# US 10,766,915 B2 · Metal-based coordination complexes as photodynamic compounds and their use

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,766,915 B2
- Document ID: US10766915B2
- Status: Granted
- Kind: B2
- Application number: 14/777,169
- Filed: 2014-03-17
- Published: 2016-02-11
- Granted: 2020-09-08
- Earliest claimed: 2013-03-15
- Applicants: Sherri Ann McFarland
- Inventors: Sherri Ann McFarland
- Web page: https://patentgrep.com/patent/US10766915B2

## CPC

- C07F 15/0053: {without a metal-carbon linkage}
- A61K 31/473: ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
- A61K 41/0057: {Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent}
- A61P 35/00: Antineoplastic agents
- C07F 15/0026: {without a metal-carbon linkage}
- 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

Compositions of the invention include metal-based coordination complexes, which are preferably tunable photodynamic compounds. The compositions and complexes are useful as therapeutic agents and as in vivo diagnostic agents for treating or preventing diseases including those that involve hyperproliferating cells in their etiology, such as cancer. Compositions and complexes of the invention are further capable of destroying microbial cells, such as bacteria, fungi, and protozoa, and destroying viruses. The compositions and complexes are also capable of modulating cell function in other ways.

## Claims

### Claim 1

A compound having the formula (V)
including hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, wherein:
M is selected from the group consisting of osmium, manganese, molybdenum, rhenium, ruthenium, iron, cobalt, rhodium, iridium, nickel, and platinum;
X is selected from the group consisting of Cl−, PF6−, Br−, BF4−, ClO4−, CF3SO3−, and SO4−2;
n=0, 1, 2, 3, 4, or 5;
Lig3 is a bidentate ligand that at each occurrence is each independently selected from the group consisting of
R3a, R3b, R3c, R3d, R3e, R3f, R3g, R3h, R3i, R3j, R3k, and R3l at each occurrence are each independently selected from the group consisting of hydrogen, C1-6 optionally substituted alkyl, C1-6 optionally substituted branched alkyl, C1-6 optionally substituted haloalkyl, C1-6 optionally substituted alkoxy, optionally substituted phenyl, and CO2R8;
R8 at each occurrence is independently selected from the group consisting of hydrogen and optionally substituted alkyl;
wherein: (a) the compound is not Os(biq)3(ClO4)2·H2O, where biq is 2,2′-biquinoline, and (b) when M is ruthenium: (i) no more than two substituents on M are identical, and (ii) no more than one substituent on M is 2,2′-biquinoline.

### Claim 2

A compound having the formula [Os(biq)2(Lig)]Xn, where:
X is selected from the group consisting of Cl−, PF6−, Br−, BF4−, ClO4−, CF3SO3−, and SO4−2;
n=0, 1, 2, 3, 4, or 5;
Lig is a bidentate ligand other than unsubstituted biq selected from the group consisting of
R1 is selected from the group consisting of hydrogen, optionally substituted phenyl, optionally substituted aryl, optionally substituted heteroaryl, 4-pyridyl, 3-pyridyl, 2-thiazole, 2-pyrolyl, 2-furanyl,
u is an integer;
R2a, R2b, R2c, R2d, R2e, R2f, R2g, R2h, R2i, R2j, R2k, and R2l at each occurrence are each independently selected from the group consisting of hydrogen, C1-6 optionally substituted alkyl, C1-6 optionally substituted branched alkyl, C3-7 optionally substituted cycloalkyl, C1-6 optionally substituted haloalkyl, C1-6 optionally substituted alkoxy, CO2R5, CONR62, NR72, SO3H, sulfate, sulfonate, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, and optionally substituted heterocycle;
R3a, R3b, R3c, R3d, R3e, R3f, R3g, R3h, R3i, R3j, R3k, and R3l at each occurrence are each independently selected from the group consisting of hydrogen, C1-6 optionally substituted alkyl, C1-6 optionally substituted branched alkyl, C1-6 optionally substituted haloalkyl, C1-6 optionally substituted alkoxy, optionally substituted phenyl, and CO2R8;
R4a, R4b, and R4c at each occurrence are each independently selected from the group consisting of hydrogen, C1-6 optionally substituted alkyl, C1-6 optionally substituted branched alkyl, C1-6 optionally substituted cycloalkyl, C1-6 optionally substituted haloalkyl, C1-6 optionally substituted alkoxy, CO2R5, CONR62, NR72, sulfate, sulfonate, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, and optionally substituted heterocycle;
R4a and R4b at each occurrence on a thiophene ring are taken together with the atom to which they are bound to form an optionally substituted ring having from 6 ring atoms containing 2 oxygen atoms;
R5 at each occurrence are each independently selected from the group consisting of hydrogen and optionally substituted alkyl;
R6 at each occurrence are each independently selected from the group consisting of hydrogen and optionally substituted alkyl;
R7 at each occurrence are each independently selected from the group consisting of hydrogen and optionally substituted alkyl;
R8 at each occurrence are each independently selected from the group consisting of hydrogen and optionally substituted alkyl; and
biq is 2,2′-biquinoline.

### Claim 3 (depends on 2)

The compound of claim 2, wherein Lig is 1,10-phenanthroline, imidazo[4,5-f][1,10]phenathroline or benzo[i]dipyrido[3,2-α:2′,3′-c]phenazine.

### Claim 4 (depends on 3)

The compound of claim 3, wherein X is Cl− and n is 2.