CA2865941A1 - Bis-quaternary cinchona alkaloid salts as asymmetric phase transfer catalysts - Google Patents
Bis-quaternary cinchona alkaloid salts as asymmetric phase transfer catalysts Download PDFInfo
- 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
- Authority
- 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
Links
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
-
- 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (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 (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 (https=) |
| EP (4) | EP4019516A1 (https=) |
| JP (1) | JP6140266B2 (https=) |
| KR (2) | KR102061180B1 (https=) |
| CN (1) | CN104144929B (https=) |
| AU (6) | AU2013232191B2 (https=) |
| BR (1) | BR112014021828B8 (https=) |
| CA (1) | CA2865941A1 (https=) |
| ES (1) | ES2806150T3 (https=) |
| MX (1) | MX351657B (https=) |
| RU (1) | RU2667909C2 (https=) |
| WO (1) | WO2013138413A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI501968B (zh) * | 2010-11-12 | 2015-10-01 | 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 |
| RU2019123406A (ru) | 2014-02-05 | 2019-10-03 | Мерк Шарп И Доум Корп. | Технология приготовления таблеток для cgrp-активных соединений |
| EP3463929B1 (en) | 2016-06-07 | 2020-05-13 | Pirelli Tyre S.p.A. | Tire for vehicle wheels |
| EP4406609A3 (en) | 2017-05-30 | 2024-10-02 | Day One Biopharmaceuticals, 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 |
| IL297522A (en) * | 2020-05-06 | 2022-12-01 | Amgen Inc | Synthesis of vinylic intermediates |
| CN116390712A (zh) | 2020-07-29 | 2023-07-04 | 阿勒根制药国际有限公司 | 治疗偏头痛 |
| CA3206184A1 (en) | 2020-12-22 | 2022-06-30 | Allergan Pharmaceuticals International Limited | Treatment of migraine |
| EP4408418A1 (en) | 2021-09-27 | 2024-08-07 | 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)
| 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 KR KR1020147025142A patent/KR102061180B1/ko active Active
- 2013-03-13 US US14/384,355 patent/US9376431B2/en active Active
- 2013-03-13 WO PCT/US2013/030688 patent/WO2013138413A1/en not_active Ceased
- 2013-03-13 JP JP2015500539A patent/JP6140266B2/ja active Active
- 2013-03-13 RU RU2014141166A patent/RU2667909C2/ru active
- 2013-03-13 EP EP21202495.4A patent/EP4019516A1/en not_active Withdrawn
- 2013-03-13 EP EP20154142.2A patent/EP3680240A1/en not_active Withdrawn
- 2013-03-13 BR BR112014021828A patent/BR112014021828B8/pt active IP Right Grant
- 2013-03-13 CA CA2865941A patent/CA2865941A1/en active Pending
- 2013-03-13 ES ES13761100T patent/ES2806150T3/es active Active
- 2013-03-13 EP EP13761100.0A patent/EP2825536B1/en active Active
- 2013-03-13 MX MX2014010999A patent/MX351657B/es active IP Right Grant
- 2013-03-13 KR KR1020197038179A patent/KR102153850B1/ko active Active
- 2013-03-13 AU AU2013232191A patent/AU2013232191B2/en active Active
- 2013-03-13 EP EP23217661.0A patent/EP4357020A3/en active Pending
- 2013-03-13 CN CN201380013400.XA patent/CN104144929B/zh active Active
-
2017
- 2017-06-29 AU AU2017204464A patent/AU2017204464B2/en active Active
-
2019
- 2019-07-17 AU AU2019206049A patent/AU2019206049B2/en active Active
-
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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180219 |
|
| MFA | Maintenance fee for application paid |
Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 12TH ANNIV.) - STANDARD Year of fee payment: 12 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20241221 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT Effective date: 20241221 Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL Effective date: 20241221 |
|
| MFA | Maintenance fee for application paid |
Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 13TH ANNIV.) - STANDARD Year of fee payment: 13 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20251217 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL Effective date: 20251217 |