Labeled inhibitors of prostate specific membrane antigen (PSMA), their use as imaging agents and pharmaceutical agents for the treatment of prostate cancer

• US 10,398,791 B2
• Filed: 08/28/2018
• Issued: 09/03/2019
• Est. Priority Date: 10/18/2013
• Status: Active Grant

• Current Assignee: Novartis Ag
• Original Assignee: Deutsches Krebsforschungszentrum
• Inventors: Eder, Matthias, Kopka, Klaus, Schafer, Martin, Bauder-Wust, Ulrike, Haberkorn, Uwe, Eisenhut, Michael, Mier, Walter, Benesova, Martina
• Primary Examiner(s): Hartley, Michael G.
• Assistant Examiner(s): Samala, Jagadishwar R
• Application Number:
  US16/114,988
• Publication Number:
  US 20190060491A1
• Time in Patent Office: 371 Days
• CPC Class Codes: A61K 51/0402 carboxylic acid carriers, fatty acids amino acids A61K51/0406
• CPC Class Codes: A61K 51/0482 chelates from cyclic ligands, e.g. DOTA
• CPC Class Codes: A61K 51/0497 conjugates with a carrier being an organic compounds
• CPC Class Codes: A61P 13/08 of the prostate
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/04 specific for metastasis
• CPC Class Codes: C07B 59/002 Heterocyclic compounds
• CPC Class Codes: C07D 257/02 not condensed with other rings
• CPC Class Codes: C07D 295/145 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

Abstract

The present invention generally relates to the field of radiopharmaceuticals and their use in nuclear medicine as tracers, imaging agents and for the treatment of various disease states of prostate cancer. Thus, the present invention concerns compounds that are represented by the general Formulae (Ia) or (Ib).

Claims

1. A compound of the formula:

2. The compound or salt thereof according to claim 1, wherein the compound or salt is lyophilized.

3. A composition comprising:

(1) the compound and/or a salt thereof according to claim 1; and

(2) optionally a pharmaceutically acceptable carrier.

4. The composition of claim 3,

wherein the composition further comprises an excipient, and

wherein the excipient is different from said pharmaceutically acceptable carrier.

5. The composition of claim 3, wherein the composition is a buffered solution.

6. The composition of claim 3, wherein the compound and/or a salt thereof, and optionally the pharmaceutically acceptable carrier, are lyophilized.

9. A composition comprising:

(1) the compound and/or a salt thereof according to claim 7; and

(2) optionally a pharmaceutically acceptable carrier.

10. The composition of claim 9,

wherein the composition further comprises an excipient, and

wherein the excipient is different from said pharmaceutically acceptable carrier.

11. The composition of claim 9, wherein the composition is a buffered solution.

20. The composition of claim 9, wherein the compound and/or a salt thereof, and optionally the pharmaceutically acceptable carrier, are lyophilized.

23. A composition comprising:

(1) the compound and/or a salt thereof according to claims 21; and

(2) optionally a pharmaceutically acceptable carrier.

24. The composition of claim 23,

wherein the composition further comprises an excipient, and

wherein the excipient is different from said pharmaceutically acceptable carrier.

25. The composition according to claim 23, wherein the composition is a buffered solution.

26. The composition of claim 23, wherein the compound and/or a salt thereof, and optionally the pharmaceutically acceptable carrier, are lyophilized.

28. A composition comprising:

(1) the compound and/or a salt thereof according to claims 27; and

(2) optionally a pharmaceutically acceptable carrier.

29. The composition of claim 28,

wherein the composition further comprises an excipient, and

wherein the excipient is different from said pharmaceutically acceptable carrier.

30. The composition of claim 28, wherein the composition is a buffered solution.

7. A compound of the formula:

8. The compound or salt thereof according to claim 7, wherein the compound or salt is lyophilized.

21. The compound of claim 7 having the formula:

22. The compound or salt thereof according to claim 21, wherein the compound or salt is lyophilized.

12. A compound of the formula:

13. A composition comprising:

(1) the compound and/or a salt thereof according to claim 12; and

(2) optionally a pharmaceutically acceptable carrier.

14. The composition of claim 13,

wherein the composition further comprises an excipient, and

wherein the excipient is different from said pharmaceutically acceptable carrier.

15. The composition of claim 13, wherein the composition is a buffered solution.

16. A compound of the formula:

17. A composition comprising:

(1) the compound and/or a salt thereof according to claim 16; and

(2) optionally a pharmaceutically acceptable carrier.

18. The composition of claim 17,

wherein the composition further comprises an excipient, and

wherein the excipient is different from said pharmaceutically acceptable carrier.

19. The composition of claim 17, wherein the composition is a buffered solution.

27. The compound of claim 16 having the formula: