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US 5,489,673 AGranted
Iodinated borane cage molecules as X-ray contrast media
AssigneeUniversity of Washington
InventorD. Scott Wilbur
Life of this patent
Estimating the term…
Abstract
Highly iodinated borane and carborane cage molecules, having from 60% to 90% w/w iodine, are disclosed as new and useful X-ray contrast media when combined with a pharmaceutically acceptable carrier. The inclusion of appropriate functional group substituents, such as hydrophilic moieties, increases solubility and lowers toxicity.
Claims57
A diagnostic composition suitable for enteral or parenteral administration to a mammal comprising:
- a diagnostically effective amount of a stable iodinated borane cage compound having a formula:
- [I.sub.x B.sup.cm R.sub.y ].sup.z
- wherein B.sup.cm is a stable borane cage moiety containing from 9 to 12 boron atoms in either a closo- or nido- cage structure and containing up to 3 carbon atoms as part of the cage structure which replace respective boron atoms of the cage structure;
- I represents iodine atoms of x number substituted on boron atoms of B.sup.cm and x is from 6 to 12;
- and R is a substituent of either a boron atom or carbon atom of B.sup.cm which contains functional groups that alter the overall charge or improve water solubility of the stable iodinated borane cage compound and y is from 0 to 6;
- and z represents the overall charge of the stable iodinated borane cage compound ranging from -4 to +4;
- and
- a pharmaceutically acceptable carrier.
5 more elements
A compound having the formula:
- [I.sub.x (B.sub.y R.sub.z)H.sub.[y-(x+z+n)] ]M.sub.n
- wherein B.sub.y is a closo-borane cage moiety in which there are y boron atoms in the cage structure and y is in the range from 9 to 12;
- I are iodine atoms present in x number substituted on boron atoms of the borane cage moiety and x is in the range from 6 to 12;
- R are substituents, other than iodine or hydrogen atoms, present in z number substituted on boron atoms of the borane cage moiety, which contain functional groups that alter the overall charge of the compound or improve water solubility of the compound, wherein R is selected from the group consisting of alkyl amine, dialkyl amine, trialkyl amine, alkyl carboxylate, alkyl alcohol, ester, alkyl ester, cyclic heteroalkyl polyalcohol, acyclic heteroalkyl polyalcohol, and combination thereof and where z is in the range from 1 to 6;
- H are hydrogen atoms of y-(x+z+n) number attached to boron atoms of the borane cage moiety, wherein y-(x+z+n) is in the range from 0 to 6;
- and M are cationic or anionic counterions and n is adjusted from 0 to 4 to balance the net overall charge on the iodinated borane cage moiety.
3 more elements
A compound having the formula:
- [I.sub.x (C.sub.1 B.sub.y R.sub.z)H.sub.[Y+1-(x+z+n)] ]M.sub.n
- wherein C.sub.1 B.sub.y is a closo or nido-monocarbon carborane cage moiety in which there are y boron atoms and 1 carbon atom in the cage structure and y is in the range from 8 to 11;
- I are iodine atoms present in x number substituted on boron atoms of the borane cage moiety and x is in the range from 6 to 11;
- R are alkyl or heterocyclic substituents, other than iodine or hydrogen atoms, present in z number substituted on boron or carbon atoms of the borane cage moiety, which contain functional groups that alter the overall charge of the compound or improve water solubility of the compound and where z is in the range from 0 to 5;
- H are hydrogen atoms of y+1-(x+z+n) number attached to boron atoms of the borane cage moiety, wherein y+1-(x+z+n) is in the range from 0 to 6;
- and M are cationic or anionic counterions and n is adjusted from 0 to 4 to balance the net overall charge on the iodinated borane cage moiety.
3 more elements
A compound having the formula:
- [I.sub.x (C.sub.2 B.sub.y R.sub.z)H.sub.[h+2-(x+z+n)] ]M.sub.n
- wherein C.sub.2 B.sub.y is a closo or nido-dicarbon carborane cage moiety in which there are y boron atoms and 2 carbon atoms in the cage structure and y is in the range from 7 to 10;
- I are iodine atoms present in x number substituted on boron atoms of the borane cage moiety and x is in the range from 6 to 10;
- R are alkyl or heterocyclic substituents, other than iodine or hydrogen atoms, present in z number substituted on boron or carbon atoms of the borane cage moiety, which contain functional groups that alter the overall charge of the compound or improve water solubility of the compound and where z is in the range from 0 to 5;
- H are hydrogen atoms of y+2-(x+z+n) number attached to boron atoms of the borane cage moiety, wherein y+2-(x+z+n) is in the range from 0 to 6;
- and M are cationic or anionic counterions and n is adjusted from 0 to 4 to balance the net overall charge on the iodinated borane cage moiety.
3 more elements
Dependencies are inferred from the claim text.