PSMA imaging agents

Patent metadata

Field	Value
Publication number	US-12139554-B2
Application number	US-202016999563-A
Country	US
Kind code	B2
Filing date	Aug 21, 2020
Priority date	Aug 22, 2011
Publication date	Nov 12, 2024
Grant date	Nov 12, 2024

Abstract

Compounds for targeting and agents for imaging, prostate-specific membrane antigen (PSMA) are disclosed. Methods of synthesizing compounds and imaging agents, as well as methods for imaging PSMA are also disclosed. The imaging agents disclosed are suitable for PET and SPECT imaging.

First claim

We claim:

1. A compound of Formula VI:

and pharmaceutically acceptable salts and stereoisomers thereof,
wherein:
X 1 is CH or N;
X 19 is selected from the group consisting of: NO 2 and (CH 2 ) 1-10 -R 16 wherein at least one CH 2 of (CH 2 ) 1-10 is optionally replaced by CONH, aryl, heteroaryl;
X 20 is selected from the group consisting of: H, NO 2 , (CH 2 ) 1-10 -R 16 wherein at least one CH 2 of (CH 2 ) 1-10 is optionally replaced by CONH, aryl, heteroaryl;
X 21 is selected from the group consisting of (CH 2 ) 1-3 wherein at least one CH 2 of (CH 2 ) 1-3 is optionally replaced by heteroaryl,
and
R 16 is selected from the group consisting of N 3 , alkyne, protecting group, halo and radioisotope.

2. The compound of claim 1 , wherein in Formula VI, X 1 is N.

3. The compound of claim 1 , wherein in Formula VI, X 20 is H and X 19 is (CH 2 ) 1-10 -R 16 wherein at least one CH 2 of (CH 2 ) 1-10 is replaced by CONH.

4. The compound of claim 1 , wherein in Formula VI, at least one CH 2 of (CH 2 ) 1-10 -R 16 of either X 19 or X 20 is replaced by triazole.

5. The compound of claim 1 , wherein in Formula VI, R 16 is a radioisotope.

6. A compound of Formula VIII:

and pharmaceutically acceptable salts and stereoisomers thereof,
wherein:
X 1 is CH or N;
X 24 is selected from the group consisting of (CH 2 ) 1-6 wherein at least one CH 2 of (CH 2 ) 1-6 is optionally replaced by at least one selected from the group consisting of NH, O, S;
X 25 is N or CH;
X 26 is NH or CH 2 ;
X 27 is selected from the group consisting of: H, NO 2 , (CH 2 ) 1-10 -R 16 wherein at least one CH 2 of (CH 2 ) 1-10 is optionally replaced by O, CONH, aryl, heteroaryl; and
R 16 is selected from the group consisting of N 3 , alkyne, protecting group, halo and radioisotope.

7. The compound of claim 6 , wherein in Formula VIII, X 1 is N.

8. The compound of claim 6 , wherein in Formula VIII, X 1 is CH.

9. The compound of claim 6 , wherein in Formula VIII, at least one CH 2 of (CH 2 ) 1-6 is optionally replaced by O.

10. The compound of claim 6 , wherein in Formula VIII, X 25 is N.

11. The compound of claim 6 , wherein in Formula VIII, X 25 is CH.

Assignees

• Siemens Medical Solutions Usa Inc

Inventors

• Wang Eric
• Kolb Hartmuth C
• Szardenings Anna Katrin
• Liu Changhui
• Walsh Joseph C
• Chen Gang
• Sinha Anjana
• Kasi Dhanalakshmi
• Yu Chul
• Gangadharmath Umesh B
• Zhang Wei
• Zhao Tieming
• Mocharla Vani P

Classifications

• C07D249/04

  1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles · CPC title

• A61K51/0453

  having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole · CPC title

• A61K51/0497

  conjugates with a carrier being an organic compounds · CPC title

• A61K51/0402

  carboxylic acid carriers, fatty acids (amino acids A61K51/0406) · CPC title

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title