JP6140266B2 - 不斉相間移動触媒としてのビス四級シンコナアルカロイド塩 - Google Patents
不斉相間移動触媒としてのビス四級シンコナアルカロイド塩 Download PDFInfo
- Publication number
- JP6140266B2 JP6140266B2 JP2015500539A JP2015500539A JP6140266B2 JP 6140266 B2 JP6140266 B2 JP 6140266B2 JP 2015500539 A JP2015500539 A JP 2015500539A JP 2015500539 A JP2015500539 A JP 2015500539A JP 6140266 B2 JP6140266 B2 JP 6140266B2
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- JP
- Japan
- Prior art keywords
- alkyl
- mmol
- bis
- nmr
- heteroaryl
- 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.)
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Classifications
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- 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
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- 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
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- 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
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- 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
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- 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)
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2015516945A JP2015516945A (ja) | 2015-06-18 |
| JP2015516945A5 JP2015516945A5 (enExample) | 2016-05-12 |
| JP6140266B2 true JP6140266B2 (ja) | 2017-05-31 |
Family
ID=49161748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015500539A Active JP6140266B2 (ja) | 2012-03-14 | 2013-03-13 | 不斉相間移動触媒としてのビス四級シンコナアルカロイド塩 |
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) |
Families Citing this family (14)
| 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 |
| 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)
| 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 |
-
2013
- 2013-03-13 BR BR112014021828A patent/BR112014021828B8/pt active IP Right Grant
- 2013-03-13 RU RU2014141166A patent/RU2667909C2/ru active
- 2013-03-13 JP JP2015500539A patent/JP6140266B2/ja active Active
- 2013-03-13 KR KR1020147025142A patent/KR102061180B1/ko active Active
- 2013-03-13 US US14/384,355 patent/US9376431B2/en active Active
- 2013-03-13 EP EP20154142.2A patent/EP3680240A1/en not_active Withdrawn
- 2013-03-13 AU AU2013232191A patent/AU2013232191B2/en active Active
- 2013-03-13 CN CN201380013400.XA patent/CN104144929B/zh active Active
- 2013-03-13 WO PCT/US2013/030688 patent/WO2013138413A1/en not_active Ceased
- 2013-03-13 KR KR1020197038179A patent/KR102153850B1/ko active Active
- 2013-03-13 EP EP21202495.4A patent/EP4019516A1/en not_active Withdrawn
- 2013-03-13 EP EP13761100.0A patent/EP2825536B1/en active Active
- 2013-03-13 EP EP23217661.0A patent/EP4357020A3/en active Pending
- 2013-03-13 MX MX2014010999A patent/MX351657B/es active IP Right Grant
- 2013-03-13 CA CA2865941A patent/CA2865941A1/en active Pending
- 2013-03-13 ES ES13761100T patent/ES2806150T3/es active Active
-
2017
- 2017-06-29 AU AU2017204464A patent/AU2017204464B2/en active Active
-
2019
- 2019-07-17 AU AU2019206049A patent/AU2019206049B2/en active Active
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2021
- 2021-07-01 AU AU2021204629A patent/AU2021204629A1/en not_active Abandoned
-
2023
- 2023-10-24 AU AU2023254886A patent/AU2023254886A1/en not_active Abandoned
-
2025
- 2025-08-25 AU AU2025220879A patent/AU2025220879A1/en active Pending
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