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

Five-membered heteroaromatics tolylene glucoside and preparation method and use thereof

A technology of glucopyranoside and heterocycle, which is applied in the field of type 2 sodium glucose transporter inhibitor and its preparation, and can solve problems such as liver toxicity and body weight

Inactive Publication Date: 2009-06-03
TIANJIN INSTITUTE OF PHARMA RESEARCH
View PDF0 Cites 22 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have good therapeutic effects, but long-term treatment has safety issues such as hepatotoxicity and weight gain

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
  • Five-membered heteroaromatics tolylene glucoside and preparation method and use thereof
  • Five-membered heteroaromatics tolylene glucoside and preparation method and use thereof
  • Five-membered heteroaromatics tolylene glucoside and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] 2-[(4-Amino-3-methylthio-1,3,4-triazol-5-yl)methyl]phenol (IIIa-1)

[0067]

[0068] Add 2.22g (10mmol) of compound IVa-1 and 20mL of methanol to a 50mL round bottom flask, add 0.40g (10mmol) of solid NaOH under stirring at room temperature, stir for 10 minutes, then add dropwise 1.26g (10mmol) of freshly distilled MeOH 2 SO 4 5 mL of methanol solution, after the dropwise addition, stirred at room temperature for 1 hour. The reaction mixture was poured into 200mL saturated brine, acidified with concentrated hydrochloric acid to pH=4-5, extracted with 50mL×3 chloroform, the organic phase was washed with saturated brine, anhydrous Na 2 SO 4 After drying, the solvent was evaporated on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IIIa-1. Colorless crystals, 1.91g, 81%. IR(KBr), 3421, 3328, 3245, 1597, 1503cm -1 .

[0069] Compounds IVa-1 and IIIa-1 are one of the compounds having the general formula IVa and ...

Embodiment 2

[0071] 3-[(4-Amino-3-ethylthio-1,3,4-triazol-5-yl)methyl]phenol (IIIa-2)

[0072]

[0073] Add 2.22g (10mmol) of compound IVa-2 and 20mL of methanol to a 50mL round bottom flask, add 0.40g (10mmol) of solid NaOH under stirring at room temperature, stir for 10 minutes, then add dropwise 1.54g (10mmol) of newly distilled Et 2 SO 4 5 mL of methanol solution, after the dropwise addition, stirred at room temperature for 1 hour. The reaction mixture was poured into 200mL saturated brine, acidified with concentrated hydrochloric acid to pH=4-5, extracted with 50mL×3 chloroform, the organic phase was washed with saturated brine, anhydrous Na 2 SO 4 After drying, the solvent was evaporated on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IIIa-2. Colorless crystals, 2.10g, 84%. IR(KBr), 3426, 3322, 3243, 1598, 1502cm -1 .

[0074] Compounds IVa-2 and IIIa-2 are one of the compounds having the general formula IVa and the g...

Embodiment 3

[0076] 2-[(2-Methylthio-1,3,4-oxadiazol-5-yl)methyl]phenol (IIIb-1)

[0077]

[0078] Add 2.08g (10mmol) of compound IVb-1 and 20mL of methanol to a 50mL round bottom flask, add 0.40g (10mmol) of solid NaOH under stirring at room temperature, stir for 10 minutes, then dropwise add 1.26g (10mmol) of freshly distilled MeOH 2 SO 4 5 mL of methanol solution, after the dropwise addition, stirred at room temperature for 1 hour. The reaction mixture was poured into 200mL saturated brine, acidified with concentrated hydrochloric acid to pH=4-5, extracted with 50mL×3 chloroform, the organic phase was washed with saturated brine, anhydrous Na 2 SO 4 After drying, the solvent was evaporated on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IIIb-1. Colorless crystals, 2.02g, 91%. IR(KBr), 3427, 1599, 1501cm -1 .

[0079] Compounds IVb-1 and IIIb-1 are one of the compounds having the general formula IVb and the general formul...

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 the field of diabetes-related drugs, in particular to an SGLT2 inhibitor containing the structure of five-membered heteroaromatics tolylene glucoside and the preparation method thereof and application thereof for preparing the drugs of diabetes, wherein, the group is defined in the specification.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a type 2 sodium glucose transporter (SGLT2) inhibitor containing a five-membered aromatic heterocyclic cresyl glucoside structure, a preparation method thereof, and a pharmaceutical composition containing them, which have a therapeutic effect on diabetes. Background technique [0002] There are currently about 170 million diabetics in the world, and the vast majority are type II (ie non-insulin-dependent) diabetics. At present, the traditional drugs used clinically to treat diabetes mainly include metformin, sulfonylureas and insulin drugs, as well as thiazolidinedione drugs, α-glucosidase inhibitors and dipeptidyl peptidase-IV that have been on the market in recent years. Inhibitors etc. These drugs have good therapeutic effects, but long-term treatment has safety issues such as hepatotoxicity and weight gain. [0003] Sodium glucose t...

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): C07H15/26A61K31/7056A61P3/10
Inventor 赵桂龙徐为人王玉丽汤立达王致峰刘巍张士俊刘冰妮谭初兵邹美香
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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