Claims
- 1. A compound of the formula ##STR229## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkoxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, amino, (C.sub.1 -C.sub.6)alkylamino, di(C.sub.1 -C.sub.6)alkylamino, aryl(C.sub.1 -C.sub.6)alkylamino, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, aryl(C.sub.1 -C.sub.6)alkylcarbonyloxy; with the proviso that when halo is present another substituent is present;
- R.sup.1 is hydrogen, (C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, arylo[w]xycarbonyl, aryl(C.sub.1 -C.sub.6)alkoxycarbonyl, aminocarbonyl, (C.sub.1 -C.sub.6)alkylaminocarbonyl or di(C.sub.1 -C.sub.6)alkylaminocarbonyl; and ##STR230## R.sup.2 is where R.sup.6 is hydrogen, (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkylcarbonyl, aryl(C.sub.1 -C.sub.6)alkylcarbonyl or (C.sub.1 -C.sub.6)alkoxycarbonyl; or
- R.sup.1 and R.sup.2 together with the nitrogen to which they are attached form the ring ##STR231## where R.sup.7 is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.3 -C.sub.6)alkynyl, phenyl, aryl(C.sub.1 -C.sub.6)alkyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or quinolinyl; R.sup.8 and R.sup.9 are independently hydrogen, (C.sub.1 -C.sub.6)alkyl or aryl(C.sub.1 -C.sub.6)alkyl;
- m is an integer from 2 to 7;
- n is an integer from 1 to 3;
- p is an integer from 1 to 3;
- s is an integer from 0 to 6;
- and pharmaceutically acceptable addition salts thereof and optical and geometric isomers and racemic mixtures thereof.
- 2. The compound of claim 1 of the formula ##STR232## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.1 is hydrogen (C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, aryloxycarbonyl, aryl(C.sub.1 -C.sub.6)alkoxycarbonyl, aminocarbonyl, (C.sub.1 -C.sub.6)alkylaminocarbonyl, or di(C.sub.1 -C.sub.6)alkylaminocarbonyl;
- R.sup.6 is hydrogen, (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkylcarbonyl, aryl(C.sub.1 -C.sub.6)alkylcarbonyl or (C.sub.1 -C.sub.6)alkoxycarbonyl;
- m is an integer from 2 to 7;
- n is an integer from 0 to 3; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomer or racemic mixture thereof.
- 3. The compound of claim 2 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.1 is hydrogen or (C.sub.1 -C.sub.6)alkyl;
- R.sup.6 is aryl(C.sub.1 -C.sub.6)alkyl;
- n is 1 or 2; and
- m is 2, 3 or 4.
- 4. The compound of claim 3 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy;
- R.sup.1 is hydrogen or methyl;
- R.sub.6 is phenylmethyl; and
- m is 2.
- 5. The compound of claim 4 which is 6-methoxy-N-methyl-N-[2-[1-(4-phenylmethyl)piperazinyl]ethyl]-1,2-benzisoxazol-3-amine difumarate and its pharmaceutically acceptable acid addition salts.
- 6. A compound which is 6-methoxy-3-(1-piperazinyl)-1,2-benzisoxazole hemihydrate and its pharmaceutically acceptable acid addition salts.
- 7. The compound of claim 1 of the formula ##STR233## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy; and
- n is an integer from 0 to 3; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomer or racemic mixture thereof.
- 8. The compound of claim 7 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy; and
- n is 1 or 2.
- 9. The compound of claim 8 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy.
- 10. The compound of claim 9 which is 6-methoxy-3-[1-[4-(2-propynyl)]piperazinyl]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 11. The compound of claim 1 of the formula ##STR234## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy; and
- n is an integer from 0 to 3; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomer or racemic mixture thereof.
- 12. The compound of claim 11 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy; and
- n is 1 or 2.
- 13. The compound of claim 12 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy.
- 14. The compound of claim 13 which is 6-methoxy-3-[1-(N-phenylpiperazinyl]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 15. A compound of the formula ##STR235## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, or tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.11 is (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, hydroxy, halogen, nitro or trifluoromethyl;
- n is an integer from 0 to 3;
- r is an integer from 0 to 2; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomers or racemic mixture thereof.
- 16. The compound of claim 15 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.11 is (C.sub.1 -C.sub.6)alkyl or halogen;
- n is 1 or 2; and
- r is 0 or 1.
- 17. The compound of claim 16 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy
- R.sup.11 is methyl or hydrogen; and
- r is 0 or 1.
- 18. The compound of claim 17 which is 6-methoxy-3-[1-(4-pyridyl)piperazinyl)]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 19. The compound of claim 17 which is 3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazol-6-ol and it pharmaceutically acceptable acid addition salts.
- 20. The compound of claim 17 which is 3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazol-6-yl dimethylcarbamate and it pharmaceutically acceptable acid addition salts.
- 21. The compound of claim 17 which is 6-methoxy-3-[1-(2-pyridyl)piperazinyl]-1,2-benzisoxazole and it pharmaceutically acceptable acid addition salts.
- 22. The compound of claim 1 of the formula ##STR236## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.11 is halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, hydroxy, nitro or trifluoromethyl;
- n is an integer from 0 to 3;
- r is an integer from 0 to 2; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomers or racemic mixture thereof.
- 23. The compound of claim 22 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy or di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.11 is (C.sub.1 -C.sub.6)alkyl or halo;
- n is 1 or 2; and
- r is 0 or 1.
- 24. The compound of claim 23 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy; and
- R.sup.11 is chloro or hydrogen.
