1,3-substituted cycloalkenes and cycloalkanes as central nervous system agents

Claim 2

A compound of Formula I Z--CH.sub.2 --Y I wherein Z is ##STR41## wherein R is aryl, 2-, 3-, or 4-pyridinyl or 2-, 3-, or 4-pyridinyl substituted by lower alkyl, lower alkoxy, hydroxy, or halogen, and m is an integer of 1, 2, or 3, ##STR42## wherein R and m are as defined above, ##STR43## wherein R and m are as defined above, ##STR44## wherein R is as defined above; Y is ##STR45## whrein R is as defined above; and corresponding isomers thereof; or a pharmaceutically acceptable acid addition salt thereof.

Claim 3

A compound according to claim 1, in which R is phenyl, phenyl substituted by lower alkyl, lower alkoxy, lower dialkoxy, halogen, hydroxy, dihydroxy, amino, lower alkyl amino, lower dialkyl amino, 2- or 3-pyridinyl, or 2- or 3-pyridinyl substituted by lower alkyl, lower alkoxy, or halogen; m is an integer of 1 or 2; and Y is ##STR46## wherein R is as defined above.

Claim 4

A compound according to claim 2, in which R is phenyl, phenyl substituted by para-halogen, para-methoxy, ortho or para lower alkyl, para mono- or di-lower alkyl amino, or 2- or 3-pyridinyl; m is an integer of 2; and Y is ##STR47## wherein R is as defined above.

Claim 5

A compound according to claim 3 selected from the group consisting of: (±)-1,2,3,6-Tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen01-yl)methyl]pyridine; (±)-1,2,3,6-Tetrahydro-4-phenyl-1-[(3-phenyl-2-cyclohexen-1-yl)methyl]pyridine; (±)-1-[[3-(4-Fluorophenyl)-3-cyclohexen-1-yl]methyl]-1,2,3,6-tetrahydro-4-phenylpyridine; (±)-1-[[3-(4-Fluorophenyl)-2-cyclohexen-1-yl]methyl]-1,2,3,6-tetrahydro-4phenylpyridine; (+)-1,2,3,6-Tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine; (-)-1,2,3,6-Tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine; (R)-1-[[3-(4-chlorophenyl)-3-cyclohexen-1-yl]methyl]-1,2,3,6-tetrahydro9-4-phenylpyridine; (R)-1-[[3-(4-chlorophenyl)-2-cyclohexen-1-yl]methyl]-1,2,3,6-tetrahydro-4-phenylpyridine; (R)-1-[[3-(4-fluorophenyl)-3-cyclohexen-1-yl]methyl]-1,2,3,6-tetrahydro-4-phenylpyridine; (R)-1,2,3,6-tetrahydro-1-[[3-(4-methylphenyl)-3-cyclohexen-1-yl]methyl]-4-phenylpyridine; (R)-1,2,3,6-tetrahydro-1-[[3-(4-methoxyphenyl)-3-cyclohexen-1-yl]methyl]-4-phenylpyridine monohydrochloride; (R)-3-[5-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-1-cyclohexen-1-yl]pyridine monohydrochloride; (R)-3-[3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-1-cyclohexen-1-yl]pyridine dihydrochloride; (R)-1,2,3,6-tetrahydro-1-[[3-(2-methylphenyl)-2-cyclohexen-1-yl]methyl]-4-phenylpyridine; (R)-1,2,3,6-tetrahydro-1-[[3-(2-methylphenyl)-3-cyclohexen-1-yl]methyl]-4-phenylpyridine; (R)-4-[5-[(f3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-1-cyclohexen-1-yl]-N,N-dimethylbenzeneamine; (R)-4-[3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-1-cyclohexen-1-yl]-N,N-dimethylbenzeneamine; (1S-cis)-N-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexyl]benzamide; (1R-Cis)-1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenylcyclohexyl)methyl]pyridine monohydrochloride; and (1R-Trans)-1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenylcyclohexyl)methyl]pyridine monohydrochloride.

Claim 6

A compound having the name (+)-1,2,3,6-Tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine.

Claim 7

A compound having the name (+)-1,2,3,6-Tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine.

Claim 8

A method of treating schizophrenia comprising administering to a host suffering therefrom a therapeutic effective amount of a compound according to claim 1 in unit dosage form.

Claim 9

A pharmaceutical composition adapted for administration as a dopaminergic, antipsychotic, or antihypertensive agent comprising a therapeutic effective amount of a compound according to claim 1 in admixture with a pharmaceutically acceptable excipient, diluent, or carrier.