# US 5,332,732 A · Thiophene and pyridine antipsychotic agents

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- Number: US 5,332,732 A
- Document ID: US5332732A
- Status: Granted
- Kind: A
- Application number: 07/943,662
- Filed: 1992-09-11
- Granted: 1994-07-26
- Earliest claimed: 1992-09-11
- Assignees: McNeilab, Inc.
- Inventors: Malcolm K. Scott; Allen B. Reitz; Frank J. Villani, Jr.; C. Royce Rasmussen
- Web page: https://patentgrep.com/patent/US5332732A

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 333/24: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 409/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 409/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of the general formula I ##STR1## wherein A is N; Ar is aryl, substituted aryl or benzofuranyl, wherein the substituents are selected from C.sub.1 -C.sub.8 alkoxy; B is CO or CH.sub.2 and HET is selected from any of piperizine, piperidine, hexahydroazepine, morpholine, thiomorpholine or pyrrolidine, which may be substituted with one of more oxo groups are disclosed as novel antipsychotic agents. Pharmaceutical compositions and methods of treating convulsions employing such compounds of formula I are also disclosed.

## Claims

### Claim 1

A compound of the formula I: ##STR7## wherein A is N
Ar is aryl substituted aryl or benzofuranyl, wherein the aryl substituents are seleted from C.sub.1 -C.sub.8 alkoxy;
B is CO or CH.sub.2 ;
W is thiophene or pyridine;
HET is selected from any of piperizine, piperidine, hexahydroazepine, morpholine, thiomorpholine or pyrrolidine, which may be substituted with one or more oxo groups, or the pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein B is CO.

### Claim 3 (depends on 1)

The compound of claim 1, wherein W is thiophene.

### Claim 4 (depends on 1)

The compound of claim 1, wherein W is pyridine.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the HET ring substituent is a single oxo group.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the HET ring is a substituted or unsubstituted piperidine or hexahydroazepine ring.

### Claim 7 (depends on 6)

The compound of claim 6, wherein B is CO.

### Claim 8 (depends on 5)

The compound of claim 5, wherein the HET ring is piperidine and the substituent is a single oxo group.

### Claim 9 (depends on 1)

The compound of claim 1, wherein Ar is substituted aryl or benzofuranyl.

### Claim 10 (depends on 9)

The compound of claim 9, wherein Ar is substituted with C.sub.1 -C.sub.8 alkoxy.

### Claim 11 (depends on 10)

The compound of claim 10, wherein the substituent is isopropoxy.

### Claim 12 (depends on 1)

The compound of claim 1 having the name 1-[[5-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]-3-thienyl]carbo nyl]piperidine.

### Claim 13 (depends on 1)

The compound of claim 1, having the name hexahydro-1-[[5-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]-3-thi enyl]carbonyl]-1H-azepine.

### Claim 14 (depends on 1)

The compound of claim 1, having the name 1-[[5-[[1(7-benzofuranyl)-4-piperazinyl]-2-thienyl]-2-piperidinone.

### Claim 15 (depends on 1)

The compound of claim 1, having the name 1-[[5-[[1-[2-(1-methlethoxy)phenyl]-4-piperazinyl]methyl]-2-thienyl]carbon yl]piperidine.

### Claim 16 (depends on 1)

The compound of claim 1 having the name hexahydro-1-[[5-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]-2-thi enyl]carbonyl]-1H-azepine.

### Claim 17 (depends on 1)

The compound of claim 1 having the name 1-[[6-[[1-[2-(methylethoxy)phenyl]-4-piperazinyl]methyl]pyridinyl]methyl]- 2-piperidinone.

### Claim 18 (depends on 1)

The compound of claim 1 having the name 1-[[5-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]-2-thienyl]methy l]-2-piperidinone.

### Claim 19 (depends on 1)

A composition for treating psychotic conditions in mammals comprising the compound of claim 1 and a pharmaceutically acceptable carrier, said compound being present in a therapeutically effective amount for treating psychotic conditions in mammals.

### Claim 20 (depends on 1)

A method for treating psychotic conditions in mammals comprising administering to a mammal in need of such treatment the compound of claim 1 in an amount sufficient to treat such conditions.

### Claim 21 (depends on 20)

The method of claim 20, wherein the condition is schizophrenia.

### Claim 22 (depends on 20)

The method of claim 20, wherein the effective amount is about 0.5 to 5 mg/kg per day.