# US 10,766,882 B2 · 1,2-naphthoquinone based derivative and method of preparing the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,766,882 B2
- Document ID: US10766882B2
- Status: Granted
- Kind: B2
- Application number: 15/959,419
- Filed: 2018-04-23
- Published: 2018-09-13
- Granted: 2020-09-08
- Earliest claimed: 2013-12-30
- Assignees: Yungjin Pharm. Co., Ltd.
- Applicants: Yungjin Pharm. Co., Ltd.
- Inventors: Whee Seong Lee; Mi Jung Lee; Bo Jung Kim; Tae Cheul Roh; Seung Hoon Lee; Kyu Dae Lee; You-Hui Lee; Tae Hwan Kwak
- Web page: https://patentgrep.com/patent/US10766882B2

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/498: Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 13/12: of the kidneys
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07C 231/12: by reactions not involving the formation of carboxamide groups
- C07C 231/14: by formation of carboxamide groups together with reactions not involving the carboxamide groups
- C07C 309/04: containing only one sulfo group
- C07D 235/02: condensed with carbocyclic rings or ring systems
- C07D 241/38: with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed are a compound represented by Formula (1), or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, tautomer, enantiomer, or pharmaceutically acceptable diastereomer thereof, a method of preparing the same, and a pharmaceutical composition, which have effects for treatment or prevention of metabolic syndromes, comprising the same: wherein R1 to R6, X1 to X4, and n are the same as defined in claim 1.

## Claims

### Claim 1

A method of preparing 2-isopropyl-1H-naphtho[2,1-d]imidazole-4,5-dione comprising the following steps:
1) synthesizing compound B-1 by reacting compound A and isobutyric anhydride under basic conditions formed using pyridine;
2) reacting compound B-1 and HNO3 under acidic conditions formed using acetic acid anhydride;
3) reducing compound B-2 using Pd/C and hydrazine;
4) cyclizing compound B-3 under acidic conditions formed using acetic acid; and
5) oxidation of compound B-4 using 2-iodoxybenzoic acid (IBX) under basic conditions formed using DMF to generate 2-isopropyl-1H-naphtho[2,1-d]imidazole-4,5-dione (compound B-5):