62883-00-5

Basic information

• Product Name: Iopamidol
• Synonyms: N,N'-BIS(1,3-DIHYDROXYPROPAN-2-YL)-5-(2-HYDROXYPROPANOYLAMINO)-2,4,6-TRIIODO-BENZENE-1,3-DICARBOXAMIDE;Iopamidol;N,N'-Bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydroxy-1-oxopropyl)amino)-2,4,6-triiodo-1,3-Benzenedicarboxamide;1-N,3-N-bis(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxamide;N,N'-bis(2-hydroxy-1-methylol-ethyl)-2,4,6-triiodo-5-lactamido-isophthalamide;N1,N3-bis(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanoylamino)-2,4,6-triiodo-benzene-1,3-dicarboxamide;1,3-BenzenedicarboxaMide,N1,N3-bis[2-hydroxy-1-(hydroxyMethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)aMino]-2,4,6-triiodo-
• CAS NO: 62883-00-5
• Molecular Formula: C17H22I3N3O8
• Molecular Weight: 777.09
• EINECS: 262-093-6
• Product Categories: Other APIs
• Mol File: 62883-00-5.mol

Chemical Properties

• Boiling Point: 785.3 °C at 760 mmHg
• Flash Point: 428.8 °C
• Appearance: /
• Density: 2.281 g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Water (Slightly)
• PKA: pKa 10.70(H2O,t = 25.0) (Uncertain)
• CAS DataBase Reference: Iopamidol(CAS DataBase Reference)
• NIST Chemistry Reference: Iopamidol(62883-00-5)
• EPA Substance Registry System: Iopamidol(62883-00-5)

Safety Data

• Hazardous Substances Data: 62883-00-5(Hazardous Substances Data)

Usage

Uses

Used in Diagnostic Imaging:
Iopamidol is used as a diagnostic aid for radiological procedures, functioning as a radiopaque medium. It improves the visualization of blood vessels, organs, and other internal structures during X-ray, CT, and other imaging techniques by increasing their radiodensity.
Used in Medical Contrast Agents:
Iopamidol is utilized as a nonionic medical contrast agent in various radiological applications. It helps in providing clearer images of the vascular system, urinary tract, and other body parts, facilitating more accurate diagnoses and treatment planning.

Upstream product

• 60166-98-5 S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-amino-2,4,6-triiodo-1,3-benzenedicarboxamide 
• 267881-76-5 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide 
• 25351-79-5 5-amino-isophthalic acid dibutyl ester 
• 10552-75-7 dibutyl 5-nitroisophthalate 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 
• 60166-91-8 S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride 
• 35453-19-1 2,4,6-triiodo-5-aminoisophthalic acid 
• 534-03-2 serinol 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF IOPAMIDOL

The present invention provides a process for the preparation of a compound of Formula (II) wherein the process comprises: (i) reacting a compound of Formula (I) with pyridine and 2-acetyloxypropanoyl chloride (APC) to give a compound of Formula (II), wherein the compound of Formula (I) has the following structure.

MECHANOCHEMICAL SYNTHESIS OF RADIOGRAPHIC AGENTS INTERMEDIATES

The present invention generally relates to a process using a mechanochemical approach exploiting the mechanical milling of reactants for the manufacturing of acetyl Iopamidol and, more generally, of key intermediates of radiographic contrast agents, and of the contrast agents themselves.

