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

Furanone derivatives, preparation methods and uses

A kind of technology of furanone and compound, applied in the field of furanone derivative, preparation and use

Active Publication Date: 2019-04-16
BEIJING ORBIEPHARM
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The discovery of COX-2 enabled the synthesis of selective COX-2 inhibitors

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
  • Furanone derivatives, preparation methods and uses
  • Furanone derivatives, preparation methods and uses
  • Furanone derivatives, preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] Example 1: Preparation of 2,2-dimethyl-5-[5-(methylsulfonyl)-2-pyridyl]-4-benzo-3(2H)-furanone Prepare (Compound A-001).

[0166]

[0167] Step 1: Preparation of 2-bromo-5-(methylsulfonyl)pyridine (compound 2)

[0168] 2,5-Dibromopyridine (50 g, 211 mmol) was dissolved in 175 mL THF, and cooled to 0° C. in an ice bath. Isopropylmagnesium chloride (2M THF solution, 274mmol) was slowly added to the above solution, and the temperature was controlled not to exceed 8°C. The reaction mixture was stirred at 0°C for 45 minutes and then cooled to minus 15°C. The THF (40 mL) solution of methanesulfonyl chloride was slowly added to the above reaction solution, the temperature was controlled not to exceed 5°C, and the solution was stirred for 30 minutes after dropping, and then water was added to separate the layers. The aqueous phase is extracted twice with methyl tert-butyl ether. The organic phases were combined and washed with water. Concentrated under reduced press...

Embodiment 2 to 28

[0182] Examples 2 to 28 can all be prepared by referring to the method of Example 1, and can also be prepared by other methods, which should not be construed as a limitation of the present invention. The corresponding compounds are shown in Tables 1-1 and 1-2, and the structure confirmation data of the compounds are shown in Table 1-3.

[0183] The chemical structural formula of table 1-1 embodiment 1-28

[0184]

[0185]

[0186] Table 1-2 Chemical names of A-001~A-028

[0187]

[0188]

[0189] The structural confirmation data of some compounds in Table 1-3 Examples 2-28

[0190]

Embodiment 29

[0191]Example 29: Preparation of 2,2-dimethyl-5-[6-(methylsulfonyl)-3-pyridine]-4-benzo-3(2H)-furanone (Compound B-001)

[0192]

[0193] 5-Bromo-2-methylthiopyridine (Compound S1)

[0194] 2,5-Dibromopyridine (35 g, 0.15 mol) was dissolved in 50 mL DMF. In the above solution, add 150mLNaSCH 3 aqueous solution (20%, 0.43mol). The reaction mixture was heated to 85°C for 24 hours. After cooling, the mixture was washed with CH 2 Cl 2 extraction. The organic phase was washed with saturated brine. After removing the solvent, the crude product was purified by column chromatography to obtain compound S1 (15 g, 50%, white solid). 1 H-NMR (300MHz, CDCl 3 ):δ8.49(s,1H),7.597(d,1H),7.280(d,1H),2.530(s,3H); LCMS[M+H] + :204; Purity (LCMS)>95%.

[0195] 6-Methylthio-3-formylpyridine (Compound S2)

[0196] Compound S1 was dissolved in 20 mL THF and cooled to -78 °C. Add n-BuLi (2 mL, 10.3 mmol, 2.5 M) slowly to the above solution, and stir for 2 hours. Then DMF (0.9 g, 1...

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
purityaaaaaaaaaa
Login to View More

Abstract

The invention relates to a novel selective cyclooxygenase-2 inhibitor compound, a preparation method and use and belongs to the field of chemical drugs. The compound represented by a formula (I) shown in the description can be used for inhibiting cyclooxygenase and interfering with the biotransformation of in-vivo arachidonic acid to prostaglandin, so that the compound and pharmaceutical compositions thereof can be used for treating cyclooxygenase mediated related diseases, i.e., can be used for treating and relieving animal and human inflammations and inflammation caused various diseases such as arthritis, neurodegenerative disease, depression, schizophrenia disease and cancers (including non-small-cell lung cancer, liver cancer, pancreatic cancer, colon cancer, breast cancer, ovarian cancer, prostatic cancer, cervical cancer, skin cancer, head and neck cancer and the like).

Description

technical field [0001] The invention relates to the application of a new class of furanone derivatives and its pharmaceutical composition in the treatment of cyclooxygenase-related diseases. The compounds in the present invention can inhibit cyclooxygenase and interfere with the biotransformation of arachidonic acid to prostaglandins in the body. Therefore, they can be used to treat and relieve inflammation in animals and humans and various diseases caused by inflammation, such as cancer ( Including non-small cell lung cancer, liver cancer, pancreatic cancer, colon cancer, breast cancer, ovarian cancer, prostate cancer, cervical cancer, skin cancer, head and neck cancer, etc.), arthritis, neurodegenerative diseases, depression, schizophrenia, Analgesia after surgery. Background technique [0002] Metabolites of arachidonic acid are involved in many acute and chronic inflammatory processes. And this large class of fatty arachidonic acid metabolites is obtained under the act...

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): C07D405/04A61K31/443A61P29/00A61P19/02A61P15/00A61P25/24A61P25/18A61P35/00A61P9/10A61P25/08A61P25/28
CPCC07D405/04
Inventor 李靖
Owner BEIJING ORBIEPHARM
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