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Title:
PROCESS FOR THE PREPARATION OF TREPROSTINIL AND DERIVATIVES THEREOF
Document Type and Number:
WIPO Patent Application WO/2013/174848
Kind Code:
A3
Abstract:
A method for the preparation of treprostinil and its derivatives is described. In contrast to prior art, this method utilizes an easily scalable enzymatic resolution of a key intermediate for making these compounds. Another significant improvement of the described method over prior methods is the regioselective Claisen rearrangement of a 5-allyloxy-benzaldehyde precursor, which is facilitated by a bromo substituent in 2-position.

Inventors:
JAIN, Nareshkumar F. (The Chemistry Research Solution LLC, 360 George Patterson Blvd.Suite 108, P, Bristol Pennsylvania, 19007, US)
KIRKUP, Michael P. (The Chemistry Research Solution LLC, 360 George Patterson Blvd.Suite 108, P, Bristol PA, 19007, US)
MARELLA, Michael A. (The Chemistry Research Solution LLC, 360 George Patterson Blvd.Suite 108, P, Bristol PA, 19007, US)
GHONE, Sanjeevani, A. (The Chemistry Research Solution LLC, 360 George Patterson Blvd.Suite 108, P, Bristol PA, 19007, US)
Application Number:
EP2013/060472
Publication Date:
June 26, 2014
Filing Date:
May 22, 2013
Export Citation:
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Assignee:
SCIPHARM SÀRL (26-28, rue Edward Steichen, Luxembourg, L-2540, LU)
International Classes:
C07C67/29; C07C47/565; C07C47/575; C07C51/377; C07C59/72; C07C69/18; C07F7/18; C12P41/00
Domestic Patent References:
WO2011153363A12011-12-08
WO2012009816A12012-01-26
Foreign References:
US6700025B22004-03-02
US20110118213A12011-05-19
US6242482B12001-06-05
Other References:
MORIARTY ROBERT M ET AL: "The Intramolecular Asymmetric Pauson-Khand Cyclization as a Novel and General Stereoselective route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil)", JOURNAL OF ORGANIC CHEMISTRY, ACS, US, vol. 69, no. 6, 1 January 2004 (2004-01-01), pages 1890 - 1902, XP002523983, ISSN: 0022-3263, [retrieved on 20040219], DOI: 10.1021/JO0347720
BRUCE ET AL: "Claisen rearrangement of meta-substituted allyl phenyl ethers", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 10, 1 January 1981 (1981-01-01), pages 2677 - 2679, XP002198137, ISSN: 0300-922X, DOI: 10.1039/P19810002677
Attorney, Agent or Firm:
GASSNER, Birgitta et al. (REDL Life Science Patent Attorneys, Donau-City-Straße 1, Vienna, A-1220, AT)
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