# US 11,897,910 B2 · Mito-honokiol compounds and methods of synthesis and use thereof

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- Number: US 11,897,910 B2
- Document ID: US11897910B2
- Status: Granted
- Kind: B2
- Application number: 17/099,268
- Filed: 2020-11-16
- Published: 2021-03-11
- Granted: 2024-02-13
- Earliest claimed: 2015-06-11
- Assignees: The Medical College of Wisconsin, Inc.; Aix-Marseille Universite
- Applicants: The Medical College of Wisconsin, Inc.; Aix-Marseille Universite
- Inventors: Balaraman Kalyanaraman; Jacek Michal Zielonka; Gang Cheng; Micael J. Hardy; Olivier Ouari; Ming You
- Web page: https://patentgrep.com/patent/US11897910B2

## CPC

- C07F 9/5456: {Arylalkanephosphonium compounds}
- A61K 31/66: Phosphorus compounds
- A61P 35/04: specific for metastasis
- C07F 9/5442: {Aromatic phosphonium compounds (P-C aromatic linkage)}
- A61K 31/19: Carboxylic acids, e.g. valproic acid (salicylic acid A61K31/60)
- A61K 31/7004: Monosaccharides having only carbon, hydrogen and oxygen atoms
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides mito-honokiol or mito-magnolol compounds, pharmaceutical compositions thereof, and methods of using the mito-honokiol or mito-magnolol compounds in the treatment of cancer.

## Claims

### Claim 1

A mito-magnolol compound according to the following structures:
wherein L1 is
wherein n is an integer from 1-15, and
wherein L2 is
or H, wherein n is an integer from 1-15.

### Claim 2 (depends on 1)

The compound of claim 1 wherein n is an integer from 1-12.

### Claim 3 (depends on 1)

The compound of claim 1, wherein n is 9 or 10.

### Claim 4 (depends on 1)

The compound of claim 1, wherein L2 is
wherein n is an integer from 1-15.

### Claim 5 (depends on 4)

The compound of claim 4, wherein n is 9 or 10.

### Claim 6 (depends on 1)

The compound of claim 1, wherein L2 is H.

### Claim 7 (depends on 6)

The compound of claim 6, wherein n of L1 is an integer from 1-12.

### Claim 8 (depends on 7)

The compound of claim 7, wherein n is 9 or 10.

### Claim 9 (depends on 1)

The compound of claim 1, where the compound is:

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is

### Claim 11 (depends on 1)

A method of reducing or inhibiting tumor growth in a subject comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition comprising at least one mito-magnolol compound of claim 1, wherein the tumor is melanoma, lung cancer, colon cancer or pancreatic cancer.

### Claim 12 (depends on 11)

The method of claim 11, wherein the tumor is a lung cancer.

### Claim 13 (depends on 11)

The method of claim 11, wherein the tumor is a metastatic tumor.

### Claim 14 (depends on 11)

The method of claim 11, wherein the method further comprises treatment of the patient with an antiglycolytic agent and other standard-of-care drug.

### Claim 15 (depends on 11)

The method of claim 11, wherein the antiglycolytic agent is selected from the group consisting of 2-deoxyglucose or 3-bromopyruvate.

### Claim 16 (depends on 11)

The method of claim 11, wherein the method further comprises treating the patient with surgery, radiation therapy (RT), or chemotherapy (CT) prior to or concurrently with administering the pharmaceutical composition.

### Claim 17 (depends on 1)

A method of inhibiting, or reducing metastasis of a cancer comprising administering an effective amount of a pharmaceutical composition comprising at least one mito-magnolol of claim 1 to inhibit or reduce metastasis of cancer in the patient, wherein the cancer is selected from the group consisting of melanoma, colon cancer, lung cancer and pancreatic cancer.

### Claim 18 (depends on 17)

The method of claim 17, wherein the metastasis is in a lymph node or distal organ.

### Claim 19 (depends on 1)

The compound of claim 1, wherein then of both L1 and L2 is an integer from 1-12.