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Details for Patent: 5,977,140

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Details for Patent: 5,977,140

Title: N-[(4-Heteroaryl-1-Piperidinyl)Alkly] Phthalimides and related compounds and their therapeutic utility
Abstract:Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. The compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. Depot derivatives of the compounds are useful for providing long acting effects of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.
Inventor(s): Glamkowski; Edward J. (Warren, NJ), Chiang; Yulin (Covent Station, NJ), Strupczewski; Joseph T. (Flemington, NJ), Nemoto; Peter A. (Raritan, NJ), Tegeler; John J. (Bridgewater, NJ)
Assignee: Hoechst Marion Roussel, Inc. (Kansas City, MO)
Filing Date:Jun 06, 1995
Application Number:08/465,863
Claims:1. A compound of the formula ##STR133## wherein, X is --O--, --S--, --NH--, or --N(R.sub.2)--; R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, alkoxycarbonyl, and phenysulfonyl groups;

aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino;

A is --C(.dbd.O)--, --C(.dbd.S)--, --C(.dbd.CH.sub.2)--, --C(.dbd.O)CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CR.sub.26 .dbd.N--, or --CR.sub.25 R.sub.26 --;

R.sub.25 is hydrogen, (C.sub.1 -C.sub.6)alkyl, hydroxy, or (C.sub.1 -C.sub.8) alkanoyloxy;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is CH or N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 --(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 -- where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24 --, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkoxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR134## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2, or halogen, and p is as previously defined, and wherein aryl is as defined hereinafter; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR135## where Z.sub.1 is as previously defined, and p is as previously defined, wherein aryl is as defined hereinafter;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S;

with the proviso that R.sub.23 is not hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR136## when R.sub.27 is hydrogen and R.sub.24 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR137## with the proviso that R.sub.24 is not hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR138## when R.sub.27 is hydrogen and n is 0; or when R.sub.27 is hydrogen and R.sub.23 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR139## or when R.sub.1 is --CHR.sub.24 --CH.dbd.CH--CHR.sub.24 -- or --CHR.sub.24 --C.tbd.C--CHR.sub.24 --;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, nitro, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl, wherein aryl is as defined hereinafter;

in which aryl is phenyl or ##STR140## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.1 -C.sub.18)alkanoyl group, in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

all geometric, optical, and stereoisomers thereof; or a pharmaceutically acceptable acid addition salt thereof.

2. A compound of the formula ##STR141## wherein, X is --O--, --S--, --NH--, or --N(R.sub.2)--; R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, alkoxycarbonyl, and phenysulfonyl;

aryl is as defined hereinafter;

p is 2;

Y is lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino when X is --S--, --NH--, or --N(R.sub.2)--;

Y is lower alkyl, trifluoromethyl, nitro, or amino when X is --O--;

A is --C(.dbd.O)--, --C(.dbd.S)--, --C(.dbd.CH.sub.2)--, --C(.dbd.O)CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CR.sub.26 .dbd.N--, or --CR.sub.25 R.sub.26 --;

R.sub.25 is hydrogen, (C.sub.1 -C.sub.6)alkyl, hydroxy, or (C.sub.1 -C.sub.8) alkanoyloxy;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is CH or N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 --(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 -- where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24 --, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkoxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR142## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, NH.sub.2, or halogen, and p is as previously defined, and wherein aryl is as defined hereinafter; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub..sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR143## where Z.sub.1 is as previously defined, and p is as previously defined, and wherein aryl is as defined hereinafter;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, nitro, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl, wherein aryl is as defined hereinafter;

in which aryl is phenyl or ##STR144## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 -C.sub.18)alkanoyl group, in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

all geometric, optical, and stereoisomers thereof; or a pharmaceutically acceptable acid addition salt thereof.

3. A compound of the formula ##STR145## wherein, X is --O--, --S--, --NH--, or --N(R.sub.2)--; R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, alkoxycarbonyl, and phenysulfonyl groups;

aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino;

A is --C(.dbd.O), --C(.dbd.S)--, --C(.dbd.CH.sub.2)--, --C(.dbd.O)CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CR.sub.26 .dbd.N--, or --CR.sub.25 R.sub.26 --;

