CA2865941A1 - Bis-quaternary cinchona alkaloid salts as asymmetric phase transfer catalysts - Google Patents

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

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Publication number
CA2865941A1
CA2865941A1 CA2865941A CA2865941A CA2865941A1 CA 2865941 A1 CA2865941 A1 CA 2865941A1 CA 2865941 A CA2865941 A CA 2865941A CA 2865941 A CA2865941 A CA 2865941A CA 2865941 A1 CA2865941 A1 CA 2865941A1
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CA
Canada
Prior art keywords
4alkyl
amino
halogen
heteroaryl
group
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.)
Pending
Application number
CA2865941A
Other languages
English (en)
French (fr)
Inventor
Bangping Xiang
Nobuyoshi Yasuda
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.)
Merck Sharp and Dohme LLC
Original Assignee
Merck Sharp and Dohme LLC
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 and Dohme LLC filed Critical Merck Sharp and Dohme LLC
Publication of CA2865941A1 publication Critical patent/CA2865941A1/en
Pending legal-status Critical Current

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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)
CA2865941A 2012-03-14 2013-03-13 Bis-quaternary cinchona alkaloid salts as asymmetric phase transfer catalysts Pending CA2865941A1 (en)

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

Publications (1)

Publication Number Publication Date
CA2865941A1 true CA2865941A1 (en) 2013-09-19

Family

ID=49161748

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2865941A Pending CA2865941A1 (en) 2012-03-14 2013-03-13 Bis-quaternary 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) KR102153850B1 (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)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US12168004B2 (en) 2014-02-05 2024-12-17 Merck Sharp & Dohme Llc Treatment of migraine
CN105960397B (zh) 2014-02-05 2020-09-04 默沙东公司 Cgrp-活性化合物的片剂制剂
US11717515B2 (en) 2020-12-22 2023-08-08 Allergan Pharmaceuticals International Limited Treatment of migraine
CN109195810B (zh) * 2016-06-07 2021-02-02 倍耐力轮胎股份公司 车轮用轮胎
MX391164B (es) 2017-05-30 2025-03-21 Dot Therapeutics 1 Inc Metodo para producir compuesto opticamente activo
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
MX2022013872A (es) * 2020-05-06 2022-11-30 Amgen Inc Sintesis de productos intermedios de alcohol vinilico.
CA3190176A1 (en) 2020-07-29 2022-02-03 Allergan Pharmaceuticals International Limited Treatment of migraine
WO2023049920A1 (en) 2021-09-27 2023-03-30 Allergan Pharmaceuticals International Limited Combination comprising atogepant for treating migraine
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0438796B1 (en) 1990-01-22 1998-08-26 HOECHST MARION ROUSSEL, Inc. Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine
ATE259807T1 (de) 1996-06-05 2004-03-15 Lindner Wolfgang Prof Dr Auf cinchonan basierte chirale selektoren zur trennung von stereoisomeren
US6596870B2 (en) 2000-07-13 2003-07-22 Brandeis University Asymmetric synthetic methods based on phase transfer catalysis
ATE520661T1 (de) * 2003-06-27 2011-09-15 Univ Maryland Heterocyclische verbindungen mit quaternärem stickstoff zum nachweis von wässrigen monosacchariden in physiologischen flüssigkeiten
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
AU2019206049B2 (en) 2021-04-01
RU2014141166A (ru) 2016-05-10
WO2013138413A1 (en) 2013-09-19
AU2023254886A1 (en) 2023-11-16
KR102061180B1 (ko) 2019-12-31
CN104144929A (zh) 2014-11-12
AU2013232191A1 (en) 2014-08-21
MX351657B (es) 2017-10-23
CN104144929B (zh) 2016-09-14
JP2015516945A (ja) 2015-06-18
RU2667909C2 (ru) 2018-09-25
AU2017204464A1 (en) 2017-07-20
BR112014021828B8 (pt) 2023-04-18
EP4019516A1 (en) 2022-06-29
EP2825536A4 (en) 2015-10-28
BR112014021828B1 (pt) 2019-04-24
AU2013232191B2 (en) 2017-03-30
EP2825536B1 (en) 2020-06-17
AU2019206049A1 (en) 2019-08-01
EP4357020A3 (en) 2024-06-26
KR20200003243A (ko) 2020-01-08
ES2806150T3 (es) 2021-02-16
JP6140266B2 (ja) 2017-05-31
EP2825536A1 (en) 2015-01-21
KR20140138704A (ko) 2014-12-04
AU2025220879A1 (en) 2025-09-11
KR102153850B1 (ko) 2020-09-08
US9376431B2 (en) 2016-06-28
AU2021204629A1 (en) 2021-07-29
EP3680240A1 (en) 2020-07-15
AU2017204464B2 (en) 2019-04-18
US20150031891A1 (en) 2015-01-29
EP4357020A2 (en) 2024-04-24
MX2014010999A (es) 2014-10-13

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