IP Library Granted Patent US 10,980,900
Granted Patent B2
US 10,980,900 · App. 14/983,075 · Granted Apr 20, 2021

Imaging of meningiomas using phenylbenzothiazole, stilbene, or biphenylalkyne derivatives

Inventors: Geoffrey B. Johnson (Rochester, MN); Val J. Lowe (Rochester, MN); Mark A. Nathan (Rochester, MN); Joseph E. Parisi (Rochester, MN)
Assignee: Mayo Foundation for Medical Education and Research
A61K51/0453A61K51/04A61K51/0446A61K51/0455A61K51/0497
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Quick Facts
Patent No.
US 10,980,900
App. No.
14/983,075
Granted
Apr 20, 2021
Kind
B2
Abstract

Methods for detecting or ruling out a meningioma in a patient using a phenylbenzothiazole derivative or a stilbene derivative or a biphenylalkyne derivative, and a medical imaging technique such as positron emission tomography/computed tomography are disclosed. In one version of the method, the stilbene derivative is a compound of formula (X):

Claims (57)

1. A method for detecting or ruling out a meningioma in a patient, the method comprising:

(a) administering to a patient a detectable amount of a compound of formula (VI):

wherein the compound is targeted to any meningiomas in the patient,

wherein R 4 is selected from the group consisting of H, OH, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, and substituted or unsubstituted carboxylate,

wherein n is an integer from 0 to 10,

wherein X is selected from the group consisting of 3 H, 11 C, 13 C, 14 C, 13 N, 15 O, 75 Br, 76 Br, 18 F, 19 F, 68 Ga, 82 Rb, 111 In, 123 I, 125 I, 131 I, 201 Tl, and 99m Tc; and

(b) acquiring an image of the patient;

(c) evaluating the image to detect meningiomas that do not contain amyloid; and

(d) detecting the meningioma in the patient based on detected meningiomas that do not contain amyloid.

2. The method of claim 1 wherein:

R 4 is methylamino or dimethylamino.

3. The method of claim 1 wherein:

R 4 is methylamino, and

X is 18 F.

4. The method of claim 3 wherein:

n is 3.

5. The method of claim 1 wherein step (b) comprises acquiring the image using an imaging method selected from positron emission tomography imaging, single photon emission computed tomography imaging, positron emission tomography with computed tomography imaging, positron emission tomography with magnetic resonance imaging, single photon emission computed tomography with computed tomography imaging, or any combination thereof.

6. The method of claim 1 wherein step (b) comprises acquiring the image using positron emission tomography imaging.

7. The method of claim 1 wherein step (b) comprises acquiring the image using single photon emission computed tomography imaging.

8. The method of claim 1 wherein step (b) comprises acquiring the image using positron emission tomography with computed tomography imaging.

9. The method of claim 1 wherein step (b) comprises acquiring the image using positron emission tomography with magnetic resonance imaging.

10. The method of claim 1 wherein step (b) comprises acquiring the image using single photon emission computed tomography with computed tomography imaging.

11. The method of claim 1 wherein the presence of any meningiomas in the patient is indicated by an image in which meningiomas showed activity of the compound greater than normal adjacent tissues imaged.

12. The method of claim 1 wherein:

the presence of any meningiomas in the patient is indicated by a brain image in which meningiomas showed activity of the compound greater than any other intracranial tumors imaged.

13. The method of claim 1 wherein:

the presence of any meningiomas in the patient is indicated by a brain image in which meningiomas showed activity of the compound greater than any metastases, pituitary macroadenomas, schwannomas, or ependymomas imaged.

14. The method of claim 1 wherein:

the presence of any meningiomas in the patient is indicated by an image in which meningiomas showed activity of the compound greater than any metastases imaged.

15. A method for detecting or ruling out a meningioma in a patient, the method comprising:

(a) administering to a patient a detectable amount of a compound of formula (VIII):

wherein the compound is targeted to any meningiomas in the patient,

wherein R 4 is selected from the group consisting of H, OH, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, and substituted or unsubstituted carboxylate,

wherein n is an integer from 0 to 10,

wherein X is selected from the group consisting of 3 H, 11 C, 13 C, 14 C, 13 N, 15 O, 75 Br, 76 Br, 18 F, 19 F, 68 Ga, 82 Rb, 111 In, 123 I, 125 I, 131 I, 201 Tl, and 99m Tc; and

(b) acquiring an image of the patient;

(c) evaluating the image to detect meningiomas that do not contain amyloid; and

(d) detecting the meningioma in the patient based on detected meningiomas that do not contain amyloid.

16. The method of claim 15 wherein:

R 4 is methylamino or dimethylamino.

17. The method of claim 15 wherein:

R 4 is methylamino, and

X is 18 F.

18. A method for detecting or ruling out a meningioma in a patient, the method comprising:

(a) administering to a patient a detectable amount of a compound of formula (IX):

wherein the compound is targeted to any meningiomas in the patient,

wherein R 4 is selected from the group consisting of H, OH, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, and substituted or unsubstituted carboxylate,

wherein n is an integer from 0 to 10,

wherein X is selected from the group consisting of 3 H, 11 C, 13 C, 14 C, 13 N, 15 O, 75 Br, 76 Br, 18 F, 19 F, 68 Ga, 82 Rb, 111 In, 123 I, 125 I, 131 I, 201 Tl, and 99m Tc; and

(b) acquiring an image of the patient;

(c) evaluating the image to detect meningiomas that do not contain amyloid; and

(d) detecting the meningioma in the patient based on detected meningiomas that do not contain amyloid.

19. The method of claim 18 wherein:

R 4 is methylamino or dimethylamino.

20. The method of claim 18 wherein:

R 4 is methylamino, and

X is 18 F.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2020
From: JOHNSON, GEOFFREY B.; LOWE, VAL J.; NATHAN, MARK A.; PARISI, JOSEPH E.
To: MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH
Reel/Frame 054736/0288 →
CONFIRMATORY LICENSE Recorded Jun 13, 2016
From: MAYO CLINIC ROCHESTER
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 038965/0600 →
Continuity (3)
Division 13878689
Provisional Application 61392282 · Oct 12, 2010
Related Publication 20160144060A1 · May 26, 2016