Tricyclicdicarboximides
AssigneeMerck & Co., Inc.
InventorsKenneth L. Shepard, William J. Paleveda, Jr.
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Abstract
Tricyclicdicarboximides representatively prepared by the Diels-Alder condensation of a cyclic diene such as cycloheptatriene, cyclooctatetraene and the like with a dienophile such as substituted N-phenylmaleimide and the like are disclosed having pharmaceutical utility as minor tranquilizers and anti-convulsants. Also disclosed are processes for the preparation of such tricyclicdicarboximides; pharmaceutical compositions comprising such compounds and their salt, ester and amide derivatives, and methods of treatment comprising administering such compounds and compositions.
Claims4
A compound having the formula:
- ##STR5## wherein:
- R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are hydrogen,
- X is --CH.sub.2 -- or --CH.dbd.CH--;
- R is --CH.sub.2 C.tbd.CH or ##STR6## wherein Y is hydrogen, or halogen and R.sup.5 is amino, acetamido, propionamido or valeramido;
- or a non-toxic pharmaceutically acceptable salt thereof.
The compound selected from the group consisting of
- N-(4-acetamidophenyl)-anti-tricyclo[3.2.2.0.sup.2,4 ]non-8-ene-endo-6,endo-7-dicarboximide;
- N-(4-acetamidophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide;
- N-(3-acetamidophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide;
- N-(propargyl)-anti-tricyclo[3.2.2.0.sup.2,4 ]non-8-ene-endo-6,endo-7-dicarboximide;
- N-(3-chloro-4-valeramidophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide;
- N-(4-valeramidophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide;
- N-(4-aminophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide;
- N-(3-acetamidophenyl)-anti-tricyclo[3.2.2.0.sup.2,4 ]non-8-ene-endo-6,endo-7-dicarboximide;
- N-(3-aminophenyl)-anti-tricyclo[3.2.2.0.sup.2,4 ]non-8-ene-endo-6,endo-7-dicarboximide;
- N-(4-propionamidophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide;
- N-(4-acetamido-3-chlorophenyl)-anti-tricyclo[4.2.2.0.sup.2,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide.
A pharmaceutical composition for treating anxiety comprising a therapeutically effective amount in unitary dosage form of a compound having the formula:
- ##STR7## wherein:
- R.sup.1 R.sup.2, R.sup.3 and R.sup.4 are hydrogen;
- X is --CH.sub.2 -- or --CH.dbd.CH--;
- R is --CH.sub.2 C.tbd.CH or ##STR8## wherein Y is hydrogen, or halogen;
- and R.sup.5 is amino, acetamido, propionamido or valeramido;
- or a non-toxic pharmaceutically acceptable salt thereof and a pharmaceutical carrier thereof.
A method of treatment of anxiety comprising administering to a patient in need of such treatment a therapeutically effective amount in unitary dosage form of a compound having the formula:
- ##STR9## wherein:
- R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are hydrogen;
- X is --CH.sub.2 -- or --CH.dbd.CH--;
- R is --CH.sub.2 C.tbd.CH or ##STR10## wherein Y is hydrogen, or halogen;
- and R.sup.5 is amino, acetamido, priopionamido or valeramido;
- or a non-toxic pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.