Substituted 2-amidotetralins as melatonin agonists and antagonists
AssigneeNorthwestern University
InventorsAlan S. Horn, Margarita L. Dubocovich
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Abstract
The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.
Claims7
Compounds of the formula:
- ##STR10## wherein:
- R.sub.1 is hydrogen, halogen, amino, amido, a C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, or C.sub.1-4 alkoxyl-C.sub.6 -aryl;
- R.sub.2 is hydrogen, halogen, amino, amido, C.sub.6 aryl, mono- or di- C.sub.1-4 alkylamino, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkoxyl-C.sub.6 -aryl, or C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxyl;
- R.sub.3 is hydrogen, C.sub.6 aryl, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkyl, C.sub.2-4 alkenyl, or C.sub.2-4 alkynyl;
- R.sub.4 is C.sub.6 aryl, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkyl, halo-C.sub.1-4 alkyl, or C.sub.3-6 cycloalkyl;
- R.sub.5 is hydrogen, halogen, oxo, C.sub.6 aryl, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkyl;
- wherein aryl substitutents of R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may optionally be halogen, hydroxyl, amino, mono- or di- C.sub.1-4 alkylamino, or C.sub.1-4 alkyl or C.sub.1-4 alkoxyl substituted, provided that when R.sub.1 is methoxy, and R.sub.2, R.sub.3, and R.sub.5 are hydrogen, R.sub.4 is not methyl.
A pharmaceutical composition for use in treatment of disorders associated with abnormal melatonin activity in an organism, said composition comprising a pharmaceutically acceptable solvent, diluent, adjuvant or carrier and, as the active ingredient, from about 0.001 mg to about 100 mg per kg of body weight of said organism of a compound of the formula:
- ##STR11## wherein:
- R.sub.1 is hydrogen, halogen, amino, amido, a C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, or C.sub.1-4 alkoxyl-C.sub.6 -aryl:
- R.sub.2 is hydrogen, halogen, amino, amido, C.sub.6 aryl, mono- or di- C.sub.1-4 alkylamino, C.sub.1-4 alkyl-C.sub.6 -aryl, or -C.sub.1-4 alkoxyl-C.sub.6 -aryl, or C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxyl;
- R.sub.3 is hydrogen, -C.sub.6 aryl, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkyl, C.sub.2-4 alkenyl, or C.sub.2-4 alkynyl;
- R.sub.4 is C.sub.6 aryl, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkyl, halo-C.sub.1-4 -alkyl, or C.sub.3-6 cycloalkyl;
- R.sub.5 is hydrogen, halogen, oxo, C.sub.6 aryl, C.sub.1-4 alkyl-C.sub.6 -aryl, or C.sub.1-4 alkyl;
- wherein aryl substitutents of R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may optionally be halogen, hydroxyl, amino, mono- or di- C.sub.1-4 alkylamino, or C.sub.1-4 alkyl or C.sub.1-4 alkoxyl substituted.
Dependencies are inferred from the claim text.