IP Library › Patent Application 16510495
Patent Application
App. No. 16/510,495

LABELED INHIBITORS OF PROSTATE SPECIFIC MEMBRANE ANTIGEN (PSMA), THEIR USE AS IMAGING AGENTS AND PHARMACEUTICAL AGENTS FOR THE TREATMENT OF PROSTATE CANCER

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Quick Facts
Patent No.
US None
App. No.
16/510,495
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 (55)

1 . A compound of Formula (Ia) or (Ib):

with:

n:

0,1

m:

1,2,3,4

Z:

—CO 2 H, —SO 2 H, —SO 3 H, —SO 4 H, —PO 2 H, —PO 3 H,

—PO 4 H 2

X:

Naphthyl, Phenyl, Biphenyl, Indolyl (=2,3-benzopyrrolyl),

Benzothiazolyl

Y:

Aryl, Alkylaryl, Cyclopentyl, Cyclohexyl, Cycloheptyl

Che-

1,4,7,10-tetraazacyclododecane-N,N′,N″,N′″-tetraacetic acid

lator:

(=DOTA),

N,N″-bis[2-hydroxy-5-(carboxyethyl)benzyl]ethylenediamine-

N,N″-diacetic acid (=HBED-CC),

1,4,7-triazacyclononane-1,4,7-triacetic acid (=NOTA),

2-(4,7-bis(carboxymethyl)-1,4,7-triazonan-1-yl)pentanedioic acid

(NODAGA),

2-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-

yl)pentanedioic acid

(DOTAGA),

1,4,7-triazacyclononane phosphinic acid (TRAP),

1,4,7-triazacyclononane-1-[methyl(2-carboxyethyl)phosphinic

acid]-4,7-bis[methyl(2-hydroxymethyl)phosphinic acid] (NOPO),

3,6,9,15-tetraazabicyclo[9.3.1.]pentadeca-1(15),11,13-triene-3,6,9-

triacetic acid (=PCTA),

N′-{5-[Acetyl(hydroxy)amino]pentyl}-N-[5-({4-[(5-

aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N-

hydroxysuccinamide (DFO),

Diethylenetriaminepentaacetic acid (DTPA)

Trans-cyclohexyl-diethylenetriaminepentaacetic acid (CHX-DTPA)

1-oxa-4,7,10-triazacyclododecane-4,7,10-triacetic acid (oxo-Do3A)

p-isothiocyanatobenzyl-DTPA (SCN-Bz-DTPA)

1-(p-isothiocyanatobenzyl)-3-methyl-DTPA (1B3M)

2-(p-isothiocyanatobenzyl)-4-methyl-DTPA (1M3B)

1-(2)-methyl-4-isocyanatobenzyl-DTPA (MX-DTPA)

2 . The compound of claim 1 having the structure R′-Linker-R with R′=DOTA and R=. Glu-Urea-Lys:

wherein the linker is selected from:

3 . The compound of claim 1 , selected from the following:

4 . A radiolabeled compound comprising the compound of claim 1 .

5 . A metal complex comprising a radionuclide and a compound of claim 1 .

6 . The metal complex of claim 5 , wherein the radionuclide is 111 In, 90 Y, 68 Ga, 177 Lu, 99m Tc, 64 Cu, 153 Gd, 155 Gd, 157 Gd, 213 Bi, 225 Ac or Fe.

7 . A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt, or ester thereof, and a pharmaceutically acceptable carrier.

8 . The compound of claim 1 for use in a method of imaging in a patient.

9 . The compound of claim 1 for use in a method of diagnosing prostate cancer and/or metastasis thereof.

10 . The compound of claim 1 for use in a method of treating prostate cancer and/or metastasis thereof.

11 . A pharmaceutical composition comprising the metal complex of claim 5 , or a pharmaceutically acceptable salt, or ester thereof, and a pharmaceutically acceptable carrier.

12 . The metal complex of claim 5 for use in a method of imaging in a patient.

13 . The metal complex of claim 5 for use in a method of diagnosing prostate cancer and/or metastasis thereof.

14 . The metal complex of claim 5 for use in a method of treating prostate cancer and/or metastasis thereof.

Assignments (6)
DECLARATION OF BRENDA HERSCHBACH JARRELL Recorded Apr 12, 2022
From: RUPRECHT-KARLS-UNIVERSITÄT HEIDELBERG; DEUTSCHES KREBSFORSCHUNGSZENTRUM
To: RUPRECHT-KARLS-UNIVERSITÄT HEIDELBERG; DEUTSCHES KREBSFORSCHUNGSZENTRUM
Reel/Frame 059690/0218 →
DECLARATION TO CORRECT ASSIGNMENT RECORD AFTER ATTEMPT BY A THIRD PARTY TO RECORD AN IMPROPER ASSIGNMENT IN APPLICATION NO. 16/510,495 AT REEL 051989/FRAME 0187 Recorded Nov 20, 2021
From: RUPRECHT-KARLS-UNIVERSITÄT HEIDELBERG; DEUTSCHES KREBSFORSCHUNGSZENTRUM
To: RUPRECHT-KARLS-UNIVERSITÄT HEIDELBERG; DEUTSCHES KREBSFORSCHUNGSZENTRUM
Reel/Frame 058896/0557 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2020
From: KRATOCHWIL, CLEMENS WALTER
To: RUPRECHT-KARLS-UNIVERSITÄT HEIDELBERG
Reel/Frame 052956/0769 →
CONFIRMATION OF OWNERSHIP (AS FILING RELATES TO COMPOUNDS THAT ARE "DERIVATIVES") Recorded Feb 21, 2020
From: UNIVERSITY OF HEIDELBERG
To: MOLECULAR INSIGHT PHARMACEUTICAL, INC.
Reel/Frame 051989/0187 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2019
From: EDER, MATTHIAS; KOPKA, KLAUS; SCHÄFER, MARTIN; BAUDER-WÜST, ULRIKE; EISENHUT, MICHAEL; BENESOVA, MARTINA
To: DEUTSCHES KREBSFORSCHUNGSZENTRUM
Reel/Frame 049750/0158 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2019
From: HABERKORN, UWE; MIER, WALTER
To: RUPRECHT-KARLS-UNIVERSITÄT HEIDELBERG
Reel/Frame 049750/0312 →