Granted Patent B2

US 12,324,845 · App. 17/587,454 · Granted Jun 10, 2025

Inventors: Ajay Purohit (Sudbury, MA); Thomas D. Harris (Salem, NH); Heike S. Radeke (South Grafton, MA); Simon P. Robinson (Stow, MA); Ming Yu (Chelmsford, MA); David S. Casebier (Carlisle, MA); Michael T. Azure (Renlop, AL)

Assignee: Lantheus Medical Imaging, Inc.

A61K51/04A61K51/0453A61K51/0459C07B59/001C07C215/60C07C217/70C07C279/06C07C279/08C07B2200/05

Abstract

Claims (30)

1. A method of imaging, the method comprising administering, to a subject, a compound of Structure Alpha, of the formula:

or a pharmaceutically acceptable salt thereof, wherein:

n is 0;

R, R 1 , and R 3 are independently selected from the group consisting of H, OR 4 , F, Cl, Br, I, CF 3 , alkyl (C 1 -C 4 ), aryl, heteroaryl, C(═O)R 4 , CO 2 R 4 , N(R 4 ) 2 , CN, C(═NR 4 )OR 5 , NR 4 C(═NR 5 )NHR 6 , C(═NR 4 )NHR 5 , C(═O)NHR 4 , NR 4 C(═O)NR 5 , NR 4 NR 5 , SO 2 OR 4 , and imaging moiety Im;

R 2 is absent;

R 4 , R 5 , and R 6 are independently selected from the group consisting of H, alkyl, aryl and heteroaryl substituents; wherein the alkyl, aryl, or heteroaryl may be substituted with imaging moiety Im, wherein optionally any two of R 4 , R 5 , and R 6 form a cyclic structure selected from the group consisting of —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 , —CH═CH—, —X═CH—, and —X—CH═CH—, wherein X is selected from the group consisting of O, NH, and NR 7 , and wherein R 7 is selected from the group consisting of alkyl, aryl, and heteroaryl substituents;

W, X, Y and Z are independently selected from the group consisting of H, OR 4 , N(R 4 ) 2 , F, Cl, Br, I, CF 3 , imaging moiety Im, aryl, and heteroaryl;

A is O or absent; and

selected from the group consisting of 18 F, 76 Br, 124 I, 131 I, 99m Tc, 153 Gd, and 111 In;

and acquiring at least one image of the subject.

2. The method of claim 1 , wherein the method utilizes PET imaging techniques to acquire the at least one image.

3. The method of claim 1 , wherein the method utilizes SPECT imaging techniques to acquire the at least one image.

4. The method of claim 1 , wherein:

A is absent;

X, W, R and R 3 are hydrogen;

R 1 is NHC(═NH)NH 2 ;

Y is H, F, Cl, or Br; and

Z is OR 4 , wherein R 4 is alkyl substituted with 18 F.

5. The method of claim 1 , wherein any two of R 4 , R 5 , and R 6 form a cyclic structure selected from the group consisting of —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 , —CH═CH—, —X═CH—, and —X—CH═CH—,

wherein X is selected from the group consisting of O, NH, and NR 7 , and

wherein R 7 is selected from the group consisting of alkyl, aryl and heteroaryl substituents.

6. The method of claim 1 , wherein A is absent.

7. The method of claim 1 , wherein X and R 3 are hydrogen.

8. The method of claim 1 , wherein the imaging moiety Im is 18 F.

9. The method of claim 1 , wherein the compound of Structure Alpha has the structure:

or a pharmaceutically acceptable salt thereof.

10. The method of claim 1 , wherein the compound of Structure Alpha has the structure:

or a pharmaceutically acceptable salt thereof.

11. The method of claim 1 , wherein the compound of Structure Alpha has the structure:

or a pharmaceutically acceptable salt thereof.

Assignments (5)

Continuity (5)

References Cited (283)