# US 4,391,978 A · Phenyl-quinolizidines

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- Number: US 4,391,978 A
- Document ID: US4391978A
- Status: Granted
- Kind: A
- Application number: 06/252,540
- Filed: 1981-04-09
- Granted: 1983-07-05
- Earliest claimed: 1980-04-11
- Assignees: Hoffmann-La Roche Inc.
- Inventors: Rene Imhof; Emilio Kyburz
- Web page: https://patentgrep.com/patent/US4391978A

## CPC

- C07D 211/76: attached in position 2 or 6
- C07D 455/02: containing not further condensed quinolizine ring systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Phenyl-quinolizidines of the general formula ##STR1## wherein X is hydrogen, fluorine, chlorine, lower-alkoxy, lower-alkyl or trifluoromethyl; Y is hydrogen, fluorine, chlorine, lower-alkoxy or lower-alkyl; and R.sup.1 is acyl, acylamino or a group A of the formula ##STR2## wherein R.sup.2 is oxygen or sulfur; R.sup.3 is hydrogen or lower-alkyl; and one of R.sup.4 and R.sup.5 is hydrogen and the other is bromine, iodine, cyano, lower-alkoxycarbonyl or sulfamoyl, as racemates or enatiomers, as well as acid addition salts thereof, utilizing various intermediates, are described. The foregoing compounds are useful as neuroleptic, antiemetic and analgesic agents.

## Claims

### Claim 1

A compound of the formula ##STR31## wherein X is hydrogen, fluorine, chlorine, lower-alkoxy, lower-alkyl or trifluoromethyl; Y is hydrogen, fluorine, chlorine, lower-alkoxy, or lower-alkyl; R.sup.2 is oxygen or sulfur; R.sup.3 is hydrogen or lower-alkyl; and one of R.sup.4 and R.sup.5 is hydrogen and the other is bromine, iodine, cyano, lower-alkoxycarbonyl or sulfamoyl
in the form of its racemate or its enantiomers, as well as a pharmaceutically acceptable acid addition salt thereof.

### Claim 2 (depends on 1)

A compound in accordance with claim 1, which is rac-1-[(9a.beta.H)-7.beta.-(o-Fluorophenyl)-octahydro-2H-quinolin-2.alpha. -yl]-5-bromo-2-benzimidazolinone in the form of its racemate or its enantiomers, as well as a pharmaceutically acceptable acid addition salt thereof.

### Claim 3 (depends on 1)

A compound, in accordance with claim 1, which is rac-1-[(9a.beta.H)-7.beta.-(o-Fluorophenyl)-octahydro-2H-quinolizin-2.alph a.-yl]-5-iodo-2-benzimidazolinone in the form of its racemate or its enantiomers, as well as a pharmaceutically acceptable acid addition salt thereof.

### Claim 4 (depends on 1)

A compound, in accordance with claim 1, which is rac-1-[(9a.beta.H)-7.beta.-(o-Fluorophenyl)-octahydro-2H-quinolizin-2.alph a.-yl]-5-cyano-2-benzimidazolinone in the form of its racemate or its enantiomers, as well as a pharmaceutically acceptable acid addition salt thereof.

### Claim 5

A compound of the formula ##STR32## wherein X is hydrogen, fluorine, chlorine, lower-alkoxy, lower-alkyl or trifluoromethyl; Y is hydrogen, fluorine, chlorine, lower-alkoxy or lower-alkyl; and one of R.sup.4 and R.sup.5 is hydrogen and the other is bromine, iodine, cyano, lower-alkoxycarbonyl or sulfamoyl,
in the form of its racemate or its enantiomers, as well as a pharmaceutically acceptable acid addition salt thereof.