# US 6,297,282 B1 · Substituted derivatives of benzosulphonamides as inhibitors of the enzyme cyclooxygenase II

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- Number: US 6,297,282 B1
- Document ID: US6297282B1
- Status: Granted
- Kind: B1
- Application number: 09/355,722
- Filed: 1999-10-26
- Granted: 2001-10-02
- Earliest claimed: 1997-02-03
- Assignees: Nycomed Austria GmbH
- Inventors: Michael Hartmann; Peter Kremminger; Heinz Blaschke; Dagmar Stimmeder; Harald Fellier; Franz Rovenszky
- Web page: https://patentgrep.com/patent/US6297282B1

## CPC

- C07C 323/67: containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present application relates to compounds of formula (I) wherein A represents oxygen, sulfur or —NH—, m is 0-2, and R1, R2, R3, R6 and R7 have the meanings given in the specification, to a process for their preparation, as well as to their use in the inhibition of cyclooxygenase II.

## Claims

### Claim 1

Compounds of formula I
wherein
A denotes oxygen, sulphur or NH,
R1 denotes an optionally unsaturated alkyl or alkyloxyalkyl group, optionally mono- or polysubstituted or mixed substituted by halogen, alkoxy, oxo or cyano, a cycloalkyl, aryl or heteroaryl group optionally mono- or polysubstituted or mixed substituted by halogen, alkyl, CF3, cyano or alkoxy,
R2 and R3, independently from one another, denote hydrogen, an optionally polyfluorinated alkyl group, an aralkyl, aryl or heteroaryl group or a group (CH2)n—X, or R2 and R3, together with the N- atom denotes a 3- to 7- membered saturated, partially or completely unsaturated heterocycle with one or more heteroatoms N, O or S, which may optionally be substituted by oxo, an alkyl, alkylaryl or aryl group, or a group (CH2)n—X, X denotes halogen, NO2, —OR4, —COR4, —CO2R4, —OCO2R4, —CN, —CONR4OR5, —CONR4R5, SR4, —S(O)R4, —S(O)2R4, —NR4R5, —NCH(O)R4, NHS(O)2R4,
n is a whole number from 0 to 6,
R6 denotes a straight-chained or branched alkyl group with 1-10 C-atoms, a vinyl group, a cycloalkyl group, an alkylene carboxyl group, an aryl group, aralkyl group, a heteroaryl or beteroaralkyl group, which may optionally be substituted by halogen or alkoxy,
R7 denotes hydrogen, halogen, hydroxy, a straight-chained or branched alkyl, alkoxy, acyloxy or alkyloxycarbonyl group with 1-6 C-atoms, which may optionally be mono- or polysubstituted by halogen, —NO2, —OR4, —COR4, —CO2R4, —OCO2R4, —CN, —CONR4OR5, —CONR4R5, —SR4, —S(O)R4, —S(O)2R4, —NR4R5, —NHC(O)R4, —NHS(O)2R4, or a polyfluoroalkyl group, R4 and R5, independently from one another, denote hydrogen, alkyl, aralkyl or aryl, and
m is a whole number from 0 to 2,
and the pharmaceutically-acceptable salts thereof.

### Claim 2 (depends on 1)

Compounds of formula I according to claim 1, wherein R7 denotes halogen, hydroxy or an alkyl or alkoxycarbonyl group with 1-4 C-atoms which may optionally be substituted by halogen or hydroxy.

### Claim 3 (depends on 1)

Compounds of formula I according to claim 1, wherein R1 may optionally be an unsaturated alkyl or alkyloxyalkyl group which may optionally bemono- or polysubstituted or mixed substituted by halogen, alkoxy, oxo or cyano.

### Claim 4 (depends on 2)

Compounds of formula I according to claim 2, wherein R1 may optionally be an unsaturated alkyl or alkyloxyalkyl group which may optionally be mono- or polysubstituted or mixed substituted by halogen, alkoxy, oxo or cyano.

### Claim 5 (depends on 1)

A pharmaceutical composition containing as an active ingredient at least one compound of formula I according to claim 1.

### Claim 6 (depends on 1)

A method of treatment and alleviation of diseases or disorders which can be healed or alleviated by inhibition of the enzyme cyclooxygenase II which comprises administering to a patient in need of same the compound of formula I according to claim 1.

### Claim 7 (depends on 1)

A method for treatment or alleviation of inflammatory processes which comprises administering to a patient in need of same the compound of formula I according to claim 1.

### Claim 8 (depends on 1)

A method for treatment of pain which comprises administering to a patient in need of same the compound of formula I according to claim 1.