# US 2013/0158066 A1 · 4-azaindole inhibitors of crac

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- Number: US 2013/0158066 A1
- Document ID: US20130158066A1
- Status: Published application
- Kind: A1
- Application number: 13/713,733
- Filed: 2012-12-13
- Published: 2013-06-20
- Earliest claimed: 2011-12-20
- Assignees: Hoffmann-La Roche Inc.
- Inventors: Muzaffar Alam; Daisy Jo Du Bois; Ronald Charles Hawley; Ana Elena Minatti; Joshua Kennedy-Smith; Kshitij Chhabilbhai Thakkar; Robert Stephen Wilhelm
- Web page: https://patentgrep.com/patent/US20130158066A1

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed are compounds of Formula (I): useful for treatment of autoimmune and inflammatory diseases associated with IL-2 inhibition via modulation of calcium release-activated calcium (CRAC) channels. Also disclosed are methods of making and using the compounds for treatment of diseases associated with CRAC channels.

## Claims

### Claim 1

A compound of Formula (I):
wherein:
Ar is phenyl, unsubstituted or substituted with one, two or three substituents independently selected from halogen and alkoxy; and
Ar′ is phenyl, unsubstituted or substituted with one or two substituents independently selected from lower alkyl, haloalkyl, —SO2N(CH3)2, —CN and halogen, or heteroaryl, unsubstituted or substituted with one or two substituents independently selected from lower alkyl, haloalkyl and halogen,
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein Ar is phenyl substituted with one, two or three substituents independently selected from chlorine, fluorine and —OCH3.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein Ar is phenyl substituted with one or two substituents independently selected from chlorine and fluorine.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein Ar′ is phenyl substituted with one or two substituents independently selected from methyl, —CF3, —SO2N(CH3)2, —CN, chlorine and fluorine.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein Ar′ is pyrazolyl or pyridinyl, substituted with one or two substituents independently selected from methyl and —CF3.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein said compound is:
[2-[(E)-2-(2-Chloro-phenyl)-vinyl]-6-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-pyridin-3-yl]-methyl-amine;
2-(2-Chloro-6-fluoro-phenyl)-5-(6-chloro-4-methyl-pyridin-3-yl)-1H-pyrrolo[3,2b]pyridine;
2-(2-Chloro-6-fluoro-phenyl)-5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-1H-pyrrolo[3,2-b]pyridine;
2-(2-chloro-6-fluorophenyl)-5-(2-methyl-4-(trifluoromethyl)phenyl)-1H-pyrrolo[3,2-b]pyridine;
4-(2-(2-chloro-6-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-3-methylbenzonitrile;
4-(2-(2-chloro-6-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N,N,3-trimethylbenzenesulfonamide;
4-[2-(2-Chloro-phenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-3,N,N-trimethyl-benzenesulfonamide;
2-(2-Chloro-4-fluoro-phenyl)-5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-1H-pyrrolo[3,2-b]pyridine;
4-[2-(2-Chloro-4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-3,N,N-trimethyl-benzenesulfonamide;
4-[2-(2,6-Difluoro-phenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-3,N,N-trimethyl-benzenesulfonamide;
4-[2-(2,6-Difluoro-phenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-3-methyl-benzonitrile;
2-(2,6-Difluoro-phenyl)-5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-1H-pyrrolo[3,2-b]pyridine; or
4-(2-(2,6-difluoro-4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N,N,3-trimethylbenzenesulfonamide.

### Claim 7 (depends on 1)

A pharmaceutical composition, comprising a therapeutically effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.

### Claim 8 (depends on 1)

A method for treating arthritis, comprising the step of administering a therapeutically effective amount of a compound according to claim 1 to a subject in need thereof.

### Claim 9 (depends on 1)

A method for treating a respiratory disorder, comprising the step of administering a therapeutically effective amount of a compound according to claim 1 to a subject in need thereof.

### Claim 10 (depends on 9)

The method according to claim 9, wherein said respiratory disorder is chronic obstructive pulmonary disorder (COPD), asthma or bronchospasm.