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Claims for Patent: 4,804,663

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Claims for Patent: 4,804,663

Title: 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles
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.
Inventor(s): Kennis; Ludo E. J. (Turnhout, BE), Vandenberk; Jan (Beerse, BE)
Assignee: Janssen Pharmaceutica N.V. (Beerse, BE)
Application Number:06/826,517
Patent Claims: 1. 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.

2. A chemical compound according to claim 1, wherein Q is a radical of formula (a) wherein R.sup.3 is hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, hydroxy, amino or azido and R.sup.4 is hydrogen; or Q is a radical of formula (b) wherein R.sup.5 is 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 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or C.sub.1-6 alkyl.

3. A chemical compound according to claim 2, wherein R is hydrogen, R.sup.1 is hydrogen or halo and R.sup.2 is hydrogen, halo, hydroxy or C.sub.1-6 alkyloxy.

4. A chemical compound according to claim 3, wherein Q is a radical of formula (a) wherein R.sup.3 is hydrogen, halo or methyl and Y.sup.1 is O; or Q is a radical of formula (b) wherein --Z--A-- is --S--CH.sub.2 --CH.sub.2 --, --S--(CH.sub.2).sub.3 --, --S--CR.sup.8 .dbd.CR.sup.9 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or methyl, --CH.dbd.CH--CR.sup.8 .dbd.CR.sup.9 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or methyl, or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --.

5. A chemical compound according to claim 4, wherein R.sup.1 is hydrogen, and R.sup.2 is hydrogen, halo, hydroxy or methoxy.

6. A chemical compound according to claim 1 wherein the compound is 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetr ahydro-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one or 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2-methyl-4H- pyrido[1,2-a]pyrimidin-4-one.

7. 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.

8. A pharmaceutical composition according to claim 7 wherein Q is a radical of formula (a) wherein R.sup.3 is hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, hydroxy, amino or azido and R.sup.4 is hydrogen; or Q is a radical of formula (b) wherein R.sup.5 is 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 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or C.sub.1-6 alkyl.

9. A pharmaceutical composition according to claim 8 wherein R is hydrogen, R.sup.1 is hydrogen or halo and R.sup.2 is hydrogen, halo, hydroxy or C.sub.1-6 alkyloxy.

10. A pharmaceutical composition according to claim 9 wherein Q is a radical of formula (a) wherein R.sup.3 is hydrogen, halo or methyl and Y.sup.1 is O; or Q is a radical of formula (b) wherein --Z--A-- is --S--CH.sub.2 --CH.sub.2 --, --S--(CH.sub.2).sub.3 --, --S--CR.sup.8 .dbd.CR.sup.9 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or methyl, --CH.dbd.CH--CR.sup.8 .dbd.CR.sup.9 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or methyl, or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --.

11. A pharmaceutical composition according to claim 10 wherein R.sup.1 is hydrogen, and R.sup.2 is hydrogen, halo, hydroxy or methoxy.

12. A pharmaceutical composition according to claim 7 wherein the compound is 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetr ahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one or 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2-methyl-4H- pyrido[1,2-a]pyrimidin-4-one.

13. 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.

14. A method according to claim 13 wherein Q is a radical of formula (a) wherein R.sup.3 is hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, hydroxy, amino or azido and R.sup.4 is hydrogen; or Q is a radical of formula (b) wherein R.sup.5 is 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 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or C.sub.1-6 alkyl.

15. A method according to claim 14 wherein R is hydrogen, R.sup.1 is hydrogen or halo and R.sup.2 is hydrogen, halo, hydroxy or C.sub.1-6 alkyloxy.

16. A method according to claim 15 wherein Q is a radical of formula (a) wherein R.sup.3 is hydrogen, halo or methyl and Y.sup.1 is O; or Q is a radical of formula (b) wherein --Z--A-- is --S--CH.sub.2 --CH.sub.2 --, --S--(CH.sub.2).sub.3 --, --S--CR.sup.8 .dbd.CR.sup.9 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or methyl, --CH.dbd.CH--CR.sup.8 .dbd.CR.sup.9 -- wherein R.sup.8 and R.sup.9 are each independently hydrogen or methyl, or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --.

17. A method according to claim 16 wherein R.sup.1 is hydrogen, and R.sup.2 is hydrogen, halo, hydroxy or methoxy.

18. A method according to claim 13 wherein the compound is 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetr ahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one or 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2-methyl-4H- pyrido[1,2-a]pyrimidin-4-one.
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