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

'Sqiqu site' derivative and its preparing method as well as its activity of anti asthma

A technology of sestrolast and derivatives, applied in the fields of sestrolast derivatives and their preparation and anti-asthma activity, can solve problems such as unsatisfactory therapeutic effect of inhibitors and the like

Inactive Publication Date: 2005-05-04
CHINA PHARM UNIV
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Judging from the results of the current research on inflammatory mediator inhibitors, the therapeutic effect of a single inhibitor is not very satisfactory.

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
  • 'Sqiqu site' derivative and its preparing method as well as its activity of anti asthma
  • 'Sqiqu site' derivative and its preparing method as well as its activity of anti asthma
  • 'Sqiqu site' derivative and its preparing method as well as its activity of anti asthma

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0119] (±)-N-[3-(2,4-dimethylphenyl)-1,2,3,4-oxatriazol-5-yl]-7-(2,4,5-trimethyl -3,6-dioxo-1,4-cyclohexadien-1-yl)phenylheptimide (I-1A 1 )

[0120] 3-(2,4-Dimethylphenyl)-1,2,3,4-oxatriazole-5-imine hydrochloride (38mg, 0.168mmol), 2mlNaHCO 3 The saturated solution and 2ml of dichloromethane were added to a 25ml two-neck flask, and under nitrogen protection with vigorous stirring, a solution of SD-COCl (about 0.168mmol) dissolved in 2ml of anhydrous dichloromethane was added dropwise. After reacting for 2 hours, separate the organic layer, wash with water (10ml×3), dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain a yellow solid, add 5ml of ether and stir for 10 minutes, then suction filter, the filter cake is light yellow powder The solid was dried to obtain 70 mg, yield 79.5%, mp 114°C-116°C.

[0121] IR (KBr, cm -1 ): 1702 (amide), 1642 (C=O);

[0122] ESI-MS: 527[M+H] + , 549[M+Na] + ;

[0123] 1 HNMR (500MHz, CDCl 3 ), δ(ppm): 1...

Embodiment 2

[0125] (±)-7-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)phenylheptanoic acid (N-4-methylphenyl -N'-hydroxyguanidine) ester (I-2A 1 )

[0126] Add SD (0.1g, 0.28mmol), p-methylphenyl-N-hydroxyguanidine (0.05g, 0.31mmol), DMAP pellets and 5ml of dichloromethane into a 10ml eggplant-shaped bottle, stir to dissolve, then add in batches DCC (0.069g, 0.34mmol) was stirred overnight at room temperature, and a white precipitate formed. Filtration, column chromatography [petroleum ether (60 ° C ~ 90 ° C): acetone: glacial acetic acid = 4: 1: 0.01 (v: v: v)], to obtain a light yellow powdery solid 0.085 g, yield 60.5%, mp 106°C~108°C.

[0127] IR (KBr, cm -1 ): 3376 (NH), 1731 (ester), 1642 (C=O);

[0128] ESI-MS: 502[M+H] + , 524[M+Na] +

[0129] 1 HNMR (300MHz, d-DMSO), δ (ppm): 1.24~1.68 (m, 6H, 3×CH 2 ), 1.87 (s, 3H, CH 3 ), 1.91 (s, 3H, CH 3 ), 1.98 (s, 3H, CH 3 ), 2.10~2.18 (m, 2H, C 6 -CH 2 ), 2.19 (s, 3H, CH 3 ), 2.30~2.35(t, 2H, J=7.5Hz, C 2 -CH 2 ), 4....

Embodiment 3

[0133] (±)-7-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)phenylheptanoic acid (N-4-chlorophenyl- N'-Hydroxyguanidine) ester (I-2A 2 )

[0134] Refer to I-2A 1 The preparation method is obtained from p-chlorophenyl-N-hydroxyguanidine. Column chromatography [petroleum ether (60°C-90°C): acetone: glacial acetic acid = 4:1:0.01 (v:v:v)] gave a light yellow powdery solid with a yield of 56.8%, mp 44°C-46 ℃.

[0135] IR (KBr, cm -1 ): 3310 (NH), 1731 (ester), 1643 (C=O);

[0136] ESI-MS: 522[M+H] + , 544[M+Na] + ;

[0137] 1 HNMR (300MHz, CD 3 COCD 3 ), δ(ppm): 1.24~1.68(m, 6H, 3×CH 2 ), 2.00 (s, 3H, CH 3 ), 2.02(s, 3H, CH 3 ), 2.03(s, 3H, CH 3 ), 2.10~2.18 (m, 2H, C 6 -CH 2 ), 2.34~2.39(t, 2H, J=7.5Hz, C 2 -CH 2 ), 4.34~4.35(q, 1H, CH), 5.48(s, 2H, NH 2 ), 7.14~7.25(m, 5H, ArH); 7.30~7.32(m, 2H, ArH), 7.49~7.52(m, 2H, ArH);

[0138] Anal.C 29 h 32 ClN 3 o 4 0.4H 2 O Found (%): N 7.46 C 66.12 H 6.67

[0139] Calcd...

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 discloses the general formula I of anti-asthma drug Seratrodast (Seratrodast, SD) coupled derivatives, which include the nitric oxide donor type imide compound (I-1) of SD, the nitric oxide donor Body type ester compound (I-2) and amide compound (I-3); screened by guinea pig asthma model, the above compounds show anti-asthmatic activity equivalent to or enhanced by SD. ∴

Description

technical field [0001] The present invention relates to different types of NO donors and groups with PAF receptor antagonistic activity and LTs inhibitory activity respectively combined with anti-asthma drug TXA through imide bond, ester bond or amide bond 2 A receptor antagonist seratrodast (Seratrodast, referred to as SD)-coupled compound, its preparation method and its application in the preparation of anti-asthma drugs. [0002] Background technique [0003] Asthma is a common respiratory disease. Studies in recent years have shown that the infiltration of inflammatory cells into the airway by inflammatory mediators is an important cause of asthma. Asthma treatment drugs have been compatible with the original inhaled steroid hormones β 2 - Receptor agonists, gradually expanding to the application of some new inflammatory mediator inhibitors, such as 5-lipoxygenase (5-LO) inhibitors, leukotriene (LTs) receptor antagonists, thromboxane A 2 (TXA 2 ) receptor antagoni...

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): C07D273/00C07D271/08C07D317/14C07D339/06C07D237/04C07C279/02C07C259/06C07C311/37A61K31/41A61K31/155A61K31/16A61P11/06
Inventor 张奕华张治国季晖邱苏赣
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