Drug – bio-affecting and body treating compositions – In vivo diagnosis or in vivo testing – X-ray contrast imaging agent
Patent
1994-11-21
1997-03-11
Kumar, Shailendra
Drug, bio-affecting and body treating compositions
In vivo diagnosis or in vivo testing
X-ray contrast imaging agent
564153, A61K 4904, C07C23305
Patent
active
056098510
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR93/00175, filed Feb. 22, 1993.
The present invention relates to compounds which can be used in contrast media for radiography.
BACKGROUND
Iodobenzene compounds having on the benzene ring several iodine atoms, in general 3 iodine atoms per benzene ring and various other substituents, have been used for a long time as contrast agents. These other substituents are pharmacologically acceptable groups which allow administration of the compounds to man and to animals. These substituents are generally chosen, on the one hand, to confer on the compounds a sufficient water-solubility for administering these compounds in aqueous solution and, on the other hand, to confer on these compounds sufficient tolerance by the human body.
To this effect, nonionic compounds, that is to say substituted iodobenzenes possessing nonionic substituents, have been proposed.
SUMMARY OF THE INVENTION
The object of the present invention is to provide new nonionic compounds which are well tolerated by the human body, which are stable in aqueous solution, which possess good water-solubility and which, in aqueous solution, possess low viscosity.
To this effect, the present invention provides compounds having formula I: ##STR2## wherein: R.sub.1 represents a group selected from ##STR3## R.sub.4 representing --CH.sub.3, --CH.sub.2 --CH.sub.2 OH, --CH.sub.2 --CHOH--CH.sub.2 OH or --CH--(CH.sub.2 OH).sub.2, ##STR4## R.sub.4 being as defined above, ##STR5## R.sub.5 representing --H or R.sub.4, ##STR6## R.sub.16 representing R.sub.4 or --CH.sub.2 (CHOH).sub.2 CH.sub.2 OH ##STR7## R.sub.4 being as defined above, ##STR8## representing a linear or branched (C.sub.4 -C.sub.8)alkylene group, a linear or branched hydroxy- or polyhydroxy (C.sub.1 --C.sub.4)alkylene group, a linear or branched (C.sub.1 -C.sub.4)alkoxy(C.sub.4 -C.sub.8)alkylene group, a linear or branched hydroxy- or polyhydroxdroxy(C.sub.1 -C.sub.4)alkoxy(C.sub.4 -C.sub.8)alkylene group, ##STR9## R.sub.1 being as defined above and R.sub.7 and R.sub.8, which are identical or different, representing a group selected from --H, a linear or branched (C.sub.1 -C.sub.6)alkyl, a linear or branched hydroxy- or polyhydroxy(C.sub.1 -C.sub.6 )alkyl group, a linear or branched (C.sub.1 -C.sub.4)alkoxy(C.sub.1 -C.sub.6)alkyl group and a linear or branched hydroxy- or polyhydroxy(C.sub.1 -C.sub.4)alkoxy(C.sub.1 -C.sub.6)alkyl group, ##STR10## R.sub.9 and R.sub.10 representing R.sub.7 and R.sub.8, a group of formula ##STR11## a group of formula ##STR12## R.sub.10 being as defined above and R.sub.11 having the seine meanings as R.sub.10 except --H.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Polyhydroxy group is understood to mean a group containing 2 to 5 --OH groups.
Among the preferred ##STR13## groups, there may be mentioned those possessing 2 to 4 hydroxyl groups and containing 5 to 6 members, especially: ##STR14##
A first group of preferred compounds according to the invention is that having the following formula II: ##STR15## wherein R.sub.4 is --CH.sub.2 CH.sub.2 OH or --CH.sub.2 --CHOH--CH.sub.2 OH and R.sub.10 is --H or --CH.sub.3.
The compound of the following formula IIa is particularly preferred: ##STR16##
A second group of preferred compounds according to the invention is that having the following formula III: ##STR17## wherein R.sub.2 is ##STR18## R.sub.4 is as defined above for formula I, and R.sub.10 represents --H or --CH.sub.3.
The compounds of the following formula IIIa, IIIb, IIIc, IIId and IIIe are particularly preferred: ##STR19##
A third group of preferred compounds according to the invention is that having the following formula IV: ##STR20## wherein R.sub.2 is selected from the groups ##STR21## R.sub.5 is as defined above for the formula I and R.sub.10 represents --H or --CH.sub.3.
The compounds of the following formula IVa, IVb, IVc, IVd, IVe and IVf are particularly preferred: ##STR22##
A fourth group of preferred compounds according to the invention is that having the following formula V: ##STR23## wherein: R.sub.2 is --CONHCH.sub.3, #
REFERENCES:
patent: 4547357 (1985-10-01), Pfeiffer et al.
patent: 5043152 (1991-08-01), Schaefer et al.
T. Nakanishi, "Hydrophilic Elastomers", Chemical Abstracts, vol. 88, No. 4, Jan. 23, 1978, Abstract No. 24102c.
Bennani Fatima Z.
le Greneur Soizic
Meyer Dominique
Simonot Christian
Guerbet S A.
Kumar Shailendra
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