# US 2014/0193344 A1 · Imaging contrast agents and uses thereof

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- Number: US 2014/0193344 A1
- Document ID: US20140193344A1
- Status: Published application
- Kind: A1
- Application number: 14/116,270
- Filed: 2012-05-11
- Published: 2014-07-10
- Earliest claimed: 2011-05-11
- Assignees: The Research Foundation of State University of New York
- Inventors: Janet R. Morrow; Pavel Tsitovich; Sarina Dorazio; Abiola Olatunde
- Web page: https://patentgrep.com/patent/US20140193344A1

## CPC

- A61K 49/106: {the complex-forming compound being cyclic, e.g. DOTA}
- C07D 213/53: Nitrogen atoms
- C07D 213/58: Amidines
- C07D 213/59: with at least one of the bonds being to sulfur
- C07D 213/68: attached in position 4
- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 471/04: Ortho-condensed systems
- G01N 33/52: Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper {and including single- and multilayer analytical elements (immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72)}
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

Provided are macrocyclic compounds having a macrocyclic core which has at least one macrocyclic donor and at least one pendant group which has at least one donor group. The macrocyclic compounds can be complexed to Fe(II) and Ni(II). The macrocyclic compounds can be used in imaging methods. For example, the compounds can be used MRI paraCEST contrast agents.

## Claims

### Claim 1

A macrocyclic compound having a macrocyclic core comprising from 9 to 15 atoms, wherein at least one of the atoms in the macrocyclic core is a N atom, at least two carbon atoms separate a heteroatom selected from the group consisting of: N atom, O atom, or S atom, and one or more of the following pendant groups as substituents on the macrocyclic core:
wherein each R4 is independently selected from H, C1 to C12 alkyl groups, PEG groups, thioether groups, or CH2CO2R8, each R5 is independently selected from H, C1 to C12 alkyl groups, PEG groups, thioether groups, CH2CO2R8, or OCH3, R6 is H or OCH3, R7 is H, OCH3, or CO2H, and each R8 and R9 is independently selected from H, C1 to C12 alkyl groups, PEG groups, thioether groups, the macrocyclic compound has at least one exchangeable proton, and a Fe(II) or Ni(II) cation is complexed to the macrocyclic core and/or at least one pendant group substituent of the macrocyclic compound.

### Claim 2 (depends on 1)

The macrocyclic compound of claim 1, wherein the macrocyclic compound has the following structure:
wherein each R1 is independently H, CH3, or a pendant group, each R2 is independently H or CH3, and each R3 is independently H or CH3.

### Claim 3 (depends on 1)

The macrocyclic compound of claim 1, wherein the macrocyclic compound has the following structure:
wherein n is from 6 to 17.

### Claim 4 (depends on 1)

A composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method to obtain an image of at least a portion of a cell, organ, vasculature or tissue comprising the steps of:
contacting the cell, organ, vasculature, or tissue with a compound of claim 1, and imaging at least a portion of the cell, organ, vasculature, or tissue to obtain an image of the portion of a cell, organ, vasculature, or tissue,
wherein the image is obtained by using magnetic resonance.

### Claim 6 (depends on 5)

The method of claim 5, wherein the cell, organ, vasculature, or tissue is part of an individual.

### Claim 7 (depends on 5)

The method of claim 5, wherein the image is obtained using magnetic resonance imaging (MRI).

### Claim 8 (depends on 5)

The method of claim 5, wherein the image is obtained using chemical exchange saturation transfer (CEST).

### Claim 9 (depends on 5)

The method of claim 5, wherein the image is obtained using paramagnetic chemical exchange saturation transfer (paraCEST).

### Claim 10 (depends on 5)

The method of claim 5, wherein the image is obtained using magnetic resonance spectroscopy imaging (MRSI).

### Claim 11 (depends on 5)

The method of claim 5, wherein the image is obtained using thermometry.

### Claim 12 (depends on 5)

The method of claim 5, wherein the image is obtained using pH mapping.