# US 11,110,109 B2 · Water soluble O-glycosyl flavonoid compositions and methods for preparing same

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- Number: US 11,110,109 B2
- Document ID: US11110109B2
- Status: Granted
- Kind: B2
- Application number: 16/660,111
- Filed: 2019-10-22
- Published: 2021-04-22
- Granted: 2021-09-07
- Earliest claimed: 2019-10-22
- Assignees: Alps Pharmaceutical Ind. Co., Ltd.
- Applicants: Alps Pharmaceutical Ind. Co., Ltd.
- Inventors: Naoto Yamaguchi; Yui Sudaka; Mitsunori Ono
- Web page: https://patentgrep.com/patent/US11110109B2

## CPC

- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A23L 33/125: containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates (indigestible substances A23L33/21)
- A23L 33/15: Vitamins
- A23L 33/175: Amino acids
- A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)}
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 9/145: {with organic compounds}
- A61K 9/28: Dragees; Coated pills or tablets {, e.g. with film or compression coating (A61K9/2072 takes precedence, e.g. partially coated tablets A61K9/2072, coated multilayer tablets A61K9/2086, tablets with drug-coated core A61K9/209)}
- A61K 9/4891: {Coated capsules; Multilayered drug free capsule shells (with drug coating for immediate release A61K9/4808; osmotic devices A61K9/0004)}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE 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)

## Abstract

A water-soluble composition including an O-glycosyl flavonoid compound, L-arginine, a sugar alcohol, and ascorbic acid or an alkali salt of ascorbic acid. The O-glycosyl flavonoid compound is rutin, isoquercitrin, or hesperidin, and a molar ratio between the O-glycosyl flavonoid compound and the sugar alcohol is 1:4.0-12.0. Also provided is a method for making the above-described water-soluble composition by combining the O-glycosyl flavonoid compound, L-arginine, the sugar alcohol, and ascorbic acid or an alkali salt thereof to form a mixture, and heating it at 110° C.-140° C. to melt the mixture.

## Claims

### Claim 1

A water-soluble composition comprising an O-glycosyl flavonoid compound, L-arginine, a sugar alcohol, and an alkali salt of ascorbic acid, wherein the O-glycosyl flavonoid compound is selected from the group consisting of rutin, isoquercitrin, and hesperidin, the sugar alcohol is selected from the group consisting of maltitol, erythritol, xylitol, and sorbitol, the molar ratio between the O-glycosyl flavonoid compound and the L-arginine is 1:0.5-2.0 and the molar ratio between the glycosyl compound and the sugar alcohol is 1:4.0-12.0.

### Claim 2 (depends on 1)

The water-soluble composition of claim 1, wherein the molar ratio between the O-glycosyl flavonoid compound and the sugar alcohol is 1:4.0-8.0.

### Claim 3 (depends on 1)

The water-soluble composition of claim 1, wherein the molar ratio between the O-glycosyl flavonoid compound and the L-arginine is 1:0.7-1.5.

### Claim 4 (depends on 1)

The water-soluble composition of claim 1, wherein the molar ratio between the O-glycosyl flavonoid compound and the alkali salt of ascorbic acid is 1:0.02-0.5.

### Claim 5 (depends on 4)

The water-soluble composition of claim 4, wherein the molar ratio between the O-glycosyl flavonoid compound and the alkali salt of ascorbic acid is 1:0.1-0.5.

### Claim 6 (depends on 1)

The water-soluble composition of claim 1, further comprising vitamin B1, vitamin B3, vitamin B6, vitamin B9, or vitamin B12.

### Claim 7 (depends on 1)

The water-soluble composition of claim 1, wherein the composition is a pharmaceutical drug, a dietary supplement, a natural health product, a cosmetic product, a food product, or a beverage.

### Claim 8 (depends on 7)

The water-soluble composition of claim 7, wherein the composition is an oral formulation selected from the group consisting of a liquid, a capsule, a tablet, a pill, and a gel.

### Claim 9 (depends on 8)

The water-soluble composition of claim 8, wherein the composition is in a capsule or a tablet, each formed with an enteric coating.

### Claim 10 (depends on 7)

The water-soluble composition of claim 7, wherein the composition is in a topical formulation selected from the group consisting of a solution, a liniment, a lotion, a cream, an ointment, a paste, a gel, and an emulgel.

### Claim 11 (depends on 10)

The water-soluble composition of claim 10, wherein the composition is a cosmetic product, a skin care product, or a pharmaceutical drug.

### Claim 12

A method for producing a water-soluble O-glycosyl flavonoid composition, the method comprising combining an O-glycosyl flavonoid compound, L-arginine, a sugar alcohol, and an alkali salt of ascorbic acid to form a mixture, and heating the mixture at 110° C.-140° C. for a time sufficient to melt the mixture, wherein the O-glycosyl flavonoid compound, the L-arginine, the sugar alcohol, and the alkali salt of ascorbic acid are each in solid form; the O-glycosyl flavonoid compound is selected from the group consisting of rutin, isoquercitrin, and hesperidin, the sugar alcohol is selected from the group consisting of maltitol, compound and the L-arginine is 1:0.5-2.0, and the molar ratio between the O-glycosyl flavonoid compound and the sugar alcohol is 1:4.0-12.0.