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

9-Azabicyclo[3.3.1]nonane-coupled iodine-rich compounds and their preparation methods and uses

An azabicyclo and compound technology, which is applied in the field of 9-azabicyclo[3.3.1]nonane coupled iodine-rich compounds, can solve problems such as early diagnosis and discovery of unfavorable tumors, and achieve high product yield and high product yield. Affinity, convenient post-processing effect

Active Publication Date: 2020-09-11
CHINA JILIANG UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most organic X-ray contrast agents are non-targeted contrast agents, which have no tissue-organ distribution specificity, which is not conducive to the early diagnosis and discovery of tumors. Therefore, the research on targeted contrast agents has gradually increased in recent years.

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
  • 9-Azabicyclo[3.3.1]nonane-coupled iodine-rich compounds and their preparation methods and uses
  • 9-Azabicyclo[3.3.1]nonane-coupled iodine-rich compounds and their preparation methods and uses
  • 9-Azabicyclo[3.3.1]nonane-coupled iodine-rich compounds and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、9

[0034] Example 1, 9-aza[6'-(2,4,6)-triiodophenylacetamide-α-amino]hexylamino-9-azabicyclo[3.3.1]nonane-3α-alkyl The synthetic method of phenyl carbamate compound, carries out following steps successively:

[0035] 1), take aniline (1.74g, 0.018mol) and dissolve in 68mL distilled water to obtain aniline aqueous solution;

[0036] Another NaCl (3.9g, 0.067mol) was dissolved in 14mL of distilled water, and ICl (10g, 0.062mol) was weighed and slowly added to the NaCl aqueous solution under stirring (the purpose of slow addition was to keep the temperature not higher than 30°C), to obtain mixed solution;

[0037] Add 2 / 3 of the mixed solution dropwise to the aniline aqueous solution under stirring (the purpose of the dropwise addition is to keep the temperature not higher than 80°C); add the remaining 1 / 3 of the mixed solution dropwise (the purpose of the dropwise addition is to make the temperature not higher than 90°C ), stirred and reacted for 3 hours, naturally cooled to room...

Embodiment 2

[0049] In Example 2, the raw material aniline in Example 1 was changed to 5-aminoisophthalic acid, and the molar weight remained unchanged, and the rest were identical to steps 1) to 3) of Example 1.

[0050] Its step 1), step 2) corresponding reaction formula is:

[0051]

[0052] The name of the product (S2) obtained in step 1) is: 3,5-dicarboxy(2,4,6)triiodoaniline;

[0053] The name of the product obtained in step 2) is: chloroacetyl 3,5-dicarboxy(2,4,6)triiodoaniline.

[0054] The final product is 9-aza[6'-(2,4,6)-triiodoisophthaloacetamide-α-amino]hexylamino-9-azabicyclo[3.3.1]nonane-3α- Alkyl phenyl carbamate, brown solid, yield 87%, m.p.112°C; 1 H NMR (500MHz, CDCl3) δ 10.21(d, 2H), 8.16(d, J=5.3Hz, 3H), 7.26(s, 2H), 6.75(s, 2H), 5.55(s, 1H), 3.82( d, J=18.0Hz, 3H), 3.59(s, 2H), 3.42(s, 2H), 3.15–2.93(m, 2H), 2.83(d, J=64.7Hz, 3H), 2.43–2.13(m ,3H), 1.93(s,4H),1.71(d,J=5.5Hz,4H),1.63–1.33(m,8H); Elementalanal.For C 33 h 41 o 8 N 4 I 3 (%), calculated: C,39....

Embodiment 3

[0059] The product (S2)3,5-dicarboxy (2,4,6)triiodoaniline (10g, 0.018mol) obtained in step 1) of Example 2 was dissolved in 40mL ethyl acetate, and 60mL SOCl2( 8.6g, 0.072mol) was slowly added dropwise (the purpose of dropping is to control the temperature not to exceed 10°C), after the dropwise addition was completed, the temperature was raised to 80°C, and the reaction was refluxed for 20 hours, and about half of the volume of the solvent was evaporated, left to stand for 2 hours, and filtered , and dried (dried at 85° C. until the water content ≤ 1.5%) to obtain a brownish-brown powdery compound (S3).

[0060] The above brownish brown powdery solid compound (10g, 16.8mmol) was dissolved in 10mL DMAc, mixed with 3-amino-1,2-propanediol (3.8g, 41.8mmol) and triethylamine (5.1g, 50.5mmol), iced React in the bath for 30 minutes, raise the temperature to 50°C, and react for 3 hours. Cool to room temperature, add 10 mL of water, adjust the pH to 5 with 10% hydrochloric acid, ev...

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
molecular weightaaaaaaaaaa
molecular weightaaaaaaaaaa
Login to View More

Abstract

The invention discloses 9-aza-bicyclo[3.3.1] nonane coupled iodine-rich compounds. A preparation method of the compound comprises steps as follows: 9-nitrogen(6'-amino)hexylamine-9-9-aza-bicyclo[3.3.1] nonane-3 alpha-alkylamidophenyl formate and a chloroacetyl triiodoaniline derivative are mixed in an organic solvent in the mole ratio being 1:(1.0-1.5) and subjected to a reaction at the room temperature under the catalytic action of cesium hydroxide for 20-30 h, and a product, namely, the 9-aza-bicyclo[3.3.1] nonane coupled iodine-rich compounds, is obtained. The invention also discloses an application of the 9-aza-bicyclo[3.3.1] nonane coupled iodine-rich compounds as a contrast medium for early diagnosis of breast cancer.

Description

technical field [0001] The invention belongs to the technical field of 9-azabicyclo[3.3.1]nonane coupling iodine-rich compounds. The full name of 9-azabicyclo[3.3.1]nonane coupling iodine-rich compounds is: 9-nitrogen [6'-(2,4,6)-triiodophenylacetamide-α-amino]hexylamino-9-azabicyclo[3.3.1]nonane-3α-alkylcarbamate phenyl ester compounds. Background technique [0002] Imaging based on the X-ray principle is a widely used medical diagnostic method, and most diagnostic imaging today is based on this principle. Due to the large atomic number of iodine atoms, the ability to block X-rays is relatively strong. Therefore, organic iodine compounds are currently commonly used clinical X-ray contrast agents. Most organic X-ray contrast agents are non-targeted contrast agents, which have no tissue-organ distribution specificity, which is not conducive to early diagnosis and detection of tumors. Therefore, research on targeted contrast agents has gradually increased in recent years. Th...

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): C07D471/08A61K49/04
CPCA61K49/0438C07D471/08
Inventor 吴志平白雪燕吴雨琦
Owner CHINA JILIANG 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