# US 5,346,904 A · Sulphonyl compound

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- Number: US 5,346,904 A
- Document ID: US5346904A
- Status: Granted
- Kind: A
- Application number: 07/945,975
- Filed: 1992-11-04
- Granted: 1994-09-13
- Earliest claimed: 1990-05-16
- Assignees: Byk Gulden Lomberg Chemische Fabrik GmbH
- Inventors: Dieter Flockerzi; Kurt Klemm
- Web page: https://patentgrep.com/patent/US5346904A

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 11/08: Bronchodilators
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compound of the formula I ##STR1## wherein the substituents have the meanings given in the description, are new active bronchodilators.

## Claims

### Claim 1

A compound of formula I ##STR8## wherein R1 denotes 1-4C-alkyl,
R2 denotes hydrogen (H), 1-4C-alkyl or 1-4C-alkoxy,
R3 denotes hydrogen (H), 1-4C-alkyl or 1-4C-alkoxy,
R4 denotes hydrogen (H), methyl or methoxy,
R5 denotes hydrogen (H) or 1-4C-alkyl and
R6 denotes 1-4C-alkyl, phenyl or substituted phenyl with one or two identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, hydroxyl and halogen,
or a salt thereof.

### Claim 2 (depends on 1)

A compound of the formula I according to claim 1, in which
R1 denotes 1-4C-alkyl,
R2 denotes 1-4C-alkoxy,
R3 denotes 1-4C-alkoxy,
R4 denotes hydrogen or methyl,
R5 denotes hydrogen or 1-4C-alkyl and
R6 denotes 1-4C-alkyl, phenyl or substituted phenyl with one substituent selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy and halogen,
or a salt thereof.

### Claim 3 (depends on 1)

A compound of formula I according to claim 1, in which
R1 denotes methyl,
R2 denotes methoxy,
R3 denotes methoxy and
R4 denotes hydrogen or methyl, the radical -N(R5)SO.sub.2 R6 is in the 4-position of the phenyl radical bonded in the 6-position on the benzo-naphthyridine ring,
R5 denotes hydrogen, methyl or ethyl and
R6 denotes methyl, 4-methylphenyl, 4-methoxyphenyl or 4-fluorophenyl,
or a salt thereof.

### Claim 4

A compound of claim: which is rac-cis-8,9-Dimethoxy-1,2,3,4,4a,10b-hexahydro-6-(4-methylsulphonamidophen yl)-2-methylbenzo[c][1,6]naphthyridine, or a salt thereof.

### Claim 5 (depends on 1)

A compound of claim 1: which is rac-cis-8,9-Dimethoxy-1,2,3,4,4a,10b-hexahydro-2-methyl-6-[4-(p-toluenesul phonamido)-phenyl]-benzo[c][1,6]naphthyridine, or a salt thereof.

### Claim 6 (depends on 1)

A compound of claim 1: which is (-)-cis-8,9-Dimethoxy-1,2,3,4,4a,10b-hexahydro-2-methyl-6-[4-(p-toluenesul phonamido)-phenyl]-benzo[c][1,6]naphthyridine, or a salt thereof.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising an effective amount of a compound of claim 1 and/or of a pharmacologically tolerated salt thereof, and pharmaceutically acceptable diluent or carrier therefor.

### Claim 8 (depends on 1)

In a process for treating a disease of the bronchi which comprises administering an effective amount of an active ingredient to a mammal afflicted with said disease, the improvement wherein the active ingredient is a compound of claim 1 or a pharmacologically-tolerated salt thereof.

### Claim 9 (depends on 1)

In a method of compounding a pharmaceutical composition comprising an active ingredient for the treatment of a disease of the bronchi, the improvement comprising incorporating in the composition a compound of claim 1, or a pharmacologically-tolerated salt thereof, as the active ingredient.