# US 2018/0022771 A1 · Cymanquine compounds and derivatives thereof and uses thereof

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- Number: US 2018/0022771 A1
- Document ID: US20180022771A1
- Status: Published application
- Kind: A1
- Application number: 15/541,300
- Filed: 2016-01-04
- Published: 2018-01-25
- Earliest claimed: 2015-01-02
- Assignees: University of Vermont and State Agricultural College
- Applicants: University of Vermont and State Agricultural College
- Inventors: William E. GEIGER; Kevin LAM; Jon E. RAMSEY; Claire F. VERSCHRAEGEN
- Web page: https://patentgrep.com/patent/US20180022771A1

## CPC

- C07F 13/00: Compounds containing elements of Groups 7 or 17 of the Periodic Table
- A61K 31/555: containing heavy metals, e.g. hemin, hematin, melarsoprol
- 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)

## Abstract

Organometallic compounds comprising a chloroquinoline moiety and uses the compounds. The compounds are, for example, manganese or rhenium complexes of a ligand comprising a chloroquinoline moiety. The compounds can be used in, for example, methods of inhibiting cell growth.

## Claims

### Claim 1

A compound having the formula:
where:
M is Mn or Re,
L is a neutral, two-electron donor ligand,
R1 is H or an amine-substituted alkyl group,
R2 is H, (CH2)nCH3, wherein n is 0 to 20, OMe, OEt, OPh, Ph, CHO, COMe, COPh, CH2OH, CO2H, CO2Me, CO2Et, CH2Ph, NH2, NMe2, NEt2, C6H4Me, C6H4OMe, NH2COMe, F, Cl, Br, or I; and
E is a linker moiety connecting the cyclopentadienyl moiety with the chloroquinoline moiety.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is (CH2)nNR3R4, where n is an integer from 1 to 20 and R3 and R4 are independently H or an C1-Cx alkyl group, wherein x is an integer from 2 to 20.

### Claim 3 (depends on 1)

The compound of claim 1, wherein L is selected from —CO, phosphines, phosphites, aryl amines, and carbenes.

### Claim 4 (depends on 1)

The compound of claim 1, wherein E is —NH(CH2)n—, NH(CH2)nNH— where n is an integer from 1 to 10.

### Claim 5 (depends on 1)

The compound of claim 1, wherein a CO ligand is replaced by a second neutral, two-electron donor.

### Claim 6 (depends on 1)

The compound of claim 1, wherein M is Mn and R1 is an amine-substituted alkyl group.

### Claim 7 (depends on 1)

The compound of claim 1, wherein M is Re and R1 is an amine-substituted alkyl group.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound has the following structure:

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound has the following structure:

### Claim 10 (depends on 1)

A composition comprising one or more compounds of claim 1 and a pharmaceutical carrier.

### Claim 11 (depends on 1)

A method for treating cancer comprising administering to an individual who has been diagnosed with, is suffering from, or is at risk of developing cancer comprising administering to the individual a therapeutically effective amount of a composition comprising one of more compounds of claim 1.

### Claim 12 (depends on 11)

The method of claim 11, further comprising subjecting the individual to one or more of the following:
i) surgically removing a malignant tumor,
ii) radiation, and
iii) additional chemotherapy.

### Claim 13 (depends on 1)

A method for inhibiting the growth of cells comprising contacting the cells with a compound of claim 1.

### Claim 14 (depends on 1)

A kit comprising one or more containers or packaging having a compound of claim 1 and instructions for use.

### Claim 15 (depends on 14)

The kit of claim 14, wherein the kit comprises a plurality of individualized sealed packets, each individual packets representing a dose of the composition for a single use.

### Claim 16 (depends on 11)

The method of claim 11, wherein the composition further comprises a pharmaceutical carrier.

### Claim 17 (depends on 13)

The method of claim 13, wherein the compound is present in a pharmaceutical carrier.

### Claim 18 (depends on 14)

The kit of claim 14, further comprising a pharmaceutical carrier.

### Claim 19 (depends on 18)

The kit of claim 18, wherein the kit comprises a plurality of individualized sealed packets, each individual packets representing a dose of the composition for a single use.