R.sub.25 is hydrogen, (C.sub.1 -C.sub.6)alkyl, hydroxy, or (C.sub.1 -C.sub.8)alkanoyloxy;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is CH or N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 --(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 -- where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24 --, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, [phenyl(C.sub.1 -C.sub.6)alkoxy,] aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR146## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2, or halogen, and p is as previously defined, and wherein aryl is as defined hereinafter; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR147## where Z.sub.1 is as previously defined, and p is as previously defined, and wherein aryl is as defined hereinafter;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, nitro, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR148## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 -C.sub.18)alkanoyl group, in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

with the proviso that when A is --C(.dbd.O), R.sub.23 is not hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR149## when R.sub.27 is hydrogen and R.sub.24 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR150## with the proviso that when A is --C(.dbd.O), R.sub.24 is not hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR151## when R.sub.27 is hydrogen and n is 0; or when R.sub.27 is hydrogen and R.sub.23 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR152## or when R.sub.1 is --CHR.sub.24 --CH.dbd.CH--CHR.sub.24 -- or --CHR.sub.24 --C.tbd.C--CHR.sub.24 --;

with the proviso that when A is --CH.sub.2 CH.sub.2 --, or when A is --CR.sub.25 R.sub.26 and R.sub.25 and R.sub.26 are both hydrogen or (C.sub.1 -C.sub.6)alkyl, then B.sub.y and B.sub.z are not both CH, unless X is --NR.sub.2 and R.sub.2 is not alkyl, or unless R.sub.1 is subject to the proviso that R.sub.23 is not hydrogen or (C.sub.1 -C.sub.18)linear alkyl when R.sub.27 is hydrogen and R.sub.24 is hydrogen or (C.sub.1 -C.sub.18)linear alkyl, and the proviso that R.sub.24 is not hydrogen or (C.sub.1 -C.sub.18)linear alkyl when R.sub.27 is hydrogen and n is 0, or when R.sub.27 is hydrogen and R.sub.23 is hydrogen or (C.sub.1 -C.sub.18)linear alkyl, or when R.sub.1 is --CHR.sub.24 --CH.dbd.CH--CHR.sub.24 -- or --CHR.sub.24 --C.tbd.C--CHR.sub.24 --;

with the proviso that A is not --CR.sub.26 .dbd.N-- when B.sub.y and B.sub.z are both CH;

all geometric, optical, and stereoisomers thereof; or a pharmaceutically acceptable acid addition salt thereof.

4. A compound of the formula ##STR153## wherein, X is --O--, --S--, --NH--, or --N(R.sub.2)--; R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, alkoxycarbonyl, and phenysulfonyl groups;

aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino;

A is --C(.dbd.O)--, --C(.dbd.S)--, --C(.dbd.CH.sub.2)--, --C(.dbd.O)CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CR.sub.26 .dbd.N--, or --CR.sub.25 R.sub.26 --;

R.sub.25 is hydrogen, (C.sub.1 -C.sub.6)alkyl, hydroxy, or (C.sub.1 -C.sub.8) alkanoyloxy;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 --(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 -- where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24 --, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR154## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2, or halogen, and p is as previously defined, and wherein aryl is as defined hereinafter; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR155## where Z.sub.1 is as previously defined, and p is as previously defined, and wherein aryl is as defined hereinafter;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, nitro, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR156## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 -C.sub.18)alkanoyl group, in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

with the proviso that U is O, then A is not C.dbd.O;

all geometric, optical, and stereoisomers thereof; or a pharmaceutically acceptable acid addition salt thereof.

5. The compound of any one of claims 1 or 3, wherein A is C.dbd.O, B.sub.y and B.sub.z are CH, and U is O.

6. The compound of claim 5, wherein X is --O--.

7. The compound of claim 5, wherein X is --S--.

8. The compound of claim 5, wherein X is --NH--.

9. The compound of claim 6, which is N-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-hydroxy-1-propyl ]phthalimide and its pharmaceutically acceptable acid addition salts.

10. The compound of claim 6, which is 1-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-3-phthalimido-2-propy l decanoate and its pharmaceutically acceptable acid addition salts.

11. The compound of claim 6, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-4-(1-decanoy l)oxyphthalimide and its pharmaceutically acceptable acid addition salts.

12. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 10.

13. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 11.

14. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition claim 12 sufficient to produce a long acting antipsychotic effect.

15. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition claim 13 sufficient to produce a long acting antipsychotic effect.

16. The compound of any one of claims 1 or 3, wherein A is --CH(OH)--, B.sub.y and B.sub.z are CH, and U is O.

17. The compound of claim 16, wherein X is --O--.

18. The compound of claim 16, wherein X is --S--.

19. The compound of claim 16, wherein X is --NH--.

20. The compound of claim 17, which is 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2,3-dihydro- 3-hydroxy-1H-isoindol-1-one and its pharmaceutically acceptable acid addition salts.

21. The compound of claim 18, which is 2-[2-[4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]ethyl]-2,3-dihydr o-3-hydroxy-1H-isoindol-1-one and its pharmaceutically acceptable acid addition salts.

22. The compound of any one of claims 1 or 3, wherein A is C(.dbd.S), B.sub.y and B.sub.z are CH, and U is O.

23. The compound of claim 22, wherein X is --O--.

24. The compound of claim 23, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]thiaphthalimi de and its pharmaceutically acceptable acid addition salts.

