# US 4,396,770 A · 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy -4-phenylpiperidines

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- Number: US 4,396,770 A
- Document ID: US4396770A
- Status: Granted
- Kind: A
- Application number: 06/366,247
- Filed: 1982-04-09
- Granted: 1983-08-02
- Earliest claimed: 1982-04-09
- Assignees: Hoechst-Roussel Pharmaceuticals Inc.
- Inventors: Larry Davis; Joseph T. Klein
- Web page: https://patentgrep.com/patent/US4396770A

## CPC

- C07D 261/20: condensed with carbocyclic rings or ring systems
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C07C 45/46: Friedel-Crafts reactions
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Novel 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-phenylpiperidines , processes for the preparation thereof, and methods of treating psychoses and alleviating pain employing compounds and compositions thereof are disclosed.

## Claims

### Claim 1

A compound of the formula ##STR7## wherein X is hydrogen, loweralkyl of 1 to 5 carbon atoms, loweralkoxy of 1 to 5 carbon atoms, halogen or trifluoromethyl; Y is hydrogen or trifluoromethyl with the proviso that Y is hydrogen when X is hydrogen, loweralkyl of 1 to 5 carbon atoms, loweralkoxy of 1 to 5 carbon atoms, or trifluoromethyl and Y is hydrogen or trifluoromethyl when X is halogen; the optical antipode thereof, or pharmaceutically acceptable acid addition salt thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein X is halogen and Y is hydrogen.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein the halogen is bound to the 4-position of the benzene ring.

### Claim 4 (depends on 1)

The compound according to claim 1 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-phenylpiperidine.

### Claim 5 (depends on 2)

The compound according to claim 2 which is 4-(3-chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxyp iperidine.

### Claim 6 (depends on 3)

The compound according to claim 3 which is 4-(4-chlorophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxyp iperidine.

### Claim 7 (depends on 3)

The compound according to claim 3 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-fluorophenyl)-4-hydroxyp iperidine.

### Claim 8 (depends on 1)

The compound according to claim 1 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(2-methylphenyl)p iperidine.

### Claim 9 (depends on 1)

The compound according to claim 1 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(4-tolyl)piperidi ne.

### Claim 10 (depends on 1)

The compound according to claim 1 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(4-methoxyphenyl) piperidine.

### Claim 11 (depends on 1)

The compound according to claim 1 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(3-trifluoromethy lphenyl)piperidine.

### Claim 12 (depends on 1)

The compound according to claim 1 which is 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(4-trifluoromethy lphenyl)piperidine.

### Claim 13 (depends on 1)

The compound according to claim 1 which is 4-(4-chloro-3-trifluoromethylphenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl) propyl]-4-hydroxypiperidine.

### Claim 14 (depends on 3)

The compound according to claim 3 which is 4-(4-bromophenyl)-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypi peridine.