# US 2024/0189433 A1 · Superabsorbent hydrogels

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- Number: US 2024/0189433 A1
- Document ID: US20240189433A1
- Status: Published application
- Kind: A1
- Application number: 18/551,592
- Filed: 2022-03-23
- Published: 2024-06-13
- Earliest claimed: 2021-03-23
- Assignees: Junion Labs Pte. Ltd.
- Applicants: Junion Labs Pte. Ltd.
- Inventors: Jingnan LUO; Hongqian BAO; Bo Huai Moses LEE
- Web page: https://patentgrep.com/patent/US20240189433A1

## CPC

- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- A23L 29/262: Cellulose; Derivatives thereof, e.g. ethers
- A23L 33/21: Addition of substantially indigestible substances, e.g. dietary fibres
- A23L 33/24: Cellulose or derivatives thereof
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)}
- A61K 9/48: Preparations in capsules, e.g. of gelatin, of chocolate {(A61K9/0004 takes precedence; bite capsules A61K9/0056)}
- A61P 3/04: Anorexiants; Antiobesity agents
- C08B 15/10: Crosslinking of cellulose
- C08J 3/075: Macromolecular gels
- C08J 3/12: Powdering or granulating
- C08L 1/08: Cellulose derivatives
- C08L 1/286: {substituted with acid radicals, e.g. carboxymethyl cellulose [CMC] (C08L1/282 takes precedence)}
- C08J 2301/08: Cellulose derivatives
- C08J 2301/28: Alkyl ethers
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention relates to polymer comprising a polysaccharide crosslinked with a spacer crosslinker, wherein the spacer crosslinker comprises a first optionally substituted aliphatic moiety terminated at each end with a second moiety comprising at least two carboxylic acid groups. The present invention also relates to a hydrogel, a method of forming the polymer or hydrogel, a composition and capsule comprising the polymer or hydrogel and a method treating obesity, pre-diabetes, diabetes, non-alcoholic fatty liver disease or chronic idiopathic constipation, or of reducing caloric intake or improving glycemic control using the polymer or hydrogel and a method of weight-loss or improving the body appearance in a healthy subject.

## Claims

### Claim 1

A polymer comprising a polysaccharide crosslinked with a spacer crosslinker, wherein the spacer crosslinker comprises a first optionally substituted aliphatic moiety terminated at each end with a second moiety comprising at least two carboxylic acid groups.

### Claim 2 (depends on 1)

The polymer according to claim 1, wherein the spacer crosslinker has the following formula (I):
A-L-Z-L-A (I)
wherein
Z is the first optionally substituted aliphatic moiety;
A is the second moiety comprising at least two carboxylic acid groups; and
L is a linking group.

### Claim 3 (depends on 1)

The polymer according to claim 1, wherein the first optionally substituted aliphatic moiety is derived from a first optionally substituted aliphatic molecule comprising at least two hydroxy groups.

### Claim 4 (depends on 3)

The polymer according to claim 3, wherein the first optionally substituted aliphatic molecule has a molecular weight in the range of about 0.1 kDa to about 100 kDa.

### Claim 5 (depends on 3)

The polymer according to claim 3, wherein the first optionally substituted aliphatic molecule is a hydrophilic polymer, preferably selected from the group consisting of polyether, polyacrylamide, polyethyleneimine, polyacrylate, polymethacrylate, polyvinyl pyrrolidone and polyvinyl alcohol, each further comprising at least two hydroxy groups.

### Claim 6 (depends on 1)

The polymer according to claim 1, wherein the first optionally substituted aliphatic moiety has the following structure
wherein Q is —CH2—, —O— or —NH2—,
R is hydrogen, —OH, optionally substituted C1 to C6 alkyl, —C(O)OM, —C(O)NR2R3 or optionally substituted heterocycloalkyl,
R2 and R3 are independently hydrogen or optionally substituted C1 to C6 alkyl,
M is R2, Na or K, p in an integer in the range of 1 to 6,
n is an integer in the range of 2 to 2000 and
* indicates where the moiety attaches to the rest of the spacer crosslinker.

