# US 4,399,299 A · Bis(substituted phenoxyacetates) of N-alkyl-dialcanolamines and pharmaceutical compositions thereof

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- Number: US 4,399,299 A
- Document ID: US4399299A
- Status: Granted
- Kind: A
- Application number: 06/256,167
- Filed: 1981-04-21
- Granted: 1983-08-16
- Earliest claimed: 1980-04-03
- Assignees: Agence Nationale de Valorisation de la Recherche (ANVAR)
- Inventors: Jean-Jacques Godfroid; Jean Thuillier
- Web page: https://patentgrep.com/patent/US4399299A

## CPC

- C07C 219/06: having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
- A61P 25/00: Drugs for disorders of the nervous system
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to bis(substituted phenoxyacetates) of N-alkyl-dialkanolamines. These compounds are of the formula: ##STR1## wherein: X is chlorine, fluorine or trifluoromethyle, n is in the range from 1 to 3 and is preferably 2, R is a lower alkyl group, such as methyl or ethyl group, and the pharmaceutically acceptable salts of said compounds. Application: prevention and treatment of cerebral disorders.

## Claims

### Claim 1

A compound selected from the group consisting of N-alkyl-dialkanolamine-bis-(substituted phenoxyacetate) of the formula ##STR6## wherein X is selected from the group consisting of chlorine, fluorine and --CF.sub.3, n is an integer from 1 to 3, R is lower alkyl and their non-toxic, pharmaceutically acceptable acid addition salts.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R is methyl or ethyl.

### Claim 3 (depends on 1, 2)

A compound of claim 1 or 2 wherein n is 2.

### Claim 4 (depends on 1)

A compound of claim 1 selected from the group consisting of N-methyl-diethanolamine-bis-(4-chlorophenoxy-acetate) and N-methyl-diethanolamine-bis-(3-trifluoromethylphenoxy-acetate) and their non-toxic, pharmaceutically acceptable acid addition salts.

### Claim 5 (depends on 4)

A compound of claim 4 wherein the acid addition salt is selected from the group consisting of hydrochloride, oxalate, maleate and methanesulfonate.

### Claim 6 (depends on 1)

A compound of claim 1 which is the methanesulfonate of N-methyl-diethanolamine-bis-(4-chlorophenoxyacetate).

### Claim 7 (depends on 11)

A composition for treatment or prevention of ceberal disorders comprising an amount of a compound of claim 11 sufficient to prevent or treat ceberal disorders and a pharmaceutical carrier.

### Claim 8 (depends on 7)

A composition of claim 7 wherein R is methyl or ethyl.

### Claim 9 (depends on 7, 8)

A composition of claim 7 or 8 wherein n is 2.

### Claim 10 (depends on 7)

A composition of claim 7 wherein the active compound is selected from the group consisting of N-methyl-diethanolamine-bis-(4-chlorophenoxyacetate) and N-methyl-diethanolamine-bis-(3-trifluoromethylphenoxyacetate) and their non-toxic, pharmaceutically acceptable acid addition salts.

### Claim 11 (depends on 7)

A composition of claim 7 wherein the active compound is the methanesulfonate of N-methyl-diethanolamine-bis-(4-chlorophenoxyacetate).

### Claim 12 (depends on 1)

A method of treating or preventing ceberal disorders in warm-blooded animals comprising administering to warm-blooded animals an amount of a compound of claim 1 sufficient to prevent or treat ceberal disorders.

### Claim 13 (depends on 12)

The method of claim 12 wherein R is methyl or ethyl.

### Claim 14 (depends on 12, 13)

The method of claim 12 or 13 wherein n is 2.

### Claim 15 (depends on 12)

The method of claim 12 wherein the compound is selected from the group consisting of N-methyl-diethanolamine-bis-(4-chlorophenoxyacetate) and N-methyl-diethanolamine-bis-(3-trifluoromethylphenoxyacetate) and their non-toxic, pharmaceutically acceptable acid addition salts.

### Claim 16 (depends on 12)

The method of claim 12 wherein the compound is the methanesulfonate of N-methyl-diethanolamine-bis-(4-chlorophenoxyacetate).