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Schwerelementhaltige amphiphile Block- und Pfropf-Copolymere, Verfahren zu ihrer Herstellung und ihre Verwendung als Roentgenkontrastmittel

Amphiphilic block or graft copolymers with heavy element-containing groups such as tri-iodophenyl attached to the hydrophobic block, used in micellar suspension as X-ray media for computer tomography.
: Thünemann, A.F.; Kozlowski, C.; Storsberg, J.; Jaeger, W.; Laschewsky, A.; Kubowicz, S.

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DE 102004005304 A: 20040203
DE 2004-102004005304 A: 20040203
WO 2005-EP990 A: 20050201
DE 102004005304 A1: 20050818
Patent, Elektronische Publikation
Fraunhofer IAP ()

Die vorliegende Erfindung betrifft amphiphile Block- oder Pfropf-Copolymere, aufgebaut aus den oder unter Verwendung der Struktureinheiten (A): $F1 und (B) $F2 in einem Anteil von zusammen mindestens 70 Gew.-%, worin R1 -(X)-COOR', -(X)-OP(O)OR', -(X)-NHC(O)R'', -(X)-NR''C(O)R'', -(X)-C(O)NHR'', -(X)-C(O)N(R'')2, oder -(X)-OH ist, R2 Wasserstoff, eine Methylgruppe oder ein Rest -CH2COOR', -CH2C(O)NHR'', -CH2C(O)N(R'')2, -CH2OC(O)R'', -CH2NHR''C(O)R'' bzw. -CH2C(O)N(R'')2 ist, R3 Wasserstoff ist und ausserdem dann, wenn R2 Wasserstoff ist, ein Rest -COOR', -C(O)NHR'' oder -C(O)N(R'')2 sein kann, R' Wasserstoff, ein einwertiges Metallkation, ein entsprechender Anteil eines mehrwertigen Metallkations, R'' oder eine Gruppe (CH2CH2O)nR7 ist, wobei mehrere Reste R' dieselbe oder unterschiedliche Bedeutung (en) haben koennen, R'' eine Alkylgruppe mit vorzugsweise 1 bis 8 Kohlenstoffatomen, eine Benzylgruppe, eine Arylgruppe mit vorzugsweise 6 bis 8 Kohlenstoffatomen, oder eine Gruppe (CH2CH2O)nR7 ist, wobei mehrere Reste R'' dieselbe oder unterschiedliche Bedeutung (en) haben koennen, (X) eine Einfachbindung, -OC(O)R8-, -OC(O)O-R8-, -C(O)OR8-, NR7C(O)R8-, -C(O)NR7R8-, -NR7C(O)OR8-, -N(R8-)C(O)OR7-OC(O)NHR8-, -N(R8-)C(O)R7 oder -R9- ist, wobei R7 und/oder R8 sowie -R9- Substituenten tragen koennen, -OP(O)(OR')2, -P(O)(OR')2, -NR7C(O)R7, -C(O)NR7R'', -OH, -S(O)CH3 und ...


DE1004005304 A UPAB: 20051014 NOVELTY - Amphiphilic block or graft copolymers with heavy element-containing groups attached to the hydrophobic block. DETAILED DESCRIPTION - Amphiphilic block or graft copolymers (I) containing at least 70 wt% structural units of formula (A) and (B), R1 = -X-COOR', -X-OP(O)OR', -X-NHCOR, -X-NRCOR, -X-CONHR, -X-CONR2 or -X-OH; R2 = H, methyl, -CH2COOR', -CH2CONHR, -CH2CONR2, -CH2OCOR, -CH2NRCOR or -CH2CONR2; R3 = H or (if R2 is H) -COOR', -CONHR or -CONR2; R' = H, a monovalent metal cation or the equivalent proportion of a multivalent metal cation; R = -(CH2CH2O)nR7, or 1-8C alkyl (linear, branched or cyclic), benzyl or 6-8C aryl (optionally alkyl-substituted); X = a single bond, -OCOR8-, -OCOOR8-, -COOR8-, -NR7COR8-, -CONR7-R8-, -NR7COOR8-, -N(R8-)COOR7, -OCONH-R8-, -N(R8-)COR7 or -R9- (all optionally substituted with -COOR', -SO3R', -OSO3R', -N+R4, -OP(O)(OR')2, -P(O)(OR')2, -NR7COR7, -CONR7R, -OH, -S(O)CH3 or -CO(OCH2CH2)r-OR7); R4-R6 = H, -R, -OR, -OCOR, -OCOOR, -COOR, -NR7COR, -CONR7R, -NHCOOR, -OCONHR, -R10-R10', -R10'-R10, -R10-CH2-R10', -R10-CH2O-R10', -R10'-CH2-R10 or -R10'-CH2O-R10, with the proviso that at least one of the groups R4, R5 or R6 is one of the last four groups listed; R7 = H, 1-12C alkyl (linear, branched or cyclic) or 6-24C aryl (all optionally substituted); R8 = optionally substituted 1-12C (cyclo)alkylene or optionally alkyl-substituted 6-24C arylene, alkylarylene or aralkylene; R9 = optionally alkyl-substituted 6-10C arylene; R10' = optionally alkyl-substituted 6-24C aryl or arylene which is mono- or poly-substituted with a heavy element; p, q = 2-1000; n, r = 1-1000 . INDEPENDENT CLAIMS are also included for (1) micellar suspensions containing micelles of (I) in an aqueous solvent (2) a method for the production of (I) by polymerising a monomer of formula X(CH2)m-R9-CR5=CR6 (sic) to give a product (II) with a reactive chain end, polymerising a compound of formula R1-CR2=CR3 (sic) either in a first polymerisation stage with subsequent linkage of the product to (II) or by direct polymerisation onto the reactive chain end of (II), and then reacting a compound of formula R10'-(CH2)o-Y with the group X-(CH2)m-R9- in the resulting product to form the group R4. X = Cl or OH; m = 0 or 1; (o + m) = 1; Y = a suitable reaction partner (especially OH or Cl) for linking R10' with R10 directly or via an ether link. USE - Micellar suspensions of these copolymers are used as X-ray contrast media (claimed). A preferred application is in computer tomography. ADVANTAGE - An X-ray contrast agent in which the heavy element-containing group is attached to the polymer structure by covalent bonds only. The agent is hydrolytically stable under physiological conditions, and forms low-viscosity micellar suspensions which cause less pain on injection and in which the structural integrity of the micelles is preserved even at high dilution.