AU2013232191B2 - Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts - Google Patents

Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts Download PDF

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Publication number
AU2013232191B2
AU2013232191B2 AU2013232191A AU2013232191A AU2013232191B2 AU 2013232191 B2 AU2013232191 B2 AU 2013232191B2 AU 2013232191 A AU2013232191 A AU 2013232191A AU 2013232191 A AU2013232191 A AU 2013232191A AU 2013232191 B2 AU2013232191 B2 AU 2013232191B2
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Australia
Prior art keywords
bis
cinchona alkaloid
halogen
phase transfer
mmol
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AU2013232191A
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AU2013232191A1 (en
Inventor
Bangping Xiang
Nobuyoshi Yasuda
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Merck Sharp and Dohme LLC
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Merck Sharp and Dohme LLC
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Priority to AU2017204464A priority Critical patent/AU2017204464B2/en
Priority to AU2019206049A priority patent/AU2019206049B2/en
Priority to AU2021204629A priority patent/AU2021204629A1/en
Assigned to MERCK SHARP & DOHME LLC reassignment MERCK SHARP & DOHME LLC Request to Amend Deed and Register Assignors: MERCK SHARP & DOHME CORP.
Priority to AU2023254886A priority patent/AU2023254886A1/en
Priority to AU2025220879A priority patent/AU2025220879A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0204—Ethers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4272—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type via enolates or aza-analogues, added as such or made in-situ, e.g. ArY + R2C=C(OM)Z -> ArR2C-C(O)Z, in which R is H or alkyl, M is Na, K or SiMe3, Y is the leaving group, Z is Ar or OR' and R' is alkyl
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/98—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases
    • B01J2531/985—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases in a water / organic solvent system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
AU2013232191A 2012-03-14 2013-03-13 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts Active AU2013232191B2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2017204464A AU2017204464B2 (en) 2012-03-14 2017-06-29 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2019206049A AU2019206049B2 (en) 2012-03-14 2019-07-17 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2021204629A AU2021204629A1 (en) 2012-03-14 2021-07-01 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2023254886A AU2023254886A1 (en) 2012-03-14 2023-10-24 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2025220879A AU2025220879A1 (en) 2012-03-14 2025-08-25 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261610746P 2012-03-14 2012-03-14
US61/610,746 2012-03-14
PCT/US2013/030688 WO2013138413A1 (en) 2012-03-14 2013-03-13 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2017204464A Division AU2017204464B2 (en) 2012-03-14 2017-06-29 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts

Publications (2)

Publication Number Publication Date
AU2013232191A1 AU2013232191A1 (en) 2014-08-21
AU2013232191B2 true AU2013232191B2 (en) 2017-03-30

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Family Applications (6)

Application Number Title Priority Date Filing Date
AU2013232191A Active AU2013232191B2 (en) 2012-03-14 2013-03-13 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2017204464A Active AU2017204464B2 (en) 2012-03-14 2017-06-29 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2019206049A Active AU2019206049B2 (en) 2012-03-14 2019-07-17 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2021204629A Abandoned AU2021204629A1 (en) 2012-03-14 2021-07-01 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2023254886A Abandoned AU2023254886A1 (en) 2012-03-14 2023-10-24 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2025220879A Pending AU2025220879A1 (en) 2012-03-14 2025-08-25 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts

Family Applications After (5)

Application Number Title Priority Date Filing Date
AU2017204464A Active AU2017204464B2 (en) 2012-03-14 2017-06-29 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2019206049A Active AU2019206049B2 (en) 2012-03-14 2019-07-17 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2021204629A Abandoned AU2021204629A1 (en) 2012-03-14 2021-07-01 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2023254886A Abandoned AU2023254886A1 (en) 2012-03-14 2023-10-24 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts
AU2025220879A Pending AU2025220879A1 (en) 2012-03-14 2025-08-25 Bis-quarternary cinchona alkaloid salts as asymmetric phase transfer catalysts

Country Status (12)

Country Link
US (1) US9376431B2 (enExample)
EP (4) EP3680240A1 (enExample)
JP (1) JP6140266B2 (enExample)
KR (2) KR102061180B1 (enExample)
CN (1) CN104144929B (enExample)
AU (6) AU2013232191B2 (enExample)
BR (1) BR112014021828B8 (enExample)
CA (1) CA2865941A1 (enExample)
ES (1) ES2806150T3 (enExample)
MX (1) MX351657B (enExample)
RU (1) RU2667909C2 (enExample)
WO (1) WO2013138413A1 (enExample)

