US 10,766,882 B2Granted

1,2-naphthoquinone based derivative and method of preparing the same

AssigneeYungjin Pharm. Co., Ltd.

InventorsWhee Seong Lee, Mi Jung Lee, Bo Jung Kim, Tae Cheul Roh, Seung Hoon Lee, Kyu Dae Lee, You-Hui Lee, Tae Hwan Kwak

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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.

Claims1

Dependent claims

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):

3 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/959,419Filed 23 Apr 2018 · division
Priority: KR 10-2013-016658530 Dec 2013
Published: US 2018/0258079 A113 Sep 2018
Granted: 8 Sep 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification28 codes

C07D 405/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61K 31/4184
1,3-Diazoles: condensed with carbocyclic rings, e.g. benzimidazoles
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
A61K 31/498
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: pyrazines or piperazines…

Family

PCT/KR2014/013040Parent of this division · filed 30 Dec 2014
US 2018/0258079 A1Pre-grant publication · published 13 Sep 2018
Application15/102,968Parent of this division
US 9,975,883 B2Parent of this division
US 2016/0376258 A1Published application
US 10,766,882 B2This patent

From the US filing history. Foreign family members aren’t listed.

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