IP Library Granted Patent US 9,920,063
Granted Patent B2
US 9,920,063 · App. 15/251,889 · Granted Mar 20, 2018

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: BIOVENTURES, LLC; THE REGENTS OF THE UNIVERSITY OF COLORADO
C07D493/04
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Quick Facts
Patent No.
US 9,920,063
App. No.
15/251,889
Granted
Mar 20, 2018
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 (28)

1. A method for inhibiting growth of a cancer cell, the method comprising contacting the cancer cell with an amount of a compound comprising Formula (I), or a salt thereof, effective to inhibit growth of the cancer cell, the 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;

wherein the cancer cell is an acute myelogenous leukemia (AML) cancer cell or a solid tumor cell; and

wherein the solid tumor cell is selected from the group consisting of non-small cell lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer.

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

wherein:

R 15 is selected from the group consisting of:

6. The method 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. The method of claim 1 , wherein the cancer cell is in vivo or in vitro.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2017
From: BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS
To: BIOVENTURES, LLC
Reel/Frame 041137/0734 →
Continuity (4)
Division 14676537 · Apr 1, 2015
Continuation In Part 14537389 · Nov 10, 2014
Provisional Application 61901714 · Nov 8, 2013
Related Publication 20160368928A1 · Dec 22, 2016