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

A kind of new rosiglitazone analogue and its preparation method and application

A technology of reaction and scheme, applied in the field of compound and its preparation, to achieve the effect of simple preparation method

Active Publication Date: 2021-04-27
北京安博睿达医药科技有限公司
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the pharmacological activity of rosiglitazone still needs to be further improved

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
  • A kind of new rosiglitazone analogue and its preparation method and application
  • A kind of new rosiglitazone analogue and its preparation method and application
  • A kind of new rosiglitazone analogue and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Example 1: (E)-5-(4-(2-(cyclopropyl(pyridin-2-yl)amino)ethoxy)benzylidene)thiazolidine-2,4-dione (compound II-1 )

[0099]

[0100] step 1:

[0101]

[0102] Add A1 (50g, 0.3286mol, 1eq) and 1,2-dibromoethane (500g, double as solvent and raw material, excess) in a 500ml single-necked flask, and add potassium carbonate (63.0g, 0.4558mol, 1.3eq), the temperature was raised to 120°C, and the reaction was carried out overnight, monitored by TLC until the reaction was complete. Stop heating, cool down, evaporate 1,2-dibromoethane under reduced pressure with an oil pump at 70°C, evaporate to dryness, add water to dissolve, extract with 800ml dichloromethane, dry over anhydrous magnesium sulfate, concentrate by suction filtration, pack 250g silica gel column, wet The method was used to load the sample, and 70 g of slightly pure light yellow oil (solid after standing for a long time) was obtained, and the yield was 82.35%.

[0103] Step 2:

[0104]

[0105] Add A2 (7...

Embodiment 2

[0129] Example 2: 5-(4-(2-cyclopropyl(pyridin-2-yl)amino)ethoxy)benzylthiazolidine-2,4-dione (compound I-1)

[0130]

[0131] On the basis of Example 1, step 9 is further included, and the product A9 is further reduced using palladium carbon catalytic hydrogenation. MS (m / z): 384.1 (M+H).

Embodiment 3

[0132] Example 3: 5-(4-(2-cyclopropyl(pyrimidin-2-yl)amino)ethoxy)benzylthiazolidine-2,4-dione (compound 1-2)

[0133]

[0134] The preparation method is the same as in Example 2, except that Step 4 and Step 5 are omitted, and the raw material in Step 3 is 2-bromopyrimidine. MS (m / z): 386.1 (M+H).

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 relates to a rosiglitazone analogue, a preparation method and application thereof. Described compound has the structure shown in following formula (I), R 1 represents C that is unsubstituted or optionally substituted by 3‑10 Cycloalkyl: halogen, nitro, cyano, hydroxyl, mercapto, C 1‑6 Alkyl, C 1‑6 Alkoxy, halo C 1‑6 Alkyl; A 1 、A 2 The same or different, independently of each other represents C that is unsubstituted or optionally substituted by 6‑14 Aryl or 5‑14 membered heteroaryl: halogen, nitro, cyano, hydroxyl, mercapto, C 1‑6 Alkyl, C 1‑6 Alkoxy, halo C 1‑6 Alkyl; n is an integer of 0-5; R 2 means H or C 1‑6 Alkyl; R 3 Represents H; X, Z, W are the same or different, and independently represent S or O; represent a single bond or a double bond, and when it is a single bond, there is R 3 ; When double bond, R is absent 3 . The invention also provides its preparation method and its application in the preparation of medicines for treating or preventing diabetes.

Description

technical field [0001] The invention relates to a novel rosiglitazone analogue and its preparation method and application, and belongs to the technical field of compounds and its preparation method and application. Background technique [0002] Rosiglitazone [chemical name 5-{4-[2-(methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedione (structural formula as formula (a) shown)] or rosiglitazone hydrochloride (Rosiglitazone hydrochloride, also referred to as rosiglitazone) [chemical name 5-{4-[2-(methyl-2-pyridylamino)ethoxy]benzyl}- 2,4-thiazolidinedione hydrochloride (structural formula shown in formula (b))]: [0003] [0004] It belongs to the thiazolidinedione class of antidiabetic drugs, which can effectively control blood sugar by improving insulin sensitivity. [0005] However, the pharmacological activity of rosiglitazone still needs to be further improved. Contents of the invention [0006] The purpose of the present invention is to overcome the shortcom...

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 Patents(China)
IPC IPC(8): C07D417/12C07D277/82C07D277/42C07D413/12A61K31/4427A61K31/506A61K31/428A61K31/426A61P3/10A61P3/06A61P9/12A61P9/00
CPCA61P3/06A61P3/10A61P9/00A61P9/12C07D277/42C07D277/82C07D413/12C07D417/12
Inventor 闫京波李松钟武肖军海王刚
Owner 北京安博睿达医药科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com