# US 12,006,338 B2 · Antimicrobial organosilanes

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- Number: US 12,006,338 B2
- Document ID: US12006338B2
- Status: Granted
- Kind: B2
- Application number: 18/087,555
- Filed: 2022-12-22
- Published: 2023-09-21
- Granted: 2024-06-11
- Earliest claimed: 2019-10-18
- Assignees: Topikos Scientific, Inc.
- Applicants: Topikos Scientific, Inc.
- Inventors: Gary Allred; Lanny Liebeskind; William R. Cast; Carl Hilliard
- Web page: https://patentgrep.com/patent/US12006338B2

## CPC

- A61L 15/44: Medicaments
- C07F 7/1896: {Compounds having one or more Si-O-acyl linkages}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61L 15/26: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof {(A61L15/225 takes precedence)}
- A61L 27/34: Macromolecular materials
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61L 29/085: {Macromolecular materials}
- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A61L 31/10: Macromolecular materials
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- 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

Organosilicon quaternary ammonium compounds, their formulations, including powdered and solid formulations, and methods of use to treat infections in humans and animals.

## Claims

### Claim 1

A quaternary ammonium compound of Formula:
or pharmaceutically acceptable salt thereof,
wherein
a is 3;
R1 is independently at each occurrence selected from the group consisting of C6-C22alkyl and C6-C22alkanoyl;
R2, R3, and R4 are independently at each occurrence selected from the group consisting of:
R8 is H or CH2OH;
R9 is H or C1-C8alkyl,
X3 is OH or CH2OR7;
R10, R11, and R12 are independently at each occurrence selected from the group consisting of hydrogen, —CH2OR7, CON(R7)2, COOR7, C(O)R7, C1-C8alkyl, C1-C8hydroxyalkyl, and C1-C8alkanoyl;
R13 is selected from the group consisting of CH2OR7, CON(R7)2, COOR7, C(O)R7, C1-C8alkyl, C1-C8hydroxyalkyl, and C1-C8alkanoyl;
R7 is independently at each occurrence selected from hydrogen, C1-C8alkyl, C1-C8hydroxyalkyl, and C1-C8alkanoyl;
X1 is NR17, CH2, or C(O);
X4 is selected from the group consisting of hydroxyl, CH2OR7, CON(R7)2, COOR7, C(O)R7, C1-C8hydroxyalkyl, and C1-C8alkanoyl;
R16 is C1-C4alkyl;
R17 is hydrogen, C1-C8hydroxyalkyl, or C1-C8alkanoyl;
X− is an anion.

### Claim 2 (depends on 1)

The quaternary ammonium compound of claim 1, wherein X− is selected from the group consisting of chloride, fluoride, iodide, bromide, hydroxide, chlorite, chlorate, hydroxide, formate, acetate, lactate, benzoate, methane sulfonate and salicylate anion.

### Claim 3 (depends on 1)

The quaternary ammonium compound of claim 1, wherein R2, R3, and R4 are
and X3 is OH.

### Claim 4 (depends on 1)

The quaternary ammonium compound of claim 1, wherein R2, R3, and R4 are
and R8 is CH2OH and R9 is C1-C8alkyl.

### Claim 5 (depends on 4)

The quaternary ammonium compound of claim 4, wherein X4 is OH and X1 is C(O).

### Claim 6 (depends on 4)

The quaternary ammonium compound of claim 4, wherein R1 is octadecyl and R16 is CH3.

### Claim 7 (depends on 4)

The quaternary ammonium compound of claim 4, wherein X4 is OH and X1 is CH2.

### Claim 8 (depends on 1)

The quaternary ammonium compound of claim 1 selected from the group consisting of:

### Claim 9 (depends on 8)

The quaternary ammonium compound of claim 8 of structure:

### Claim 10 (depends on 8)

The quaternary ammonium compound of claim 8 of structure:

### Claim 11 (depends on 8)

The quaternary ammonium compound of claim 8 of structure:

### Claim 12 (depends on 8)

The quaternary ammonium compound of claim 8 of structure:

### Claim 13

An antimicrobial composition comprising a quaternary ammonium compound selected from the group consisting of:
and a pharmaceutically acceptable carrier.

### Claim 14 (depends on 13)

The antimicrobial composition according to claim 13, wherein the pharmaceutically acceptable carrier is selected from the group consisting of alcohol, aqueous solution, and glycerin solution.

### Claim 15 (depends on 13)

The antimicrobial composition of claim 13, wherein the composition is suitable for topical delivery.

### Claim 16 (depends on 13)

The antimicrobial composition of claim 13, wherein the quaternary ammonium compound is

### Claim 17 (depends on 13)

The antimicrobial composition of claim 13, wherein the quaternary ammonium compound is

### Claim 18 (depends on 13)

The antimicrobial composition of claim 13, wherein the quaternary ammonium compound is

### Claim 19 (depends on 13)

The antimicrobial composition of claim 13, wherein the quaternary ammonium compound is

### Claim 20 (depends on 13)

The antimicrobial composition of claim 13, wherein the quaternary ammonium compound is

### Claim 21 (depends on 13)

The antimicrobial composition of claim 13, wherein the quaternary ammonium compound is

### Claim 22 (depends on 1)

The quaternary ammonium compound of claim 1 selected from the group consisting of:
wherein anion X− is a methane sulfonate anion.

### Claim 23 (depends on 13)

The antimicrobial composition according to claim 13, wherein the pharmaceutically acceptable carrier is an aqueous solution.

### Claim 24

An antimicrobial composition comprising a quaternary ammonium compound selected from the group consisting of:
and a pharmaceutically acceptable carrier;
wherein anion X− is a methane sulfonate anion.

### Claim 25 (depends on 24)

The antimicrobial composition of claim 24, wherein the quaternary ammonium compound is
wherein anion X− is a methane sulfonate anion.

### Claim 26 (depends on 24)

The antimicrobial composition according to claim 24, wherein the pharmaceutically acceptable carrier is selected from the group consisting of alcohol, aqueous solution, and glycerin solution.

### Claim 27 (depends on 24)

The antimicrobial composition of claim 24, wherein the composition is suitable for topical delivery.

### Claim 28 (depends on 24)

The antimicrobial composition according to claim 24, wherein the pharmaceutically acceptable carrier is an aqueous solution.