WO2008100651A3 - Preparation of darifenacin and its salts - Google Patents

Preparation of darifenacin and its salts Download PDF

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Publication number
WO2008100651A3
WO2008100651A3 PCT/US2008/050388 US2008050388W WO2008100651A3 WO 2008100651 A3 WO2008100651 A3 WO 2008100651A3 US 2008050388 W US2008050388 W US 2008050388W WO 2008100651 A3 WO2008100651 A3 WO 2008100651A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
darifenacin
salts
reaction
salt
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2008/050388
Other languages
French (fr)
Other versions
WO2008100651A2 (en
Inventor
Srinivas Katkam
Pattabhiramayya Vaddadi
Vishnuvardhan Sunkara
Muralimohan Muttavarapu
Lalitha Dattatray Kulkarni
Rajeshwar Reddy Sagyam
Jaya Prakash Pitta
Ravinder Buchnikonda
Sridhar Munagala
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
Original Assignee
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
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 Dr Reddys Laboratories Ltd, Dr Reddys Laboratories Inc filed Critical Dr Reddys Laboratories Ltd
Priority to EP08772573A priority Critical patent/EP2109601A2/en
Publication of WO2008100651A2 publication Critical patent/WO2008100651A2/en
Publication of WO2008100651A3 publication Critical patent/WO2008100651A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Provided are various processes and compounds related to darifenacin and/or its salts. For example, there is provided a process for preparing a free base of darifenacin: Formula, or the salt thereof, the process including reacting 3-(S)-(cyanodiphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl) ethyl] pyrrolidine of the Formula (IV), or a salt thereof: Formula (IV) with a base effective to convert the nitrile group of the compound of the Formula (IV) to the amide group of the darifenacin in an organic solvent, the reaction being carried out in the organic solvent, with a proviso that the solvent is not 2-methyl-butan-2-ol, and with further proviso that the reaction produces less than about 0.5 % of the compound of the Formula (Ic): Formula (Ic) in the reaction mass, as measured by HPLC. Various embodiments and variants are provided.
PCT/US2008/050388 2007-01-05 2008-01-07 Preparation of darifenacin and its salts Ceased WO2008100651A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08772573A EP2109601A2 (en) 2007-01-05 2008-01-07 Preparation of darifenacin and its salts

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
IN34/CHE/2007 2007-01-05
IN34CH2007 2007-01-05
US89471107P 2007-03-14 2007-03-14
US60/894,711 2007-03-14
IN2060CH2007 2007-09-13
IN2060/CHE/2007 2007-09-13

Publications (2)

Publication Number Publication Date
WO2008100651A2 WO2008100651A2 (en) 2008-08-21
WO2008100651A3 true WO2008100651A3 (en) 2008-11-20

Family

ID=39277318

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/050388 Ceased WO2008100651A2 (en) 2007-01-05 2008-01-07 Preparation of darifenacin and its salts

Country Status (2)

Country Link
EP (1) EP2109601A2 (en)
WO (1) WO2008100651A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109641822B (en) * 2016-08-12 2022-03-11 拜耳作物科学股份公司 Process for preparing substituted styrene derivatives

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008126106A2 (en) * 2007-04-16 2008-10-23 Manne Satyanarayana Reddy Novel and improved processes for the preparation of intermediates of darifenacin, darifenacin and its pharmaceutically acceptable salts
US20100204296A1 (en) * 2007-06-08 2010-08-12 Actavis Group Ptc Ehf Novel Polymorphs of Darifenacin Free Base and its Hydrobromide Salt
WO2009010846A2 (en) * 2007-07-13 2009-01-22 Medichem, S.A. Amorphous form of darifenacin hydrobromide and processes for the preparation thereof
JP2012041277A (en) * 2010-08-13 2012-03-01 Kaneka Corp Improved method for producing 1, 3-disubstituted pyrrolidine compound or salt thereof
CN101973971A (en) * 2010-09-26 2011-02-16 山东邹平大展新材料有限公司 Method for preparing 5-halogenated ethyl-2,3-dihydrobenzofuran

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5096890A (en) * 1989-03-17 1992-03-17 Pfizer Inc. Pyrrolidine derivatives
WO2003080599A1 (en) * 2002-03-26 2003-10-02 Novartis International Pharmaceutical Ltd. Stable hydrate of a muscarinic receptor antagonist
WO2007076158A2 (en) * 2005-12-27 2007-07-05 Teva Pharmaceutical Industries Ltd. Processes for preparing darifenacin hydrobromide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5096890A (en) * 1989-03-17 1992-03-17 Pfizer Inc. Pyrrolidine derivatives
US5096890B1 (en) * 1989-03-17 1995-03-28 Pfizer Pyrrolidine derivatives
WO2003080599A1 (en) * 2002-03-26 2003-10-02 Novartis International Pharmaceutical Ltd. Stable hydrate of a muscarinic receptor antagonist
US6930188B2 (en) * 2002-03-26 2005-08-16 Novartis International Pharmaceutical, Ltd. Stable hydrate of a muscarinic receptor antagonist
WO2007076158A2 (en) * 2005-12-27 2007-07-05 Teva Pharmaceutical Industries Ltd. Processes for preparing darifenacin hydrobromide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109641822B (en) * 2016-08-12 2022-03-11 拜耳作物科学股份公司 Process for preparing substituted styrene derivatives

Also Published As

Publication number Publication date
EP2109601A2 (en) 2009-10-21
WO2008100651A2 (en) 2008-08-21

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