Thienopyridine derivatives, production method and use thereof

A compound and mixture technology, applied in organic chemistry methods, chemical instruments and methods, drug combinations, etc., can solve problems such as long-term use shortage, arthritis ineffectiveness, side effects, etc.

Inactive Publication Date: 2009-10-28
TAKEDA PHARMA CO LTD
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But some of these agents have shown serious side effect problems, or are difficult to use for a long time, insufficient effect, or ineffective for already developed arthritis, etc.

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
  • Thienopyridine derivatives, production method and use thereof
  • Thienopyridine derivatives, production method and use thereof
  • Thienopyridine derivatives, production method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0289] The present invention is described in more detail below by the following reference examples, examples, preparation examples and experimental examples, these reference examples, examples, preparation examples and experimental examples should not be construed as limiting, and can The scope of the premise varies.

[0290] Unless otherwise stated, the elution of column chromatography in Reference Examples and Examples was performed under observation of TLC (thin layer chromatography). TLC observation using silica gel 60F produced by Merck 254 A solvent that was used as a TLC plate and eluted using column chromatography was used as a developing solvent. Detection utilizes a UV detector. Silica gel 60 (70-230 mesh size) produced by Merck was used as silica gel for column chromatography. The room temperature here generally refers to a temperature of about 10°C to 35°C. In addition, sodium sulfate or magnesium sulfate is used to dry the extract.

[0291] Abbreviations used...

reference example 1

[0344] 4-Methoxybenzoylacetonitrile

[0345]

[0346] Sodium methoxide (3.046 kg) and acetonitrile (2.135 kg) were added to a dimethyl sulfoxide solution (21.6 L) of methyl 4-methoxybenzoate (7.2 kg), and the mixture was stirred at 110° C. for 2 hours . Water (10.83 L) was added dropwise at not exceeding 15°C, and acetonitrile (14.4 L) was added. Then 6N HCl was added to adjust the pH to 7.9 without exceeding 20°C, and the mixture was extracted with ethyl acetate (72 L). The aqueous layer was further extracted with ethyl acetate (36.32 L). The organic layers were combined and concentrated until the weight of the concentrate was 17.39 kg. Methanol (17.84 L) was added to the mixture, and then water (17.84 L) was added dropwise. The mixture was stirred at 5°C for 1 hr, and the precipitated crystals were collected by filtration and washed with methanol-water (1:1) to obtain the title compound (6.40 kg, 82.7%).

[0347] 1 H-NMR (CDCl 3 ) δ; 3.90 (3H, s), 4.03 (2H, s), 6.9...

reference example 2

[0349] 2-Amino-4,5,6,7-tetrahydro-3-(4-methoxybenzoyl)-1-benzothiophene-6-carboxylic acid ethyl ester

[0350]

[0351]4-Methoxybenzoyl acetonitrile (13.6g), cyclohexanone-4-carboxylic acid ethyl ester (14.0g), sulfur (2.7g), morpholine (7.3g) obtained in Reference Example 1 And ethanol (300ml) was stirred under reflux for 3 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The obtained residue was purified by column chromatography (developing solvent: ethyl acetate-hexane (1:1, v / v)), and the title compound (25.0 g , 87%). Melting point: 102-103°C.

[0352] 1 H-NMR (CDCl 3 )δ; 1.26 (3H, t, J=7.0Hz), 1.50-1.70 (1H, m), 1.87-2.18 (3H, m), 2.61-2.87 (3H, m), 3.86 (3H, s), 4.15 (2H, q, J = 7.0 Hz), 6.30 (2H, brs), 6.90 (2H, d, J = 8.8 Hz), 7.51 (2H, d, J = 8.8 Hz).

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
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to view more

Abstract

The invention relates to thienopyridine derivatives, production method and use thereof. A compound represented by the formula (I) wherein R is a hydrogen atom or a C1-4 alkyl group, and X is CH2, O or S, or a salt thereof. The present invention provides a novel thienopyridine derivative having an anti-inflammatory effect, a bone resorption suppressing effect, an immune cytokine production suppressing effect and the like, and useful as a pharmaceutical agent such as an agent for the prophylaxis or treatment of arthritis such as rheumatoid arthritis and the like.

Description

[0001] This application is a divisional application of the Chinese invention application "thienopyridine derivatives, their preparation methods and their uses" with the filing date of May 13, 2005 and the application number of 200580023747.8. technical field [0002] The present invention relates to novel thienopyridine derivatives having anti-inflammatory activity, bone resorption-inhibitory activity, immune cytokine production-inhibitory activity, etc., which can be used as medicaments such as for the prevention or treatment of arthritis such as rheumatoid arthritis etc., its preparation method and its use. Background technique [0003] Arthritis is an inflammatory disease of joints, which includes rheumatoid arthritis as a major disease and its related diseases related to inflammation in joints. [0004] Specifically, rheumatoid arthritis, also called rheumatoid arthritis, is chronic polyarthritis with inflammatory changes in the synovial membrane in the inner capsule lay...

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 Applications(China)
IPC IPC(8): C07D495/04C07B53/00A61K31/4365A61P29/00A61P19/02
Inventor 马场厚生安间常雄多和田紘之山下诚
Owner TAKEDA PHARMA CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap