Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1993-10-25
1997-04-01
Kumar, Shailendra
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564152, C07C23303, C07C23304, C07C23305
Patent
active
056167989
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/Fr 92/00172 filed Feb. 25, 1992.
The present invention relates to novel poly-iodinated compounds utilizable in contrast media for radiography.
The invention also relates to a process for the preparation of these compounds as well as the contrast media containing them.
The invention thus relates to poly-iodinated compounds of formula: ##STR3## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10, identical or different, are selected from an iodine atom, a group of formula ##STR4## in which R.sub.11 and R.sub.12, identical or different, represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 alkyl group, a linear or branched C.sub.1 -C.sub.6 hydroxy- or polyhydroxy-alkyl group, bearing optionally in addition one or more C.sub.1 -C.sub.6 alkoxy groups, in particular methoxy or ethoxy, a linear or branched C.sub.1 -C.sub.6 alkoxy - C.sub.1 -C.sub.6 -alkyl group or a linear or branched C.sub.1 -C.sub.6 hydroxy- or polyhydroxy-alkoxy --C.sub.1 -C.sub.6 -alkyl group bearing two to five --OH groups, a group of formula ##STR5## wherein R.sub.11 and R.sub.12 identical or different are as defined previously or represent hydroxy and n and m are integers selected so that the sum n+m is an integer from 3 to 6, a group COO.sup.- M.sup.+ or --COOH, M.sup.+ representing a mineral or organic physiologically acceptable cation, a group of formula ##STR6## a group of formula ##STR7## and a group of formula ##STR8## in which R.sub.13 and R.sub.14, identical or different, represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 alkyl group, a linear or branched C.sub.1 -C.sub.6 hydroxy- or polyhydroxy-alkyl group, bearing optionally in addition one or more C.sub.1 -C.sub.6 alkoxy groups, in particular methoxy or ethoxy, a linear or branched C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 -alkyl group or a linear or branched C.sub.1 -C.sub.6 hydroxy- or polyhydroxy-alkoxy C.sub.1 -C.sub.6 -alkyl group bearing two to five --OH groups, or R.sub.13 and R.sub.14 form together a C.sub.4 -C.sub.8 alkylene, a C.sub.4 -C.sub.8 hydroxy alkylene or a C.sub.4 -C.sub.8 polyhydroxyalkylene group with a linear or branched chain, such that R.sub.13 and R.sub.14 form with the nitrogen atom to which they are attached a 5 or 6-membered nitrogenous heterocycle, optionally substituted by one or more hydroxy or C.sub.1 -C.sub.4 hydroxyalkyl groups, and R.sub.15 has the same meaning than R.sub.13 excepted an hydrogen atom, provided that at least two of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 groups represent an iodine atom.
The invention is particularly concerned with poly-iodinated compounds of general formula I in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10, identical or different, are selected from an iodine atom, a group of formula ##STR9## in which R.sub.11 and R.sub.12, identical or different represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 alkyl group, a linear or branched C.sub.1 -C.sub.6 hydroxy- or polyhydroxyalkyl group, optionally bearing in addition one or more C.sub.1 -C.sub.6 alkoxy groups, a linear or branched C.sub.1 -C.sub.6 alkoxyalkyl group, or linear or branched C.sub.1 -C.sub.6 hydroxy- or polyhydroxy- alkoxyalkyl group containing from two to five --OH groups, and a group of formula ##STR10## in which R.sub.13 and R.sub.14, identical or different, are as R.sub.11 and R.sub.12 defined above, provided that at least two of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 groups represent an iodine atom.
A first group of preferred compounds comprises the tetraiodinated compounds of general formula II: ##STR11## in which R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8 and R.sub.10 are as defined previously.
A second group of preferred compounds comprises the hexaiodinated compounds of general formula III: ##STR12## in which R.sub.1, R.sub.3, R.sub.7 and R.sub.9 are as define
REFERENCES:
patent: 4102924 (1978-07-01), Kalk et al.
patent: 4348377 (1982-09-01), Felder et al.
patent: 5232685 (1993-08-01), Speck et al.
Dugast-Zrihen Maryse
Meyer Dominique
Guerbet S.A.
Kumar Shailendra
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