IP Library Granted Patent US 8,901,117
Granted Patent B2
US 8,901,117 · App. 13/336,047 · Granted Dec 2, 2014

Small molecule inhibitors of MDM2 and the uses thereof

Inventors: Shaomeng Wang (Saline, MI); Ke Ding (Guangzhou, CN); Yipin Lu (Ann Arbor, MI); Zaneta Nikolovska-Coleska (Ann Arbor, MI); Su Qiu (Ann Arbor, MI); Guoping Wang (Ann Arbor, MI); Dongguang Qin (Ann Arbor, MI); Sanjeev Kumar (Ann Arbor, MI)
Assignee: The Regents of The University of Michigan
C07D209/54C07D491/10C07D487/10
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Quick Facts
Patent No.
US 8,901,117
App. No.
13/336,047
Granted
Dec 2, 2014
Kind
B2
Abstract

The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

Claims (14)

1. A method of treating or ameliorating colon cancer or prostate cancer in an animal, comprising administering to said animal a therapeutically effective amount of a compound having Formula X:

or a pharmaceutically acceptable salt thereof, wherein:

R 1 is optionally substituted cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclic, CO 2 R′, OCOR′, CONR′R″, NR″COR′, NR′SO 2 R″, SO 2 NR′R″, (C═NR′)NR″R′″, or NR′R″;

R 5 and R 7 are independently H or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclic, CO 2 R′, OCOR′, CONR′R″, NR″COR′, NR′SO 2 R″, SO 2 NR′R″, (C═NR′)NR″R′″, or NR′R″;

R 9 is one to four groups independently selected from H, F, Cl, Br, I, OH, NO 2 , alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclic, OR′, CO 2 R′, OCOR′, CONR′R″, NR″COR′, NR′SO 2 R″, SO 2 NR′R″, (C═NR′)NR″R′″, or NR′R″; and

each R′, R″ and R′″ is independently H or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic; or

R′ and R″, or R″ and R′″, form a ring;

R 10 and R 11 are independently H, (CH 2 ) n —R′, (CH 2 ) n —NR′R″, (CH 2 ) n —NR′COR″, (CH 2 ) n —NR′SO 2 R″, (CH 2 ) n —NR′(C═NR″)NR′″, (CH 2 ) n —COOH, (CH 2 ) n —COOR′, (CH 2 ) n —CONR′R″, (CH 2 ) n —OR′, (CH 2 ) n —SR′, (CH 2 ) n —COR′, (CH 2 ) n —SO 3 H, (CH 2 ) n —SONR′R″, (CH 2 ) n —SO 2 NR′R″, (CH 2 CH 2 O) n —(CH 2 ) m —OH, (CH 2 CH 2 O) n —(CH 2 ) m —OR′, (CH 2 CH 2 O) n —(CH 2 ) m —COOR′, (CH 2 CH 2 O) n —(CH 2 ) m —CONR′R″, (CH 2 CH 2 O) n —(CH 2 ) m —NR′R″, (CH 2 CH 2 O) n —(CH 2 ) m —NR′COR″, (CH 2 CH 2 O) n —(CH 2 ) m —NR′(C═NR″)NR′″, (CH 2 CH 2 O) n —(CH 2 ) m —NR′SO 2 R″, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —OH, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —OR′, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —COOR′, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —CONR′R″, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —NR′R″, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —NR′COR″, (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —NR′(C═NR″)NR′″, or (CH 2 ) p —(CH 2 CH 2 O) n —(CH 2 ) m —NR′SO 2 R″; and n, m, and p are each independently 1-6.

2. The method of claim 1 , further comprising administering an additional agent(s).

3. The method of claim 2 , wherein said additional agent(s) is a chemotherapeutic agent.

4. The method of claim 2 , wherein said additional agent(s) is radiation.

5. The method of claim 2 , wherein said compound is administered prior to said additional agent(s).

6. The method of claim 2 , wherein said compound is administered after said additional agent(s).

7. The method of claim 2 , wherein said compound is administered concurrently with said additional agent(s).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2011
From: WANG, SHAOMENG; DING, KE; LU, YIPIN; NIKOLOVSKA-COLESKA, ZANETA; QIU, SU; WANG, GUOPING; QIN, DONGGUANG; KUMAR, SANJEEV
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 027440/0014 →
Continuity (5)
Division 12822829 · Jun 24, 2010
Division 11360485 · Feb 22, 2006
Provisional Application 60749023 · Dec 8, 2005
Provisional Application 60655135 · Feb 22, 2005
Related Publication 20120101092A1 · Apr 26, 2012