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

C13 deuterated methyl telmisartan and preparation method and application thereof

A technology of telmisartan and methyl substitution, which is applied in the field of carbon 13 deuterated methyl telmisartan and its preparation, and achieves the effects of high yield, reduced production cost, and reduced death

Inactive Publication Date: 2018-06-29
QINZHOU UNIV
View PDF4 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, there is no literature report on the synthesis of carbon-13 deuterium instead of misartan

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
  • C13 deuterated methyl telmisartan and preparation method and application thereof
  • C13 deuterated methyl telmisartan and preparation method and application thereof
  • C13 deuterated methyl telmisartan and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0038]A kind of carbon 13 deuterium replaces the preparation method of misartan, it comprises the following steps:

[0039] 1): Mix carbon-13 deuterated methanol and iodine, and catalyze carbon-13 deuterated methyl iodide by refluxing red phosphorus (Ⅱ)

[0040]

[0041] 2): Dissolving compound (Ⅲ) in a solvent, adding base, and adding carbon 13 deuterated methyl iodide to react to obtain compound (Ⅳ)

[0042]

[0043] 3): Dissolving compound (Ⅳ) in a solvent, adding reaction base and catalyst, and preparing compound (Ⅴ) through Suzuki coupling reaction

[0044]

[0045] 4): Dissolving compound (Ⅴ) in a solvent, adding a reaction base, and obtaining carbon-13 deuterium instead of misartan through hydrolysis reaction

[0046]

[0047] As a preferred version, the above-mentioned deuterium replaces misartan-C 13 d 3 The preparation method, in the reaction described in step 1, the reaction mass ratio of carbon-13 deuterated methanol to iodine and red phosphorus is 1...

Embodiment 1

[0054] Step 1, the preparation of compound (II):

[0055]

[0056] Mix iodine element (19.5g) with carbon-13 deuterated methanol (5.0g) and place it in a 150mL constant pressure dropping funnel. , first drop a small amount of deuterated methanol mixture that dissolves part of the iodine in the constant pressure dropping funnel into the round bottom flask, then heat to reflux, and when the temperature rises to about 50°C, drop the remaining mixed solution into the round bottom flask in batches in the flask. The dropwise addition was completed in about 30 minutes. The reflux continued to dissolve the iodine and drop it in. After all the iodine in the dropping funnel was dissolved, stop heating and cool to room temperature. After stirring at room temperature for 1 h, distill at atmospheric pressure, collect fractions at 41 to 44 ° C, and use saturated Na 2 S 2 o 3 Wash 3 times, wash 2 times with saturated brine, add anhydrous CaCl 2 After drying, 13.8 g of carbon-13 deut...

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 belongs to the field of organic medicinal synthesis, and discloses C13 deuterated methyl telmisartan and a preparation method and application thereof. According to the preparation method, with C13 deuterated methanol as a C13 deuterated raw material, the C13 deuterated telmisartan is synthesized through a four-step reaction. The preparation method comprises the following steps: iodizing the C13 deuterated methanol to obtain C13 deuterated iodomethane; performing a substitution reaction on the C13 deuterated iodomethane and a compound (III) to obtain a compound (IV); performing aSuzuki coupling reaction on the compound (IV) and 2-boro methylbenzoate to obtain a compound (V); performing esterolysis on the compound (V) under an alkaline condition to obtain the C13 deuterated telmisartan. The preparation method is easy and convenient to operate; by the preparation method, a C13 deuterated reagent is saved, the cost is low and purification is easy; a purified product is obtained after rapid preparation and chromatographic purification. A standard deuterated telmisartan substance prepared by the preparation method provided by the invention is high in purity and stable in chemical properties, and can be applied to preparation of an analytical standard substance.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the technical field of organic drug synthesis, in particular to a carbon-13 deuterated methyl telmisartan and a preparation method and application thereof. Background technique [0002] Telmisartan, as an angiotensin (AT1) II receptor antagonist, is a new type of antihypertensive drug. The compound was developed by Boehringer Ingethiem in Germany, and it was first launched in the United States in March 1999, and in Germany in the same year. Non-peptide angiotensin II receptor antagonists can selectively and irreversibly block ATI receptors without affecting other receptor systems. For mild to moderate high blood pressure. Telmisartan is a new type of antihypertensive drug and a specific angiotensin II receptor (ATI type) antagonist for the treatment of essential hypertension. The alternative angiotensin II receptor binds with high affinity to the ATI receptor subtype (the kno...

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): C07D235/18A61K31/4184A61P9/12A61P9/10A61P3/10A61P13/12A61P9/04
CPCC07D235/18
Inventor 孔亚芬范和良庞庭才尹艳镇
Owner QINZHOU 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