25. The compound of any one of claims 1 or 3, wherein A is C(.dbd.S), B.sub.y and B.sub.z are CH,and U is S.

26. The compound of claim 25, wherein X is --O--.

27. The compound of claim 27, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-1,3-bis-thia phthalimide and its pharmaceutically acceptabele acid addition salts.

28. The compound of any one of claims 1 or 3, wherein A is C(CH.sub.3)OH, B.sub.y and B.sub.z are CH, and U is O.

29. The compound of claim 28, wherein X is --O--.

30. The compound of claim 29, which is 2,3-dihydro-2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidyinyl]ethyl] -3-hydroxy-3-methyl-1-H-isoindol-1-one and its pharmaceutically acceptable acid addition salts.

31. The compound of any one of claims 1 or 3, wherein A is CH(CH.sub.3), B.sub.y and B.sub.z are CH, and U is O.

32. The compound of any one of claims 1 or 3, wherein A is C.dbd.CH.sub.2, B.sub.y and B.sub.z are CH, and U is O.

33. The compound of claim 32, wherein X is --O--.

34. The compound of claim 33, which is 2,3-dihydro-2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]- 3-methylene-1H-isoindol-1-one and its pharmaceutically acceptable acid addition salts.

35. The compound of any one of claims 1 or 3, wherein A is CH.sub.2, B.sub.y and B.sub.z are CH, and U is O.

36. The compound of any one of claims 1 or 3, wherein A is --C(.dbd.O)CH.sub.2 --, B.sub.y and B.sub.z are CH, and U is O.

37. The compound of claim 36, wherein X is --O--.

38. The compound of claim 37, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-1,2,3,4-tetr ahydroisoquinolin-1,3-dione and its pharmaceutically acceptable acid addition salts.

39. The compound of any one of claims 1 or 4, wherein A is C.dbd.O, B.sub.y is CH, B.sub.z is N, and U is O.

40. The compound of any one of claims 1 or 3, wherein A is --CR.sub.26 .dbd.N--, B.sub.y and B.sub.z are CH, and U is O.

41. The compound of any one of claims 1, 2, 3 or 4, wherein X is --NR.sub.2 --.

42. An antipsychotic composition, which comprises the compound of any one of claims 2, 3 or 4 in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier.

43. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of the compound of any one of claims 1-4.

44. An analgesic composition, which comprises the compound of any one of claims 1, 2, 3 or 4 in an amount sufficient to produce a pain-relieving effect and a pharmaceutically acceptable carrier.

45. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of the compound of any one of claims 1, 2, 3 or 4.

46. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of any one of claims 1, 2, 3 or 4, wherein the compound contains an acylated hydroxy group, or an acylated amino group.

47. The compound of claim 41, wherein R.sub.2 is (C.sub.1 -C.sub.18)alkanoyl or (C.sub.1 -C.sub.18)alkoxycarbonyl.

48. The depot pharmaceutical composition of claim 46, wherein the hydroxy group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group, or the amino group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group or a (C.sub.4 -C.sub.18)alkoxycarbonyl group.

49. The composition of claim 46, which contains a pharmaceutically acceptable oil.

50. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 46 sufficient to produce a long acting antipsychotic effect.

51. The composition of claim 49, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols.

52. The composition of claim 48, which contains a pharmaceutically acceptable oil.

53. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 48 sufficient to produce a long acting antipsychotic effect.

54. The composition of claim 52, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols.

55. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 54 sufficient to produce a long acting antipsychotic effect.

56. A compound having the formula: ##STR157## wherein, X is --O--, --S--, ##STR158## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, and phenylsulfonyl groups, wherein aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;

Y is lower alkoxy, hydroxy or halogen when p is 2 and X is --O--;

in which (R.sub.1) is R.sub.20, R.sub.21 or R.sub.22, wherein:

R.sub.20 is --(CH.sub.2).sub.n --, where n is 2, 3, 4 or 5;

R.sub.21 is

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --C.tbd.C--CH.sub.2 --,

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2,

--CH.sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --C.tbd.C--CH.sub.2 --CH.sub.2 --, or

--CH.sub.2 --CH.sub.2 --C.tbd.C--CH.sub.2 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1 -C.sub.6 linear alkyl group, phenyl group or ##STR159## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, mono- or dialkylamino, C.sub.1 -C.sub.3 acyl amino, C.sub.1 -C.sub.6 alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, ##STR160## (C.sub.1 -C.sub.12 straight or branched chain) alkyl, or ##STR161## in which aryl is phenyl or ##STR162## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy;

q is 1, 2, 3, or 4;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

all geometric, optical, and stereoisomers thereof, or a pharmaceuticaly acceptable acid addition salt thereof.

57. The compound of claim 56, wherein X is --N(R.sub.2)--.

58. The compound of claim 56, wherein R.sub.1 is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH(CH.sub.3)--, or --CH(CH.sub.3)CH.sub.2 --.

