# US 10,765,763 B2 · Radioligands for myelin

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- Number: US 10,765,763 B2
- Document ID: US10765763B2
- Status: Granted
- Kind: B2
- Application number: 16/083,747
- Filed: 2017-03-09
- Published: 2019-05-09
- Granted: 2020-09-08
- Earliest claimed: 2016-03-09
- Assignees: Case Western Reserve University
- Applicants: Case Western Reserve University
- Inventors: Yanming Wang; Chunying Wu
- Web page: https://patentgrep.com/patent/US10765763B2

## CPC

- A61K 51/04: Organic compounds
- A61K 51/0453: {having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole}
- G01N 33/58: involving labelled substances (G01N33/53 takes precedence)
- G01N 2800/285: Demyelinating diseases; Multipel sclerosis
- G01N 2800/52: Predicting or monitoring the response to treatment, e.g. for selection of therapy based on assay results in personalised medicine; Prognosis
- 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)
- 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

A radioligand for labeling myelin includes a fluorescent trans-stilbene derivative.

## Claims

### Claim 1

A method of detecting myelin in vivo in a subject's tissue, the method comprising:
(i) administering to the subject a radioligand including a compound having the formula:
R2 is H, or NHR′, where R′ is a lower alkyl group;
R3 is a radiolabeled lower alkyl group, alkylene group, alkenyl group, alkynyl group, or alkoxy group;
wherein R3 includes a radiolabeled group having a radiolabel selected from the group consisting of 18F, 123I, 125I, and 99mTc; or a pharmaceutically acceptable salt thereof; and
(ii) detecting the location, distribution, and/or amount of the radioligand that is bound to and/or labels myelin to detect myelin in the tissue.

### Claim 2 (depends on 1)

The method of claim 1, wherein the radioligand has the formula:
wherein R2 is H, or NHR′, where R′ is a lower alkyl group;
X1 is a lower alkyl group, alkylene group, alkenyl group, alkynyl group, or alkoxy group;
Y1 is a radiolabel selected from the group consisting of 18F, 123I, 125I, and 99mTc; or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein the radioligand has the formula:
R2 is H, or NHR′, where R′ is a lower alkyl group;
n1 is 1 to 6;
Y1 is a radiolabel selected from the group consisting of 18F, 123I, 125I, and 99mTc; or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the radioligand has the formula:
or pharmaceutically acceptable salts thereof.

### Claim 5 (depends on 1)

The method of claim 1, the radioligand is detected by in Positron Emission Tomography (PET) imaging or micro Positron Emission Tomography (microPET) imaging.

### Claim 6 (depends on 1)

The method of claim 1, further comprising the step of administering the radioligand to the subject parenterally.

### Claim 7 (depends on 1)

The method of claim 1, wherein the radioligand further comprises a chelating group or a near infrared imaging group.

### Claim 8

A method of detecting a myelin related disorder in a subject in need thereof, the method comprising the steps of:
(i) administering to the subject a radioligand that includes a compound having the formula:
R2 is H, or NHR′, where R′ is a lower alkyl group;
R3 is a radiolabeled lower alkyl group, alkylene group, alkenyl group, alkynyl group, or alkoxy group;
wherein R3 includes a radiolabeled group having a radiolabel selected from the group consisting of 18F, 123I, 125I, and 99mTc; or a pharmaceutically acceptable salt thereof;
(ii) detecting the distribution and/or amount of the radioligand in a region of interest in tissue of the subject; and
(iii) comparing the detected distribution and/or amount of the radioligand to a control, wherein a decreased distribution and/or amount of the radioligand compared to the control is indicative of a decrease in myelination of the tissue and the presence of myelination related disorder.

### Claim 9 (depends on 8)

The method of claim 8, wherein the radioligand has the formula:
or pharmaceutically acceptable salts thereof.

### Claim 10 (depends on 8)

The method of claim 8, wherein the radioligand is detected using Positron Emission Tomography (PET) or micro Positron Emission Tomography (microPET) imaging modality.

### Claim 11 (depends on 8)

The method of claim 8, further comprising the step of administering the radioligand to the subject parenterally.

### Claim 12 (depends on 8)

The method of claim 8, wherein the radioligand further comprises a chelating group or a near infrared imaging group.

### Claim 13 (depends on 8)

The method of claim 8, wherein the myelin related disorder is a neurodegenerative autoimmune disease.

### Claim 14 (depends on 13)

The method of claim 13, wherein the neurodegenerative autoimmune disease is multiple sclerosis.