# US 10,245,332 B2 · Contrast agents for applications including perfusion imaging

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- Number: US 10,245,332 B2
- Document ID: US10245332B2
- Status: Granted
- Kind: B2
- Application number: 15/153,502
- Filed: 2016-05-12
- Published: 2016-12-15
- Granted: 2019-04-02
- Earliest claimed: 2008-02-29
- Assignees: Lantheus Medical Imaging, Inc.
- Applicants: Lantheus Medical Imaging, Inc.
- Inventors: Simon P. Robinson; David S. Casebier; Ming Yu; Mikhail Kagan; Joel Lazewatsky
- Web page: https://patentgrep.com/patent/US10245332B2

## CPC

- A61K 51/0459: {having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine}
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 35/00: Antineoplastic agents
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention is directed, in part, to compounds and methods for imaging the central nervous system or cancer, comprising administering to a subject a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the subject using diagnostic imaging.

## Claims

### Claim 1

A method of imaging cancer in a subject, comprising:
administering to a subject with cancer a contrast agent which comprises an imaging moiety and a compound bound to the imaging moiety, scanning the patient using diagnostic imaging to produce an image of at least a portion of the cancer, wherein the contrast agent has a structure as in Formula (II),
wherein:
J is selected from N(R27) S, O, C(═O), C(═O)O, NHCH2CH2O, a bond, or C(═O)N(R27);
K and L, when present, are independently selected from hydrogen, alkoxyalkyl, alkyloxy, aryl, alkyl, heteroaryl, and an imaging moiety, each of which is optionally substituted;
M is selected from hydrogen, alkoxyalkyl, alkyloxy, aryl, alkyl, heteroaryl, and an imaging moiety, each of which is optionally substituted, or
L and M, together with the atom to which they are attached, form a ring, optionally substituted;
Q is halo or haloalkyl;
n is 0, 1, 2, or 3;
R21, R22, R23, R24, R25, R26, and R27 are independently selected from hydrogen, alkyl,
optionally substituted, and an imaging moiety;
R29 is alkyl, optionally substituted; and
Y is selected from a bond, carbon, and oxygen; provided that when Y is a bond, K and L are
absent and M is selected from aryl and heteroaryl, each of which is optionally substituted; and
provided that when Y is oxygen, K and L are absent and M is selected from hydrogen, alkoxyalkyl,
aryl, alkyl, and heteroaryl, each of which is optionally substituted,
wherein at least one imaging moiety is present in Formula (II) and is 18F.

### Claim 2 (depends on 1)

The method as in claim 1, wherein the image is used in the diagnosis of a subject.

### Claim 3 (depends on 2)

The method as in claim 2, wherein the diagnosis is a diagnosis of a cancer.

### Claim 4 (depends on 1)

The method as in claim 1, wherein the image is used to determine the stage of a cancer.

### Claim 5 (depends on 1)

The method as in claim 1, further comprising selecting a treatment of a cancer in the subject based at least in part on the image of at least a portion of the cancer.

### Claim 6 (depends on 1)

The method as in claim 1, further comprising evaluating a treatment of a cancer in the subject based at least in part on the image of at least a portion of the cancer.

### Claim 7 (depends on 1)

The method as in claim 1, wherein the cancer is a primary tumor or neoplasia.

### Claim 8 (depends on 1)

The method as in claim 1, wherein the cancer is a metastatic growth.

### Claim 9 (depends on 1)

The method as in claim 1, wherein J is O and R29 is C1-C6 alkyl.

### Claim 10 (depends on 1)

The method as in claim 1, wherein R29 is tert-butyl.

### Claim 11 (depends on 1)

The method as in claim 1, wherein M is alkoxyalkyl, optionally substituted with an imaging moiety.

### Claim 12 (depends on 1)

The method as in claim 1, wherein the contrast agent is selected from the following group:

### Claim 13 (depends on 1)

The method as in claim 1, wherein the contrast agent is:

### Claim 14 (depends on 2)

The method as in claim 2, wherein the contrast agent is:

### Claim 15 (depends on 3)

The method as in claim 3, wherein the contrast agent is:

### Claim 16 (depends on 4)

The method as in claim 4, wherein the contrast agent is:

### Claim 17 (depends on 5)

The method as in claim 5, wherein the contrast agent is:

### Claim 18 (depends on 6)

The method as in claim 6, wherein the contrast agent is:

### Claim 19 (depends on 7)

The method as in claim 7, wherein the contrast agent is:

### Claim 20 (depends on 8)

The method as in claim 8, wherein the contrast agent is: