Granted Patent B2

US 12,545,701 · App. 18/149,696 · Granted Feb 10, 2026

Inventors: Melean Visnick (Irving, TX); Xin Jiang (Coppell, TX); Martha R. Hotema (Hurst, TX); Chitase Lee (Ann Arbor, MI); Bradley William Caprathe (Livonia, MI); William H. Roark (Ann Arbor, MI); Gary L. Bolton (Ann Arbor, MI)

Assignee: REATA PHARMACEUTICALS, INC.

C07J63/008A61P29/00C07J71/0005

Abstract

Claims (54)

1 . A compound of the formula:

wherein:

R 3 is hydrogen, hydroxy, or R 3 is taken together with Y as described below;

Y is heteroaryl (C≤8) or substituted heteroaryl (C≤8) ;

—C(O)R c , wherein

R c is: hydroxy, alkoxy (C≤8) , substituted alkoxy (C≤8) , alkylamino (C≤8) , substituted alkylamino (c≤8) , dialkylamino (C≤8) , or substituted dialkylamino (C≤8) ;

—NR d C(O)R e , wherein

R d is hydrogen; and

R e is alkyl (C≤8) , alkoxy (C≤8) , or a substituted version of either group; or

Y is taken together with R 3 and is-C(O)O—; and

R 5 is acyloxy (C≤8) or substituted acyloxy (C≤8) ;

wherein when the terms alkyl, alkoxy, acyloxy, alkylamino, dialkylamino, and heteroaryl are used with the substituted modifier, one or more hydrogen atom has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —NHCH 3 , —NHCH 2 CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —C(O)NHCH 3 , —C(O)N(CH 3 ) 2 , —OC(O)CH 3 , —NHC(O)CH 3 , —S(O) 2 OH, or —S(O) 2 NH 2 ;

or a pharmaceutically acceptable salt thereof.

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

wherein:

R 3 is hydrogen, hydroxy, or R 3 is taken together with Y as described below;

Y is heteroaryl (C≤8) or substituted heteroaryl (C≤8) ;

—C(O)R c , wherein

R c is: alkylamino (C≤8) , dialkylamino (C≤8) , or a substituted version of either group;

—NR d C(O)R e , wherein

R d is hydrogen; and

R e is alkyl (C≤8) , alkoxy (C≤8) , or a substituted version of either group; or

Y is taken together with R 3 and is —C(O)O—; and

R 5 is acyloxy (C≤8) or substituted acyloxy (C≤8) ;

or a pharmaceutically acceptable salt thereof.

3 . The compound of claim 1 , wherein the compound is further defined as:

wherein:

R 3 is hydrogen or hydroxy;

Y is —C(O)R c , wherein R c is:

hydroxy, alkoxy (C≤8) , or substituted alkoxy (C≤8) ; and

R 5 is acyloxy (C≤8) or substituted acyloxy (C≤8) ;

or a pharmaceutically acceptable salt thereof.

4 . The compound of claim 1 , wherein the compound is further defined as:

wherein:

R 3 is hydrogen or hydroxy;

Y is —C(O)R c , wherein R c is alkoxy (C≤8) , or substituted alkoxy (C≤8) ; and

R 5 is acyloxy (C≤8) or substituted acyloxy (C≤8) ;

or a pharmaceutically acceptable salt thereof.

5 . The compound of claim 1 , wherein the compound is further defined as:

wherein:

R 3 is hydrogen or hydroxy; and

Y is —C(O)R c , wherein R c is:

hydroxy, alkoxy (C≤8) , or substituted alkoxy (C≤8) ; and

R 5 is acyloxy (C≤8) ;

or a pharmaceutically acceptable salt thereof.

6 . The compound of claim 1 , wherein R 5 is acyloxy (C≤8) .

7 . The compound of claim 1 , wherein the compound is further defined as:

or a pharmaceutically acceptable salt thereof.

8 . A pharmaceutical composition comprising:

(A) a compound of claim 1 ; and

(B) an excipient or a pharmaceutically acceptable carrier.

9 . A method of treating an autoimmune disease selected from the group consisting of psoriasis, multiple sclerosis, scleroderma, rheumatoid arthritis, lupus, psoriatic arthritis, ankylosing spondylitis, Sjögren syndrome, vitiligo, uveitis, systemic sclerosis, type 1 diabetes, myasthenia gravis, and inflammatory bowel disease, in a patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound of claim 1 .

10 . The compound of claim 7 , wherein the compound is further defined as:

or a pharmaceutically acceptable salt thereof.

Assignments (7)

Continuity (3)

References Cited (400)