Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1990-04-10
1992-06-30
Griffin, Ronald W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
424 5, 424 4, 514 59, A61K 2902, A61K 4904, C08B 3702, C08G 7300
Patent
active
051264404
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to iodinated polymers which can be used in radiography as contrast products and, in particular, as injectable contrast products.
The compounds used as injectable contrast products must not only absorb X-rays but also possess various properties and in particular
Up to now it has been necessary to inject considerable amounts of contrast products into patients in order to obtain a correct diagnosis starting from the radiographic image. Also, the researches have been oriented towards derivatives with a more suitable osmolarity and reduced toxicity. Two new categories of products have thus made their appearance: ionic products of low osmolarity and non-ionic products
More recently, one has tried to develop another approach consisting of slowing down the diffusion of the contrast products in the extra-vascular space.
For this purpose, different iodinated polymers have been suggested. it is thus that U.S. Pat. No. 3,852,341 describes iodinated polymers obtained by copolymerization of a 3,5-diacylamino-2,4,6-triiodobenzene acid with bifunctional compounds such as a diepoxide. These polymers are soluble in water. FR-A-2,200,018 describes related copolymers which are cross-linked and insoluble in water.
U.S. Pat. No. 4,406,878 describes an iodinated polymer which is obtained by reaction of tetraiodphthalic anhydride on polyvinyl alcohol and cross-linking.
The applicant has already developed iodinated polymers which comprise a skeleton constituted by a dextran on which are grafted groups displaying a triiodobenzene residue.
These polymers are obtained in particular by conversion of the hydroxy groups of the dextran into grafting groups of the carboxymethyloxy type and reaction of the grafting groups of the carboxymethyloxy type thus obtained with amines containing a triiodobenzene residue.
The applicant has observed that the grafting of the amines onto the grafting groups of the carboxymethyloxy type is not complete and that 20 to 70% of the grafting groups of the carboxymethyloxy type do not react.
The applicant has now discovered that by making an aliphatic amine react on the grafting groups of the carboxymethyloxy type or analogous grafting groups which remain after reaction with an amine with a triiodobenzene residue, it was possible to obtain an iodinated polymer which exhibits a better tolerance.
Consequently, the object of the present invention is iodinated polymers comprising a skeleton constituted by a dextran on which are grafted groups of general formula: ##STR1## in which
X is selected from among the groups ##STR2##
n is equal to 0 to 4 and the R groups are simultaneously
a) iodinated groups of formula ##STR3## in which m is an integer from 1 to 5
R.sub.1 is a group selected from among the COOH group, the COOH group made into a salt by a pharmaceutically acceptable base and the groups of formula ##STR4## and
R.sub.2 is a group selected from among the groups of formula ##STR5## formulae in which
R.sub.3 and R.sub.5 are selected from among C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 hydroxyalkyl, C.sub.1 to C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.6) alkoxy (C.sub.1 -C.sub.6) alkyl and (C.sub.1 -C.sub.6) alkoxy (C.sub.1 -C.sub.6) hydroxyalkyl groups,
R.sub.4 and R.sub.6 are selected from among a hydrogen atom and C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 hydroxyalkyl, C.sub.1 to C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.6) alkoxy (C.sub.1 -C.sub.6) alkyl and (C.sub.1 -C.sub.6) alkoxy (C.sub.1 -C.sub.6) hydroxylakyl groups,
R.sub.3 being, in addition, a group of formula ##STR6##
m' being an integer from 1to 5 and
R.sub.1 and R.sub.2 having the meaning given previously,
b) non-iodinated groups of formula -C.sub.4 hydroxyalkyl and (C.sub.1 -C.sub.4) polyhydroxyalkyl groups. and
c) less than 20% of hydroxy groups.
The dextran which serves as support for the triiodobenzene groups is a polymer usually obtained from sucrose by the action of Leuconostoc mesenteroides.
The dextrans are polymers constitute by .alpha.-D-glucose units. The glycosyl units of chains are linked essential
REFERENCES:
patent: 2708174 (1955-05-01), Stavely
patent: 4069306 (1978-01-01), Rothman
patent: 4406878 (1983-09-01), DeBoer
patent: 4822594 (1989-04-01), Gibby
Doucet Didier
Meyer Dominique
Paris Dominique
Schaefer Michel
Griffin Ronald W.
Guerbert S.A.
Leary Louise
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