Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of pyrrolopyrimidine compound

A compound and oxidation reaction technology, applied in the field of medicine, can solve the problem of a single type of JAK inhibitor, and achieve the effects of high yield, simple reaction and simple operation

Active Publication Date: 2022-06-07
GUANGZHOU JOYO PHARMATECH CO LTD
View PDF7 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the single defect of existing JAK inhibitors. The present invention provides a preparation method of pyrrolopyrimidine compounds. and TYK2 kinase both have inhibitory effect, and the preparation method in the application has simple reaction, high yield, simple operation, mild conditions and wide industrial application prospect

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
  • Preparation method of pyrrolopyrimidine compound
  • Preparation method of pyrrolopyrimidine compound
  • Preparation method of pyrrolopyrimidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] The synthetic method of compound 12 is as follows

[0096]

[0097] Step 9:

[0098] The product 8 (60g) in Example 1, the compound of formula (7-1) (107.0g), DMSO (600ml) and DIPEA (85.6g) were added to the reactor, the temperature was raised to 100-110°C, and after stirring for 8h, Cool to 20-30°C, add water (150ml), stir for 1h, filter and dry to obtain product 9; purity 86%, yield 73%;

[0099] Step 10:

[0100] To the reactor were added dichloromethane (200 g), product 9 (15 g), 2,2,6,6-tetramethylpiperidine-nitrogen-oxide (TEMPO, 0.52 g), iodobenzene diacetate (11.7 g) ), reacted at room temperature for 10h, added triethylamine (12g) after the reaction, stirred for 1h, filtered and dried to obtain product 10; purity, 96.1%, yield: 89%;

[0101] Step 11:

[0102] Product 10 (73g), ammonia water (25ml), iodine (124g), THF (730mL) were added to the reactor, stirred at room temperature for 12h, after the reaction was completed, ethyl acetate (100ml) and saturat...

Embodiment 2

[0106] Condition screening as shown in Table 1 is carried out to the reaction in step 9 of Example 1. Except for the screening condition, other conditions are as described above:

[0107] Table 1

[0108]

[0109] 10V and 5V in this application respectively represent: the volume weight ratio of solvent to raw material is 10mL / g and 5mL / g, for example, the volume weight ratio of solvent to product 8 is 10mL / g here.

Embodiment 3

[0111] The reaction in step 10 of Example 1 is screened by the conditions shown in Table 2. Except for the screening conditions, other conditions are as described above:

[0112] Table 2

[0113]

[0114]

[0115] When manganese dioxide is used as the oxidant, there are problems such as difficult post-treatment, heavy metal residues, environmental protection, and unsuitability for large-scale production. The optimized oxidant has the advantages of simple post-treatment, high yield, and environmental protection.

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 discloses a preparation method of a pyrrolopyrimidine compound. The pyrrolopyrimidine compound provided by the invention has an inhibition effect on JAK1, JAK2, JAK3 and TYK2 kinase, has characteristic high permeability, has good oral bioavailability and relatively high exposure in mice, is beneficial to generation of a good in-vivo drug effect and has an effect of treating arthritis. In addition, the preparation method is simple in reaction, high in yield, simple to operate, mild in condition and wide in industrial application prospect.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to a method for preparing a pyrrolopyrimidine compound as a JAK inhibitor. Background technique [0002] Janus kinases (JAKs) are cytoplasmic tyrosine kinases that transmit cytokine signaling. From membrane receptors to STAT transcription factors. The JAK family consists of four members, JAK1, JAK2, JAK3 and TYK2. The JAK-STAT pathway transmits extracellular signals from a variety of cytokines, growth factors and hormones to the nucleus and is responsible for the expression of thousands of protein-coding genes. The JAK-STAT pathway involves several steps in translating extracellular signals into transcriptional responses: 1) When the cytokine receptors on the cell surface bind to their respective cytokine ligands, their conformation changes, resulting in dimerization of the receptor molecules, This brings receptor-coupled JAK kinases into close proximity and is activated...

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): C07D487/04
CPCC07D487/04Y02P20/55
Inventor 王春娟李永国董建明贾国慧舒诗会
Owner GUANGZHOU JOYO PHARMATECH CO LTD
Features
  • R&D
  • 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