# US 4,393,069 A · 8-Arylalkyl-3-phenyl-3-nortropanols and salts thereof

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- Number: US 4,393,069 A
- Document ID: US4393069A
- Status: Granted
- Kind: A
- Application number: 06/324,680
- Filed: 1981-11-25
- Granted: 1983-07-12
- Earliest claimed: 1980-12-04
- Assignees: C. H. Boehringer Sohn
- Inventors: Adolf Langbein; Herbert Merz; Rainer Sobotta; Rudolf Bauer; Hans M. Jennewein; Joachim Mierau
- Web page: https://patentgrep.com/patent/US4393069A

## CPC

- C07D 451/06: Oxygen atoms
- A61P 5/00: Drugs for disorders of the endocrine system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of the formula ##STR1## wherein Ar is ##STR2## R.sub.1 is hydrogen, fluorine, bromine, methyl or methoxy; X is .dbd.CO, .dbd.CH--CN, .dbd.CH--OH, --O--, --S--, --NH--, ##STR3## and R is hydrogen, 4-fluoro, 4-chloro, 4-trifluoromethyl, 3-trifluoromethyl, 3-trifluoromethyl-4-chloro, 4-methyl or 4-methoxy; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as neuroleptics.

## Claims

### Claim 1

A compound of the formula ##STR166## wherein Ar is ##STR167## R.sub.1 is hydrogen, fluorine, bromine, methyl or methoxy; X is .dbd.CO, .dbd.CH--CN, .dbd.CH--OH, --O--, --S--, --NH--, ##STR168## and R is hydrogen, 4-fluoro, 4-chloro, 4-trifluoromethyl, 3-trifluoromethyl, 3-trifluoromethyl-4-chloro, 4-methyl or 4-methoxy;
or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 2 (depends on 1)

A compound of claim 1
wherein
Ar is 4-fluoro-phenyl;
X is .dbd.CO, .dbd.CH--CN, .dbd.CH--OH or ##STR169## and R is halogen;
or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 3 (depends on 1)

A compound of claim 1, wherein
A is 4-fluoro-phenyl;
X is .dbd.CO or .dbd.CH--CN; and
R is halogen;
or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 4 (depends on 1)

A compound of claim 1, which is 8-(4-p-fluorophenyl-4-oxo-butyl)-3-(4-chloro-phenyl)-3-nortropol or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 5 (depends on 1)

A neuroleptic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective neuroleptic amount of a compound of claim 1.

### Claim 6 (depends on 1)

The method of depressing the central nervous system of a warm-blooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective neuroleptic amount of a compound of claim 1.