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TWI487706B (zh) * 2010-11-12 2015-06-11 Merck Sharp & Dohme 六氫吡啶酮甲醯胺氮雜茚滿ｃｇｒｐ受體拮抗劑
US9487523B2 (en) 2012-03-14 2016-11-08 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists
US9174989B2 (en) 2012-05-09 2015-11-03 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists
CA2937315A1 (en) 2014-02-05 2015-08-13 Merck Sharp & Dohme Corp. Tablet formulation for cgrp-active compounds
US12168004B2 (en) 2014-02-05 2024-12-17 Merck Sharp & Dohme Llc Treatment of migraine
MX384019B (es) * 2016-06-07 2025-03-14 Pirelli Neumatico para ruedas de vehiculos.
CA3065683A1 (en) 2017-05-30 2018-12-06 Millennium Pharmaceuticals, Inc. Method for producing optically active compound
US12383545B1 (en) 2018-06-08 2025-08-12 Allergan Pharmaceuticals International Limited Treatment of migraine
CN109180606B (zh) * 2018-09-30 2021-04-06 浙江工业大学 一类具有光学活性的β-氨基酮的合成方法
CA3181189A1 (en) * 2020-05-06 2021-11-11 Amgen Inc. Synthesis of vinylic alcohol intermediates
AU2021319090A1 (en) 2020-07-29 2023-03-02 Allergan Pharmaceuticals International Limited Treatment of migraine
AU2021409718A1 (en) 2020-12-22 2023-07-13 Allergan Pharmaceuticals International Limited Treatment of migraine
JP2024533756A (ja) 2021-09-27 2024-09-12 アラガン ファーマスーティカルズ インターナショナル リミテッド アトゲパントを含む片頭痛の併用療法
CN115974867B (zh) * 2023-01-31 2025-11-28 成都大学 一种手性相转移催化剂及其制备方法和应用

Family Cites Families (9)

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Publication number Priority date Publication date Assignee Title
ATE170173T1 (de) * 1990-01-22 1998-09-15 Hoechst Marion Roussel Inc Verfahren zur enantioselektiven synthese alkylierter oxindole zur verwendung als zwischenprodukte bei der herstellung von physostigminen
US6313247B1 (en) * 1996-06-05 2001-11-06 Wolfgang Lindner Cinchonan based chiral selectors for separation of stereoisomers
US6596870B2 (en) * 2000-07-13 2003-07-22 Brandeis University Asymmetric synthetic methods based on phase transfer catalysis
WO2005000109A2 (en) * 2003-06-27 2005-01-06 University Of Maryland Biotechnology Institute Quaternary nitrogen heterocyclic compounds for detecting aqueous monosaccharides in physiological fluids
GB0601286D0 (en) * 2006-01-23 2006-03-01 Sandoz Ag Asymmetric synthesis
PL213306B1 (pl) * 2008-02-04 2013-02-28 Politechnika Lodzka Sposób otrzymywania wzbogaconych enancjomerycznie produktów kondensacji z kwasów racemicznych lub kwasów o niskiej czystosci enancjomerycznej
WO2011005731A2 (en) * 2009-07-08 2011-01-13 Merck Sharp & Dohme Corp. Process for making cgrp receptor antagonist
US9487523B2 (en) 2012-03-14 2016-11-08 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists
US9174989B2 (en) 2012-05-09 2015-11-03 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists

Also Published As

Publication number Publication date
KR20140138704A (ko) 2014-12-04
AU2013232191A1 (en) 2014-08-21
MX2014010999A (es) 2014-10-13
EP3680240A1 (en) 2020-07-15
JP6140266B2 (ja) 2017-05-31
KR102153850B1 (ko) 2020-09-08
AU2025220879A1 (en) 2025-09-11
BR112014021828B8 (pt) 2023-04-18
CN104144929B (zh) 2016-09-14
EP2825536A1 (en) 2015-01-21
ES2806150T3 (es) 2021-02-16
US9376431B2 (en) 2016-06-28
AU2017204464B2 (en) 2019-04-18
EP2825536B1 (en) 2020-06-17
MX351657B (es) 2017-10-23
JP2015516945A (ja) 2015-06-18
AU2019206049B2 (en) 2021-04-01
CA2865941A1 (en) 2013-09-19
EP4357020A2 (en) 2024-04-24
KR20200003243A (ko) 2020-01-08
EP2825536A4 (en) 2015-10-28
WO2013138413A1 (en) 2013-09-19
AU2017204464A1 (en) 2017-07-20
RU2667909C2 (ru) 2018-09-25
AU2021204629A1 (en) 2021-07-29
KR102061180B1 (ko) 2019-12-31
BR112014021828B1 (pt) 2019-04-24
AU2019206049A1 (en) 2019-08-01
EP4357020A3 (en) 2024-06-26
CN104144929A (zh) 2014-11-12
AU2023254886A1 (en) 2023-11-16
EP4019516A1 (en) 2022-06-29
RU2014141166A (ru) 2016-05-10
US20150031891A1 (en) 2015-01-29

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Owner name: MERCK SHARP & DOHME LLC

Free format text: FORMER NAME(S): MERCK SHARP & DOHME CORP.