### Claim 7 (depends on 1)

The polymer according to claim 1, wherein the second moiety comprising at least two carboxylic acid groups is derived from a second molecule having at least three carboxylic acid groups.

### Claim 8 (depends on 7)

The polymer according to claim 7, wherein the second molecule having at least three carboxylic acid groups is selected from the group consisting of citric acid, pyromellitic acid, butanetetracarboxylic acid, and benzoquinonetetracarboxylic acid.

### Claim 9 (depends on 1)

The polymer according to claim 1, wherein the second moiety comprising at least two carboxylic acid groups is selected from the group consisting of:
wherein * indicates where the moiety attaches to the rest of the spacer crosslinker.

### Claim 10 (depends on 2)

The polymer according to claim 2, wherein L is selected from the group consisting of an amide, ester, acid anhydride and thioester.

### Claim 11 (depends on 1)

The polymer according to claim 1, wherein the polysaccharide is selected from the group consisting of starch, cellulose, galactomannan and alginate, or is carboxymethylcellulose.

### Claim 12 (depends on 1)

The polymer according to claim 1, wherein the polymer is in the form of a powder having a particle size in the range of about 0.05 mm to about 5 mm.

### Claim 13 (depends on 1)

A hydrogel comprising the polymer according to claim 1 and a liquid.

### Claim 14 (depends on 1)

A method of forming the polymer according to claim 1, comprising steps of:
a) reacting a first optionally substituted aliphatic molecule comprising at least two hydroxyl groups with a second molecule comprising at least three carboxylic acid groups to form a spacer crosslinker; and
b) crosslinking the spacer crosslinker with a polysaccharide to form the polymer of claim 1.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the reacting step (a) further comprises a polymer additive.

### Claim 16 (depends on 14)

The method according to claim 14, wherein the reacting step (a) and crosslinking step (b) are independently performed at a temperature in the range of 80° C. to 180° C.

### Claim 17 (depends on 15)

The method according to claim 15, further comprising the following steps (a1), (a2) and (a3) between the reacting step (a) and the crosslinking step (b):
a1) mixing the spacer crosslinker and the polysaccharide in a solvent to form a homogenized mixture,
a2) drying the homogenized mixture at a temperature in the range of 40° C. to 90° C. to remove the solvent, and
a3) grinding the dried homogenized mixture to form a powder having a particle size in the range of about 0.05 mm to about 5 mm.

### Claim 18 (depends on 17)

The method according to claim 17, wherein the mixing step (a1) further comprises the polymer additive.

### Claim 19 (depends on 14)

The method according to claim 14, further comprising a step of adding a liquid to the polymer.

### Claim 20 (depends on 1)

A composition comprising the polymer according to claim 1 and a pharmaceutically acceptable excipient.

### Claim 21 (depends on 20)

The composition according to claim 20, further comprising a polymer additive.

### Claim 22 (depends on 1)

A capsule comprising the polymer according to claim 1.

### Claim 23 (depends on 1)

A method of treating obesity, pre-diabetes, diabetes, non-alcoholic fatty liver disease (NAFLD), or chronic idiopathic constipation, or of reducing caloric intake or improving glycemic control in a subject in need thereof, comprising a step of orally administering to subject a therapeutically effective amount of the polymer according to claim 1.

### Claim 24 (depends on 1)

A use, comprising using the polymer according to claim 1 in a treatment of obesity, pre-diabetes, diabetes, non-alcoholic fatty liver disease (NAFLD), or chronic idiopathic constipation, or for reducing caloric intake or improving glycemic control.

### Claim 25 (depends on 1)

A use, comprising using the polymer according to claim 1 in the manufacture of a medicament for a treatment of obesity, pre-diabetes, diabetes, non-alcoholic fatty liver disease (NAFLD), or chronic idiopathic constipation, or for reducing caloric intake or improving glycemic control.

### Claim 26 (depends on 23)

The method of claim 23, wherein the polymer is administered or is to be administered orally.

### Claim 27 (depends on 23)

The method of claim 23, wherein a dosage unit form of the polymer comprises 1 g to 6 g of the polymer.

### Claim 28 (depends on 1)

A method of weight-loss or improving the body appearance in a healthy subject, comprising a step of orally administering to a subject the polymer according to claim 1.