Process for the monotopic preparation of intermediate organo-iodinated compounds for the synthesis of ioversol

A technology of compounds and intermediates, applied in the field of preparation of organic iodide compounds, to achieve the effect of cheap preparation methods

Pending Publication Date: 2021-03-23
GUERBET SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For this acylation step alone, a yield limited to about 87.5% was obtained

Method used

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  • Process for the monotopic preparation of intermediate organo-iodinated compounds for the synthesis of ioversol
  • Process for the monotopic preparation of intermediate organo-iodinated compounds for the synthesis of ioversol
  • Process for the monotopic preparation of intermediate organo-iodinated compounds for the synthesis of ioversol

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example

[0140] The term "V" is understood to mean the volume ratio, ie the volume of reagent or solvent relative to 1 kg of AATI.

[0141] The term "eq." is understood to mean the number of molar equivalents, ie the ratio between the number of moles of reagent and the number of moles of AATI.

example 1

[0142] Example 1: Synthesis of Ioversol Synthetic Intermediates According to the Invention

[0143] Synthetic scheme

[0144] - MP602 from AATI

[0145]

[0146] Acylation step:

[0147] 2-Chloro-2-oxoethyl acetate (also known as AAC) (281 g, 1.15 eq.) was dissolved in dimethylacetamide (DMAC) (1.35 l) and AATI (1 kg , 1.0eq.). The reaction medium is mixed for 6 hours at 50°C. Propylene carbonate (1.151) was added and the reaction was cooled to 5°C.

[0148] Chlorination step:

[0149] Add thionyl chloride SOCl within 2 h at 5 °C 2 (745 g, 3.5 eq.) and the reaction medium was mixed for 5 hours at 5°C.

[0150] The reaction medium is added to an aqueous solution of sodium acetate (AcONa) in order to precipitate the "DiCOA-like" synthesis intermediate. The suspension was filtered and the solid part was redissolved in DMAC (1.5ml) to obtain a solution.

[0151] Amidation steps:

[0152] A mixture of aminopropylene glycol (APD) (359 g, 2.2 eq.) and 30% aqueous sodi...

example 2

[0155] Example 2: Synthesis of ioversol by the synthetic intermediate obtained according to the present invention

[0156] The compound obtained in Example 1 is then alkylated using 2-chloroethanol or ethylene oxide. The compound thus obtained is then purified and dried to obtain ioversol.

[0157]

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Abstract

The invention relates to a process for the preparation of organo-iodinated compounds as well as the preparation intermediates thereof. More specifically, the invention relates to a process for the preparation of organo-iodinated compounds useful as preparation intermediates in the synthesis of the contrast product ioversol.

Description

technical field [0001] The present invention relates to a process for the preparation of organic iodinated compounds, and also intermediates for their preparation. More specifically, the present invention relates to a method for the preparation of iodinated contrast agent ioversol A method for the preparation of organoiodinated compounds used as intermediates in the synthesis of . Background technique [0002] In patent US 4,396,598, ioversol is described as a non-ionic contrast agent. [0003] Currently, most methods for the synthesis of iodinated contrast agents, and notably those involving ioversol, use 5-amino-2,4,6-triiodoisophthalic acid dichloride (also known as DiCOCl) as an intermediate product: [0004] [0005] During the synthesis of iodinated contrast agents, lengthy isolation and purification steps are required in order to obtain synthetic intermediates of good purity. These steps greatly increase the time to perform the synthesis, and thus the costs in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/69
CPCC07C231/02C07C233/69
Inventor 斯蒂芬·佩林盖利米里亚姆·佩塔
Owner GUERBET SA
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