Process for the preparation of iopamidol and the new...

Details Process for the preparation of iopamidol and the new... Process for the preparation of iopamidol and the new...

2008-05-06

2008-05-06

Hartley, Michael G. (Department: 1618)

Drug, bio-affecting and body treating compositions

In vivo diagnosis or in vivo testing

X-ray contrast imaging agent

C564S153000, C549S370000, C424S009450

Reexamination Certificate

active

07368101

ABSTRACT:
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) starting 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 R1is a hydrogen atom, a C1÷C4straight or branched alkoxy group, R2is hydrogen, a C1÷C4straight or branched alkoy group and R3 ?is a C1÷C4straight 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.

REFERENCES:
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patent: 616 403 (1980-03-01), None
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patent: WO 00 50385 (2000-08-01), None
Greene, T. and Wuts, P., Protective Groups in Organic Synthesis, 1999, John Wiley and Sons, p. 201-237.
Felder, E. et al.; “Iopamidol”, Analytical Profiles of Drug Substances, Academic Press, London, GB, vol. 17, pp. 115-154.
PCT International Search Report for PCT/EP01/13939 dated Mar. 19, 2002.
PCT International Preliminary Examination Report for PCT/EP01/13939 dated Oct. 2, 2002.

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