# US 5,346,916 A · Alkoxy-3-[(Toluenesulfonylaminoalkyl)amino] chroman compounds

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- Number: US 5,346,916 A
- Document ID: US5346916A
- Status: Granted
- Kind: A
- Application number: 08/033,156
- Filed: 1993-03-16
- Granted: 1994-09-13
- Earliest claimed: 1990-04-09
- Assignees: Adir et Compagnie
- Inventors: Gerald Guillaumet; Beatrice Guardiola
- Web page: https://patentgrep.com/patent/US5346916A

## CPC

- C07D 405/12: linked by a chain containing hetero atoms as chain links
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/12: Antihypertensives
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/24: Antidepressants
- A61P 25/26: Psychostimulants, e.g. nicotine, cocaine
- C07D 311/58: other than with oxygen or sulphur atoms in position 2 or 4
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to compounds of the formula (I): ##STR1## in which: Z represents an oxygen atom or a sulfur atom, R.sub.1 represents a hydrogen atom or an alkyl group, R.sub.2 represents a hydrogen atom or an alkyl group, n is one to six, inclusive, R.sub.3 represents an amino group, substituted with phenylsulfonyl, and medicinal products containing the same.

## Claims

### Claim 1

A compound selected from those of formula (I): ##STR39## in which: Z represents oxygen or sulfur,
R.sub.1 represents hydrogen or (C.sub.1 -C.sub.6) alkyl,
R.sub.2 represents hydrogen or (C.sub.1 -C.sub.6) alkyl,
n is an integer of 1 to 6 inclusive,
R.sub.3 represents an amino group substituted with:
an phenylsulfonyl optionally substituted with alkyl, alkoxy, hydroxyl, or halogen,
its enantiomers, diastereoisomers and epimers and its pharmaceutically-acceptable acid addition salts.

### Claim 2 (depends on 1)

A compound as claimed in claim 1, wherein R.sub.1 is a methyl group.

### Claim 3 (depends on 1)

A compound as claimed in claim 1, wherein R.sub.2 is an n-propyl group.

### Claim 4 (depends on 1)

A compound as claimed in claim 1, wherein R.sub.1 is in the 5-position.

### Claim 5 (depends on 1)

A compound as claimed in claim 1, wherein R.sub.2 is a hydrogen atom.

### Claim 6 (depends on 1)

A compound as claimed in claim 1, selected from 5-methoxy-3-{N-propyl-N-[2-(4-toluenesulfonylamino)ethyl]amino}chroman, its isomers and its addition salts with a pharmaceutically-acceptable acid.

### Claim 7 (depends on 1)

A compound as claimed in claim 1, selected from 5-methoxy-(+)-3-{N-propyl-N-[2-(4-toluenesulfonylamino)ethyl]amino}chroman , and its addition salts with a pharmaceutically-acceptable acid.

### Claim 8 (depends on 1)

A compound as claimed in claim 1, selected from 5-methoxy-(-)-3-{N-propyl-N-[2-(4-toluenesulfonylamino)ethyl]amino}chroman , and its addition salts with a pharmaceutically-acceptable acid.

### Claim 9 (depends on 1)

A compound as claimed in claim 1, selected from 5-methoxy-3-{N-n-propyl-N-[4-(4-toluenesulfonylamino)butyl]amino}chroman, its isomers and its addition salts with a pharmaceutically-acceptable acid.

### Claim 10 (depends on 1)

A compound as claimed in claim 1, selected from 5-methoxy-(+)-3-{N-n-propyl-N-[4-(4-toluenesulfonylamino)butyl]amino}chrom an, and its addition salts with a pharmaceutically-acceptable acid.

### Claim 11 (depends on 1)

A compound as claimed in claim 1, selected from 5-methoxy-(-)-3-{N-n-propyl-N-[4-(4-toluenesulfonylamino)butyl]amino}chrom an, and its addition salts with a pharmaceutically-acceptable acid.

### Claim 12 (depends on 1)

A pharmaceutical composition comprising the active principle as claimed in claim 1, which is useful in the treatment of depression, stress, psychoses, anxiety, pain, schizophrenia, hypertension, or atheroma, and as an agent modifying feeding and sexual behavior, together with a pharmaceutically-acceptable diluent.

### Claim 13 (depends on 1)

A method for treating a living animal afflicted with a disorder of the serotoninergic system comprising the step of administering to the said living animal an amount of a compound of claim 1 which is suitable for the alleviation of said condition.