# US 5,708,007 A · 2-(piperidin-4-yl, pyridin-4-yl and tetrahydropyridin-4-yl) benzofuran-7-ol and carbamate derivatives for treating memory dysfunction

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,708,007 A
- Document ID: US5708007A
- Status: Granted
- Kind: A
- Application number: 08/703,843
- Filed: 1996-08-27
- Granted: 1998-01-13
- Earliest claimed: 1993-08-05
- Assignees: Hoechst Marion Roussel, Inc.
- Inventors: Gerard J. O'Malley; Udo Hedtmann
- Web page: https://patentgrep.com/patent/US5708007A

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 25/02: for peripheral neuropathies
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 307/86: with an oxygen atom directly attached in position 7
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

These are disclosed novel 2-(piperidin-4-yl, pyridin-4-yl and tetrahydropyridin-4-yl)benzofuran-7-ol and carbamate derivatives of the formula ##STR1## where the substituents are as defined in the specification, which are useful as acetylcholinesterase inhibitors and as such may be useful for the treatment of Alzheimer's disease and other senile dementias.

## Claims

### Claim 1

A compound of the formula ##STR32## wherein R.sub.1 is CONHR.sub.11 or CONR.sub.6 R.sub.7
R.sub.2 is hydrogen, cyano, CH.sub.2 NR.sub.8 R.sub.9, CONHR.sub.5 or CONR.sub.6 R.sub.7 ;
R.sub.3 is ##STR33## where R.sub.10 is hydrogen, loweralkyl, arylloweralkyl, CONHR.sub.5, CONR.sub.6 R.sub.7, acyl, acyloxyloweralkyl or acyloxyarylloweralkyl;
R.sub.4 is hydrogen, halogen, loweralkyl or loweralkoxy;
R.sub.5 is hydrogen, loweralkyl or arylloweralkyl;
R.sub.6 is loweralkyl or arylloweralkyl;
R.sub.7 is loweralkyl or arylloweralkyl;
R.sub.8 is hydrogen, loweralkyl, arylloweralkyl or acyl;
R.sub.9 is hydrogen, loweralkyl or arylloweralkyl;
R.sub.11 is loweralkyl, aryl or arylloweralkyl;
or a pharmaceutically acceptable acid addition salt thereof, or, where applicable, an optical or geometric isomer or racemic mixture thereof.

### Claim 2 (depends on 1)

A compound as defined in claim 1 wherein R.sub.3 is ##STR34##

### Claim 3 (depends on 1)

A compound as defined in claim 1 wherein R.sub.3 is ##STR35##

### Claim 4 (depends on 1)

A compound as defined in claim 1 wherein R.sub.3 is ##STR36##

### Claim 5 (depends on 2)

A compound as defined in claim 2 wherein R.sub.1 is CONHR.sub.11.

### Claim 6 (depends on 5)

The compound as defined in claim 5 which is 2-(4-pyridinyl)benzofuran-7-yl methyl carbamate.

### Claim 7 (depends on 5)

The compound as defined in claim 5 which is 2-(4-pyridinyl)benzofuran-7-yl butyl carbamate.

### Claim 8 (depends on 3)

A compound as defined in claim 3 wherein R.sub.1 is CONHR.sub.11.

### Claim 9 (depends on 8)

The compound as defined in claim 8 which is 2-(1-methyl-4-piperidinyl)benzofuran-7-yl methyl carbamate.

### Claim 10 (depends on 3)

A compound as defined in claim 3 wherein R.sub.1 is CONR.sub.6 R.sub.7.

### Claim 11 (depends on 10)

The compound as defined in claim 10 which is 2-(4-piperidinyl)-benzofuran-7-yl dimethyl carbamate.

### Claim 12 (depends on 1)

A pharmaceutical composition which comprises an effective amount of a compound as defined in claim 1 and a pharmaceutically acceptable carrier therefor.

### Claim 13 (depends on 1)

A method of treating memory dysfunction of the Alzheimer's type comprising administering to a patient an acetyl-cholinesterase inhibitory effective amount of a compound as defined in claim 1.