IP Library Granted Patent US 9,315,534
Granted Patent B2
US 9,315,534 · App. 12/188,641 · Granted Apr 19, 2016

Radiologic agents for monitoring alzheimer's disease progression and Evaluating a Response to Therapy and processes for the preparation of such agents

Inventors: Zbigniew P. Kortylewicz (Omaha, NE); Janina Baranowska-Kortylewicz (Omaha, NE)
Assignee: BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA
C07H19/073A61K51/0459
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Quick Facts
Patent No.
US 9,315,534
App. No.
12/188,641
Granted
Apr 19, 2016
Kind
B2
Abstract

Disclosed are certain cycloSalingenyl pyrimidine nucleoside monophosphates comprising positron emitters or gamma-emitting radiohalides, uses thereof for monitoring Alzheimer's disease progression and evaluating response to therapy and process for their preparation.

Claims (18)

1. A compound of the formula:

wherein R represents a substituted or unsubstituted, straight or branched chain, saturated or unsaturated hydrocarbyl (C 1 -C 15 ) group, radioactive halogen, non-radioactive halogen;

R a represents radioactive halogen, non-radioactive halogen, hydroxyl, one of R and Ra being radioactive halogen;

X represents hydrogen, non-radioactive halogen, radioactive halogen;

Y represents hydrogen, a straight or branched chain, substituted or unsubstituted, saturated or unsaturated hydrocarbyl (C 1 -C 4 ) group, and 11 C-containing analogues of said hydrocarbyl group; and

Z represents hydrogen, straight or branched chain, substituted or unsubstituted saturated or unsaturated hydrocarbyl (C 1 -C 4 ) group, and 11 C-containing analogues of said hydrocarbyl group.

2. The compound of claim 1 , wherein R represents straight chain alkyl (C 1 -C 8 ) or aryl; R a represents 18 F; X represents F; Y represents branched chain alkyl (C 1 -C 4 ); Z represents branched chain alkyl (C 1 -C 4 ).

3. The compound 5′-O-[cycloSaligenyl-3,5-di(tert-butyl)-6-fluoro]-3′-[ 18 F]fluoro thymidine monophosphate, according to claim 1 .

4. The compound 5′-O-[cycloSaligenyl-3,5-di(tert-butyl)-6-fluoro-2′,3′-deoxy-3′-fluoro-5-[ 125 I]iodouridine monophosphate, according to claim 1 .

5. A method for making an ante mortem diagnosis of Alzheimer's disease comprising:

a. administering to a patient suspected of having Alzheimer's disease a compound according to claim 1 in an amount of up to 20 mCi (up to 740 MBq) effective to bind to butyrylcholinesterase (BChE) present in the brain of said patient; and

b. detecting the amount of BChE bound by said compound.

6. The method of claim 5 , further comprising comparing the amount of BChE detected to a positive or negative control.

7. The method of claim 5 , wherein said detecting is carried out by imaging.

8. The method of claim 7 , wherein the imaging is positron emission tomography (PET) or single photon emission computed tomography (SPECT).

9. The method of claim 5 , wherein said compound is administered intravenously or intracarotid.

10. The method according to claim 6 , wherein steps (a) and (b) are repeated at least once after passage of a predetermined time interval, an increase in said radioactive drug uptake during said time interval being indicative of the progression of AD in said patient.

11. The method according to claim 6 , wherein steps (a) and (b) are repeated at least once after passage of a predetermined time interval during which AD therapy is administered to said patient, a decrease in said radioactive drug uptake being indicative of the effectiveness of said therapy.

Assignments (3)
CONFIRMATORY LICENSE Recorded Nov 23, 2011
From: UNIVERSITY OF NEBRASKA MEDICAL CENTER
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 027281/0070 →
CONFIRMATORY LICENSE Recorded Dec 24, 2009
From: UNIVERSITY OF NEBRASKA MEDICAL CENTER
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 023701/0500 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2009
From: BARANOWSKA-KORTYLEWICZ, JANINA; KORTYLEWICZ, ZBIGNIEW P.
To: BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA
Reel/Frame 022646/0502 →
Continuity (3)
Provisional Application 60964251 · Aug 10, 2007
Provisional Application 61010129 · Jan 4, 2008
Related Publication 20090117041A1 · May 7, 2009