Tetraiodopyrrole derivatives as contrast medium and as antisepti

Details Tetraiodopyrrole derivatives as contrast medium and as antisepti Tetraiodopyrrole derivatives as contrast medium and as antisepti

1995-05-25

1996-12-24

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548413, 548518, 548531, 548538, 548560, 548562, C07D207305

Patent

active

055874878

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP 94/04201 filed Dec. 16,1994.
X-ray imaging is a widely used diagnostic technique for an early detection of a series of anomalies and/or pathological conditions in living tissues.
A better enhancement of images obtained through this diagnostic procedure was made possible thanks to contrast media of suitable opacifying agents. These compounds became unavoidable in the study of some organs or anatomical districts, characterised by a very low absorbing power with regard to radiations which were used and therefore unable to supply clear and sharp radiographic images.
Today's contrast media preferably contain, as opacifying molecules, neutral polyiodinated aromatic compounds (an extensive and up-dated publication on the state of the art of these diagnostic agents is the work of D. P. Swanson et al. "Pharmaceuticals in Medical Imaging", 1990, Mac Millan Publ. Company). The characteristic of these products relies on the inclusion of at least one benzene nucleus where three hydrogen atoms are replaced by three iodine atoms. An acceptable absorption of X-rays requires an iodine high concentration and therefore the above mentioned contrast agents have to be used in highly concentrated solutions.
The present invention refers to new contrast media particularly suited for X-ray diagnostic procedures of the human and animal body and also to the new compounds of general formulae (I) and (II) ##STR2## wherein: m and n can independently vary between 0 and 5, branched (C.sub.1- C.sub.8 ) hydroxyalkyl with 1-7 --OH groups, or polyoxalkyl group of formula ##STR3## wherein G is H, CH.sub.3, CH.sub.2 CH.sub.3, R.sub.3 and R.sub.4 which are the same or different, have the same meanings as R.sub.2, or they are a group of formula --(CH.sub.2).sub.1-2 R.sub.5 where R.sub.5 can be one of the following groups COOH, SOH, SOH, POH, PO.sub.2 H or a derivative thereof, or they are a group of formula --CH.sub.2 CH.sub.2 R.sub.6 where R.sub.6 is a quaternary ammonium group of aliphatic or aromatic nature, or a group of formula ##STR4## wherein m has the above meanings, or again R hd 3 and R.sub.4 can be a neutral or ionic organic residue containing from one to two triiodinated aromatic nuclei, or R.sub.3 and R.sub.4 , considered together, can be a (C.sub.3 -C.sub.7) residue, possibly interrupted by atoms of, S, N, or possibly substituted by hydrophilic and/or radiopaque functional groups,
Should the compounds of formula (I) and (II) contain carboxylic and/or free phenol functions, this invention also include the salts of said compounds with physiologically acceptable organic bases, preferably selected among primary, secondary or tertiary amines, or basic amino acids, or with inorganic bases whose cations are sodium, potassium, magnesium, calcium or their mixtures.
Should compounds of formula (I) and (II) contain cationic functions, this invention also includes the salts of said compounds with anions of physiologically acceptable organic acids such as acetate, fumarate, succinate, oxalate, citrate, glutamate, aspartate or with anions of inorganic acids, such as chlorides, bromides, iodides or sulfates.
The new pyrrole derivatives of this invention are characterised in that they have four iodine atoms substituting the corresponding hydrogens. This substitution leads to a 89% iodine concentration, in the specific case of tetraiodopyrrole. Such a high iodine concentration allows the administration of the compounds of the invention at a lower concentration, thus reducing the chances of possible undesired side effects.
Up to now tetraiodopyrrole derivatives have never been used as X-ray contrast media, nor their use with this techniques has been mentioned or anticipated by the known prior art. On the contrary, in the past century tetraiodopyrrole was found to be an effective mean against syphilis, angina pectoris, diabetes and so on, thanks to its therapeutic characteristics,.
In patent literature, two patents, issued at the end of the last century, claim the tetraiodopyrrole preparation (or Iodol.sup.R). The f

REFERENCES:
patent: 5371239 (1994-12-01), Doscher

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