IP Library Granted Patent US 9,611,235
Granted Patent B2
US 9,611,235 · App. 13/102,475 · Granted Apr 4, 2017

Methods and compositions related to a retinoid receptor-selective pathway

Inventors: Xiao-kun Zhang (San Diego, CA); Ying Su (San Diego, CA); Hu Zhou (San Diego, CA); Wen Liu (La Jolla, CA); Pei-Qiang Huang (Xiamen, CN)
Assignees: SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; XIAMEN UNIVERSITY
C07D295/112A61K38/191C07C57/62C07C59/72C07C255/57C07D213/55G01N33/5011G01N2333/70567G01N2510/00
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Quick Facts
Patent No.
US 9,611,235
App. No.
13/102,475
Granted
Apr 4, 2017
Kind
B2
Abstract

Provided herein are methods and compositions related to a retinoid receptor-selective pathway. As described herein, this pathway can be targeted to manipulate a tumor microenvironment. For example, the methods and compositions described herein can be used to induce apoptosis in a cancer cell. Further, the compositions described herein, including Sulindac and analogs thereof, can be used to target this pathway for the treatment or prevention of cancer in human patients.

Claims (18)

1. A compound of formula (I), or a sodium salt thereof, having the structure:

wherein A is a phenyl, and wherein A is substituted by one or two substituents independently selected from the group consisting of C2-3 alkyl, n-butyl, iso-butyl, sec-butyl, —CF 3 , a C3-C4 cycloalkyl, and a C4-C5 cycloalkylalkyl;

wherein B is a fused phenyl, and wherein B is substituted by a fluoro;

wherein R 1 is —(CR 5 R 6 ) n COOH;

wherein R 2 is CH 3 ;

wherein R 5 and R 6 are H; and

wherein n is 1 or 2.

2. A compound of formula (II), or a sodium salt thereof, having the structure:

wherein R 1 is selected from the group consisting of CH 2 COOH and CH 2 CH 2 COOH;

wherein R 2 is CH 3 ; and

wherein R 3 is selected from the group consisting of 4-CH 2 CH 3 , and 4-CH(CH 3 ) 2 .

3. The compound of claim 2 , or a sodium salt thereof, selected from the group consisting of:

4. The compound of claim 2 , or a sodium salt thereof, selected from the group consisting of:

5. The compound of claim 2 , or a sodium salt thereof, having the structure:

6. A compound, or a sodium salt thereof, having the structure:

7. A pharmaceutical composition comprising a compound of claim 1 , or a sodium salt thereof, and a pharmaceutically acceptable excipient.

8. A pharmaceutical composition comprising a compound of claim 2 , or a sodium salt thereof, and a pharmaceutically acceptable excipient.

9. A pharmaceutical composition comprising a compound of claim 6 , or a sodium salt thereof, and a pharmaceutically acceptable excipient.

Assignments (5)
CONFIRMATORY LICENSE Recorded Apr 10, 2012
From: BURNHAM INSTITUTE
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 028023/0504 →
CONFIRMATORY LICENSE Recorded Apr 4, 2012
From: BURNHAM INSTITUTE
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 027986/0672 →
CONFIRMATORY LICENSE Recorded Oct 17, 2011
From: BURNHAM INSTITUTE
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 027068/0773 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 21, 2011
From: HUANG, PEI-QIANG
To: XIAMEN UNIVERSITY
Reel/Frame 026638/0909 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 21, 2011
From: ZHANG, XIAO-KUN; SU, YING; ZHOU, HU; LIU, WEN
To: SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE
Reel/Frame 026638/0912 →
Continuity (2)
Provisional Application 61332124 · May 6, 2010
Related Publication 20150266842A1 · Sep 24, 2015