Method for preparing 18F-BPA and intermediate

Patent metadata

Field	Value
Publication number	US-11655261-B2
Application number	US-202117171224-A
Country	US
Kind code	B2
Filing date	Feb 9, 2021
Priority date	Aug 17, 2018
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

A method for preparing 18F-BPA and an intermediate, by which high-purity 18F-BPA is obtained. The method simplifies the synthesis steps after 18F labeling, and is easy to operate and efficient.

First claim

What is claimed is:

1. A method for preparing 18 F-BPA with the structure:

comprising
reacting intermediate I-2 with a 18 F ion to obtain a 18 F-substituted compound

and
deprotecting the 18 F-substituted compound to obtain the 18 F-BPA

wherein R 10 and R 20 are OH, or taken together with a boron atom to which they are attached, represent a substituent that is hydrolyzable to —B(OH) 2 group;
R 3 or R 4 independently represents hydrogen, an amino-protecting group, or an imino group combined with an amino group for protecting the amino group; and
R 5 represents hydrogen or a carboxyl-protecting group.

2. The method according to claim 1 , wherein the reaction of the intermediate I-2 with the 18 F ion further comprises using a copper catalyst.

3. The method according to claim 1 , wherein the reaction of the intermediate I-2 with the 18 F ion is carried out at a temperature of 20-150° C.

4. The method according to claim 1 , wherein the reaction of the intermediate I-2 with the 18 F ion is carried out in a solvent comprising water, methanol, DMF, DMA, DMSO, acetonitrile, n-butanol, ethanol, dichloromethane, or any mixed solvents thereof.

5. The method according to claim 1 , further comprising: using intermediate I-1 to react with boric acid or boric ester to obtain the intermediate I-2

where both of X 1 and X 2 are halogens.

6. The method according to claim 5 , wherein X 1 or X 2 independently represents Cl, Br, or I, X 1 and X 2 are the same.

7. The method according to claim 5 , further comprising: chirally resolving the intermediate I-1, and then reacting with boric acid or boric ester respectively.

8. The method according to claim 1 , wherein the intermediate I-2 is selected from

and

Assignees

• Neuboron Medtech Ltd

Inventors

• Li shi-hong
• He Jing
• Yan Heng
• Cai Fei

Classifications

• C07F5/025 Primary

  Boronic and borinic acid compounds · CPC title

• C07C249/02

  of compounds containing imino groups · CPC title

• C07C271/22

  to carbon atoms of hydrocarbon radicals substituted by carboxyl groups · CPC title

• C07C269/00

  Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups [IMAGE cpc-sch-C07C-0964.gif], the nitrogen atom not being part of nitro or nitroso groups · CPC title

• C07B59/004

  Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium · CPC title