# US 2019/0375720 A1 · 18f-labeled triazole containing psma inhibitors

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- Number: US 2019/0375720 A1
- Document ID: US20190375720A1
- Status: Published application
- Kind: A1
- Application number: 16/233,026
- Filed: 2018-12-26
- Published: 2019-12-12
- Earliest claimed: 2016-06-28
- Applicants: Cornell University
- Inventors: John W. Babich; James M. Kelly; Alejandro Amor-Coarasa; Shashikanth Ponnala
- Web page: https://patentgrep.com/patent/US20190375720A1

## CPC

- C07D 249/06: with aryl radicals directly attached to ring atoms
- A61B 6/032: {Transmission computed tomography [CT]}
- A61B 6/037: {Emission tomography}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 51/0497: {conjugates with a carrier being an organic compounds}
- A61P 35/00: Antineoplastic agents
- C07C 275/16: being further substituted by carboxyl groups
- C07C 275/24: containing six-membered aromatic rings
- C07D 249/04: 1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61B: DIAGNOSIS; SURGERY; IDENTIFICATION (usefulness limited to only animals A61D)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present technology is directed to compounds, intermediates thereof, compositions thereof, medicaments thereof, and methods related to the imaging of mammalian tissue overexpressing PSMA. The compounds are of Formula I or a pharmaceutically acceptable salt thereof, wherein one of R1, R2, and R3 is and of Formula IV or a pharmaceutically acceptable salt thereof.

## Claims

### Claim 1

A compound of Formula I
or a pharmaceutically acceptable salt thereof, wherein
P1, P2, and P3 are each independently H, methyl, benzyl, 4-methoxybenzyl, or tert-butyl;
W1 is —C(O)— or —(CH2)n—NH—C(O)—;
one of R1, R2, and R3 is
N and the remaining two of R1, R2, and R3 are each H;
X1 is absent, O, S, or NH;
m is 0, 1, 2, or 3;
n is 1 or 2;
p is 0, 1, 2, or 3, provided that when p is 0 then X1 is absent; and
q is 1 or 2.

### Claim 2 (depends on 1)

The compound of claim 1, wherein P1, P2, and P3 are each independently H or tert-butyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein P1, P2, and P3 are each independently H.

### Claim 4 (depends on 1)

An intermediate for preparing a compound of claim 1, wherein the intermediate is of Formula II
wherein
P4, P5, and P6 are each independently H, methyl, benzyl, 4-methoxybenzyl, or tert-butyl;
W2 is —C(O)— or —(CH2—NH—C(O)—;
one of R4, R5, and R6 is
and the remaining two of R4, R5, and R6 are each H;
X2 is absent, 0, S, or NH;
r is 0, 1, 2, or 3;
s is 1 or 2; and
t is 0, 1, 2, or 3, provided that when t is 0 then X2 is absent.

### Claim 5 (depends on 3)

A composition comprising a compound of claim 3 and a pharmaceutically acceptable carrier.

### Claim 6 (depends on 3)

A pharmaceutical composition for detecting mammalian tissue overexpressing prostate specific membrane antigen (“PSMA”), the composition comprising an effective amount of the compound of claim 3 and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 6)

The pharmaceutical composition of claim 6, wherein the mammalian tissue comprises one or more of glioma, cervical carcinoma, vulvar carcinoma, endometrial carcinoma, primary ovarian carcinoma, metastatic ovarian carcinoma, non-small cell lung cancer, small cell lung cancer, bladder cancer, colon cancer, primary, gastric adenocarcinoma, primary colorectal adenocarcinoma, renal cell carcinoma, and prostate cancer.

### Claim 8 (depends on 3)

A method comprising
administering a compound of claim 3 to a subject; and
subsequent to the administering, detecting one or more of positron emission, gamma rays from positron emission and annihilation, and Cerenkov radiation due to positron emission.

### Claim 9 (depends on 8)

The method of claim 8, wherein the method comprises administering an effective amount of the compound to the subject.

### Claim 10 (depends on 8)

The method of claim 8, wherein the subject is suspected of suffering from a mammalian tissue overexpressing prostate specific membrane antigen (“PSMA”).

### Claim 11 (depends on 10)

The method of claim 10, wherein the mammalian tissue comprises one or more of glioma, cervical carcinoma, vulvar carcinoma, endometrial carcinoma, primary ovarian carcinoma, metastatic ovarian carcinoma, non-small cell lung cancer, small cell lung cancer, bladder cancer, colon cancer, primary, gastric adenocarcinoma, primary colorectal adenocarcinoma, renal cell carcinoma, and prostate cancer.

### Claim 12 (depends on 8)

The method of claim 8, wherein the administering the compound comprises parenteral administration.

### Claim 13

A compound of Formula IV
wherein
P7, P8, and P9 are each independently H, methyl, benzyl, 4-methoxybenzyl, or tert-butyl;
w is 1 or 2;
x is 0, 1, 2, or 3; and
y is 1 or 2.

### Claim at position 14

-15. (canceled)

### Claim 16 (depends on 13)

An intermediate for preparing a compound of claim 13, wherein the intermediate is of Formula V
wherein
P10, P11, and P12 are each independently H, methyl, benzyl, 4-methoxybenzyl, or tert-butyl;
b is 1 or 2; and
d is 0, 1, 2, or 3.

### Claim 17 (depends on 15)

A composition comprising a compound of claim 15 and a pharmaceutically acceptable carrier.

### Claim 18 (depends on 15)

A pharmaceutical composition for detecting a mammalian tissue overexpressing prostate specific membrane antigen (“PSMA”), the composition comprising an effective amount of the compound of claim 15 and a pharmaceutically acceptable excipient.

### Claim 19 (depends on 15)

A method comprising
administering a compound of claim 15 to a subject; and
subsequent to the administering, detecting one or more of positron emission, gamma rays from positron emission and annihilation, and Cerenkov radiation due to positron emission.

### Claim 20 (depends on 19)

The method of claim 19, wherein the method comprises administering an effective amount of the compound to the subject.

### Claim 21 (depends on 1)

The compound of claim 1, wherein the compound is
or a pharmaceutically acceptable salt thereof, or
or a pharmaceutically acceptable salt thereof.

### Claim 22 (depends on 4)

The intermediate of claim 4, wherein the intermediate is