IP Library Granted Patent US 9,487,536
Granted Patent B2
US 9,487,536 · App. 14/676,537 · Granted Nov 8, 2016

Melampomagnolide B derivatives

Inventors: Shobanbabu Bommagani (Little Rock, AR); Peter Crooks (Little Rock, AR); Narsimha Reddy Penthala (Little Rock, AR); Venumadhav Janganati (Little Rock, AR); Craig T. Jordan (Aurora, CO); Jessica Ponder (Aurora, CO)
Assignees: BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS; REGENTS OF THE UNIVERSITY OF COLORADO
C07D493/04
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Quick Facts
Patent No.
US 9,487,536
App. No.
14/676,537
Granted
Nov 8, 2016
Kind
B2
Abstract

The present disclosure provides derivatives of melampomagnolide B (MMB), including carbonates, carbamates, thiocarbamates, ester and amide derivatives of MMB. These derivatives are useful for treating cancer in humans.

Claims (26)

1. A compound comprising Formula (I):

wherein:

R is selected from the group consisting of

wherein:

R 1 is selected from the group consisting of substituted indoles, substituted heterocyclic aromatic, and substituted aromatic derivatives;

R 2 is selected from the group consisting of substituted indoles; and

R 3 is selected from the group consisting of substituted amines.

2. The compound of claim 1 , wherein Formula (I) comprises:

wherein:

X is selected from the group consisting of S, O, NH, NR 10 ;

R 9 is selected from the group consisting of OMe, Cl, Br and F; and

R 10 is selected from the group consisting of H, CH 3 , benzyl, substituted benzyl, benzoyl, substituted benzoyl, and benzylsulfonyl and substituted benzylsulfonyl.

3. The compound of claim 1 , wherein Formula (I) comprises:

wherein:

R 11 is selected from the group consisting of H, CH 3 , benzyl, substituted benzyl, benzoyl, substituted benzoyl, and benzylsulfonyl and substituted benzylsulfonyl; and

R 12 and R 13 are independently selected from the group consisting of H, F, Cl, Br, OCH 3 , CN, CH 3 , NO 2 and COOCH 3 .

4. The compound of claim 1 , wherein Formula (I) comprises:

wherein:

R 14 is selected from the group consisting of 2-thiophenyl, 3-thiophenyl, 2-pyrazine, 3-pyrazine, 2-amino nicotinic acid, indole-3-acetic acid, indole-3-acrylic acid.

5. The compound of claim 1 , wherein Formula (I) comprises:

wherein:

R 15 is selected from the group consisting of:

6. The compound of claim 1 , wherein Formula (I) comprises:

wherein:

R 1 is selected from the group consisting of substituted indoles, substituted heterocyclic aromatic, aromatic and aliphatic derivatives.

7. A pharmaceutically acceptable salt comprising a compound of claim 1 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2018
From: BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS
To: BIOVENTURES, LLC
Reel/Frame 047667/0515 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2015
From: BOMMAGANI, SHOBANBABU; JANGANATI, VENUMADHAV; PENTHALA, NARSIMHA REDDY; CROOKS, PETER A.
To: BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS
Reel/Frame 035558/0470 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2015
From: JORDAN, CRAIG T.; PONDER, JESSICA
To: THE REGENTS OF THE UNIVERSITY OF COLORADO
Reel/Frame 035558/0524 →
CONFIRMATORY LICENSE Recorded Apr 24, 2015
From: UNIV OF ARKANSAS FOR MED SCIS
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 035511/0392 →
Continuity (3)
Continuation In Part 14537389 · Nov 10, 2014
Provisional Application 61901714 · Nov 8, 2013
Related Publication 20150203508A1 · Jul 23, 2015