IP Library Granted Patent US 9,186,402
Granted Patent B2
US 9,186,402 · App. 13/944,446 · Granted Nov 17, 2015

Method for preparing largazole analogs and uses thereof

Inventors: Robert M. Williams (Fort Collins, CO); James E. Bradner (Cambridge, MA); Albert Bowers (Boston, MA); Tenaya Newkirk (Fort Collins, CO); Olaf G. Wiest (Notre Dame, IN)
Assignees: Colorado State University Research University; Dana-Farber Cancer Institute, Inc.; University of Notre Dame du Lac
A61K39/39558A61K31/429C07D498/18C07D513/18
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Quick Facts
Patent No.
US 9,186,402
App. No.
13/944,446
Granted
Nov 17, 2015
Kind
B2
Abstract

Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

Claims (21)

1. A compound of Formula (I)

wherein X is S or O;

Y is NR, wherein R is H, lower alkyl, or lower arylalkyl;

Z is S or O;

R 1 is H, lower alkyl, or lower arylalkyl;

R 2 is lower alkyl, isopropyl, n-propyl, cyclopropyl, isobutyl, n-butyl, sec-butyl, or tert-butyl;

R 4 is H, (CH 2 ) n COOH, (CH 2 ) n CONHR, (CH 2 ) n CONHOH, (CH 2 ) n SR 3 , SR 5 (wherein R 5 is lower alkyl or lower aryl),

wherein n is at least 1, and wherein R 3 is H, octanoyl, acyl, SR, a higher acyl derivative, or

or a pharmaceutically acceptable salt, solvate, clathrate, prodrug, or stereoisomer thereof.

2. The compound of claim 1 , having the Formula (III)

or a pharmaceutically acceptable salt, solvate, clathrate, prodrug, or stereoisomer thereof.

3. The compound of claim 1 , having the Formula (VIII)

or a pharmaceutically acceptable salt, solvate, clathrate, prodrug, or stereoisomer thereof.

4. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 1 and at least one pharmaceutically acceptable excipient for treating cancer in a subject.

5. The pharmaceutical composition of claim 4 , wherein the subject is human.

6. The compound of claim 1 , wherein R 1 is H or lower alkyl.

7. The compound of claim 1 , wherein R 1 is methyl.

8. The compound of claim 1 , wherein R 2 is lower alkyl.

9. The compound of claim 1 , wherein R 2 is isopropyl.

10. The compound of claim 1 , wherein X is S.

11. The compound of claim 1 , wherein Z is S.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2014
From: WILLIAMS, ROBERT M; BOWERS, ALBERT; NEWKIRK, TENAYA
To: COLORADO STATE UNIVERSITY RESEARCH FOUNDATION
Reel/Frame 032739/0835 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2014
From: BRADNER, JAMES E
To: DANA-FARBER CANCER INSTITUTE, INC.
Reel/Frame 032739/0847 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2014
From: WIEST, OLAF G
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 032739/0859 →
Continuity (5)
Continuation 13490693 · Jun 7, 2012
Division 12504508 · Jul 16, 2009
Provisional Application 61151087 · Feb 9, 2009
Provisional Application 61081653 · Jul 17, 2008
Related Publication 20140093449A1 · Apr 3, 2014