A process for the preparation of regadenoson

Patent metadata

Field	Value
Publication number	US-2016304551-A1
Application number	US-201315102505-A
Country	US
Kind code	A1
Filing date	Dec 10, 2013
Priority date	Dec 10, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

The present invention provides novel processes for the preparation of regadenoson having the formula (I). In some embodiments, the intermediates for the synthesis of regadenoson are also provided.

First claim

What is claimed is:

1 . A process for the preparation of regadenoson of formula I:

comprising:
(a) contacting a compound of formula II:

with a compound of formula IIa:

under conditions sufficient to form a compound of formula IV:

and (b) converting the compound of formula IV to the compound of formula I;
wherein
X is a leaving group;
R 2 and R 3 are independently-selected hydroxy protecting groups, or R 2 and R 3 are taken together to form a dihydroxy protecting group; and
R 4 is selected from the group consisting of hydrogen and a hydroxy protecting group.

2 . The process of claim 1 , wherein the leaving group is halogen.

3 . The process of claim 1 , wherein R 2 and R 3 are taken together to form ethane-1,1-diyl, propane-2,2-diyl, phenylmethanediyl, diphenylmethanediyl, tetramethylene or pentamethylene.

4 . The process of claim 3 , wherein R 2 and R 3 are taken together to form propane-2,2-diyl.

5 . The process of claim 1 , wherein the compound of formula II is:

6 . A process for the preparation of the compound of formula IIb

comprising:
contacting the compound of formula IIa

with acetone, 2,2-dimethoxypropane, 2-methoxypropene, or a combination thereof in the presence of an acid.

7 . The process of claim 6 , wherein the acid is HClO 4 , HCl, DL-10-camphorsulfonic acid or H 2 SO 4 .

8 . The process of claim 7 , wherein the acid is HClO 4 .

9 . The process of claim 1 , wherein formula IV is the compound of IVb:

Assignees

• Scinopharm Taiwan Ltd

Inventors

• Zhang Xiaoheng
• Mei Lijun

Classifications

• C07H19/167 Primary

  with ribosyl as the saccharide radical · CPC title

• C07H19/16 Primary

  Purine radicals · CPC title