 5-7-membered heterocycle optionally substituted with up to two substituents selected from —C1-8 alkyl, CF3, and —OR8;
- wherein aryl and heteroaryl are optionally substituted with up to two substituents selected from —C1-8 alkyl, halogen, CN, and alkoxy, and the pharmaceutically acceptable salts thereof.
20 more elements
Dependencies are inferred from the claim text.