- 25. The compound of claim 24 which is 3-[1-(4-(6-chloropyrimidyl)piperazinyl]-6-methoxy-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 26. A compound of the formula ##STR237## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.11 is halogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, hydroxy, nitro or trifluoromethyl;
- n is an integer from 0 to 3;
- r is an integer from 0 to 2; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomers or racemic mixture thereof.
- 27. The compound of claim 26 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.11 is halogen or (C.sub.1 -C.sub.6)alkyl;
- n is 1 or 2; and
- r is 0 or 1.
- 28. The compound of claim 27 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy; and
- R.sup.11 is chloro or hydrogen.
- 29. The compound of claim 28 which is 3-[1-(3-(6-chloro)pyridazinyl)piperazinyl]-6-methoxy-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 30. A compound of the formula ##STR238## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.11 is halogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, hydroxy, nitro or trifluoromethyl;
- n is an integer from 0 to 3;
- r is an integer from 0 to 2; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomers or racemic mixture thereof.
- 31. The compound of claim 30 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.11 is halo or (C.sub.1 -C.sub.6)alkyl;
- n is 1 or 2; and
- r is 0 or 1.
- 32. The compound of claim 31 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy; and
- R.sup.11 is chloro or hydrogen.
- 33. The compound of claim 32 which is 3-[1-(2-(6-chloro)pyridazinyl)piperazinyl]-6-methoxy-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 34. The compound of claim 1 of the formula ##STR239## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.11 is halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, hydroxy, nitro or trifluoromethyl;
- n is an integer from 0 to 3;
- r is an integer from 0 to 2; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomers or racemic mixture thereof.
- 35. The compound of claim 24 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.11 is (C.sub.1 -C.sub.6)alkyl;
- n is 1 or 2; and
- r is 0 or 1.
- 36. The compound of claim 35 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy; and
- p is 0 or 1; and
- R.sup.11 is methyl or hydrogen
- and pharmaceutically acceptable acid addition salts thereof and the optical and geometric isomers or racemic mixture of.
- 37. The compound of claim 36 which 6-methoxy-3-[1-(4-phenylmethyl)piperazinyl]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 38. The compound of claim 36 which is 6-methoxy-3-[1-[4-(3-methyl)phenylmethyl]piperazinyl]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 39. A compound of the formula ##STR240## wherein X is hydrogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyloxymethyleneoxy, aryl(C.sub.1 -C.sub.6)alkoxy, halo, hydroxy, (C.sub.1 -C.sub.6)alkanoylamino, aminocarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, di(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, aryl(C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.1 -C.sub.6)alkoxycarbonyloxy, tetrahydroisoquinolylcarbonyloxy or aryl(C.sub.1 -C.sub.6)alkycarbonyloxy;
- R.sup.11 is halogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, hydroxy, nitro or trifluoromethyl;
- n is an integer from 0 to 3;
- r is an integer from 0 to 2; and
- pharmaceutically acceptable acid addition salts thereof and optical and geometric isomers or racemic mixture thereof.
- 40. The compound of claim 39 wherein
- X is hydrogen, hydroxy, halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.8)alkylaminocarbonyloxy, tetrahydroisoquinolylcarbonyloxy, di(C.sub.1 -C.sub.8)alkylaminocarbonyloxy or aryl(C.sub.1 -C.sub.6)alkylaminocarbonyloxy;
- R.sup.11 is halogen or trifluoromethyl;
- n is 1 or 2; and
- r is 0 or 1.
- 41. The compound of claim 40 wherein
- X is hydrogen, 5-hydroxy, 5-methoxy, 5-methylaminocarbonyloxy, 5-dimethylaminocarbonyloxy, 5-methylethylaminocarbonyloxy, 5-bromo, 7-bromo, 5-phenylmethylaminocarbonyloxy, 6-chloro, 6-hydroxy, 6-methoxy, 6-methylaminocarbonyloxy, 6-methylethylaminocarbonyloxy, 6-dimethylaminocarbonyloxy, 6-phenylmethylaminocarbonyloxy, 5-hexylaminocarbonyloxy, 5-heptylaminocarbonyloxy, 5-tetrahydroisoquinol-2-ylcarbonyloxy, 6-hexylaminocarbonyloxy, 6-heptylaminocarbonyloxy or 6-tetrahydroisoquinol-2-ylcarbonyloxy; and
- R.sup.11 is hydrogen, trifluoromethyl or chloro.
- 42. The compound of claim 41 which is 6-methoxy-3-[1-(4-quinolinyl)piperazinyl]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 43. The compound of claim 41 which is 6-methoxy-3-[1-(4-(7-trifluoromethyl)quinolinyl)piperazinyl]-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 44. The compound of claim 41 which is 3-[1-(4-(7-chloro)quinolinyl)piperazinyl]-6-methoxy-1,2-benzisoxazole and its pharmaceutically acceptable acid addition salts.
- 45. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and a pharmaceutically effective amount of the compound of claim 1.
- 46. A method of alleviating memory dysfunction which comprises administering to a patient an effective amount of the compound of claim 1.
- 47. A method of treating depression which comprises administering to a patient an effective amount of the compound of claim 1.
Parent Case Info
This application is a divisional of U.S. appln. Ser. No. 08/150,301, filed Nov. 12, 1993, now issued U.S. Pat. No. 5,494,908; which is a continuation-in-part application of U.S. appln. Ser. No. 07/980,021, filed Nov. 23, 1992, now abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
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Divisions (1)
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Number |
Date |
Country |
Parent |
150301 |
Nov 1993 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
980021 |
Nov 1992 |
|