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

N-aryl substituted-1H-pyrrole derivative possessing cardiovascular activity

A technology of heteroaryl and alkyl, applied in the field of N-aryl-substituted-1H-pyrrole derivatives, can solve the problems of high price and many reaction steps, etc.

Inactive Publication Date: 2004-11-10
CHINA PHARM UNIV
View PDF2 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(see Levens NR, et al, Pharmacol Toxicol, 1992, 71: 241-245; Duncia JV, et al, Med Res Rev, 1992, 12: 149-158; Ashton WT, Exp. Opin. Invest. Drugs 1994, 3 , 1105; Burnier, M.Circulation 2001, 103, 904) Some AII receptor antagonist drugs (such as: losartan, valsartan, etc.) that have been developed and marketed at present all contain the structure of biphenyltetrazolium , the preparation process requires the use of selective protecting groups and other expensive raw and auxiliary materials, and there are many reaction steps and a variety of raw materials

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
  • N-aryl substituted-1H-pyrrole derivative possessing cardiovascular activity
  • N-aryl substituted-1H-pyrrole derivative possessing cardiovascular activity
  • N-aryl substituted-1H-pyrrole derivative possessing cardiovascular activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 1-(4-Methylphenyl)-1H-pyrrole

[0064] Dissolve 2,5-dimethoxy-tetrahydrofuran (25g, 0.19mol) and p-toluidine (20.6g, 0.19mol) in 80ml of ice HAc, heat to reflux for 3h, concentrate, and steam distill the residue to obtain 23g (76%) of the title compound as white crystals, mp.80-82°C.

Embodiment 2

[0066] 1-(4-Methylphenyl)-2-formyl-1H-pyrrole

[0067] Under anhydrous conditions, cool DMF (20g, 0.28mol) in an ice-salt bath, slowly add POCl dropwise 3 (43g, 0.28mol), after dropping, it was raised to room temperature, stirred for 20min, then 100ml of DMF solution of 1-(4-methylphenyl)-1H-pyrrole (22g, 0.14mol) was added dropwise thereto, and after dropping, React at 100-120°C for 3h. Cool, pour into ice, adjust PH=9 with 10% NaOH, extract with ethyl acetate 60ml×3, anhydrous Na 2 SO 4 Dry and concentrate to obtain a red oily substance, 22 g (81%) of the title compound, which is directly used in the next reaction.

Embodiment 3

[0069] 1-(4-Methylphenyl)-2-oximino-1H-pyrrole

[0070] The above red oil (15g, 0.08mol) was dissolved in methanol 110ml, heated to reflux, and dissolved in hydroxylamine hydrochloride (5.6, 0.08mol) and Na 2 CO 3 (8.5, 0.08mol) aqueous solution 55ml, dropwise, reflux for 5h, filter with suction, evaporate methanol, the residue is extracted with ethyl acetate 50ml×3, anhydrous Na 2 SO 4 Dry and concentrate to give a yellow oil as the title compound 14g (90%).

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 N-aryl substituted-1H pyrrole derivative or its salt having cardiovascular activity represented by formula (I), which has activity angiotensin II (AII) acceptor antagonism and can be applied in treating cardiovascular diseases e.g. hypertension, hyperemia heart failure, myocardium pachismus, vasospasm and other diseases or symptoms treated through blockading AII acceptor.

Description

technical field [0001] The present invention relates to an N-aryl substituted-1H-pyrrole derivative with cardiovascular activity, specifically N-[4-(substituted aromatic heterocyclic methyl)phenyl]-1H-substituted pyrrole compound containing all The pharmaceutical composition of said compound and the application of said compound in treating hypertension, congestive heart failure and treating other diseases or diseases by blocking angiotensin II (AII) receptor. Background technique [0002] Angiotensin II (AII) receptor antagonist is an important drug for the treatment of hypertension and congestive heart failure that has been researched and developed in recent years, because its target is different from the angiotensin converting enzyme (AII) that is being used clinically. ACE) inhibitors (such as: captopril, enalapril, etc.), so they do not have side effects such as angioedema and dry cough caused by ACE inhibitors, and are more easily accepted by hypertensive patients, espe...

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): A61K31/40A61P7/10A61P9/04A61P9/12C07D207/30C07D207/412C07D403/06C07D471/04
Inventor 吴晓明徐进宜王秋娟
Owner CHINA PHARM UNIV
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