WO2014060575A3 - Process for the enantioselective synthesis of a tetrahydrobenzazepine compound - Google Patents

Process for the enantioselective synthesis of a tetrahydrobenzazepine compound Download PDF

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Publication number
WO2014060575A3
WO2014060575A3 PCT/EP2013/071832 EP2013071832W WO2014060575A3 WO 2014060575 A3 WO2014060575 A3 WO 2014060575A3 EP 2013071832 W EP2013071832 W EP 2013071832W WO 2014060575 A3 WO2014060575 A3 WO 2014060575A3
Authority
WO
WIPO (PCT)
Prior art keywords
tetrahydrobenzazepine
compound
enantioselective synthesis
enantioselective
synthesis
Prior art date
Application number
PCT/EP2013/071832
Other languages
French (fr)
Other versions
WO2014060575A2 (en
Inventor
Ernesto DURAN LÓPEZ
Original Assignee
Medichem S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Medichem S.A. filed Critical Medichem S.A.
Publication of WO2014060575A2 publication Critical patent/WO2014060575A2/en
Publication of WO2014060575A3 publication Critical patent/WO2014060575A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines

Abstract

This invention relates to an improved process for the enantioselective synthesis of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
PCT/EP2013/071832 2012-10-19 2013-10-18 Process for the enantioselective synthesis of a tetrahydrobenzazepine compound WO2014060575A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201261716081P 2012-10-19 2012-10-19
US61/716,081 2012-10-19
US201261721287P 2012-11-01 2012-11-01
US61/721,287 2012-11-01

Publications (2)

Publication Number Publication Date
WO2014060575A2 WO2014060575A2 (en) 2014-04-24
WO2014060575A3 true WO2014060575A3 (en) 2014-08-14

Family

ID=49385262

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/071832 WO2014060575A2 (en) 2012-10-19 2013-10-18 Process for the enantioselective synthesis of a tetrahydrobenzazepine compound

Country Status (1)

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WO (1) WO2014060575A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104730167B (en) * 2015-03-24 2016-09-07 南京昂谷医药科技有限公司 A kind of hydrochloric acid lorcaserin enantiomerism body detecting method and quality control standard thereof
CN106432080A (en) * 2016-05-24 2017-02-22 南京医科大学 Method for resolution of R/S-lorcaserin by high performance liquid chromatography method

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005003096A1 (en) * 2003-06-17 2005-01-13 Arena Pharmaceuticals, Inc. Benzazepine derivatives useful for the treatment of 5ht2c receptor associated diseases
US6953787B2 (en) * 2002-04-12 2005-10-11 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
WO2007149728A2 (en) * 2006-06-20 2007-12-27 Alcon Research, Ltd. Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma
US20080045502A1 (en) * 2003-06-17 2008-02-21 Arena Pharmaceuticals, Inc. Processes for Preparing 3-Benzazepines
WO2008080891A2 (en) * 2006-12-31 2008-07-10 Boehringer Ingelheim International Gmbh Process for the synthesis of derivatives of 3-amino-tetrahydrofuran-3-carboxylic acid and use thereof as medicaments
WO2009105206A1 (en) * 2008-02-19 2009-08-27 Arena Pharmaceuticals, Inc. Modulators of the histamine h3 receptor useful for the treatment of disorders related thereto

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6953787B2 (en) * 2002-04-12 2005-10-11 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
WO2005003096A1 (en) * 2003-06-17 2005-01-13 Arena Pharmaceuticals, Inc. Benzazepine derivatives useful for the treatment of 5ht2c receptor associated diseases
US20080045502A1 (en) * 2003-06-17 2008-02-21 Arena Pharmaceuticals, Inc. Processes for Preparing 3-Benzazepines
WO2007149728A2 (en) * 2006-06-20 2007-12-27 Alcon Research, Ltd. Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma
WO2008080891A2 (en) * 2006-12-31 2008-07-10 Boehringer Ingelheim International Gmbh Process for the synthesis of derivatives of 3-amino-tetrahydrofuran-3-carboxylic acid and use thereof as medicaments
WO2009105206A1 (en) * 2008-02-19 2009-08-27 Arena Pharmaceuticals, Inc. Modulators of the histamine h3 receptor useful for the treatment of disorders related thereto

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SMITH B M ET AL: "Discovery and SAR of new benzazepines as potent and selective 5-HT2C receptor agonists for the treatment of obesity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, GB, vol. 15, no. 5, 1 March 2005 (2005-03-01), pages 1467 - 1470, XP027801904, ISSN: 0960-894X, [retrieved on 20050301] *
SMITH BRIAN M ET AL: "Discovery and structure-activity relationship of (1R)-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (lorcaserin), a selective serotonin 5-HT2C receptor agonist for the treatment of obesity", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 51, no. 2, 1 January 2008 (2008-01-01), pages 305 - 313, XP009138515, ISSN: 0022-2623, [retrieved on 20071221], DOI: 10.1021/JM0709034 *

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