59. A pharmaceutical composition which comprises the compound of claim 56 and a pharmaceutically acceptable carrier therefor.

60. An antipsychotic composition, which comprises the compound of claim 56 in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier.

61. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of the compound of claim 56.

62. An analgesic composition, which comprises the compound of claim 56 in an amount sufficient to produce a pain-relieving effect and a pharmaceutically acceptable carrier.

63. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of the compound of claim 56.

64. The compound of claim 57, wherein R.sub.2 is (C.sub.1 -C.sub.12)alkanoyl.

65. The compound of claim 61, wherein X=0.

66. The compound of claim 61, wherein X=S.

67. The compound of claim 61, wherein X=NH.

68. The compound of claim 65, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-4-fluorophth alimide and its pharmaceutically acceptable acid addition salts.

69. The compound of claim 66, which is N-[2-[4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]ethyl]-4-methylph thalimide and its pharmaceutically acceptable acid addition salts.

70. The compound of claim 66, which is N-[2-[4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]ethyl]phthalimide and its pharmaceutically acceptable acid addition salts.

71. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 68.

72. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition claim 71 sufficient to produce a long acting antipsychotic effect.

73. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of a compound of the formula ##STR163## wherein, X is --O--, --S--, --NH--, or --N(R.sub.2)--; R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, alkoxycarbonyl, and phenysulfonyl groups;

aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino;

A is --CR.sub.26 .dbd.N--;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is CH or N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 --(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 -- where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24 --, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR164## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2, or halogen, and p is as previously defined, and wherein aryl is as defined hereinafter; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR165## where Z.sub.1 is as previously defined, and p is as previously defined, and wherein aryl is as defined hereinafter;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, nitro, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR166## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 -C.sub.18)alkanoyl group, in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

all geometric, optical, and stereoisomers thereof; or a pharmaceutically acceptable acid addition salt thereof.

74. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound having the formula: ##STR167## wherein, X is --O--, --S--, ##STR168## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, and phenylsulfonyl groups, wherein aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;

Y is lower alkoxy, hydroxy or halogen when p is 2 and X is --O--; in which (R.sub.1) is R.sub.20, R.sub.21 or R.sub.22, wherein:

R.sub.20 is --(CH.sub.2).sub.n --, where n is 2, 3, 4 or 5;

R.sub.21 is

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --C.tbd.C--CH.sub.2 --,

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --,

--CH.sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --C.tbd.C--CH.sub.2 --CH.sub.2 --, or

--CH.sub.2 --CH.sub.2 --C.tbd.C--CH.sub.2 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1 -C.sub.6 linear alkyl group, phenyl group or ##STR169## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen;

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, mono- or dialkylamino, C.sub.1 -C.sub.3 acyl amino, C.sub.1 -C.sub.6 alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, ##STR170## (C.sub.1 -C.sub.12 straight or branched chain)alkyl, or ##STR171## in which aryl is phenyl or ##STR172## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy;

q is 1, 2, 3, or 4;

with the proviso that R.sub.4 is not hydrogen when Y is 6-F, X is --O--, and n is 2, 3, or 4;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 .sub.14 C.sub.18)alkanoyl group, in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof;

wherein the compound contains an acylated hydroxy group, or an acylated amino group.

75. The depot pharmaceutical composition of claim 74, wherein the hydroxy group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group, or the amino group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group or a (C.sub.4 -C.sub.18)alkoxycarbonyl group.

76. The composition of claim 74, which contains a pharmaceutically acceptable oil.

77. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 74 sufficient to produce a long acting antipsychotic effect.

78. The composition of claim 76, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols.

79. The composition of claim 75, which contains a pharmaceutically acceptable oil.

80. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 75 sufficient to produce a long acting antipsychotic effect.

81. The composition of claim 79, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols.

82. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 81 sufficient to produce a long acting antipsychotic effect.

83. The compound of claim 6, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-4-(1-decanoy l)aminophthalimide and its pharmaceutically acceptable acid addition salts.

84. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 83.

85. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition claim 84 sufficient to produce a long acting antipsychotic effect.

86. The compound which is decanoic acid 2-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-3-oxo-2,3-di hydro-1H-isoindol-1-yl ester and its pharmaceutically acceptable acid addition salts.

87. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 86.

88. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition claim 87 sufficient to produce a long acting antipsychotic effect.

89. A pharmaceutically acceptable acid addition salt of N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]phthalimide.

90. The acid addition salt of claim 89, which is N-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]phthalimide hydrochloride.

91. An antipsychotic composition, which comprises the compound of claim 89 in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier.

92. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of a compound of claim 89.

93. An antipsychotic composition, which comprises the compound of claim 90, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier.

94. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of the compound of claim 90.
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