Claims
- 1. A compound selected from the group consisting of racemic or diastereoisomer forms of a 4-benzyl-1H-indole compound of the formula ##STR24## wherein R.sub.1 and R taken together with the nitrogen to which they are attached form morpholino or piperazyinyl optionally substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, phenyl, naphthyl, aralkyl and diaralkyl of 7 to 14 carbon atoms, A is ##STR25## or --(CH.sub.2).sub.n, n is 2, 3, 4 or 5, X and Y are both hydrogen or one is hydrogen and the other is selected from the group consisting of --OH, alkoxy and alkyl of 1 to 4 carbon atoms, or X and Y together form a member of the group consisting of .dbd.O, alkylidene of 1 to 4 carbon atoms, a, b, c and d are all hydrogen or a and b form .dbd.O and c and d are hydrogen or one of a and b with one of c and d form a carbon-carbon bond and the others are both hydrogen, Z is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, alkenyl and alkynyl of 2 to 5 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms and aralkyl of 7 to 14 carbon atoms, all optionally substituted with at least one member of the group consisting of --OH, halogen and alkyl and alkoxy of 1 to 5 carbon atoms and ##STR26## R.sub.2 is alkylene of 2 to 5 carbon atoms, R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms and aralkyl of 7 to 12 carbon atoms, all optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl or alkoxy of 1 to 5 carbon atoms, hydroxy, trifluoromethyl, methylthio, nitro, amino and monoalkylamino or dialkylamino where in alkyl of 1-5 carbon atoms or taken together with the nitrogen to which they are attached form morpholino or piperazinyl optionally substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, phenyl, naphthyl and aralkyl and diaralkyl of 7 to 14 carbon atoms or its non-toxic, pharmaceutically acceptable acid addition salts.
- 2. A compound of claim 1 wherein Z is hydrogen or alkyl of 1 to 4 carbon atoms.
- 3. A compound of claim 1 wherein X and Y are both hydrogen or together are .dbd.O or alkylidene.
- 4. A compound of claim 1 wherein A is ##STR27## or --(CH.sub.2).sub.n -- and n is 2 or 3.
- 5. A compound of claim 1 wherein a and b are .dbd.O and c and d are hydrogen or one of a and b together with one of c and d form a carbon-carbon bond and the other two are hydrogen.
- 6. A compound of claim 1 wherein is (.+-.) [2-[2-hydroxy-3-(4-methyl -1-piperazinyl)-propoxy]-phenyl]-(1H-indol-4-yl)-methanone and its non-toxic, pharmaceutically acceptable acid addition salts.
- 7. An antiarhythmic composition comprising an anti-arhythmically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
- 8. A composition of claim 7 wherein in the active compound Z is hydrogen or alkyl of 1 to 4 carbon atoms.
- 9. A composition of claim 7 wherein in the active compound X and Y are both hydrogen or together are .dbd.O or alkylidene.
- 10. A composition of claim 7 wherein in A is ##STR28## or (CH.sub.2).sub.n -- and n is 2 or 3.
- 11. A composition of claim 7 wherein in the active compound a and b are .dbd.O and c and d are hydrogen or one of a and b together with one of c and d form a carbon-carbon bond and the other two are hydrogen.
- 12. A composition of claim 7 wherein the compound is (.+-.) [2-[2-hydroxy-3-(4-methyl-1-piperazinyl)-propoxy]-phenyl]-(1H-indol-4-yl)-methanone and its non-toxic, pharmaceutically acceptable acid addition salts.
- 13. A method of inducing antiarhythmic activity in warm-blooded animals comprising administering to warm-blooded animals an antiarhythmically effective amount of at least one compound of claim 1.
- 14. A method of claim 13 wherein in the active compound Z is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, alkenyl and alkynyl of 2 to 5 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms, aralkyl of 7 to 14 carbon atoms optionally having 1 to 3 substituents selected from the group consisting of --OH, halogen, and alkyl and alkoxy of 1 to 5 carbon atoms and ##STR29## wherein R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and R.sub.2 is alkylene of 2 to 5 carbon atoms.
- 15. A method of claim 13 wherein Z is hydrogen or alkyl of 1 to 4 carbon atoms.
- 16. A method of claim 13 wherein X and Y are both hydrogen or together are .dbd.O or alkylidene.
- 17. A method of claim 13 wherein A is ##STR30## or --(CH.sub.2).sub.n -- and n is 2 or 3. carbon atoms.
- 18. A method of claim 13 wherein a and b are .dbd.O and c and d are hydrogen or one of a and b together with one of c and d form a carbon-carbon bond and the other two are hydrogen.
- 19. A method of claim 13 wherein the compound is (.+-.) [2-[2-hydroxy-3-(4-methyl-1-piperazinyl)-propoxy ]-phenyl]-(1H-indol-4-yl)-methanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Priority Claims (1)
Number |
Date |
Country |
Kind |
89 05650 |
Apr 1989 |
FRX |
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PRIOR APPLICATION
This application is a division of U.S. Pat. application Ser. No. 514,695, filed Apr. 26, 1990, now U.S. Pat. No. 5,086,070.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4808609 |
Clemence et al. |
Feb 1989 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
514695 |
Apr 1990 |
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