Supercharge Your Innovation With Domain-Expert AI Agents!

Benzopyran derivatives substituted with a benzimidazole derivative, pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them

A technology of benzopyran derivatives and benzimidazoles, which can be used in drug combination, organic chemistry, metabolic diseases, etc., and can solve problems such as difficult development of new drugs

Inactive Publication Date: 2006-06-28
DONGBU HANNONG CHEMICAL CO
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] K was first discovered in myocardium ATP Widely distributed in many organs and tissues, for example, β-cells of the pancreas, smooth muscle, kidney and central nervous system, etc., so K ATP It has become a major target for the development of new drugs, but at the same time, it is difficult to develop new drugs that selectively act on specific organs or tissues

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Benzopyran derivatives substituted with a benzimidazole derivative, pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them
  • Benzopyran derivatives substituted with a benzimidazole derivative, pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them
  • Benzopyran derivatives substituted with a benzimidazole derivative, pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0125] Example 1: (2S, 3R, 4S)-6-nitro-3,4-dihydro-3-hydroxyl-2-dimethoxymethyl-2-methyl-4-(2,3-di Preparation of Hydrogen-2-cyanoimino-1H-benzimidazol-1-yl)-2H-1-benzopyran

[0126] (2S, 3R, 4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-[(2-aminobenzene Preparation of base)amino]-2H-1-benzopyran

[0127] 950 mg (3.38 mmol) of epoxy compound (2S, 3R, 4R)-6-nitro-3,4-dihydro-3,4-epoxy-2-dimethoxymethyl-2-methyl- 2H-1-benzopyran and 370mg (3.38mmol) of 1,2-phenylenediamine were dissolved in 3ml of acetonitrile (CH 3 CN), and then add 754mg (3.38mmol) magnesium chlorate [Mg(ClO 4 ) 2 ]. The reaction was stirred at room temperature for 2 h, and 10 ml of saturated NaHCO was added 3 solution, and the aqueous layer was extracted with 30 ml of ethyl acetate. The combined organic layers were washed with anhydrous MgSO 4 Dry, filter and concentrate under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=1:1) to obtain 67...

Embodiment 2

[0132] Example 2: (2R, 3R, 4S)-6-nitro-3,4-dihydro-3-hydroxyl-2-dimethoxymethyl-2-methyl-4-(2,3-di Preparation of Hydrogen-2-cyanoimino-1H-benzimidazol-1-yl)-2H-1-benzopyran

[0133] (2R, 3R, 4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-[(2-aminobenzene Preparation of base)amino]-2H-1-benzopyran

[0134] Using a method similar to Example 1 step 1, 540mg (1.92mmol) epoxy compound (2R, 3R, 4R)-6-nitro-3,4-dihydro-3,4-epoxy-2-dimethyl Oxymethyl-2-methyl-2H-1-benzopyran and 208 mg (1.92 mmol) of 1,2-phenylenediamine were reacted to obtain 404 mg of the target compound (yield: 54%).

[0135] 1 H NMR (200MHz, CDCl 3 )δ1.43(s, 3H), 3.50(s, 3H), 3.55(s, 3H), 4.14(d, 1H), 4.45(s, 1H), 4.49(d, 1H), 6.75(m, 5H ), 8.09(dd, 1H), 8.32(d, 1H)

[0136] (2R, 3R, 4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2,3-di Preparation of Hydrogen-2-cyanoimino-1H-benzimidazol-1-yl)-2H-1-benzopyran

[0137] 404 mg (1.04 mmol) of the compound prepared in the a...

Embodiment 3

[0139] Example 3: (2S, 3S, 4R)-6-nitro-3,4-dihydro-3-hydroxyl-2-dimethoxymethyl-2-methyl-4-(2,3-di Preparation of Hydrogen-2-cyanoimino-1H-benzimidazol-1-yl)-2H-1-benzopyran

[0140] (2S, 3S, 4R)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-[(2-aminobenzene Preparation of base)amino]-2H-1-benzopyran

[0141] 2g (7.11mmol) epoxy compound (2S, 3S, 4S)-6-nitro-3,4-dihydro-3,4-epoxy-2-dimethoxymethyl-2-methyl- 2H-1-benzopyran and 1.15 g (10.7 mmol) of 1,2-phenylenediamine were reacted in a manner similar to that described in Step 1 of Example 1 to obtain 2.08 g of the target compound (yield: 75%) .

[0142] 1 H NMR (200MHz, CDCl 3 )δ1.36(s, 3H), 3.58(s, 3H), 3.59(s, 3H), 4.23(d, 1H), 4.41(s, 1H), 4.51(d, 1H), 6.72-6.78(m , 4H), 6.90(d, 1H), 8.03(dd, 1H), 8.34(d, 1H)

[0143] Mass spectrum: 389, 296, 119, 108, 75

[0144] (2S, 3S, 4R)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2,3-di Preparation of Hydrogen-2-cyanoimino-1H-benzimidazol-1-yl...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to benzopyran derivatives substituted by benzimidazole derivatives or pharmaceutically acceptable salts thereof, their preparation methods and pharmaceutical compositions containing them. The benzopyran derivatives substituted by benzimidazole derivatives represented by (Formula 1) have the function of protecting the heart from ischemia-reperfusion injury without producing side effects similar to vasodilation, and therefore contain the benzopyran derivatives of the present invention. The benzopyran derivatives substituted by imidazole derivatives or pharmaceutically acceptable salts thereof as the pharmaceutical composition can be effectively used to protect tissues affected by ischemia-reperfusion, for example, to protect the heart, nerve cells, brain, Retinal cells, storage organs, etc., and used to treat diseases caused by ischemia-reperfusion.

Description

field of invention [0001] The present invention relates to benzopyran derivatives substituted by benzimidazole derivatives represented by <Formula 1>, pharmaceutically acceptable salts thereof, methods for preparing them, and pharmaceutical compositions containing them as active ingredients, the pharmaceutical compositions having protection The ability of the heart to protect against damage caused by ischemia-reperfusion. [0002] <Formula 1> [0003] [0004] (where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and * as defined in the description). Background technique [0005] Ischemic heart disease results from myocardial ischemia that develops from a critically inadequate supply of oxygen caused by interruption of blood flow to the heart for reasons similar to arteriosclerosis ( G. J. Grover, Can. J. Physiol. 75, 309, 1997; G. D. Lopaschuk et al., Science & Medicine 42, 1997). Myocardial ischemia gradually induces pathological changes in cells, leading to irr...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D405/14
CPCA61P1/16A61P3/00A61P7/02A61P9/00A61P9/04A61P9/10A61P13/12A61P25/00A61P25/28A61P27/02A61P43/00C07D405/04C07D405/14
Inventor 林弘李东厦金善玉柳圣殷李圭亮李仙卿徐知希金洛贞黄仙庚金泰美李柄皓徐浩源
Owner DONGBU HANNONG CHEMICAL CO
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com