Benzene ring-containing glucose derivative and use thereof

Patent metadata

Field	Value
Publication number	US-11865194-B2
Application number	US-202318297575-A
Country	US
Kind code	B2
Filing date	Apr 7, 2023
Priority date	Oct 13, 2020
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

Disclosed herein is a benzene ring-containing glucose derivative of formula (I):

where R 1 is each independently

and R 2 is hydrogen. This application also provides a radioactive drug, including a complex formed by the benzene ring-containing glucose derivative and a radionuclide. Use of the benzene ring-containing glucose derivative in the tumor treatment and diagnosis is further provided.

First claim

What is claimed is:

1. A benzene ring-containing glucose derivative of formula (I):

wherein one or two R 1 are located on a benzene ring in formula (I);
the one or two R 1 are each independently

when there is one R 1 , R 1 is on 3-position or 4-position of the benzene ring in formula (I); when there are two R 1 , the two R 1 are on 3-position and 4-position of the benzene ring, respectively;
R 3 is hydrogen;
m is 0 or 1; and represents chemical bonding between R 1 and the benzene ring in formula (I);
R 2 is hydrogen;
n is 0, 1 or 2; and
when m=0 and n=1, R 1 is not on the 4-position of the benzene ring.

2. The benzene ring-containing glucose derivative of claim 1 , wherein the sum of m and n is 2.

3. The benzene ring-containing glucose derivative of claim 1 , wherein there is one R 1 , and the one R 1 is on the 3-position of the benzene ring.

4. A radioactive drug, comprising:
a complex formed by a benzene ring-containing glucose derivative and a radionuclide;
wherein:
the radionuclide is 99m Tc;
the benzene ring-containing glucose derivative is represented by formula (I):

and
the complex is represented by formula (II):

wherein in formula (I) and formula (II):
one or two R 1 are located on each of benzene rings;
the one or two R 1 are each independently

wherein when there is one R 1 , R 1 is on 3-position or 4-position of each of the benzene rings; when there are two R 1 , the two R 1 are on 3-position and 4-position of each of the benzene rings, respectively;
R 3 is hydrogen:
m is 0 or 1; and represents chemical bonding between R 1 and each of the benzene rings;

R 2 is hydrogen;
n is 0, 1 or 2; and
when m=0 and n=1, R 1 is not on the 4-position of each of the benzene rings.

5. A tumor imaging method, comprising:
administering the radioactive drug of claim 4 to a subject in need thereof; and
performing imaging of the subject by single photon emission computed tomography (SPECT).

Assignees

• Univ Beijing Normal

Inventors

• Zhang Junbo
• Gan Qianqian
• Wang Qianna
• Zhang Xuran
• Ruan Qing
• Jiang Yuhao
• Wang Xuebin
• Tang Zhigang
• Lu Jie
• Zhang Zhanbin

Classifications

• A61K51/025 Primary

  inorganic Tc complexes or compounds · CPC title

• C07H13/08 Primary

  having the esterifying carboxyl radicals directly attached to carbocyclic rings · CPC title

• A61K51/0491 Primary

  Sugars, nucleosides, nucleotides, oligonucleotides, nucleic acids, e.g. DNA, RNA, nucleic acid aptamers · CPC title

• C07H5/06

  Aminosugars · CPC title

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title