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Iohexol intermediate impurity preparation method and application

An intermediate, iohexol technology, applied in the field of drug synthesis, to achieve the effect of short steps, simple preparation process and high purity

Active Publication Date: 2018-03-30
SHANGHAI STARRY PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, serious adverse reactions still occur from time to time, and the occurrence of adverse reactions is not only related to the pharmacological activity of iohexol itself, but also has a lot to do with the impurities in iohexol

Method used

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  • Iohexol intermediate impurity preparation method and application
  • Iohexol intermediate impurity preparation method and application
  • Iohexol intermediate impurity preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The preparation of embodiment 1, formula 1 compound

[0058] The formula 2 compound (10g, 0.028mol) was added to the autoclave, followed by methanol (40g), acetic acid (25g) and Rh / C (1g), 5.5MPa H 2 Reaction at room temperature, TLC monitoring completion of the reaction, suction filtration, the filtrate was concentrated to dryness under reduced pressure at 40°C to obtain 8.6 g of the crude compound of formula 1, the crude product weight yield was 86%, and the purity was 87%.

Embodiment 2

[0059] Embodiment 2, the purification of formula 1 compound

[0060]Dissolve the compound of formula 1 (0.5g, 0.0014mol) in methanol (1ml), add silica gel (0.5g, 200-300 mesh) to mix the sample, 10g of silica gel (200-300 mesh) for column, first use 25mL ethyl acetate Elution, followed by elution with 85mL of ethyl acetate:methanol with a volume ratio of 1:1, and finally with 50mL of ethyl acetate:methanol:ammonia with a volume ratio of 1:2:0.01 for elution, TLC detection and collection , the product was concentrated to dryness under reduced pressure at 40°C to obtain 0.4 g of off-white solid, which was the pure compound of formula 1. The total molar yield is 85.8%, and the purity is 98%.

Embodiment 3

[0061] Embodiment 3, confirmation of the structure of the compound of formula 1 in embodiment 2

[0062] Mass Spectrum: ESI-MS(m / z): 334.1[M+H] +

[0063] High resolution mass spectrum: m / z: 334.1974[M+H] + ;Molecular formula: C14H27N3O6

[0064] Proton NMR spectrum: 1 HNMR(400MHz,DMSO-d6)δ7.72-7.70(t,2H),5.10-4.05(bs,4H),3.46-3.43(m,2H),3.27-3.22(m,4H),3.16-3.12( m,2H),2.98-2.93(m,2H),2.55-2.53(m,1H),2.23-2.19(t,2H),1.76-1.74(d,2H),1.63-1.60(m,1H), 1.37-1.41(m,1H),1.09-1.03(m,2H).

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Abstract

The invention belongs to the technical field of pharmaceutical synthesis and specifically relates to a preparation method of iohexol intermediate impurity 5-amino-N,N'-bis(2,3-dihydroxy propyl)-cyclohexane-1,3-dicarboamide. The impurity can be applied to detecting mass of iohexol intermediate.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, in particular, relates to an intermediate impurity 5-amino-N,N'-bis(2,3-dihydroxypropyl)-cyclohexane-1 in the preparation process of iohexol , The preparation method of 3-dicarboxamide. Background technique [0002] Iohexol (Iohexol), which belongs to the second generation of non-ionic monomer contrast agent, is named "Omnipaque" (Omnipaque), and was developed and listed by Nycomed Company of Norway in the early 1980s. In 1982, Omnipaque was first launched in Norway and Sweden. In 1985, it was approved by the US FDA to be launched in the United States. With the rapid development of imaging diagnostic equipment in the world, X-CT contrast agents based on iodine contrast agents have achieved unprecedented development. Iohexol has many advantages such as high safety, high contrast, low osmotic pressure and low human toxicity. It has become the best-selling contrast agent in the internat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/24C07C231/12C07C231/24G01N30/02G01N30/06
CPCC07C231/12C07C231/24C07C237/24G01N30/02G01N30/06
Inventor 程寿玲吴金韦
Owner SHANGHAI STARRY PHARMA CO LTD
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