# US 11,027,029 B2 · Peptide thiourea derivative, radioisotope labeled compound containing same, and pharmaceutical composition containing same as active ingredient for treating or diagnosing prostate cancer

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- Number: US 11,027,029 B2
- Document ID: US11027029B2
- Status: Granted
- Kind: B2
- Application number: 15/774,632
- Filed: 2016-11-09
- Published: 2018-11-29
- Granted: 2021-06-08
- Earliest claimed: 2015-11-09
- Assignees: Cellbion Co., Ltd.
- Applicants: Cellbion Co., Ltd
- Inventors: Jae Min Jeong; Sung-Hyun Moon; Yun-Sang Lee
- Web page: https://patentgrep.com/patent/US11027029B2

## CPC

- A61K 51/044: {having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins (rifampin A61K51/0459)}
- A61K 31/41: having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K 51/0402: {carboxylic acid carriers, fatty acids (amino acids A61K51/0406)}
- A61K 51/0482: {chelates from cyclic ligands, e.g. DOTA}
- A61K 51/0497: {conjugates with a carrier being an organic compounds}
- A61P 35/00: Antineoplastic agents
- C07D 255/02: not condensed with other rings
- C07D 257/02: not condensed with other rings
- C07F 5/003: {without C-Metal linkages}
- G01N 33/575: for cancer
- G01N 33/60: involving radioactive labelled substances
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

The present invention relates to a peptide thiourea derivative, a pharmaceutically acceptable salt thereof, a radioisotope labeled compound comprising the same, and a pharmaceutical composition for treating or diagnosing prostate cancer comprising the same as an active ingredient. The peptide thiourea derivative of the present invention is excellent in stability in human serum when it is administered in vivo and not only binds well to PSMA expressed in prostate cancer but also inhibits excellently PSMA at a low concentration. Besides, the derivative of the invention has a high water-solubility and can be excreted through the kidney not through the bile passage so that a clear image of the tumor region of prostate cancer can be obtained. Therefore, the derivative of the present invention can be effectively used as a pharmaceutical composition for treating and diagnosing prostate cancer.

## Claims

### Claim 1

A compound represented by formula 1 below or a pharmaceutically acceptable salt of the same:
wherein
X is single bond;
n is an integer of 3;
Y is —N(CH2COOH)(CH2)aCH2CH2—,
m is an integer of 1 or 2; and
a, b and c are independently an integer of 0 or 1.

### Claim 2 (depends on 1)

The compound or the pharmaceutically acceptable salt of the same according to claim 1, wherein X is single bond; and

### Claim 3 (depends on 1)

A preparation method of the compound represented by formula 1 of claim 1 comprising the step of preparing the compound represented by formula 1 by reacting the compound represented by formula 2 and the compound represented by formula 3 (step 1), as shown in reaction formula 1 below:

### Claim 4 (depends on 1)

A labeled compound prepared by coordinating a metallic radio-isotope to the compound represented by formula 1 of claim 1 or the pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 4)

The labeled compound according to claim 4, wherein the metallic radio-isotope is 67Ga, 68Ga, 62Cu, 64Cu, 67Cu, 111In, 90Y, 177Lu, or 117mSn.

### Claim 6 (depends on 4)

A pharmaceutical composition for treating or diagnosing prostate cancer comprising the labeled compound of claim 4 as an active ingredient.

### Claim 7 (depends on 1)

A radiopharmaceutical for imaging prostate cancer comprising the compound of claim 1 or the pharmaceutically acceptable salt thereof as an active ingredient.

### Claim 8 (depends on 1)

A kit for treating or diagnosing prostate cancer comprising the compound of claim 1 or the pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 8)

The kit for treating or diagnosing prostate cancer according to claim 8, wherein the kit contains a buffer having the pH of 1 to 9 and the concentration of 1 μM to 10 M.

### Claim 10 (depends on 9)

The kit for treating or diagnosing prostate cancer according to claim 9, wherein the buffer is acetic acid, phosphoric acid, citric acid, fumaric acid, ascorbic acid, butyric acid, succinic acid, tartaric acid, carbonic acid, glucoheptonic acid, gluconic acid, glucuronic acid, glucaric acid, boric acid or their sodium salts or potassium salts.

### Claim 11 (depends on 1)

A method of treating prostate cancer of a subject comprising administering an effective amount of the compound of claim 1 or the pharmaceutically acceptable salt thereof to the subject.

### Claim 12 (depends on 1)

A method of diagnosing prostate cancer of a subject comprising administering an effective amount of the compound of claim 1 or the pharmaceutically acceptable salt thereof to the subject and detecting any absorbed compound indicative of prostate cancer tissue in the subject.