Granted Patent B2

US 7,943,778 · App. 12/426,832 · Granted May 17, 2011

Assignee: Reata Pharmaceuticals, Inc.

Abstract

Claims (26)

1. A compound of the formula:

wherein:

Y is alkanediyl (C≦8) , alkenediyl (C≦8) , alkynediyl (C≦8) , or a substituted version of any of these groups;

R a is:

hydrogen, hydroxy, halo, amino, nitro, cyano, azido, phosphate, 1,3-dioxoisoindolin-2-yl, mercapto or silyl; or

alkyl (C≦12) , alkenyl (C≦12) , alkynyl (C≦12) , aryl (C≦12) , aralkyl (C≦12) , heteroaryl (C≦12) , heteroaralkyl (C≦12) , acyl (C≦12) , alkoxy (C≦12) , alkenyloxy (C≦12) , alkynyloxy (C≦12) , aryloxy (C≦12) , aralkoxy (C≦12) , heteroaryloxy (C≦12) , heteroaralkoxy (C≦12) , acyloxy (C≦12) , alkylamino (C≦12) , dialkylamino (C≦12) , alkenylamino (C≦12) , alkynylamino (C≦12) , arylamino (C≦12) , aralkylamino (C≦12) , heteroarylamino (C≦12) , heteroaralkylamino (C≦12) , alkylsulfonylamino (C≦12) , amido (C≦12) , alkylthio (C≦12) , alkenylthio (C≦12) , alkynylthio (C≦12) , arylthio (C≦12) , aralkylthio (C≦12) , heteroarylthio (C≦12) , heteroaralkylthio (C≦12) , acylthio (C≦12) , thioacyl (C≦12) , alkylsulfonyl (C≦12) , alkenylsulfonyl (C≦12) , alkynylsulfonyl (C≦12) , arylsulfonyl (C≦12) , aralkylsulfonyl (C≦12) , heteroarylsulfonyl (C≦12) , heteroaralkylsulfonyl (C≦12) , alkylsulfinyl (C≦12) , alkenylsulfinyl (C≦12) , alkynylsulfinyl (C≦12) , arylsulfinyl (C≦12) , aralkylsulfinyl (C≦12) , heteroarylsulfinyl (C≦12) , heteroaralkylsulfiny (C≦12) , alkylphosphonyl (C≦12) , alkylphosphate (C≦12) , dialkylphosphate (C≦12) , alkylammonium (C≦12) , alkylsulfonium (C≦12) , alkylsilyl (C≦12) , or a substituted version of any of these groups; or

Y and R a form a three to seven-membered ring, such that Y and R a are further connected to one another through one or more of —O— and alkanediyl (C1-5) , further wherein Y is —CH— and R a is —CH 2 —;

or a pharmaceutically acceptable salt or tautomer thereof.

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

wherein R a is:

hydrogen, hydroxy, halo, amino, phosphate, 1,3-dioxoisoindolin-2-yl, or cyano; or

alkyl (C≦12) ,alkenyl (C≦12) , alkynyl (C≦12) , aryl (C≦12) , aralkyl (C≦12) , heteroaryl (C≦12) , heteroaralkyl (C≦12) , acyl (C≦12) , alkoxy (C≦12) , alkenyloxy (C≦12) , alkynyloxy (C≦12) , aryloxy (C≦12) , aralkoxy (C≦12) , heteroaryloxy (C≦12) , heteroaralkoxy (C≦12) , acyloxy (C≦12) , alkylamino (C≦12) , dialkylamino (C≦12) , alkenylamino (C≦12) , alkynylamino (C≦12) , arylamino (C≦12) , aralkylamino (C≦12) , heteroarylamino (C≦12) , heteroaralkylamino (C≦12) , amido (C≦12) , arylsulfonyl (C≦12) , arylsulfinyl (C≦12) , alkylphosphate (C≦12) , dialkylphosphate (C≦12) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt or tautomer thereof.

3. The compound of claim 2 , further defined as:

wherein R a is hydroxy, amino, acyl (C≦8) , substituted acyl (C≦8) , acyloxy (C≦8) , substituted acyloxy (C≦8) , amido (C≦8) , or substituted amido (C≦8) ;

or a pharmaceutically acceptable salt or tautomer thereof.

4. The compound of claim 1 , wherein Y is —C(OH)HCH 2 —.

5. The compound of claim 1 , wherein R a is —OH.

6. The compound of claim 1 , wherein R a is —Cl.

7. The compound of claim 1 , wherein R a is —Br.

8. The compound of claim 1 , wherein R a is —H.

9. The compound of claim 1 , wherein R a is acyl (C1-3) or substituted acyl (C1-3) .

10. The compound of claim 1 , wherein R a is acyloxy (C1-8) or substituted acyloxy (C1-3) .

11. The compound of claim 1 , wherein R a is alkylamino (C≦12) , dialkylamino (C≦12) , alkenylamino (C≦12) , alkynylamino (C≦12) , arylamino (C≦12) , aralkylamino (C≦12) , heteroarylamino (C≦12) , heteroaralkylamino (C≦12) , alkylsulfonylamino (C≦12) , or amido (C≦12) , or a substituted version of any of these groups.

12. The compound of claim 1 further defined as:

13. A compound of the formula:

Assignments (9)

Continuity (3)