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WO2015084693A3 - New process for preparing loratadine from a ketone intermediate - Google Patents

New process for preparing loratadine from a ketone intermediate Download PDF

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Publication number
WO2015084693A3
WO2015084693A3 PCT/US2014/067846 US2014067846W WO2015084693A3 WO 2015084693 A3 WO2015084693 A3 WO 2015084693A3 US 2014067846 W US2014067846 W US 2014067846W WO 2015084693 A3 WO2015084693 A3 WO 2015084693A3
Authority
WO
WIPO (PCT)
Prior art keywords
loratadine
ketone intermediate
new process
active carbon
salt
Prior art date
Application number
PCT/US2014/067846
Other languages
French (fr)
Other versions
WO2015084693A2 (en
Inventor
Richard Desmond
Jungchul Kim
Robert A. Reamer
Jacob H. Waldman
Feng Xu
Original Assignee
Merck Sharp & Dohme Corp.
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 Merck Sharp & Dohme Corp. filed Critical Merck Sharp & Dohme Corp.
Publication of WO2015084693A2 publication Critical patent/WO2015084693A2/en
Publication of WO2015084693A3 publication Critical patent/WO2015084693A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing alicyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This application is directed to a last step synthetic process for making loratadine from ketone intermediate. Another embodiment of the present invention provides a loratadine recrystallization process comprising: adding HCI to a loratadine mixture in DMAc to form a solution of loratadine salt; optionally adding active carbon to the loratadine salt solution followed by filtration to remove any extraneous matters and/or active carbon; and adding an aqueous pH modifier to the filtered loratadine salt solution then seeding at a temperature of about 45°C to about 55°C to form crystalline loratadine.
PCT/US2014/067846 2013-12-05 2014-12-01 New process for preparing loratadine from a ketone intermediate WO2015084693A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361912133P 2013-12-05 2013-12-05
US61/912,133 2013-12-05

Publications (2)

Publication Number Publication Date
WO2015084693A2 WO2015084693A2 (en) 2015-06-11
WO2015084693A3 true WO2015084693A3 (en) 2015-10-22

Family

ID=53274263

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/067846 WO2015084693A2 (en) 2013-12-05 2014-12-01 New process for preparing loratadine from a ketone intermediate

Country Status (1)

Country Link
WO (1) WO2015084693A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016206028A1 (en) * 2015-06-24 2016-12-29 苏州大学张家港工业技术研究院 Cyclopropyl phosphate preparation method
CN106478595B (en) * 2016-09-18 2019-05-21 西安交通大学 Loratadine crystal form and its preparation method and application

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6271378B1 (en) * 1998-12-18 2001-08-07 Schering Corporation Process for preparing tricyclic compounds having antihistaminic activity
US20080194823A1 (en) * 2006-04-04 2008-08-14 Mayur Devjibhai Khunt Preparation of loratadine form i
US7449583B2 (en) * 2001-11-05 2008-11-11 Zach System S.P.A. Process for the preparation of 4-(8-chloro-5 6-dihydro-11h-benzo-(5 6)-cyclohepta-(1 2b)-pyridin-11-ylidene-1-piperidiniecarboxylic acid ethyl ester (loratadine)
CN102336739A (en) * 2011-07-15 2012-02-01 海南灵康制药有限公司 Loratadine compound and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6271378B1 (en) * 1998-12-18 2001-08-07 Schering Corporation Process for preparing tricyclic compounds having antihistaminic activity
US7449583B2 (en) * 2001-11-05 2008-11-11 Zach System S.P.A. Process for the preparation of 4-(8-chloro-5 6-dihydro-11h-benzo-(5 6)-cyclohepta-(1 2b)-pyridin-11-ylidene-1-piperidiniecarboxylic acid ethyl ester (loratadine)
US20080194823A1 (en) * 2006-04-04 2008-08-14 Mayur Devjibhai Khunt Preparation of loratadine form i
CN102336739A (en) * 2011-07-15 2012-02-01 海南灵康制药有限公司 Loratadine compound and preparation method thereof

Also Published As

Publication number Publication date
WO2015084693A2 (en) 2015-06-11

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