IP Library Granted Patent US 12697389
Granted Patent B2
US 12697389 · App. 17/612,145 · Granted Aug 4, 2026

Use of diketone compound in photodynamic therapy or diagnosis

Inventors: Ning Jiao (Beijing, CN); Jialiang Wei (Beijing, CN); Yameng Liu (Beijing, CN)
Assignee: BEIJING WHOLESOMETECH CO., LTD.
A61K41/0057A61K8/35A61K8/365A61K8/4926A61K8/4973A61K8/69A61K31/12A61K31/121A61K31/341A61K31/444A61P35/00A61Q17/005A61Q19/00A61Q19/08G01N33/574A61K2800/81
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Quick Facts
Patent No.
US 12697389
App. No.
17/612,145
Granted
Aug 4, 2026
Kind
B2
Abstract

The disclosure belongs to the technical field of medicine, and relates to use of a diketone compound in photodynamic therapy or diagnosis. Particularly, the disclosure relates to use of a compound of formula (I), pharmaceutically acceptable salt or ester, prodrug, stereoisomer, hydrate, solvate or crystal form of the compound, metabolite of each of them, or any combination or mixture thereof in preparation of a drug or a reagent. The drug or the reagent is used for photodynamic therapy or photodynamic diagnosis of a disease or is used for skin beauty by means of photodynamic therapy.

Claims (76)

1 . A photodynamic method of treating a disease in a subject suffering from the disease, the method comprising administering a compound of Formula (I):

a pharmaceutically acceptable salt or ester, a stereoisomer, or a crystal form, or any combination or mixture thereof; and irradiating the subject with a light after the administering;

wherein the disease is selected from breast cancer, cervical cancer, colon cancer, and skin cancer; and

wherein R 1 and R 2 of Formula (I) are each independently a linear or branched alkyl with 1 to 6 carbon atoms, a halogenated linear or branched alkyl with 1 to 6 carbon atoms, a hydroxyl group, or the following groups optionally substituted with one or more same or different substituents comprising aryl with 6 to 14 carbon atoms, 5- to 6-membered heteroaryl, 5- to 6-membered heterocyclyl, and 3- to 6-membered cycloalkyl, wherein the substituents are each independently selected from a hydroxyl group, a carboxyl group, a sulfonic group, a halogen atom, an amino group, a mercapto group, a nitro group, —C(O)O-(linear or branched alkyl with 1 to 4 carbon atoms), —S(O) 2 O-(linear or branched alkyl with 1 to 4 carbon atoms), or —O-(linear or branched alkyl with 1 to 4 carbon atoms); and

wherein the compound of Formula (I), a pharmaceutically acceptable salt or ester, a stereoisomer, or a crystal form, or any combination or mixture thereof is administered as the only active ingredient.

2 . The method according to claim 1 ,

wherein R 1 is selected from a linear or branched alkyl with 1 to 4 carbon atoms or an aryl with 6 to 14 carbon atoms; or

wherein R 2 is selected from a linear or branched alkyl with 1 to 4 carbon atoms, a halogenated linear or branched alkyl with 1 to 4 carbon atoms, or hydroxy.

3 . The method according to claim 1 , wherein the compound is characterized in that

(1) R 1 represents a linear or branched alkyl with 1 to 4 carbon atoms and R 2 represents a linear or branched alkyl with 1 to 4 carbon atoms;

(2) R 1 represents a linear or branched alkyl with 1 to 4 carbon atoms or a phenyl and R 2 represents a hydroxy;

(3) R 1 represents a linear or branched alkyl with 1 to 4 carbon atoms and R 2 represents a halogenated linear or branched alkyl with 1 to 4 carbon atoms;

(4) R 1 and R 2 each represent a phenyl, and the phenyl is optionally substituted with one or more substituents which are the same or different; or

(5) R 1 and R 2 are each independently a nitrogen-containing 5- to 6-membered heteroaryl, and the nitrogen-containing 5- to 6-membered heteroaryl is optionally substituted with one or more substituents which are the same or different.

4 . The method according to claim 1 , wherein the compound is selected from the following:

No.

