IP Library Granted Patent US 9,452,992
Granted Patent B2
US 9,452,992 · App. 14/237,625 · Granted Sep 27, 2016

Small molecule inhibitors of ebola and lassa fever viruses

Inventors: James Cunningham (Wellesley, MA); Kyungae Lee (Newton, MA); Tao Ren (West Roxbury, MA); Kartik Chandran (Brooklyn, NY)
Assignees: President and Fellows of Harvard College; The Brigham and Women's Hospital, Inc.
C07D295/185
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Quick Facts
Patent No.
US 9,452,992
App. No.
14/237,625
Granted
Sep 27, 2016
Kind
B2
Abstract

The present invention relates to compositions and methods for the treatment of infection by enveloped viruses, such as Ebola and Lassa fever viruses.

Claims (25)

1. A compound represented by formula I:

or a pharmaceutically acceptable salt, solvate, hydrate, enantiomer or stereoisomer thereof; wherein, independently for each occurrence,

W is

R is

X is

n is 1 or 2;

A is adamant-1-yl, 3-alkyladamant-1-yl, 5-alkyladamant-1-yl or 3,5-dialkyladamantyl;

R 2 is hydrogen, halo, alkyl or haloalkyl;

R 3 is hydrogen, halo, alkyl, haloalkyl, alkenyl, or aryl;

R 4 is hydrogen or alkyl;

R 5 is hydrogen, alkyl, haloalkyl or alkyl substituted with one or two substituents independently selected from halo, cyano, haloalkyl, aralkyl, hydroxy, alkyloxy, carboxy, alkyloxycarbonyl, haloalkyloxycarbonyl, carbocyclyloxycarbonyl, aryloxycarbonyl, carbocyclylalkyloxycarbonyl, and aralkyloxycarbonyl; and

R 6 is phenyl or pyridinyl, optionally substituted with one, two, three or four substituents selected from hydroxy, alkyloxy, tert-butyldimethylsilyloxy, methylenedioxy, ethylenedioxy, propylenedioxy, butylenedioxy, alkyl, haloalkyl, trifluoromethyl, fluoro, chloro, bromo, iodo, cyano, nitro, acetylamino, carboxy and alkyloxycarbonyl;

provided the compound is not

2. A compound, or pharmaceutically acceptable salt, solvate, hydrate, enantiomer or stereoisomer thereof, selected from

3. The compound of claim 1 , wherein R 1 is

4. The compound of claim 1 , wherein R 1 is phenyl, naphth-1-yl, naphth-2-yl, pyridin-2-yl or pyridin-3-yl.

5. The compound of claim 1 , wherein R 2 is hydrogen.

6. The compound of claim 1 , wherein R 3 is hydrogen.

7. The compound of claim 1 , wherein R is

and X is

8. The compound of claim 1 , wherein A is adamant-1-yl or 3,5-dialkyladamantyl.

9. The compound of claim 1 , wherein R 5 is hydrogen.

10. The compound of claim 2 , wherein the compound is

11. The compound of claim 1 , wherein R is

12. The compound of claim 1 , wherein R 6 is

Assignments (3)
CONFIRMATORY LICENSE Recorded Nov 17, 2014
From: HARVARD UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 034274/0214 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2014
From: LEE, KYUNGAE; REN, TAO
To: PRESIDENT AND FELLOWS OF HARVARD COLLEGE
Reel/Frame 033408/0964 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2014
From: CUNNINGHAM, JAMES; CHANDRAN, KARTIK
To: THE BRIGHAM AND WOMEN'S HOSPITAL, INC.
Reel/Frame 033408/0980 →
Continuity (2)
Provisional Application 61521998 · Aug 10, 2011
Related Publication 20140329834A1 · Nov 6, 2014