3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles
AssigneeJanssen Pharmaceutica NV
InventorsLudo E. J. Kennis, Jan Vandenberk
Life of this patent
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Abstract
3-Piperdinyl-1,2-benzisothiazoles and 3-piperidinyl-1,2-benzisoxazoles and their pharmaceutically acceptable acid addition salts having useful antipsychotic properties and being useful in the treatment of a variety of complaints in which serotonin release is of predominant importance.
Claims18
A chemical compound having the formula ##STR17## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C.sub.1-6 alkyl;
- R.sup.1 and R.sup.2 are each independently members selected from the group consisting of hydrogen, halo, hydroxy, C.sub.1-6 alkyloxy and C.sub.1-6 alkyl;
- X is O or S;
- Alk is C.sub.1-4 alkanediyl;
- and
- Q is a radical of formula ##STR18## wherein Y.sup.1 and Y.sup.2 are each independently O or S;
- R.sup.3 is a member selected from the group consisting of hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, nitro, cyano, hydroxy, (C.sub.1-10 alkylcarbonyl)oxy, amino, mono- and di(C.sub.1-6 alkyl)amino, (C.sub.1-10 alkylcarbonyl)amino, phenylmethoxy and azido;
- R.sup.4 is hydrogen or halo;
- or a radical of formula ##STR19## wherein R.sup.5 is hydrogen or C.sub.1-6 alkyl;
- Z is --S--, --CH.sub.2 -- or --CR.sup.6 .dbd.CR.sup.7 --;
- said R.sup.6 and R.sup.7 being each independently hydrogen or C.sub.1-6 alkyl;
- and
- A is a bivalent radical --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or --CR.sup.8 .dbd.CR.sup.9 --, said R.sup.8 and R.sup.9 being each independently hydrogen, halo, amino or C.sub.1-6 alkyl.
A pharmaceutical composition for treating psychotic diseases, comprising an inert carrier and as an active ingredient a pharmaceutically effective amount of a chemical compound having the formula ##STR20## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen or C.sub.1-6 alkyl;
- R.sup.1 and R.sup.2 are each independently members selected from the group consisting of hydrogen, halo, hydroxy, C.sub.1-6 alkyloxy and C.sub.1-6 alkyl;
- X is O or S;
- Alk is C.sub.1-4 alkanediyl;
- and
- Q is a radical of formula ##STR21## wherein Y.sup.1 and Y.sup.2 are each independently O or S;
- R.sup.3 is a member selected from the group consisting of hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, nitro, cyano, hydroxy, (C.sub.1-10 alkylcarbonyl)oxy, amino, mono- and di(C.sub.1-6 alkyl)amino, (C.sub.1-10 alkylcarbonyl)amino, phenylmethoxy and azido;
- R.sup.4 is hydrogen or halo;
- or
- a radical of formula ##STR22## wherein R.sup.5 is hydrogen or C.sub.1-6 alkyl;
- Z is --S--, --CH.sub.2 -- or --CR.sup.6.dbd.CR.sup.7 --;
- said R.sup.6 and R.sup.7 being each independently hydrogen or C.sub.1-6 alkyl;
- and
- A is a bivalent radical --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or --CR.sup.8 .dbd.CR.sup.9 --, said R.sup.8 and R.sup.9 being each independently hydrogen, halo, amino or C.sub.1-6 alkyl.
A method of treating warm-blooded animals suffering from psychotic diseases which comprises the administration thereto of a pharmaceutically effective amount of a chemical compound having the formula ##STR23## or a pharmaceutical acceptable acid addition salt thereof, wherein R is hydrogen or C.sub.1-6 alkyl;
- R.sup.1 and R.sup.2 are each independently members selected from the group consisting of hydrogen, halo, hydroxy, C.sub.1-6 alkyloxy and C.sub.1-6 alkyl;
- X is O or S;
- Alk is C.sub.1-4 alkanediyl;
- and
- Q is a radical of formula ##STR24## wherein Y.sup.1 and Y.sup.2 are each independently O or S;
- R.sup.3 is a member selected from the group consisting of hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, nitro, cyano, hydroxy, (C.sub.1-10 alkylcarbonyl)oxy, amino, mono- and di(C.sub.1-6 alkyl)amino, (C.sub.1-10 alkylcarbonyl)amino, phenylmethoxy and azido;
- R.sup.4 is hydrogen or halo;
- or a radical of formula ##STR25## wherein R.sup.5 is hydrogen or C.sub.1-6 alkyl;
- Z is --S--, --CH.sub.2 -- or --CR.sup.6 .dbd.CR.sup.7 --;
- said R.sup.6 and R.sup.7 being each independently hydrogen or C.sub.1-6 alkyl;
- and
- A is a bivalent radical --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or --CR.sup.8 .dbd.CR.sup.9 --;
- said R.sup.8 and R.sup.9 being each independently hydrogen, halo, amino or C.sub.1-6 alkyl.
Dependencies are inferred from the claim text.