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US 2024/0228524 A1Published application
Iron(iii) macrocyclic complexes with mixed hyroxyl pendants as mri contrast agents
OwnerJanet R. MORROW, Eric M. SNYDER +3inventors
InventorsJanet R. MORROW, Eric M. SNYDER, Patrick BURNS, Elizabeth A. KRAS, Jaclyn RAYMOND
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Abstract
The present application describes novel Fe(III) macrocyclic complexes that have hydroxy pendants with a third anionic ancillary group for improved MR imaging in vivo. The complexes have the following general structure: (I) or (II) where high spin Fe(III) is chelated thereto. The present application also describes novel Fe(III) macrocyclic complexes that have hydroxypropyl pendants with a third anionic ancillary group for improved MR imaging in vivo. The complexes have the following general structure.
Claims33
A macrocyclic complex comprising a macrocyclic core with the following structure:
- wherein
- R1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group wherein the substituted or unsubstituted alkyl group is not a methyl group,
- Z1, Z2, and Z3 are independently chosen from one or more of the following pendant groups:
- and protonated, partially deprotonated, or deprotonated species thereof,
- wherein Q3, Q4 and Q5 are each independently anionic groups or chosen from —H, —NR2, —NO2, —CN, —(CH2)mNR2, OH, OR, —P(O)OH2, —(CH2)mPO(OH)2, —SO3H, and deprotonated species thereof, wherein m is 1 or 2 and R is an alkyl group, CF3 group, aryl group, alkyl carboxylate, or alkyl carboxylic acid;
- and
- the macrocyclic complex has two of any of 1, 1′, 2, 3, 4, 8, 10, or a combination thereof and not all the pendant groups are the same, and
- a high-spin Fe(III) cation complexed to the macrocyclic core and/or at least one pendant group substituent of the macrocyclic compound,
- with the provisos:
- i) when two of the pendant groups are structures 1, 1′, 2, 3, or any combination thereof, then the third pendent group is not 1, 1′, 2, or 3;
- ii) when two of the pendant groups are structures 1, 1′, 2, 3, 8, 14 or any combination thereof, then the third pendent group is not 1, 1′, 2, 3, 8, or 14;
- iii) when two of the pendant groups are structures 1, 1′, 2, 3, 10, or any combination thereof and R of structures 1 and/or structure 1′ is phenyl, then the R1 is not a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl group;
- iv) the macrocyclic core does not have the following structure:
- and
- v) the macrocyclic complex does not have the following structure:
- wherein the Fe(III) is high spin Fe(III).
13 more elements
A macrocyclic complex having the following structure:
- where the tri(hydroxy)butyl group(s) and —(CH2)nR groups are pendant groups and each R is independently selected from alkyl groups;
- aryl groups;
- heteroaryl groups;
- alkyl groups comprising one or more —OH groups, one or more sulfonic acid groups, one or more carboxylic acid groups, one or more phosphonic acid groups, one or more alkyl groups, or combinations thereof, aryl groups comprising one or more —OH groups, one or more sulfonic acid groups, one or more carboxylic acid groups, one or more phosphonic acid groups, one or more alkyl groups, or combinations thereof, heteroaryl groups comprising one or more —OH groups, one or more sulfonic acid groups, one or more carboxylic acid groups, one or more phosphonic acid groups, one or more alkyl groups, or combinations thereof, and H;
- or a salt, a partial salt, a hydrate, a polymorph, or a stereoisomer thereof;
- n is 1, 2, or 3,
- wherein a high-spin Fe(III) cation is complexed to the macrocyclic core and/or at least one pendant group substituent of the macrocyclic compound.
4 more elements
A macrocyclic compound having the following structure:
- where the tri(hydroxy)butyl group(s) and —(CH2)nR groups are pendant groups and each R is independently selected from alkyl groups;
- aryl groups;
- heteroaryl groups;
- alkyl groups comprising one or more —OH groups, one or more sulfonic acid groups, one or more carboxylic acid groups, one or more phosphonic acid groups, one or more alkyl groups, or combinations thereof, aryl groups comprising one or more —OH groups, one or more sulfonic acid groups, one or more carboxylic acid groups, one or more phosphonic acid groups, one or more alkyl groups, or combinations thereof, heteroaryl groups comprising one or more —OH groups, one or more sulfonic acid groups, one or more carboxylic acid groups, one or more phosphonic acid groups, one or more alkyl groups, or combinations thereof, and H;
- or a salt, a partial salt, a hydrate, a polymorph, or a stereoisomer thereof;
- n is 1, 2, or 3.
3 more elements
Dependencies are inferred from the claim text.