Structural formula

BJMU-201

BJMU-202

BJMU-203

BJMU-204

BJMU-205

BJMU-206

BJMU-207

BJMU-208

BJMU-209

BJMU-210

BJMU-211

BJMU-212

BJMU-213

BJMU-214

.

5 . The method according to claim 1 , wherein the method is characterized by one or more of the following:

(1) the light being a single-wavelength light or a mixed light;

(2) at least part of the wavelength of the light being in a range of 10 nm to 1 mm;

(3) irradiating for 1 s to 12 h; or

(4) irradiating at a light density of 1 to 2000 mW/cm 2 .

6 . The photodynamic method of claim 1 , wherein the linear or branched alkyl with 1 to 6 carbon atoms is a linear or branched alkyl with 1 to 4 carbon atoms;

wherein the aryl with 6 to 14 carbon atoms is a phenyl or a naphthyl;

wherein the halogenated linear or branched alkyl with 1 to 6 carbon atoms is a fluoro-, chloro-, bromo- or iodo-linear or branched alkyl with 1 to 6 carbon atoms;

wherein the 5- to 6-membered heteroaryl contains 1 to 3 ring atoms selected from nitrogen, oxygen, and sulfur; or

wherein the 5- to 6-membered heterocyclyl contains 1 to 3 ring atoms selected from nitrogen, oxygen, and sulfur.

7 . The photodynamic method of claim 1 , wherein the linear or branched alkyl with 1 to 6 carbon atoms is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl.

8 . The photodynamic method according to claim 1 ,

wherein R 1 is methyl, ethyl or phenyl; or

wherein R 2 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, bromomethyl, bromoethyl, and hydroxy.

9 . The photodynamic method according to claim 1 , wherein the skin cancer is non-melanoma skin cancer or melanoma.

10 . The photodynamic method according to claim 9 , wherein the non-melanoma skin cancer is squamous cell carcinoma.

11 . A photodynamic method of treating a disease in a subject suffering from the disease, the method comprising administering a compound of Formula (I):

a pharmaceutically acceptable salt or ester, a stereoisomer, or a crystal form, or any combination or mixture thereof; and irradiating the subject with a light after the administering;

wherein the disease is related to a microorganism infection, and the microorganism is selected from human papilloma virus, Propionibacterium acnes and Escherichia coli ; and

wherein R 1 and R 2 of Formula (I) are each independently a linear or branched alkyl with 1 to 6 carbon atoms, a halogenated linear or branched alkyl with 1 to 6 carbon atoms, a hydroxyl group, or the following groups optionally substituted with one or more same or different substituents comprising aryl with 6 to 14 carbon atoms, 5- to 6-membered heteroaryl, 5- to 6-membered heterocyclyl, and 3- to 6-membered cycloalkyl, wherein the substituents are each independently selected from a hydroxyl group, a carboxyl group, a sulfonic group, a halogen atom, an amino group, a mercapto group, a nitro group, —C(O)O-(linear or branched alkyl with 1 to 4 carbon atoms), —S(O) 2 O-(linear or branched alkyl with 1 to 4 carbon atoms), or —O-(linear or branched alkyl with 1 to 4 carbon atoms); and

wherein the compound of Formula (I), a pharmaceutically acceptable salt or ester, a stereoisomer or a crystal form, or any combination or mixture thereof is administered as the only active ingredient.

12 . The method according to claim 11 , wherein the compound is selected from the following:

No.

Structural formula

BJMU-201

BJMU-202

BJMU-203

BJMU-204

BJMU-205

BJMU-206

BJMU-207

BJMU-208

BJMU-209

BJMU-210

BJMU-211

BJMU-212

BJMU-213

BJMU-214

.

13 . The method according to claim 11 , wherein the method is characterized by one or more of the following:

(1) the light being a single-wavelength light or a mixed light;

(2) at least part of the wavelength of the light being in a range of 10 nm to 1 mm;

(3) irradiating for 1 s to 12 h; or

(4) irradiating at a light density of 1 to 2000 mW/cm 2 .