# US 7,410,994 B2 · Indole derivatives as anti-inflammatory agents

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- Number: US 7,410,994 B2
- Document ID: US7410994B2
- Status: Granted
- Kind: B2
- Application number: 11/391,655
- Filed: 2006-03-02
- Published: 2006-08-10
- Granted: 2008-08-12
- Earliest claimed: 2001-09-27
- Assignees: Roche Palo Alto LLC
- Inventors: Chris Allen Broka; Jeffrey Allen Campbell
- Web page: https://patentgrep.com/patent/US7410994B2

## CPC

- C07D 209/42: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A61P 15/06: Antiabortive agents; Labour repressants
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/06: Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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 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
- C07D 209/10: with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D 209/30: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D 209/36: in position 3, e.g. adrenochrome
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to compounds, which are generally anti-inflammatory and analgesic compounds, and which are represented by Formula I: wherein A is a —CH2—, —O—, —S—, or —S(O)—; and the other substituents are as defined in the specification; or individual isomers, mixtures of isomers, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds and methods for their use as therapeutic agents

## Claims

### Claim 1

A compound selected from the group of compounds represented by Formula I
wherein:
A is —CH2—, or —O—;
Ar is an optionally substituted phenyl;
R1 is hydrogen, alkyl, alkoxy, hydroxy, hydroxyalkyl, alkylthio, halo, cyano, —C(O)NR5R6, —NR5R6, —(CR′R″)0-3OC(O)R5, —(CR′R″)0-3SO2R5, and —(CR′R″)0-3NSO2R5, wherein R5, R6, R′ and R″ are each independently in each occurrence hydrogen or alkyl, with the proviso that when A is —CH2—, then R1 is not —C(O)NR5R6;
R2 is hydrogen, alkyl, alkoxy, hydroxy, halo, haloalkyl, nitro, cyano, or —NR5R6, wherein R5 and R6 are as defined previously;
R3 is —SOR7, —SO2R7, or —SO2NR5R6 wherein R7 is alkyl, hydroxyalkyl, alkoxyalkyl, or alkoxycarbonylalkyl; and R5 and R6 are as defined previously;
R4 is hydrogen or alkyl;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein Ar is phenyl optionally substituted at one or two substituents independently selected from the group consisting of halo and alkoxy, and R3 is —SO2R7, wherein R7 is alkyl.

### Claim 3 (depends on 2)

The compound of claim 2 wherein A is —O—.

### Claim 4 (depends on 3)

The compound of claim 3 wherein R1 is alkyl or cyano.

### Claim 5 (depends on 2)

The compound of claim 2 wherein A is —CH2—.

### Claim 6 (depends on 5)

The compound of claim 5 wherein R1 is alkyl or cyano.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Ar is phenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methyl-sulfanyiphenyl, 2-chloro-4-fluorophenyl, naphthalene-2-yl, 4-methoxy-naphthalen-1-yl, 2-chloro-4-methoxyphenyl, or 4-ethoxyphenyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R1 is —CH3, —CH2OH, —CN, —CONH2, —CH2SO2CH3, —C(O)H, —CH2OC(O)CH3, —CONH-nBu, —CONH-iPr, —CONH-Et, —CON(Me)2, —CON(Et)2, —CONH-nPr, or —CONHMe.