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

Novel derivative of 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid, its preparation method and application

A technology of drugs and compounds, applied in the field of medicine, can solve problems such as unsatisfactory effect of lowering uric acid, single mechanism of action, damage and deformation of diseased joints, etc.

Active Publication Date: 2019-05-07
XIANGBEI WELMAN PHARMA CO LTD
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] (6) Chronic gouty arthritis causes fibrosis of joint tissue and deposition of tophi in articular cartilage, synovium, and ligaments caused by repeated acute arthritis attacks, which gradually destroys and deforms the diseased joints and loses motor function
[0031] However, since febuxostat exerts the effect of lowering uric acid mainly by inhibiting the production of uric acid, the mechanism of action is relatively simple, the effect of lowering uric acid is still not ideal, and there is room for further improvement. Therefore, the development of curative effect is better and the safety is better The febuxostat derivatives still have very important clinical significance

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
  • Novel derivative of 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid, its preparation method and application
  • Novel derivative of 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid, its preparation method and application
  • Novel derivative of 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] The preparation of embodiment 1 F1-1

[0085] 1.1 Preparation of p-[(dipropylamino)sulfonyl]benzoyl chloride

[0086]

[0087] 2.85g of p-[(dipropylamino)sulfonyl]benzoic acid was added to 25ml of toluene, then 1ml of thionyl chloride was added, then refluxed at 50°C for 2 hours and then concentrated to dryness under reduced pressure to obtain 3.12g The pale yellow solid was directly used in the next reaction.

[0088] 1.2 Preparation of p-[(dipropylamino)sulfonyl]benzoic acid ethylene glycol monoester

[0089]

[0090]Add 3.12g of p-[(dipropylamino)sulfonyl]benzoyl chloride and 10g of ethylene glycol into 50ml of tetrahydrofuran, stir at room temperature for 10 minutes, then add 2ml of triethylamine under stirring, then react at 50°C for 2 Stop the reaction after 1 hour, concentrate to dryness under reduced pressure, dissolve the product with 50ml ethyl acetate, wash 3×10ml with saturated brine and water successively, then dry with anhydrous sodium sulfate and ...

Embodiment 2

[0100] Example 2 Preparation of compound F2-1

[0101] 2.1 Preparation of intermediate p-[(dipropylamino)sulfonyl]benzoic acid N-methyl-N-hydroxyethyl ethyl ester

[0102]

[0103] 3.13g of p-[(dipropylamino)sulfonyl]benzoyl chloride and 35g of diethanolamine prepared according to the method described in step 1.1 of Example 1 were added to 50ml of tetrahydrofuran, and stirred at room temperature for 10 minutes under stirring Add 2ml of triethylamine, then stop the reaction at 50°C for 2 hours, concentrate to dryness under reduced pressure, dissolve the product in 50ml of ethyl acetate, wash 7×10ml with saturated brine, dry with anhydrous sodium sulfate and reduce Concentrate under pressure to constant weight to obtain 2.65 g of white powdery solid with a yield of 76.3%.

[0104] 1 H-NMR (400MHz, d 6 DMSO): δ8.24-8.26 (d, 2H), 8.08-8.10 (d, 2H), 4.37-4.40 (t, 2H), 3.61-3.64 (t, 2H), 3.15-3.19 (t, 2H), 2.82-2.85 (t, 2H), 2.52-2.55 (t, 4H), 2.11 (s, 3H), 1.48-1.52 (m, 4H),...

Embodiment 3

[0110] Example 3 Preparation of compound F3-1

[0111] 3.1 Preparation of 2-methyl-2-(4-(4-chlorobenzoyl)phenoxy)propionyl chloride

[0112]

[0113] It was prepared according to the method described in step 1.1 in Example 1, and was directly used in the next reaction.

[0114] 3.2 Preparation of intermediate 2-methyl-2-(4-(4-chlorobenzoyl)phenoxy)propanoic acid N-methyl-N-hydroxyethyl ethyl ester

[0115]

[0116] Referring to the method described in step 2.1 in Example 1, a white solid was prepared with a yield of 81%.

[0117] 1 H-NMR (400MHz, d 6 DMSO): δ7.53-7.66 (m, 4H), 7.25-7.27 (d, 2H), 7.08-7.10 (d, 2H), 4.21-4.24 (t, 2H), 3.67-3.69 (t, 2H), 2.61-2.64 (t, 2H), 2.59 (t, 2H), 2.34 (s, 3H), 1.68 (s, 6H).

[0118] 3.3 Preparation of compound F3-1

[0119]

[0120] Referring to the method described in 2.2 of Example 1, the product of step 3.1 and the product of step 3.2 were respectively used to prepare the target product, which was a white solid with a yie...

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

PropertyMeasurementUnit
Weightaaaaaaaaaa
Login to View More

Abstract

The present invention provides compounds represented by general formula (I), or pharmaceutical salts or stereomers thereof. When the compounds represented by formula (I), or the salts or stereomers thereof are applied in preventing and treating hyperuricemia, they have better effect on reducing uric acid and better safety than febuxostat.

Description

technical field [0001] The invention belongs to the field of medicine, more specifically, the invention relates to 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid derivatives and salts thereof, and stereoisomers thereof body, and a pharmaceutical preparation comprising at least one compound of formula (I) or its salt or its stereoisomer as an active ingredient, and its application in the prevention and treatment of hyperuricemia diseases. Background technique [0002] Gout is a group of syndromes caused by abnormal purine metabolism in the human body, and hyperuricemia is a stage in the development of its lesions. According to the cause of the disease, it can be divided into two types: primary gout and secondary gout. [0003] Primary gout has obvious familial genetic tendency, and it is prone to occur in middle-aged and elderly people. The peak incidence is 30 to 50 years old. About 95% of them are men, and 5% of women are often postmenopausal. The etiolo...

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): C07D277/56A61K31/427A61P19/06
CPCA61K31/427C07D277/56
Inventor 王海勇孙天宇陈晓峰
Owner XIANGBEI WELMAN PHARMA CO LTD
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