# US 11,998,530 B2 · Micelle comprising benzimidazole-carbohydrate conjugate compound, preparation method thereof and use thereof as anticancer agent or antiviral agent comprising the same

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- Number: US 11,998,530 B2
- Document ID: US11998530B2
- Status: Granted
- Kind: B2
- Application number: 17/544,514
- Filed: 2021-12-07
- Published: 2023-08-10
- Granted: 2024-06-04
- Earliest claimed: 2021-08-27
- Assignees: Biometrix Technology Inc.
- Applicants: Biometrix Technology Inc
- Inventors: Taisun Kim; Keumsoo Song; Junghun Kim
- Web page: https://patentgrep.com/patent/US11998530B2

## CPC

- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 47/549: {Sugars, nucleosides, nucleotides or nucleic acids}
- A61K 47/6907: {the form being a microemulsion, nanoemulsion or micelle}
- A61P 35/00: Antineoplastic agents
- 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

Disclosed herein are a micelle comprising a benzimidazole-carbohydrate conjugate compound represented by the following chemical formula 1, a preparation method thereof, and use thereof as an anticancer agent or an antiviral agent comprising the same: in the above formula, R1, R2, R3 and X are the same as those defined in the disclosure and claims.

## Claims

### Claim 1

A micelle comprising a benzimidazole-carbohydrate conjugate compound represented by the following chemical formula 1 and a benzimidazole-ammonium compound represented by the following chemical formula 1b:
wherein, the —NH—R1 moiety has one of the following structures:
the benzimidazole moiety has one of the following structures:
and
Y− is a conjugate base of acid (H+) and is selected from Cl−, Br−, I−, F−, NO3−, CH3COO−, HCOO−, HCO3−, CO32−, H2PO4−, HPO42−, HSO4−, SO42−, or ClO4−.

### Claim 2 (depends on 1)

The micelle of claim 1, wherein the micelle comprises one or more selected from a group consisting of 6-(propylthio)-1H-benzoimidazol-2-aminoglucose, 6-(propylthio)-1H-benzoimidazol-2-aminofructose, 6-(propylthio)-1H-benzoimidazol-2-aminogalactose, and 6-(propylthio)-1H-benzoimidazol-2-aminomannose, as an albendazole-D-carbohydrate conjugate compound;
6-(phenylthio)-1H-benzoimidazol-2-aminoglucose, 6-(phenylthio)-1H-benzoimidazol-2-aminofructose, 6-(phenylthio)-1H-benzoimidazol-2-aminogalactose, and 6-(phenylthio)-1H-benzoimidazol-2-aminomannose, as a fenbendazole-D-carbohydrate conjugate compound;
6-(4-fluorobenzoyl)-1H-benzimidazol-2-aminoglucose, 6-(4-fluorobenzoyl)-1H-benzimidazol-2-aminofructose, 6-(4-fluorobenzoyl)-1H-benzimidazol-2-aminogalactose, and 6-(4-fluorobenzoyl)-1H-benzimidazol-2-aminomannose, as a flubendazole-D-carbohydrate conjugate compound; and
6-benzoyl-1H-benzimidazol-2-aminoglucose, 6-benzoyl-1H-benzimidazol-2-aminofructose, 6-benzoyl-1H-benzimidazol-2-aminogalactose, and 6-benzoyl-1H-benzimidazol-2-aminomannose, as a mebendazole-D-carbohydrate conjugate compound.

### Claim 3 (depends on 1)

The micelle of claim 1, wherein a molar ratio of the benzimidazole-ammonium compound to the benzimidazole-carbohydrate conjugate compound is 1:500-500:1.

### Claim 4 (depends on 1)

The micelle of claim 1, wherein concentrations of a benzimidazole-ammonium compound and the benzimidazole-carbohydrate conjugate compound left in cells, into which the micelle is inserted, for 24 to 72 hours are kept higher than concentrations of the benzimidazole-ammonium compound and the benzimidazole-carbohydrate conjugate compound discharged from the cells into which the micelle is inserted, after the micelle is inserted into the cells.

### Claim 5

A preparation method of a micelle, comprising mixing a benzimidazole-carbohydrate conjugate compound represented by the following chemical formula 1 with a benzimidazole-ammonium compound represented by the following chemical formula 1b:
wherein, the —NH—R1 moiety has one of the following structures:
the benzimidazole moiety has one of the following structures:
Y− is a conjugate base of acid (H+) and selected from Cl−, Br−, I−, F−, NO3−, CH3COO−, HCOO−, HCO3−, CO32−, H2PO4−, HPO42−, HSO4−, SO42−, or ClO4−.

### Claim 6 (depends on 5)

The preparation method of claim 5 wherein the benzimidazole-ammonium compound represented by chemical formula 1b is prepared as a result of reaction of a 2-aminobenzimidazole compound of the following chemical formula 1a with acids:
wherein, the benzimidazole moiety has one of the following structures:

### Claim 7 (depends on 5)

The preparation method of claim 5, wherein the benzimidazole-carbohydrate conjugate compound represented by chemical formula 1 is obtained as a result of reaction of the 2-aminobenzimidazole compound of the following chemical formula 1a with carbohydrates to form an imine bond:
wherein, the benzimidazole moiety has one of the following structures:

### Claim 8 (depends on 7)

The preparation method of claim 7, wherein a substituent enabling an imine reaction, in the 2-aminobenzimidazole compound of chemical formula 1a, is protected or shielded in advance.

### Claim 9 (depends on 1)

A pharmaceutical composition, containing the micelle of claim 1.

### Claim 10 (depends on 9)

The pharmaceutical composition of claim 9, wherein the pharmaceutical composition suppresses formation of microtubules and absorption of carbohydrates.

### Claim 11 (depends on 9)

The pharmaceutical composition of claim 9, wherein the pharmaceutical composition shows anticancer or antiviral activity.

### Claim 12 (depends on 9)

The pharmaceutical composition of claim 9, wherein the pharmaceutical composition is absorbed through glucose transporter (GLUT) channels.