KR102061180B1 - 비대칭 상 이동 촉매로서의 비스-4급 신코나 알칼로이드 염 - Google Patents
비대칭 상 이동 촉매로서의 비스-4급 신코나 알칼로이드 염 Download PDFInfo
- Publication number
- KR102061180B1 KR102061180B1 KR1020147025142A KR20147025142A KR102061180B1 KR 102061180 B1 KR102061180 B1 KR 102061180B1 KR 1020147025142 A KR1020147025142 A KR 1020147025142A KR 20147025142 A KR20147025142 A KR 20147025142A KR 102061180 B1 KR102061180 B1 KR 102061180B1
- Authority
- KR
- South Korea
- Prior art keywords
- bis
- alkyl
- formula
- mmol
- phase transfer
- 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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- 0 CCC(C(CCCCCC1)=C1N1*)C1=O Chemical compound CCC(C(CCCCCC1)=C1N1*)C1=O 0.000 description 5
- XWNARNXISITYJG-UHFFFAOYSA-N CC(C)(C)N(C(F)(F)F)c1ncccc1 Chemical compound CC(C)(C)N(C(F)(F)F)c1ncccc1 XWNARNXISITYJG-UHFFFAOYSA-N 0.000 description 1
- RREAVDHSYGDVEE-SFHVURJKSA-N CC(C)(C)N(C([C@@]1(Cc2c3)Cc2ncc3Cl)=O)c2c1cccn2 Chemical compound CC(C)(C)N(C([C@@]1(Cc2c3)Cc2ncc3Cl)=O)c2c1cccn2 RREAVDHSYGDVEE-SFHVURJKSA-N 0.000 description 1
- FTSHSJVGEQJSDN-UHFFFAOYSA-N CC(C)(C)N1c2ncccc2C(Cc(c(CCl)c2)ncc2Cl)C1=O Chemical compound CC(C)(C)N1c2ncccc2C(Cc(c(CCl)c2)ncc2Cl)C1=O FTSHSJVGEQJSDN-UHFFFAOYSA-N 0.000 description 1
- UERXMTYSPMUSKT-UHFFFAOYSA-N CC(C)(C)N1c2ncccc2C(Cc2cc(C(F)(F)F)ccc2CO)C1=O Chemical compound CC(C)(C)N1c2ncccc2C(Cc2cc(C(F)(F)F)ccc2CO)C1=O UERXMTYSPMUSKT-UHFFFAOYSA-N 0.000 description 1
- YCMRNCFOTBJUGG-UHFFFAOYSA-N CC(C)(C)N1c2ncccc2CC1=O Chemical compound CC(C)(C)N1c2ncccc2CC1=O YCMRNCFOTBJUGG-UHFFFAOYSA-N 0.000 description 1
- IUUSRCAEQAUNMP-GUJJDVOOSA-N COc(cc1)cc(C[N](CC2)(C3[C@H](c4c(cc(cc5)OC)c5[n+](Cc(cc(cc5)OC)c5Br)cc4)O)C3(C3)C2[C@@H]3C=C)c1Br Chemical compound COc(cc1)cc(C[N](CC2)(C3[C@H](c4c(cc(cc5)OC)c5[n+](Cc(cc(cc5)OC)c5Br)cc4)O)C3(C3)C2[C@@H]3C=C)c1Br IUUSRCAEQAUNMP-GUJJDVOOSA-N 0.000 description 1
- PCMSIEWNWZBDPO-UHFFFAOYSA-N OCc1cc(Cl)cnc1Br Chemical compound OCc1cc(Cl)cnc1Br PCMSIEWNWZBDPO-UHFFFAOYSA-N 0.000 description 1
- NKWNLTSBVALPBR-UHFFFAOYSA-N OCc1ccc(C(F)(F)F)cc1Br Chemical compound OCc1ccc(C(F)(F)F)cc1Br NKWNLTSBVALPBR-UHFFFAOYSA-N 0.000 description 1
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
-
- 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)
- 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197038179A Division KR102153850B1 (ko) | 2012-03-14 | 2013-03-13 | 비대칭 상 이동 촉매로서의 비스-4급 신코나 알칼로이드 염 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140138704A KR20140138704A (ko) | 2014-12-04 |
| KR102061180B1 true KR102061180B1 (ko) | 2019-12-31 |
Family
ID=49161748
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197038179A Active KR102153850B1 (ko) | 2012-03-14 | 2013-03-13 | 비대칭 상 이동 촉매로서의 비스-4급 신코나 알칼로이드 염 |
| KR1020147025142A Active KR102061180B1 (ko) | 2012-03-14 | 2013-03-13 | 비대칭 상 이동 촉매로서의 비스-4급 신코나 알칼로이드 염 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197038179A Active KR102153850B1 (ko) | 2012-03-14 | 2013-03-13 | 비대칭 상 이동 촉매로서의 비스-4급 신코나 알칼로이드 염 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9376431B2 (enExample) |
| EP (4) | EP4019516A1 (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)
| 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 |
| RU2019123406A (ru) | 2014-02-05 | 2019-10-03 | Мерк Шарп И Доум Корп. | Технология приготовления таблеток для cgrp-активных соединений |
| US12168004B2 (en) | 2014-02-05 | 2024-12-17 | Merck Sharp & Dohme Llc | Treatment of migraine |
| BR112018074565B1 (pt) | 2016-06-07 | 2022-06-28 | Pirelli Tyre S.P.A. | Pneu para rodas de veículo |
| 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 |
| CA3181189A1 (en) * | 2020-05-06 | 2021-11-11 | Amgen Inc. | Synthesis of vinylic alcohol 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 |
|---|---|---|---|---|
| SG52631A1 (en) | 1990-01-22 | 1998-09-28 | Hoechst Roussel Pharma | Process for the enantioselection sznthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine |
| 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 |
| 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 |
-
2013
- 2013-03-13 MX MX2014010999A patent/MX351657B/es active IP Right Grant
- 2013-03-13 ES ES13761100T patent/ES2806150T3/es active Active
- 2013-03-13 EP EP21202495.4A patent/EP4019516A1/en not_active Withdrawn
- 2013-03-13 RU RU2014141166A patent/RU2667909C2/ru active
- 2013-03-13 KR KR1020197038179A patent/KR102153850B1/ko active Active
- 2013-03-13 CN CN201380013400.XA patent/CN104144929B/zh active Active
- 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 KR KR1020147025142A patent/KR102061180B1/ko active Active
- 2013-03-13 EP EP23217661.0A patent/EP4357020A3/en active Pending
- 2013-03-13 JP JP2015500539A patent/JP6140266B2/ja active Active
- 2013-03-13 EP EP13761100.0A patent/EP2825536B1/en active Active
- 2013-03-13 US US14/384,355 patent/US9376431B2/en active Active
- 2013-03-13 AU AU2013232191A patent/AU2013232191B2/en active Active
- 2013-03-13 WO PCT/US2013/030688 patent/WO2013138413A1/en not_active Ceased
-
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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