Claims
- 1. A pharmaceutical composition useful for its sedative and tranquilizing effects comprising
- (a) 1 to 200 mg. of a compound selected from the group consisting of a 1-substituted-4-benzylpiperidine of the formula ##STR9## wherein; R is selected from the group consisting of p-fluorobenzoylpropyl, p-acetyl-o-methoxyphenoxypropyl, carbamoyl, N-lower-alkylcarbamoyl, N,N-dilower-alkylcarbamoyl, N-phenylcarbamoyl, N-(m-trifluoromethylphenyl)carbamoyl, N-(.omega.-morpholino)lower-alkylcarbamoyl, N-[.omega.-(2-pyridyl)lower-alkyl]carbamoyl, 2-hydroxy-3-(o-methoxyphenoxy)propyloxycarbonyl, 2-carbamoylethyl or 4-(p-fluorobenzoyl)piperidinoethyl,
- R.sup.1 is selected from the group consisting of hydrogen or hydroxy,
- R.sup.2 is selected from the group consisting of phenyl, p-fluorophenyl, m-trifluoromethylphenyl or cyclohexyl,
- Y is selected from the group consisting of hydrogen or fluorine,
- with the proviso that when Y is hydrogen and R.sup.2 is phenyl, R is other than p-fluorobenzoylpropyl, and a pharmaceutically acceptable acid addition salt of a basic compound thereof, and
- (b) a pharmaceutically acceptable carrier therefor.
- 2. A composition of claim 1 wherein R.sup.1 represents hydroxy.
- 3. A composition of claim 2 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)-p-fluorobenzylpiperidine.
- 4. A composition of claim 2 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)benzylpiperidine.
- 5. A composition of claim 2 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)-p-fluorobenzylpiperidine.
- 6. A composition of claim 2 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-m-trifluoromethylphenyl-.alpha.-hydroxy) benzylpiperidine.
- 7. A composition of claim 2 wherein the compound is N-phenyl-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)-p-fluorobenzylpiperidine-1-carboxamide.
- 8. A composition of claim 2 wherein the compound is N-phenyl-4-(.alpha.-cyclohexyl-.alpha.-hydroxy)benzylpiperidine-1-carboxamide.
- 9. A composition of claim 2 wherein the compound is 1-acetyl-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)benzylpiperidine.
- 10. A composition of claim 1 wherein R.sup.1 represents hydrogen.
- 11. A composition of claim 10 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine.
- 12. A composition of claim 10 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine.
- 13. A composition of claim 10 wherein the compound is N-(2-morpholinoethyl)-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine-1-carboxamide.
- 14. A composition of claim 10 wherein the compound is N-[2-(2-pyridyl)ethyl]-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine-1-carboxamide.
- 15. A composition of claim 10 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-cyclohexyl)benzylpiperidine.
- 16. A composition of claim 10 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-phenyl)benzylpiperidine
- 17. A composition of claim 10 wherein the compound is 1-(2-carbamoylethyl)-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine.
- 18. A method of sedating or tranquilizing a living animal which comprises administering to said animal a compound selected from the group consisting of a 1-substituted-4-benzylpiperidine of the formula ##STR10## wherein; R is selected from the group consisting of, p-fluorobenzoylpropyl, p-acetyl-o-methoxyphenoxypropyl, carbamoyl, N-loweralkylcarbamoyl, N,N-dilower-alkylcarbamoyl, N-phenyl-carbamoyl, N-(m-trifluoromethylphenyl)carbamoyl, N-(.omega.-morpholino) lower-alkylcarbamoyl, N-[.omega.-(2-pyridyl)lower-alkyl]carbamoyl, 2-hydroxy-3-(o-methoxyphenoxy)propyloxycarbonyl, 2-carbamoylethyl or 4-(p-fluorobenzoyl)piperidinoethyl,
- R.sup.1 is selected from the group consisting of hydrogen or hydroxy,
- R.sup.2 is selected from the group consisting of phenyl, p-fluorophenyl, m-trifluoromethylphenyl or cyclohexyl,
- Y is selected from the group consisting of hydrogen or fluorine,
- with the proviso that when Y is hydrogen and R.sup.2 is phenyl, R is other than p-fluorobenzoylpropyl, and
- a pharmaceutically acceptable acid addition salt of a basic compound thereof.
- 19. A method of claim 18 wherein R.sup.1 represents hydroxy.
- 20. A method of claim 19 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)-p-fluorobenzylpiperidine.
- 21. A method of claim 19 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)benzylpiperidine.
- 22. A method of claim 19 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)-p-fluorobenzylpiperidine.
- 23. A method of claim 19 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-m-trifluoromethylphenyl-.alpha.-hydroxy) benzylpiperidine.
- 24. A method of claim 19 wherein the compound is N-phenyl-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)-p-fluorobenzylpiperidine-1-carboxamide.
- 25. A method of claim 19 wherein the compound is N-phenyl-4-(.alpha.-cyclohexyl-.alpha.-hydroxy)benzylpiperidine-1-carboxamide.
- 26. A method of claim 19 wherein the compound is 1-acetyl-4-(.alpha.-p-fluorophenyl-.alpha.-hydroxy)benzylpiperidine.
- 27. A method of claim 18 wherein R.sup.1 represents hydrogen.
- 28. A method of claim 27 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine.
- 29. A method of claim 27 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine.
- 30. A method of claim 27 wherein the compound is N-(2-morpholinoethyl)-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine-1-carboxamide.
- 31. A method of claim 27 wherein the compound is N-[2-(2-pyridyl)ethyl]-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine-1-carboxamide.
- 32. A method of claim 27 wherein the compound is 1-[3-(p-fluorobenzoyl)propyl]-4-(.alpha.-cyclohexyl)benzylpiperidine.
- 33. A method of claim 27 wherein the compound is 1-[3-(p-acetyl-o-methoxyphenoxy)propyl]-4-(.alpha.-phenyl)benzylpiperidine.
- 34. A method of claim 27 wherein the compound is 1-(2-carbamoylethyl)-4-(.alpha.-p-fluorophenyl)-p-fluorobenzylpiperidine.
Parent Case Info
This application is a divisional application of copending application Ser. No. 531,832 filed Dec. 11, 1974, now U.S. Pat. No. 3,956,296.
US Referenced Citations (6)
Divisions (1)
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Number |
Date |
Country |
Parent |
531832 |
Dec 1974 |
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