# US 7,608,737 B2 · Naphthyl(ethyl)acetamides

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- Number: US 7,608,737 B2
- Document ID: US7608737B2
- Status: Granted
- Kind: B2
- Application number: 12/112,722
- Filed: 2008-04-30
- Published: 2008-11-13
- Granted: 2009-10-27
- Earliest claimed: 2007-05-01
- Assignees: Concert Pharmaceuticasl Inc.
- Inventors: Julie F. Liu; Roger Tung
- Web page: https://patentgrep.com/patent/US7608737B2

## CPC

- C07C 233/18: having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 233/22: having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

This disclosure relates to novel melatonin analogues or naphthyl(ethyl)acetamides, their derivatives, pharmaceutically acceptable salts, solvates, and hydrates thereof. This disclosure also provides compositions comprising a compound of this disclosure and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a dual melatoninergic agonist and serotoninergic antagonist.

## Claims

### Claim 1

A compound of the Formula A:
or a pharmaceutically acceptable salt, solvate or hydrate thereof, wherein:
R1 is CD3;
R2 is selected from OH, H, D and F;
each of R3a, R3b, R4a, and R4b is independently selected from H and D; and
R5is CD3.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R2 is selected from H and D.

### Claim 3 (depends on 1)

The compound of claim 1, wherein each R3 is the same.

### Claim 4 (depends on 1)

The compound of claim 1, wherein each R4 is the same.

### Claim 5 (depends on 4)

The compound of claim 4, wherein each of R3a, R3b, R4a, and R4b is the same.

### Claim 6 (depends on 5)

The compound of claim 5, wherein each of R3a, R3b, R4a, and R4b is H.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound is:

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is:

### Claim 9 (depends on 1)

The compound of claim 1, wherein any atom not designated as deuterium is present at its natural isotopic abundance.

### Claim 10 (depends on 1)

A pyrogen-free composition comprising a compound of claim 1; and an acceptable carrier.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the composition is suitable for pharmaceutical administration and said carrier is a pharmaceutically acceptable carrier.

### Claim 12 (depends on 11)

The composition of claim 11, additionally comprising a second therapeutic agent.

### Claim 13 (depends on 12)

The composition of claim 12, wherein said second therapeutic agent is an agent useful in the treatment or prevention of a disease or condition selected from depression, anxiety, bipolar disorder, and sleep disorder.

### Claim 14 (depends on 13)

The composition of claim 13, wherein the second therapeutic agent is selected from reboxetine mesilate, citalopram hydrobromide, fluvoxamine maleate, paroxetine, fluoxetine hydrochloride, escitalopram oxalate, and sertraline hydrochloride.

### Claim 15 (depends on 10)

A method of treating a subject suffering from, or susceptible to, a disease selected from depression, anxiety, bipolar disorder, and sleep disorders comprising the step of administering to the subject in need thereof a composition of claim 10.

### Claim 16 (depends on 15)

The method of claim 15, wherein the disease or condition selected from depression, and bipolar disorder.

### Claim 17 (depends on 15)

The method of claim 15, comprising the additional step of co-administering to the subject in need thereof a second therapeutic agent.

### Claim 18 (depends on 17)

The method of claim 17, wherein the second therapeutic agent is selected from:
a. reboxetine mesilate when the subject is suffering from, or susceptible to depression; and
b. citalopram hydrobromide, fluvoxamine maleate, paroxetine, fluoxetine hydrochloride, escitalopram oxalate, and/or sertraline hydrochloride when the subject is suffering from, or susceptible to anxiety and depression.