PROCESS FOR THE PREPARATION OF IOPAMIDOL

The present invention discloses a process for the preparation of Iopamidol of formula (II) and comprising the following steps: a) reacting the Compound (I) wherein X is OR2 or R3, and wherein R2 and R3 are a Ci-C6 linear or branched alkyl, C3-C6 cycloalkyl, C6 aryl, optionally substituted with a group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl and phenyl, with the acylating agent (S)-2-(acetyloxy)propanoyl chloride in a reaction medium to provide the acetyloxy derivative of Compound (I); b) hydrolyzing the intermediate from step a) with an aqueous solution at a pH comprised from 0 to 7, by adding water or a diluted alkaline solution such as sodium hydroxide or potassium hydroxide, freeing the hydroxyls from the boron-containing protective groups, obtaining the N-(S)-2-(acetyloxy)propanoyl derivative of Compound (II); c) alkaline hydrolysis to restore the (S)-2-(hydroxy)propanoyl group and to obtain lopamidol (II) and optional recovery of the boron derivative from the solution obtained in step b). The boron-containing protective group is versatile, efficient and recyclable. A one-pot synthesis, without intermediate isolation is provided, leading to a decreasing of recovered and recycled solvents and a significant increasing in the yield, representing a significant advantage in terms of cost-effectiveness of the entire process and environmental awareness.

Manufacture of a Triiodinated Contrast Agent

A new compound, (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid, of formula II (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid. Said new compound is of use for the production of triiodinated contrast agent, especially lopamidol, with low content of acetyl and hydroxyacetyl analogs. The new compound may be formed from 5-amino-2,4,6-triiodoisophtalic acid by acylating with (S)-1-chloro-1-oxopropan-2-yl acetate. The new compound may then be converted to the respective acid dichloride by reacting with a chlorinating reagent, which is a further object of the present invention, followed by the amidation with 2-amino-1,3-propanediol and acetate hydrolysis.

Process For The Preparation Of Contrast Agents

The present invention relates to a process for the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamidic derivatives comprising the Smiles rearrangement of a suitable precursor, by contact of an aqueous solution of this latter with an anion exchanger solid phase.

MANUFACTURE OF A TRIIODINATED CONTRAST AGENT

A new compound, (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid, of formula II (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid. Said new compound is of use for the production of triiodinated contrast agent, especially lopamidol, with low content of acetyl and hydroxyacetyl analogs. The new compound may be formed from 5-amino-2,4,6-triiodoisophtalic acid by acylating with (S)-1-chloro-1-oxopropan-2-yl acetate. The new compound may then be converted to the respective acid dichloride by reacting with a chlorinating reagent, which is a further object of the present invention, followed by the amidation with 2-amino-1,3-propanediol and acetate hydrolysis.

PROCESS FOR THE PREPARATION OF CONTRAST AGENTS

The present invention relates to a process for the preparation of 5-[(2- hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamidic derivatives comprising the Smiles rearrangement of a suitable precursor, by contact of an aqueous solution of this latter with an anion exchanger solid phase.

PROCESS FOR THE PREPARATION OF IODINATED CONTRAST AGENT

The present invention relies on a process for the preparation of non ionic iodinated contrast agents and, in more details, it relates to a process for the preparation of Iopamidol in high yields and with a high degree of purity. In more details, the invention discloses a process for the preparation of a compound of formula (III) comprising the 5 condensation reaction a compound of formula (II) with 2-amino-1,3-propandiol, being said reaction carried out in an aprotic dipolar solvent and in the presence of an alkaline or alkaline rare earth metal oxide or hydroxide.

Process for the preparation of iopamidol and the new intermediated therein

A process for the preparation of (S)-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxo-propyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide (iopamidol) starling from 5-amino-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (II) which process comprises a) reacting the compound of formula (II) with a suitable protecting agent, to give a compound of formula (III) wherein R is a group of formula A or B wherein R1 is a hydrogen atom, a C1÷C4 straight or branched alkoxy group, R2 is hydrogen, a C1÷C4 straight or branched alkoxy group and R3 ?is a C1÷C4 straight or branched alkyl group, a trifuoromethyl or a trichloromethyl group; b) acylating the amino group in position 5 of the intermediate compound of formula (III), by reaction with a (S)-2-(acetyloxy)propanoyl chloride to give a compound of formula (IV) wherein R is as defined above; and c) removing all the acyl groups present in the compound of formula (IV) under basic conditions, with prior cleavage of the cyclic protections of the hydroxy groups in the carboxamido substituents under acidic conditions, when R is a group of formula A carboxamido hydroxy groups under acidic conditions. The invention also refers to the new intermediates of formula (III) and (IV) wherein —R is a group A.