# US 10,118,935 B2 · Melampomagnolide B dimers

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- Number: US 10,118,935 B2
- Document ID: US10118935B2
- Status: Granted
- Kind: B2
- Application number: 15/957,524
- Filed: 2018-04-19
- Published: 2018-08-23
- Granted: 2018-11-06
- Earliest claimed: 2014-12-03
- Assignees: BioVentures, LLC; The Regents of the University of Colorado
- Applicants: BioVentures, LLC; The Regents of the University of Colorado, A Body Corporate
- Inventors: Venumadhav Janganati; Peter Crooks; Narsimha Reddy Penthala; Craig Jordan; Shobanbabu Bommagani; Jessica Ponder
- Web page: https://patentgrep.com/patent/US10118935B2

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present disclosure provides dimers of melampomagnolide B (MMB), including carbamate, carbonate, succinic amide, ester and carboxamide dimers of MMB. These derivatives are useful for treating cancer in humans, in particular in treating leukemia, including acute myelogenous leukemia (AML).

## Claims

### Claim 1

A method for treating cancer, comprising administering a therapeutically effective amount of a compound comprising Formula (I), or a pharmaceutically acceptable salt thereof, to a patient in need thereof, according to the following formula:
wherein:
Z is independently selected from the group consisting of CH2, O, C(O), and CH, wherein when Z is CH, Z is connected to Y via a double bond and Y is N;
Y is independently selected from the group consisting of O, NR, N,
heterocycle, hydrocarbyl and substituted hydrocarbyl;
X is selected from the group consisting of (CH2)n, C(O),
—(CH2)n—W—C(O)—, —C(O)—W—C(O)—, —C(O)NH—W—NHC(O)—, —C(O)O—W—OC(O)—, carbocycle, heterocycle, alkyl, substituted alkyl, hydrocarbyl and substituted hydrocarbyl;
R is selected from the group consisting of H, alkyl, hydrocarbyl and substituted hydrocarbyl;
W is selected from the group consisting of O, S, NH, N-alkyl, heterocycle, alkyl, substituted alkyl, hydrocarbyl and substituted hydrocarbyl; and
n is an integer from 0-10.

### Claim 2 (depends on 1)

The method of any of claim 1, wherein the cancer is leukemia.

### Claim 3 (depends on 2)

The method of claim 2, wherein the leukemia is acute myelogenous leukemia (AML).

### Claim 4 (depends on 1)

The method of claim 1, wherein the cancer is a solid tumor.

### Claim 5 (depends on 4)

The method of claim 4, wherein the solid tumor is selected from the group
consisting of non small cell lung cancer, colon cancer, melanoma, ovarian cancer, renal cancer, and breast cancer.

### Claim 6

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 pharmaceutically acceptable salt thereof, effective to inhibit growth of the cancer cell, the compound comprising Formula (I):
wherein:
Z is independently selected from the group consisting of CH2, O, C(O), and CH, wherein when Z is CH, Z is connected to Y via a double bond and Y is N;
Y is independently selected from the group consisting of O, NR, N,
heterocycle, hydrocarbyl and substituted hydrocarbyl;
X is selected from the group consisting of (CH2)n, C(O),
—(CH2)n—W—C(O)—, —C(O)—W—C(O)—, —C(O)NH—W—NHC(O)—, —C(O)O—W—OC(O)—, carbocycle, heterocycle, alkyl, substituted alkyl, hydrocarbyl and substituted hydrocarbyl;
R is selected from the group consisting of H, alkyl, hydrocarbyl and substituted hydrocarbyl;
W is selected from the group consisting of O, S, NH, N-alkyl, heterocycle, alkyl, substituted alkyl, hydrocarbyl and substituted hydrocarbyl; and
n is an integer from 0-10.

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 6)

The method of claim 6, wherein the cancer cell is a leukemia cancer cell.

### Claim 9 (depends on 8)

The method of claim 8, wherein the leukemia cancer cell is an acute myelogenous leukemia (AML) cancer cell.

### Claim 10 (depends on 6)

The method of claim 6, wherein the cancer cell is a solid tumor cell.

### Claim 11 (depends on 10)

The method of claim 10, wherein the solid tumor cell is selected from the group consisting of non small cell lung cancer, colon cancer, melanoma, ovarian cancer, renal cancer, and breast cancer.

### Claim 12 (depends on 1)

The method of claim 1, wherein the compound comprises Formula (II) or a pharmaceutical acceptable salt thereof:
wherein:
X is selected from the group consisting of O or NH; and
n is an integer from 0-10.

### Claim 13 (depends on 1)

The method of claim 1, wherein the compound comprises Formula (IV):
wherein:
n is an integer from 1-10.

### Claim 14 (depends on 1)

The method of claim 1, wherein the compounds comprising Formulas (I), (II), (III), (IV) or (V) independently have an optical activity of (−) or (+); and the configuration of C-4, C-5, C-6, and C-7, respectively, is RRRR, RRSR, RRRS, RRSS, RSRR, RSSR, RSRS, RSSS, SRRR, SRSR, SRRS, SRSS, SSRR, SSSR, SSRS, or SSSS.

### Claim 15 (depends on 6)

The method of claim 6, wherein the compound comprises Formula (II) or a pharmaceutical acceptable salt thereof:
wherein:
X is selected from the group consisting of O or NH; and
n is an integer from 0-10.

### Claim 16 (depends on 6)

The method of claim 6, wherein the compound comprises Formula (IV):
wherein:
n is an integer from 1-10.

### Claim 17 (depends on 6)

The method of claim 6, wherein the compounds comprising Formulas (I), (II), (III), (IV) or (V) independently have an optical activity of (−) or (+); and the configuration of C-4, C-5, C-6, and C-7, respectively, is RRRR, RRSR, RRRS, RRSS, RSRR, RSSR, RSRS, RSSS, SRRR, SRSR, SRRS, SRSS, SSRR, SSSR, SSRS, or SSSS.