Antipsychotic agents, compositions and method of use
AssigneeHoechst Marion Roussel, Inc.
InventorsMark G. Palermo, Lawrence L. Martin, Peter A. Nemoto
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Abstract
This invention relates to compounds of the formula ##STR1## wherein X, Y, Z, m, n and p are as defined within, pharmaceutical compositions containing these compounds and to their use as antipsychotic agents, particularly in the treatment of schizophrenia. Depot derivatives of the compounds are useful for providing long acting effects of the compounds.
Claims10
A compound of the formula ##STR21## wherein X is --OH, OC(.dbd.O)(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)NH(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)O(C.sub.1 -C.sub.18)alkyl or --OC(.dbd.O)--(C.sub.3 -C.sub.12)cycloalkyl;
- Y is hydrogen, halogen, trifluoromethyl, (C.sub.1 -C.sub.6)alkoxy, cyano or nitro;
- m is 1, 2, 3, or 4;
- and
- p is 1 or 2;
- or the pharmaceutically acceptable addition salts thereof.
A process for preparing a compound of the formula:
- ##STR23## wherein X is --OH, OC(.dbd.O)(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)(C.sub.6 -C.sub.12)aryl, --OC(.dbd.O)(C.sub.6 -C.sub.2)alkyl(C.sub.6 -C.sub.10)aryl, OC(.dbd.O)NH(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)(C.sub.3 -C.sub.12)alkyl(C.sub.3 -C.sub.8)cycloakyl, --OC(.dbd.O)O(C.sub.1 -C.sub.18)alkyl or --OC(.dbd.O)--(C.sub.3 -C.sub.12)cycloalkyl;
- Y is H, halogen, trifluoromethyl, (C.sub.1 -C.sub.6)alkoxy, cyano or nitro;
- m is 1, 2, 3, or 4;
- n is 1 or 2;
- and
- p is 1 or 2;
- or the pharmaceutically acceptable addition salts thereof comprising reacting a compound of the formula:
- ##STR24## wherein X and n are defined as above, with a compound of the formula:
- ##STR25## wherein halo is Br or Cl, and Y, m and p are defined as above, in a polar non-protic organic solvent in the presence of a base and a catalyst.
A process for preparing a compound of the formula:
- ##STR26## wherein Y is H, halogen, trifluoromethyl, (C.sub.1 -C.sub.6)alkoxy, cyano or nitro;
- m is 1, 2, 3 or 4;
- n is 1 or 2;
- and
- p is 1 or 2;
- or the pharmaceutically acceptable acid addition salts thereof, comprising heating a compound of the formula:
- ##STR27## wherein X is --OC(.dbd.O)(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)(C.sub.6 --C.sub.10)aryl, --OC(.dbd.O)(C.sub.1 -C.sub.12)alkyl(C.sub.6 -C.sub.10)aryl, --OC(.dbd.O)NH(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)(C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.8)cycloalkyl, --OC(.dbd.O)O(C.sub.1 -C.sub.18)alkyl, or --OC(.dbd.O)--(C.sub.3 -C.sub.12)cycloalkyl, and Y, m, n and p are defined as above, with 48% HBr.
A depot pharmaceutical composition for treating psychosis comprising an adjuvant and as the active ingredient, a psychosis effective amount of a compound of the formula ##STR28## wherein X is --OC(.dbd.O)(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)NH(C.sub.1 -C.sub.18)alkyl, --OC(.dbd.O)O(C.sub.1 -C.sub.18)alkyl or --OC(.dbd.O)--(C.sub.3 -C.sub.12)cycloalkyl;
- Y is hydrogen or halogen
- m is 1, 2, 3, or 4;
- and
- p is 1;
- or the
- pharmaceutically acceptable addition salts thereof.
Dependencies are inferred from the claim text.