公开(公告)号：US20240158345A1

公开(公告)日：2024-05-16

申请号：US18275579

申请日：2021-02-03

Applicant: Nicox S.A.

Inventor： Nicoletta ALMIRANTE ,  Gael RONSIN ,  Khalid DIKER ,  Gilles GORINS ,  Jonathan COUSIN ,  Audrey BRUNEAU

IPC: C07C405/00 ,  A61K31/5575 ,  C07C201/02

CPC classification number: C07C405/0041 ,  A61K31/5575 ,  C07C201/02 ,  C07C2601/08

Abstract: The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I).




In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group.
The invention also relates to a process for the preparation of 6-(nitrooxy) hexanoic acid having a HPLC purity equal to or greater than 99% and containing an amount of 6-{[6-(nitrooxy)hexanoyl]oxy}hexanoic acid (compound (IXa) equal to or lower than 0.2%.