IP Library Granted Patent US 8,815,927
Granted Patent B2
US 8,815,927 · App. 13/503,366 · Granted Aug 26, 2014

Bivalent diazo bicyclic Smac mimetics and the uses thereof

Inventors: Shaomeng Wang (Saline, MI); Haiying Sun (Ann Arbor, MI)
Assignee: The Regents of the University of Michigan
C07D519/00C07D487/04
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Quick Facts
Patent No.
US 8,815,927
App. No.
13/503,366
Granted
Aug 26, 2014
Kind
B2
Abstract

The invention relates to diazo bicyclic Smac mimetics that are tethered through a covalent linker to give a bivalent species. Bivalent diazo bicyclic Smac mimetics function as inhibitors of Inhibitor of Apoptosis Proteins (IAPs). The invention also relates to the use of bivalent diazo bicyclic Smac mimetics for inducing or sensitizing cells to the induction of apoptotic cell death. Thus, compounds of the invention are useful in the treatment, amelioration, or prevention of hyperproliferative diseases such as cancer.

Claims (21)

1. A compound having the following formula:

wherein:

wherein R and R′ are hydrogen;

R 2 and R 2′ are CH 3 ;

R 3 and R 3′ are independently selected from the group consisting of hydrogen and CH 3 ;

T and T′ are each

wherein:

Q is selected from the group consisting of O, S and NR 7 ;

R 7 is hydrogen;

R 9a , R 9b , R 9c and R 9d are independently selected from the group consisting of hydrogen and

U and U′ are N;

m and m′ are 1;

n and n′ are 1;

p and p′ are 1; and

L is selected from the group consisting of

A) —(CH 2 ) q — or —CO—(CH 2 ) r —CO—, wherein: q is 2-50 and r is 1-50; and

B) —CO—(CH 2 ) v —O—(CH 2 ) w —CO—, wherein v and w are independently 1-20;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , said compound having the formula:

or a pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

Assignments (2)
CONFIRMATORY LICENSE Recorded Apr 26, 2012
From: UNIVERSITY OF MICHIGAN
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 028109/0033 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2012
From: WANG, SHAOMENG; SUN, HAIYING
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 028089/0052 →
Continuity (2)
Provisional Application 61254440 · Oct 23, 2009
Related Publication 20120263675A1 · Oct 18, 2012