# US 5,708,020 A · Arylalkyl(thio)amides

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- Number: US 5,708,020 A
- Document ID: US5708020A
- Status: Granted
- Kind: A
- Application number: 08/613,707
- Filed: 1996-03-11
- Granted: 1998-01-13
- Earliest claimed: 1992-10-02
- Assignees: Adir et Compagnie
- Inventors: Michel Langlois; Pierre Renard; Gerard Adam
- Web page: https://patentgrep.com/patent/US5708020A

## CPC

- C07D 307/79: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 25/00: Drugs for disorders of the nervous system
- 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 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07C 233/20: having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
- C07C 233/60: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C07D 319/18: Ethylenedioxybenzenes, not substituted on the hetero ring
- C07C 2601/02: with a three-membered ring
- C07C 2601/04: with a four-membered ring
- C07C 2601/08: the ring being saturated
- C07C 2601/14: The ring being saturated
- C07C 2602/10: the other ring being six-membered, e.g. tetraline
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A compound which is selected from those of formula (I) : ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.

## Claims

### Claim 1

A compound which is selected from those of formula (I) : ##STR21## in which : A represents a --CH.sub.2 --CH.sub.2 -- chain, unsubstituted or substituted with lower alkyl,
R.sub.1 represents hydrogen or lower alkyl,
R.sub.2 represents hydrogen, halogen, or lower alkyl,
R.sub.3 and R.sub.4, together with the benzene ring which carries them, form a ring-system E.sub.3 chosen from : benzothiophene, benzofuran, and benzodioxane, on the understanding that the portion of the ring-system E.sub.3 formed by R.sub.3 and R.sub.4 and the two carbon atoms of the benzene ring which carry them is :
unhydrogenated or partially hydrogenated,
and unsubstituted or substituted with one or more radicals chosen from : halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, and trifluoromethyl,
R.sub.5 represents hydrogen or lower alkyl,
R.sub.6 represents a group ##STR22## in which X represents oxygen and R.sub.7 represents a radical chosen from :
lower alkyl, unsubstituted or substituted with one or more radicals chosen from halogen, hydroxyl, and lower alkoxy,
linear or branched alkenyl having 2 to 7 carbon atoms, inclusive, unsubstituted or substituted with one or more radicals chosen from halogen, hydroxyl, and lower alkoxy, and --(CH.sub.2).sub.m -E.sub.4 in which m represents 0 or 1 to 4, inclusive, and E.sub.4 represents a mono- or bicyclic cycloalkyl having 3 to 12 carbon atoms, inclusive, unsubstituted or substituted with one or more radicals chosen from halogen, and lower alkyl, optical isomers,
and its addition salts thereof with a pharmaceutically-acceptable acid or base when R.sub.3 or R.sub.4 represents a salifiable group,
on the understanding that the terms "lower alkyl" and "lower alkoxy" denote linear or branched groups having 1 to 6 carbon atoms, inclusive, and that the terms "cycloalkenyl" and "alkenyl" denote hydrocarbon groups containing one or more double bonds.

### Claim 2 (depends on 1)

A compound as claimed in claim 1 in which R.sub.1 represents a methyl radical.

### Claim 3 (depends on 1)

A compound as claimed in claim 1 in which R.sub.3 and R.sub.4, together with the benzene ring which carries them, form a ring-system E.sub.3 chosen from: benzofuran, and benzodioxane, on the understanding that the portion of the ring-system E.sub.3 formed by R.sub.3 and R.sub.4 and the 2 carbon atoms of the benzene ring which carry them is :
unhydrogenated or partially hydrogenated,
and unsubstituted or substituted with one or more radicals chosen from: halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl and trifluoromethyl.

### Claim 4 (depends on 1)

A compound as claimed in claim 1 in which R.sub.3 and R.sub.4, together with the benzene ring which carries them, form a benzodioxane, on the understanding that the benzene ring formed by R.sub.3, R.sub.4 and the 2 carbon atoms which carry them is unsubstituted or substituted with one or more radicals chosen from halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, and trifluoromethyl.

### Claim 5 (depends on 1)

A compound as claimed in claim 1 in which R.sub.1 represents a methyl radical and R.sub.3 and R.sub.4, together with the benzene ring which carries them, form a benzofuran on the understanding that the benzene ring formed by R.sub.3 and R.sub.4 and the 2 carbon atoms which carry them is unsubstituted or substituted with one or more radicals chosen from: halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, and trifluoromethyl.

### Claim 6 (depends on 1)

A pharmaceutical composition containing as active principle a compound as claimed in claim 1, in combination with one or more pharmaceutically-acceptable excipients.

### Claim 7 (depends on 1)

A method of treating a mammal afflicted with a sleep disorder comprising the step of administering to the said mammal an amount of a compound as claimed in claim 1 which binds at melatonin receptors and is effective in the treatment of said disorder.

### Claim 8 (depends on 1)

A compound as claimed in claim 1 which is N-›2-(6-methoxy-1,4-benzodioxan-5-yl)ethyl!acetamide.

### Claim 9 (depends on 1)

A compound as claimed in claim 1 which is N-›2-(6-methoxy-3-methylbenzofuran-7-yl)ethyl!acetamide.