WO2011146610A3 - An enantioselective synthesis of chiral amines for the production of rotigotine - Google Patents

An enantioselective synthesis of chiral amines for the production of rotigotine Download PDF

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Publication number
WO2011146610A3
WO2011146610A3 PCT/US2011/036990 US2011036990W WO2011146610A3 WO 2011146610 A3 WO2011146610 A3 WO 2011146610A3 US 2011036990 W US2011036990 W US 2011036990W WO 2011146610 A3 WO2011146610 A3 WO 2011146610A3
Authority
WO
WIPO (PCT)
Prior art keywords
rotigotine
production
enantioselective synthesis
chiral amines
chiral
Prior art date
Application number
PCT/US2011/036990
Other languages
French (fr)
Other versions
WO2011146610A2 (en
Inventor
Christopher James Cobley
Tamara Fanjul Solares
Original Assignee
Dr. Reddy's Laboratories Ltd.
Dr. Reddy's 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. Reddy's Laboratories Ltd., Dr. Reddy's Laboratories, Inc. filed Critical Dr. Reddy's Laboratories Ltd.
Publication of WO2011146610A2 publication Critical patent/WO2011146610A2/en
Publication of WO2011146610A3 publication Critical patent/WO2011146610A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Methods of preparing (S)-N-(1,2,3,4-tetrahydronaphthalen-2-yl)propion amide compounds 4 from N-(3,4-dihydronaphthalen-2-yl)propionamide compounds 3: where the constituent variables are as defined.
PCT/US2011/036990 2010-05-19 2011-05-18 An enantioselective synthesis of chiral amines for the production of rotigotine WO2011146610A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US34609610P 2010-05-19 2010-05-19
US61/346,096 2010-05-19

Publications (2)

Publication Number Publication Date
WO2011146610A2 WO2011146610A2 (en) 2011-11-24
WO2011146610A3 true WO2011146610A3 (en) 2012-03-15

Family

ID=44992315

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/036990 WO2011146610A2 (en) 2010-05-19 2011-05-18 An enantioselective synthesis of chiral amines for the production of rotigotine

Country Status (1)

Country Link
WO (1) WO2011146610A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10611749B2 (en) * 2018-02-15 2020-04-07 Solara Active Pharma Sciences Limited Process for preparation of Rotigotine and intermediates thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019338A1 (en) * 1993-02-26 1994-09-01 Zeneca Limited Chemical process
WO2003016264A1 (en) * 2001-08-17 2003-02-27 Chirotech Technology Limited Process for the preparation of enantiomerically enriched n-acyl-beta-amino acid derivatives by enantioselective hydrogenation of the corresponding (z)-enamides
WO2006136944A1 (en) * 2005-06-22 2006-12-28 Pfizer Products Inc. Stereoselective hydrogenation process for preparing cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-methoxy-5,6,7,8-tetrahydronaphthalene hydrochloride
US20070225290A1 (en) * 2006-03-15 2007-09-27 Markus Berger Tetrahydronaphthalene derivates, processes for preparing them and their use as antiinflammatory agents

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019338A1 (en) * 1993-02-26 1994-09-01 Zeneca Limited Chemical process
WO2003016264A1 (en) * 2001-08-17 2003-02-27 Chirotech Technology Limited Process for the preparation of enantiomerically enriched n-acyl-beta-amino acid derivatives by enantioselective hydrogenation of the corresponding (z)-enamides
WO2006136944A1 (en) * 2005-06-22 2006-12-28 Pfizer Products Inc. Stereoselective hydrogenation process for preparing cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-methoxy-5,6,7,8-tetrahydronaphthalene hydrochloride
US20070225290A1 (en) * 2006-03-15 2007-09-27 Markus Berger Tetrahydronaphthalene derivates, processes for preparing them and their use as antiinflammatory agents

Also Published As

Publication number Publication date
WO2011146610A2 (en) 2011-11-24

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