Polyiodinated compounds, their preparation and their use as contrast media for radiology

Polyiodinated compounds of generic formula I:

• A--(X).sub.m (I)
• in which:
• A represents the residue of a polyfunctional molecule containing either a central tri- or tetrasubstituted carbon atom, a central trisubstituted phosphorus or nitrogen atom or a trisubstituted ##STR119## group and/or at least one aromatic or non-aromatic carbocycle optionally containing one or more iodine atoms, or at least one aromatic or non-aromatic heterocycle containing from 1 to 4 hetero atoms selected from O, S, N and P, to which residues are bound m groups X via functional groups selected from the group consisting of --CO--, ##STR120## --O--, and >NCOR.sub.5 ;
• the groups X, which may be identical to or different from one another are selected from the group consisting of the group consisting of:
• --Q--B.sub.1 (A),
• --Q--A.sub.1 --(Q--B.sub.1).sub.m' (B),
• m' representing from 2 to 11;
• and
• --Q--B.sub.2 --Q--B.sub.1 (C)
• m represents an integer from 3 to 12, the groups Q, which may be identical or different from one another, represent a single bond or a group selected from:
• ##STR121## in which:
• R.sub.1 is selected from the group consisting of an alkylene group having a linear or branched C.sub.1 -C.sub.10 chain, a hydroxy- or polyhydroxyalkylene group having a linear or branched C.sub.1 -C.sub.10 chain, a (C.sub.1 -C.sub.5 alkoxy)alkylene group having a linear or branched C.sub.1 -C.sub.10 chain, a hydroxy- or polyhydroxy(C.sub.1 -C.sub.5 alkoxy)alkylene group having a linear or branched chain, and a single bond, and the R.sub.2 groups identical or different being selected from the group consisting of H, an alkyl group having a linear or branched C.sub.1 -C.sub.10 chain, a hydroxy- or polyhydroxyalkyl group having a linear or branched C.sub.1 -C.sub.10 chain, a (C.sub.1 -C.sub.5 alkoxy)alkyl group having a linear or branched C.sub.1 -C.sub.10 chain and a hydroxy- or polyhydroxy(C.sub.1 -C.sub.5 alkoxy)alkyl group having a linear or branched chain;
• the groups B.sub.1, which may be identical to or different from one another, represent the residue of an aromatic group containing at least three iodine atoms, of formula:
• ##STR122## in which R.sub.3 is selected from the group consisting of:
• a group --COO.sup.- M.sup.+ with M.sup.+ representing H.sup.+ or a physiologically acceptable cation of an organic or inorganic base,
• a group ##STR123## and group ##STR124## in which R.sub.5 and R.sub.6, which may be identical to or different from one another, represent H or a linear or branched C.sub.1 -C.sub.10 alkyl, linear or branched C.sub.1 -C.sub.10 hydroxy- or polyhydroxyalkyl, linear or branched C.sub.1 -C.sub.10 (C.sub.1 -C.sub.5 alkoxy)alkyl or linear or branched C.sub.1 -C.sub.10 hydroxy- or polyhydroxy(C.sub.1 -C.sub.5 alkoxy)alkyl group,
• or R.sub.5 and R.sub.6 together form a C.sub.4 -C.sub.8 alkylene, C.sub.4 -C.sub.8 hydroxyalkylene or C.sub.4 -C.sub.8 polyhydroxyalkylene group having a linear or branched chain which is optionally interrupted by one or more atoms selected from the group consisting of S, O, P and N, so that R.sub.5 and R.sub.6, with the nitrogen atom to which they are linked, form a 5- to 12-membered nitrogenous heterocycle optionally substituted with one or more hydroxyl groups or C.sub.1 -C.sub.4 hydroxy- or polyhydroxyalkyl groups having a linear or branched chain and optionally containing one or more additional hetero atoms selected from the group consisting of S, O, P and N,
• R.sub.4 represents a group selected from the group consisting of R.sub.3 and a group of formula Q--B.sub.4, Q being as defined above and B.sub.4 representing a group:
• ##STR125## in which R.sub.7 and R.sub.8, which may be identical to or different from one another, represent R.sub.3,
• A.sub.1 is selected from the group consisting of groups A, with the proviso that at least one group --CO--, ##STR126## or >NCOR.sub.5 is replaced by a single bond, B.sub.2 is selected from the group consisting:
• ##STR127## in which R.sub.4 and R.sub.5 have the meanings given above, with the proviso that said compounds contain a zero overall electrical charge or at least two anionic charges when A.paren open-st.X).sub.m =A(QB.sub.1).sub.3, and that said compounds have a molecular weight above 2,000 and below 50,000 and a molecular concentration of iodine greater than 20%.