# US 10,869,941 B2 · Gas-generating polymer micells and manufacturing method of the same

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- Number: US 10,869,941 B2
- Document ID: US10869941B2
- Status: Granted
- Kind: B2
- Application number: 15/933,143
- Filed: 2018-03-22
- Published: 2018-10-04
- Granted: 2020-12-22
- Earliest claimed: 2017-03-22
- Assignees: Industry-University Cooperation; Foundation Hanyang University
- Applicants: Industry-University Cooperation Foundation Hanyang University
- Inventors: Kuen Yong Lee; Eun Ju Jeong
- Web page: https://patentgrep.com/patent/US10869941B2

## CPC

- A61K 49/227: {Liposomes, lipoprotein vesicles, e.g. LDL or HDL lipoproteins, micelles, e.g. phospholipidic or polymeric}
- 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 9/5192: {Processes}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 49/223: {Microbubbles, hollow microspheres, free gas bubbles, gas microspheres}
- A61K 2123/00: Preparations for testing in vivo
- 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

The present invention relates to a gas-generating micelle prepared by coupling a polyethylene glycol derivative and an alkyl chloroformate. The gas-generating micelles according to the present invention are circulated in the body and deposited on the disease site to generate carbon dioxide, and thus a more enhanced ultrasonic diagnostic image can be obtained.

## Claims

### Claim 1

A method of preparing a gas-generating micelle including a compound represented by the following Formula 1, the method comprising: mixing polyethylene glycol and an alkyl chloroformate to synthesize a polyethylene glycol derivative; wherein the polyethylene glycol derivative is represented by Formula I, and
dissolving the polyethylene glycol derivative in one solvent selected from acetonitrile, methylene chloride, chloroform, and methanol or in a solvent mixture of two or more selected therefrom and then evaporating the solvent(s), and then dispersing the polyethylene glycol derivative in an aqueous solution,
wherein R1 is a C1 to C2 alkyl group, H, —NH2, or COOH,
p is an integer ranging from 12 to 227,
q is an integer ranging from 2 to 14, and
wherein the micelle has a diameter of 150 to 500 nm.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the solvent mixture is prepared by mixing methylene chloride with acetonitrile, chloroform, or methanol in a mixing ratio of 3 to 1:1 to 3.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the polyethylene glycol has a number average molecular weight (Mn) of 550 to 10,000 g/mol.