Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators

Patent metadata

Field	Value
Publication number	US-9884809-B2
Application number	US-201514877974-A
Country	US
Kind code	B2
Filing date	Oct 8, 2015
Priority date	Dec 17, 2010
Publication date	Feb 6, 2018
Grant date	Feb 6, 2018

Abstract

Disclosed herein are novel antioxidant inflammation modulators, including those of the formula:

wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds. Methods and intermediates useful for making the compounds, and methods of using the compounds and compositions thereof are also provided.

First claim

What is claimed is:

1. A compound of the formula:

wherein:
R 1 and R 2 are each methyl; and
R 3 ,R 4 ,R 5 and R 6 are each independently:
hydrogen, hydroxy or amino, or
alkyl (c≦12) , acyl (c≦12) , alkoxy (c≦12) , aryloxy (c≦12) , alkylamino (c≦12) , dialkylamino (c≦12) , amido (c≦12) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt or tautomer thereof.

2. The compound of claim 1 , wherein R 4 ,R 5 and R 6 are each hydrogen.

3. The compound of claim 1 , wherein R 3 is hydroxy.

4. The compound of claim 1 , wherein R 3 is alkoxy (c≦6) or substituted alkoxy (c≦6) .

5. The compound of claim 4 , wherein R 3 is substituted alkoxy (c≦6) .

6. The compound of claim 5 , wherein R 3 is methoxymethoxy.

7. The compound of claim 1 , wherein carbon atom 10 is in the R configuration.

8. The compound of claim 1 , wherein carbon atom 10 is in the S configuration.

9. The compound of claim 1 , wherein carbon atom 5 is in the R configuration.

10. The compound of claim 1 , wherein carbon atom 5 is in the S configuration.

11. The compound of claim 1 , further defined as:

Assignees

• Reata Pharmaceuticals Inc

Inventors

• Anderson Eric
• Bolton Gary L
• CAPRATHE Bradley
• Jiang Xin
• Lee Chitase
• Roark William H
• Visnick Melean

Classifications

• A61P39/06

  Free radical scavengers or antioxidants · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• C07D239/70

  condensed with carbocyclic rings or ring systems · CPC title

• C07D413/04

  directly linked by a ring-member-to-ring-member bond · CPC title