# US 12,760,039 B2 · Anti-inflammatory compounds, pharmaceutical compositions, and methods of treating hemochromatosis, and other disorders

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- Number: US 12,760,039 B2
- Document ID: US12760039B2
- Status: Granted
- Kind: B2
- Application number: 19/062,919
- Filed: 2025-02-25
- Published: 2026-09-03
- Granted: 2026-10-13
- Earliest claimed: 2022-09-02
- Assignees: Miralogx LLC
- Applicants: Miralogx LLC
- Inventors: Jonnie R. Williams, Sr.
- Web page: https://patentgrep.com/patent/US12760039B2

## CPC

- C07F 3/06: Zinc compounds
- A61K 31/555: containing heavy metals, e.g. hemin, hematin, melarsoprol
- C07D 471/20: Spiro-condensed systems
- C07D 471/22: in which the condensed systems contains four or more hetero rings
- C07D 487/22: in which the condensed system contains four or more hetero rings
- C07F 1/10: Silver compounds
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Pharmaceutical compounds have anti-inflammatory activity. A pharmaceutical composition may include a therapeutically effective amount of the compound(s) and a pharmaceutically acceptable vehicle. A method of treating hemochromatosis, hyperammonemia, or a disorder associated with chronic inflammation or a cancer, involves administering the pharmaceutical composition to an individual in need thereof. In another aspect, a method of inhibiting formation of metal oxides or reducing metal reactivity comprises contacting a metal with an effective amount of the compound(s).

## Claims

### Claim 1

A compound having a structure according to Formula Ia or Formula Ib set forth below:
or a pharmaceutically acceptable ester or solvate thereof, wherein X− is an ion of an acid forming a pharmaceutically acceptable salt, wherein R1, R2, R4, R5, R6, R7, and R8 are independently selected from the group consisting of nothing, H, OH, protected hydroxyl, alkyl, alkenyl, alkynyl, acyl, aryl, heteroaryl, cycloalkyl, and heterocycle; wherein the alkyl, alkenyl, alkynyl or acyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, NRARB, —S-alkyl, —SO-alkyl, —SO2-alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, and heterocycle; wherein RA and RB are each independently selected from hydrogen and C1-4 alkyl; wherein the aryl or heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, —COOH, —C(O)—C1-4 alkyl, —C(O)O—C1-4 alkyl, NRCRD, —S-alkyl, —SO-alkyl and —SO2-alkyl; wherein RC and RD are each independently selected from hydrogen and C1-4 alkyl; and wherein represents a single bond or a double bond with the proviso that within a five-membered ring, one is a single bond and the other is a double bond.

### Claim 2

A compound having a structure according to Formula Ia or Formula Ib set forth below:
or a pharmaceutically acceptable ester or solvate thereof, wherein X− is an ion of an acid forming a pharmaceutically acceptable salt, where A1, A2, A3, and A4 are independently selected from nitrogen and carbon; provided that at least one of A3 or A4 is nitrogen, wherein R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from the group consisting of nothing, H, OH, protected hydroxyl, alkyl, alkenyl, alkynyl, acyl, aryl, heteroaryl, cycloalkyl, and heterocycle; wherein R1 is nothing if A3 is N; wherein R3 is nothing if A4 is N: wherein the alkyl, alkenyl, alkynyl or acyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, NRARB, —S-alkyl, —SO-alkyl, —SO2-alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, and heterocycle; wherein RA and RB are each independently selected from hydrogen and C1-4 alkyl; wherein the aryl or heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, —COOH, —C(O)—C1-4 alkyl, —C(O)O—C1-4 alkyl, NRCRD, —S-alkyl, —SO-alkyl and —SO2-alkyl; wherein RC and RD are each independently selected B from hydrogen and C1-4 alkyl; wherein represents a single bond or a double bond with the proviso that within a five-membered ring, one is a single bond and the other is a double bond; and
provided that at least one of R2 and/or R4 has the structure according to Formula IIa or Formula IIb:
wherein in Formula IIa and Formula IIb X−, , A1, A2, R5, R6, R7, and R8 are defined as above and the * indicates the point of attachment of Formula IIa and/or Formula IIb to Formula Ia or Formula Ib.

### Claim 3 (depends on 2)

The compound of claim 2, wherein A1 and A4 are N, and R3 is nothing.

### Claim 4 (depends on 3)

The compound of claim 3, wherein A2 is C.

### Claim 5 (depends on 3)

The compound of claim 3, wherein A3 is N.

### Claim 6 (depends on 5)

The compound of claim 5, wherein A2 is C.

### Claim 7

A compound having a structure selected from the group consisting of:
or a pharmaceutically acceptable salt-ester or solvate thereof.

### Claim 8 (depends on 7)

The compound of claim 7 having the structure:
2,4,6-tris(3,4-dihydro-2H-pyrrol-2-yl)pyridine
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 9 (depends on 1)

The compound of claim 1 which is a pharmaceutically acceptable salt having a structure according to Formula VIa, Formula VIb, Formula VIc or any combination thereof:
wherein each X2 is independently an ion of an acid forming a pharmaceutically acceptable salt, and each M is independently a transition metal selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, yttrium, zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, and gold.

### Claim 10 (depends on 9)

The compound of claim 9 wherein each M is independently zinc or silver.

### Claim 11 (depends on 9)

The compound of claim 9 having a structure selected from the group consisting of:
and a combination thereof.

### Claim 12 (depends on 9)

The compound of claim 9 having a structure selected from the group consisting of:
and a combination thereof.

### Claim 13 (depends on 1)

A pharmaceutical composition comprising an effective amount of a compound claim 1 and a pharmaceutically acceptable vehicle therefor.