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The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 12790291 B1

PDFFull Text
Date of Patent:
Nov. 10, 2026

Filed:

Jul. 06, 2023

Industrial process for the preparation of 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 and high pure product

Applicant:

Nicox SA, Sophia Antipois-Balbonne, FR;

Inventors:

Szabolcs Kovács, Budapest, HU;

Andrea Sántáné Csutor, Budapest, HU;

Irén Hortobágyi, Budapest, HU;

Judit Póti, Gyömrő, HU;

Gael Ronsin, Strasbourg, FR;

Nicoletta Almirante, Milan, IT;

Assignee:

NICOX SA, Sophia Antipois-Valbonne, FR;

Attorney:

ArentFox Schiff LLP

Primary Examiner:

Kamal A Saeed

Int. Cl.
CPC ...
C07C 235/34 (2006.01); A61K 31/5575 (2006.01); C07C 231/12 (2006.01); C07C 231/24 (2006.01); C07C 405/00 (2006.01);
U.S. Cl.
CPC ...
C07C 235/34 (2013.01); A61K 31/5575 (2013.01); C07C 231/12 (2013.01); C07C 231/24 (2013.01); C07C 405/0041 (2013.01); C07C 2531/02 (2013.01); C07C 2601/08 (2017.05);
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 In accordance with the present invention, a pharmaceutical grade Compound (I) can be efficiently prepared by a one-pot reactions preparation step that includes the esterification of the 15-OH bimatoprost by coupling bimatoprost phenyl-boronate with 6-(nitrooxy)hexanoic acid and the removal of the boronate ester protecting group, followed by an efficient purification step. The invention refers also to high purity Compound (I) substantially free of the impurity 15-(6-chlorohexanoyl) ester of bimatoprost and to ophthalmic pharmaceutical formulations containing the high purity compound.

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Kovács, Szabolcs. (2026). Industrial process for the preparation of 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 and high pure product (U.S. Patent No. 12790291). U.S. Patent and Trademark Office. https://idiyas.com/patent/badge/12790291

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