# US 7,745,492 B2 · Carboxamido opioid compounds

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- Number: US 7,745,492 B2
- Document ID: US7745492B2
- Status: Granted
- Kind: B2
- Application number: 12/182,462
- Filed: 2008-07-30
- Published: 2008-11-13
- Granted: 2010-06-29
- Earliest claimed: 2004-05-14
- Assignees: Janssen Pharmaceutical N.V.
- Inventors: John R. Carson; Philip M. Pitis
- Web page: https://patentgrep.com/patent/US7745492B2

## CPC

- C07C 237/30: having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 35/04: specific for metastasis
- C07C 237/38: having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C 2601/02: with a three-membered ring
- C07C 2601/14: The ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention is directed to carboxamido opioid compounds pharmaceutically useful as agents for treating or modulating a central nervous system disorder and methods for treating or modulating a central nervous system disorder.

## Claims

### Claim 1

A method for treatment of pain in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound selected from the group consisting of:
3-[(1-RS, 2-SR)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
(−)-3-[(1R, 2R)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
(+)-3-[(1S, 2S)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-N,N- diethylbenzamide;
N-cyclopropyl-3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide; and
3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-N-methylbenzamide.

### Claim 2 (depends on 1)

The method of claim 1, wherein the compound is selected from the group consisting of:
(−)-3-[(1R, 2R)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide and
(+)-3-[(1S, 2S)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;

### Claim 3

A pharmaceutical composition comprising a compound selected from the group consisting of:
3-[(1-RS, 2-SR)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
(−)-3-[(1R, 2R)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
(+)-3-[(1S, 2S)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide;
3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-N,N- diethylbenzamide;
N-cyclopropyl-3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide; and
3-[(1-RS, 2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-N-methylbenzamide.

### Claim 4 (depends on 3)

The composition of claim 3 wherein the compound is selected from the group consisting of:
(−)-3-[(1R, 2R)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide and
(+)-3-[(1S, 2S)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide.