IP Library Granted Patent US 10,604,492
Granted Patent B2
US 10,604,492 · App. 16/016,290 · Granted Mar 31, 2020

CFTR regulators and methods of use thereof

Inventors: Alan S. Verkman (San Francisco, CA); Marc H. Levin (San Francisco, CA); Onur Cil (San Francisco, CA); Sujin Lee (San Francisco, CA)
Assignee: THE REGENTS OF THE UNIVERSTIY OF CALIFORNIA
C07D251/52A61K31/496A61K31/53A61K31/5377A61K31/55A61K45/06A61P1/10A61P27/04C07D251/46C07D403/04C07D413/12
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Quick Facts
Patent No.
US 10,604,492
App. No.
16/016,290
Granted
Mar 31, 2020
Kind
B2
Abstract

Provided herein are compounds that activate CFTR and methods for treating constipation, dry eye disorders, and other diseases and disorders.

Claims (34)

1. A compound of Formula I:

or a pharmaceutically acceptable salt thereof,

wherein:

X is —O—;

R 2 is C 2 -C 4 haloalkyl substituted with at least four fluorines, substituted heteroalkyl, or unsubstituted heteroalkyl;

R 3 is hydrogen;

R 4 is substituted or unsubstituted alkyl;

R 5 is hydrogen; and

R 1 , R 6 , R 7 , R 8 and R 9 are each hydrogen.

2. The compound of claim 1 , wherein R 4 is —CH 3 or —CH 2 CH 3 .

3. The compound of claim 1 , wherein R 2 is C 2 -C 4 haloalkyl substituted with at least four fluorines.

4. The compound of claim 3 , wherein R 2 is —CH(CF 3 ) 2 or —CH 2 —CF 2 —CHF 2 .

5. The compound of claim 1 , wherein the compound of Formula I is:

6. A compound that is:

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 6 , wherein the compound is:

8. The compound of claim 6 , wherein the compound is a pharmaceutically acceptable salt of:

9. A pharmaceutical composition, comprising a pharmaceutically acceptable excipient, and a compound of Formula I:

or a pharmaceutically acceptable salt thereof,

wherein:

X is —O—;

R 2 is C 2 -C 4 haloalkyl substituted with at least four fluorines, substituted heteroalkyl; or unsubstituted heteroalkyl;

R 3 is hydrogen;

R 4 is substituted or unsubstituted alkyl;

R 5 is hydrogen; and

R 1 , R 6 , R 7 , R 8 and R 9 are hydrogen.

10. The pharmaceutical composition of claim 9 , wherein R 4 is —CH 3 or —CH 2 CH 3 .

11. The pharmaceutical composition of claim 9 , wherein R 2 is C 2 -C 4 haloalkyl substituted with at least four fluorines.

12. The pharmaceutical composition of claim 11 , wherein R 2 is —CH(CF 3 ) 2 or —CH 2 —CF 2 —CHF 2 .

13. The pharmaceutical composition of claim 9 , wherein the compound of Formula I is:

14. A pharmaceutical composition comprising a compound that is:

or a pharmaceutically acceptable salt thereof.

15. The pharmaceutical composition of claim 14 , wherein the compound is:

16. The pharmaceutical composition of claim 14 , wherein the compound is a pharmaceutically acceptable salt of:

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2019
From: VERKMAN, ALAN S.; LEVIN, MARC H.; CIL, ONUR; LEE, SUJIN
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 048942/0355 →
CONFIRMATORY LICENSE Recorded Apr 10, 2019
From: UNIVERSITY OF CALIFORNIA, SAN FRANCISCO
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 048853/0138 →
Cited By (2)
US 12,391,654 US 12,622,915