# US 8,785,503 B2 · Biphenyl compound or pharmaceutically acceptable salt thereof, method for preparing novel biphenyl compound or pharmaceutically acceptable salt thereof, and pharmaceutical composition containing same as active ingredient for preventing or treating diabetes complications

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- Number: US 8,785,503 B2
- Document ID: US8785503B2
- Status: Granted
- Kind: B2
- Application number: 13/816,402
- Filed: 2011-08-11
- Published: 2013-08-15
- Granted: 2014-07-22
- Earliest claimed: 2010-08-11
- Assignees: Korea Institute of Oriental Medicine
- Applicants: Jin Sook Kim; Young Sook Kim; Jung Hyun Kim; Eun Jin Shon; Ki Mo Kim; Chan-Sik Kim; Dong Ho Jung; Yun Mi Lee; Kyu Hyung Jo; Ohn Soon Kim; Nam-Hee Yoo
- Inventors: Jin Sook Kim; Young Sook Kim; Jung Hyun Kim; Eun Jin Shon; Ki Mo Kim; Chan-Sik Kim; Dong Ho Jung; Yun Mi Lee; Kyu Hyung Jo; Ohn Soon Kim; Nam-Hee Yoo
- Web page: https://patentgrep.com/patent/US8785503B2

## CPC

- C07C 43/23: containing hydroxy or O-metal groups
- A21D 2/24: Organic nitrogen compounds
- A23L 2/52: Adding ingredients (adding preservatives A23B70/10)
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A61K 36/73: Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- C07C 41/38: by liquid-liquid treatment
- A23C 2240/15: Use of plant extracts, including purified and isolated derivatives thereof, as ingredient in dairy products
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A21D: TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS (preservation of flour or dough before baking A23B40/00; preservation of bakery products A23B45/00)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- 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
- A23C: DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF (preservation thereof A23B11/00)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

The present invention provides a novel biphenyl compound or pharmaceutically acceptable salts thereof, methods for preparing the same, and pharmaceutical compositions for preventing or treating diabetic complications containing the same as an active ingredient. Novel biphenyl compounds, according to the present invention, effectively suppress generation activity of advanced glycation end products, which cause diabetic complications and are a criterion for evaluating the effectiveness of a treating agent for diabetic complications, and show an excellent therapeutic effect on retina blood vessels, increased occludin, and decreased angiogenic growth factor in actual diabetic retinopathy induced retina. Thus, novel biphenyl compounds according to the present invention can be used effectively as an active ingredient in compositions for preventing or treating diabetic complications such as diabetic retinopathy.

## Claims

### Claim 1

A biphenyl compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof:

### Claim 2 (depends on 1)

A method for preparing a biphenyl compound of claim 1, the method comprising the steps of:
(1) extracting Osteomeles schwerinae Schneid with water, an alcohol, or a mixture thereof to obtain Osteomeles schwerinae Schneid extract;
(2) suspending the Osteomeles schwerinae Schneid extract obtained from step (1) in water and then obtaining n-hexane, ethyl acetate, and n-butanol fractions of Osteomeles schwerinae Schneid by stepwise using n-hexane, ethyl acetate and n-butanol as an extraction solvent;
(3) carrying out a silica gel column chromatography on the ethyl acetate fraction of Osteomeles schwerinae Schneid obtained from step (2) to separate and purify an active fraction; and
(4) carrying out Sephadex LH-20 column chromatography on the active fraction obtained from step (3) to separate and purify the compound represented by Chemical Formula 1 of claim 1.

### Claim 3 (depends on 1)

A pharmaceutical composition for treating diabetic complications, the composition containing the biphenyl compound represented by Chemical Formula 1 of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

### Claim 4 (depends on 3)

The composition as set forth in claim 3, wherein diabetic complications are diabetic retinopathy, diabetic cataract, diabetic nephropathy, diabetic neuropathy, diabetic heart diseases, diabetic osteoporosis, or diabetic atherosclerosis.

### Claim 5 (depends on 1)

A health food composition for ameliorating diabetic complications, containing the biphenyl compound represented by Chemical Formula 1 of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

### Claim 6 (depends on 5)

The composition as set forth in claim 5, wherein diabetic complications are diabetic retinopathy, diabetic cataract, diabetic nephropathy, diabetic neuropathy, diabetic heart diseases, diabetic osteoporosis, or diabetic atherosclerosis.

### Claim 7 (depends on 1)

A method for treating diabetic complications, comprising administering the biphenyl compound represented by Chemical Formula 1 of claim 1 or pharmaceutically acceptable salt thereof to a patient in need thereof.

### Claim 8 (depends on 1)

The biphenyl compound represented by Chemical Formula 1 of claim 1 or pharmaceutically acceptable salt thereof, which are used for treating diabetic complications.
