Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Pyrroloquinoline quinone derivative or medicinal salt thereof, preparation method and application

A technology of pyrroloquinoline quinone and its derivatives, which is applied in the field of biomedicine, can solve problems affecting drugability, etc., and achieve excellent solubility and ideal drug efficacy

Pending Publication Date: 2022-07-29
CHINA PHARM UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, PQQ-TME is almost insoluble in water, affecting its druggability

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
  • Pyrroloquinoline quinone derivative or medicinal salt thereof, preparation method and application
  • Pyrroloquinoline quinone derivative or medicinal salt thereof, preparation method and application
  • Pyrroloquinoline quinone derivative or medicinal salt thereof, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of PQQ trimethyl ester: Take a single-neck flask, dissolve PQQ (3.3 g, 10 mmol) in DMF (200 mL), then add potassium carbonate (6.9 g, 50 mmol) in small portions and stir for 1 hour. Dimethyl sulfate (25 g) was dropped into the reaction suspension at room temperature, and the reaction was continued at room temperature for 5 days after the drop was completed. After DMF was evaporated with an oil pump, water (200 mL) was added to the residue and the residue was made acidic with 4N hydrochloric acid. The reaction solution was stirred at room temperature for 6 hours, and suction filtered to obtain an orange solid PQQ trimethyl ester (3.17 g, yield 85%).

[0039] Reduction of PQQ trimethyl ester: Take a single-neck flask, suspend PQQ trimethyl ester (1.86 g, 5 mmol) in acetonitrile (100 mL), add 1M sodium hydrosulfite solution (100 mL), and stir at room temperature overnight. The reaction solution was directly suction filtered, and the filter cake was dried to obtai...

Embodiment 2

[0042] Referring to the method of Example 1, the acetyl chloride in Example 1 was replaced with palmitoyl chloride to obtain compound 2 (319 mg, 75%). 1 H NMR (300MHz, Chloroform-d) δ 12.67(s, 1H), 8.94(s, 1H), 7.32(s, 1H), 4.20(s, 3H), 4.06(s, 3H), 4.03(s, 3H), 2.83 (t, J=7.6Hz, 2H), 2.75 (t, J=7.5Hz, 2H), 1.91 (dt, J=14.3, 7.2Hz, 4H), 1.30 (d, J=8.3Hz, 54H), 0.90(t, J=6.3Hz, 6H).

Embodiment 3

[0044]Referring to the method of Example 1, acetyl chloride in Example 1 was replaced with benzoyl chloride to obtain compound 3 (230 mg, 79%). 1 H NMR (300MHz, Chloroform-d) δ 12.74 (s, 1H), 8.96 (s, 1H), 8.47-8.11 (m, 4H), 7.95-6.91 (m, 7H), 4.21 (s, 3H), 4.01(s, 3H), 3.82(s, 3H).

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 invention discloses a pyrroloquinoline quinone derivative with a structure as shown in a formula (I) or a medicinal salt thereof, a preparation method and application of the pyrroloquinoline quinone derivative. The derivative has excellent solubility and / or permeability, is obviously superior to PQQ and PQQ salt (commercially available disodium salt), shows an ideal drug effect in anti-inflammatory, anti-diabetes and anti-metabolic disease models, and is superior to PQQ and PQQ salt (commercially available disodium salt). The invention also provides a preparation method of the derivative and an intermediate thereof, a pharmaceutical composition and medical application thereof.

Description

technical field [0001] The present invention relates to the field of biomedicine, in particular to a pyrroloquinoline quinone derivative or a pharmaceutically acceptable salt thereof, a preparation method and use thereof. Background technique [0002] Pyrroloquinoline quinone (PQQ) has been proven to be an important nutrient for mammals with a wide range of physiological and pharmacological activities, including growth-promoting, antioxidant, anti-diabetic, and neuroprotective effects. However, there are three carboxylic acid groups in the molecular structure of PQQ, resulting in unsatisfactory solubility and permeability. Carboxylic acid compounds can solve the solubility problem by forming salts, but the salt types of PQQ are diverse and complex, such as monosodium salt, disodium salt, trisodium salt and tetrasodium salt. Among them, only the disodium salt exists in various hydrated forms, such as trihydrate and pentahydrate; the solubility of trihydrate in water is about...

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
IPC IPC(8): C07D471/04A61K31/437A61P29/00A61P3/00A61P3/10
CPCC07D471/04A61P29/00A61P3/00A61P3/10
Inventor 王广基甄乐许亚文王健鲲
Owner CHINA PHARM UNIV
Features
  • Generate Ideas
  • 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