KR20230005243A - 헤테로사이클릭 알파-아미노 아미드의 위치선택적 산화 - Google Patents

헤테로사이클릭 알파-아미노 아미드의 위치선택적 산화 Download PDF

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KR20230005243A
KR20230005243A KR1020227040535A KR20227040535A KR20230005243A KR 20230005243 A KR20230005243 A KR 20230005243A KR 1020227040535 A KR1020227040535 A KR 1020227040535A KR 20227040535 A KR20227040535 A KR 20227040535A KR 20230005243 A KR20230005243 A KR 20230005243A
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South Korea
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formula
oxidation
range
periodate
mixture
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Korean (ko)
Inventor
지그프리트 알. 발트보겔
세바스찬 아른트
도미닉 바이스
카이 돈스바흐
알렉산더 마티아스 나우스
틸 오파츠
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파마젤 게엠베하
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/462—Ruthenium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/01—Hydro-lyases (4.2.1)
    • C12Y402/01084—Nitrile hydratase (4.2.1.84)
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B1/00—Electrolytic production of inorganic compounds or non-metals
    • C25B1/01—Products
    • C25B1/24—Halogens or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
    • C25B11/042—Electrodes formed of a single material
    • C25B11/043—Carbon, e.g. diamond or graphene
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/05—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/09—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
    • C25B9/13—Single electrolytic cells with circulation of an electrolyte
    • C25B9/15—Flow-through cells
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
    • C25B9/17—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
    • C25B9/19—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof with diaphragms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Electrochemistry (AREA)
  • Metallurgy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Hydrogenated Pyridines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Electrodes For Compound Or Non-Metal Manufacture (AREA)
KR1020227040535A 2020-04-24 2021-04-23 헤테로사이클릭 알파-아미노 아미드의 위치선택적 산화 Pending KR20230005243A (ko)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
EP20171351.8 2020-04-24
EP20171351 2020-04-24
EP20172908 2020-05-05
EP20172908.4 2020-05-05
EP20199842.4 2020-10-02
EP20199842 2020-10-02
EP20213425 2020-12-11
EP20213425.0 2020-12-11
PCT/EP2021/060639 WO2021214278A2 (en) 2020-04-24 2021-04-23 Regioselective oxidation of heterocyclic alpha-amino amides

Publications (1)

Publication Number Publication Date
KR20230005243A true KR20230005243A (ko) 2023-01-09

Family

ID=75562771

Family Applications (2)

Application Number Title Priority Date Filing Date
KR1020227040535A Pending KR20230005243A (ko) 2020-04-24 2021-04-23 헤테로사이클릭 알파-아미노 아미드의 위치선택적 산화
KR1020227040534A Pending KR20230005242A (ko) 2020-04-24 2021-04-23 광학 활성 아미노 아미드 화합물의 거울상이성질선택적 화학-효소적 합성

Family Applications After (1)

Application Number Title Priority Date Filing Date
KR1020227040534A Pending KR20230005242A (ko) 2020-04-24 2021-04-23 광학 활성 아미노 아미드 화합물의 거울상이성질선택적 화학-효소적 합성

Country Status (6)

Country Link
US (2) US20230183177A1 (enExample)
EP (2) EP4139283A2 (enExample)
JP (2) JP2023523585A (enExample)
KR (2) KR20230005243A (enExample)
CN (2) CN115956127A (enExample)
WO (2) WO2021214278A2 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114717582B (zh) * 2022-04-08 2023-09-19 云南大学 一种绿色电化学偶联制备茶碱类衍生物的方法
WO2024153910A2 (en) * 2023-01-19 2024-07-25 Bae Systems Plc Flow synthesis
CN116920880B (zh) * 2023-07-12 2025-07-18 江南大学 具有手性光学活性的硫化铜钴纳米花的制备方法及其应用
CN117000435B (zh) * 2023-08-17 2025-11-04 中南大学 一种辉钼矿抑制剂及高滑石型钼矿的选矿方法
CN120119268B (zh) * 2025-03-06 2025-12-09 南开大学 手性1-四氢萘酰胺类化合物的合成方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830941A (en) 1958-04-15 mehltretter
US2989371A (en) 1958-08-01 1961-06-20 Charles L Mehltretter Process for separation of sodium metaperiodate from sodium sulfate
DE19931847A1 (de) 1999-07-09 2001-01-11 Basf Ag Immobilisierte Lipase
NL1013348C2 (nl) 1999-10-20 2001-04-23 Univ Eindhoven Tech Werkwijze voor het bereiden van perjodaat door oxidatie van jodaat in een elektrolysecel.
DE10019373A1 (de) 2000-04-18 2001-10-31 Pfreundt Gmbh & Co Kg Vorrichtung und Verfahren zur Steuerung eines Maschinenbauteils
DE10019380A1 (de) 2000-04-19 2001-10-25 Basf Ag Verfahren zur Herstellung von kovalent gebundenen biologisch aktiven Stoffen an Polyurethanschaumstoffen sowie Verwendung der geträgerten Polyurethanschaumstoffe für chirale Synthesen
DE10258652A1 (de) 2002-12-13 2004-06-24 Degussa Ag Verfahren zur elektrolytischen Herstellung von anorganischen Persauerstoffverbindungen
US20040225116A1 (en) * 2003-05-08 2004-11-11 Payne Mark S. Nucleic acid fragments encoding nitrile hydratase and amidase enzymes from comamonas testosteroni 5-MGAM-4D and recombinant organisms expressing those enzymes useful for the production of amides and acids
WO2006095362A1 (en) * 2005-03-10 2006-09-14 Rubamin Limited Process for preparing levetiracetam
EP1842907A1 (en) * 2006-04-07 2007-10-10 B.R.A.I.N. Ag A group of novel enantioselective microbial nitrile hydratases with broad substrate specificity
WO2008077035A2 (en) * 2006-12-18 2008-06-26 Dr. Reddy's Laboratories Ltd. Processes for the preparation of levetiracetam
WO2009009117A2 (en) 2007-07-11 2009-01-15 Bioverdant, Inc. Chemoenzymatic processes for preparation of levetiracetam
CN102036956A (zh) * 2008-03-21 2011-04-27 柯罗瑞恩制药有限公司 取代的吡咯烷和哌啶化合物、它们的衍生物、以及用于治疗疼痛的方法
CN102260721A (zh) * 2010-05-31 2011-11-30 尚科生物医药（上海）有限公司 一种用酶法制备（s）-2-氨基丁酰胺的方法
EP2719760B1 (en) * 2011-06-07 2016-06-29 Mitsubishi Rayon Co., Ltd. Improved nitrile hydratase
CN104450657B (zh) * 2014-11-06 2017-10-03 浙江大学 腈水合酶及其编码基因和应用
FR3053363B1 (fr) * 2016-06-30 2021-04-09 Herakles Systeme electrolytique pour la synthese du perchlorate de sodium avec anode a surface externe en diamant dope au bore
CN106544336A (zh) * 2016-12-06 2017-03-29 江南大学 一种对脂肪族二腈区域选择性提高的腈水合酶
US11261468B2 (en) * 2017-11-14 2022-03-01 Columbia Srl Microbiological process for the preparation of amides
CN108660131B (zh) * 2018-04-27 2020-07-21 浙江工业大学 固定化腈基水合酶和(s)-n-乙基吡咯烷-2-甲酰胺的制备方法

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Publication number Publication date
JP2023522406A (ja) 2023-05-30
WO2021214283A1 (en) 2021-10-28
EP4139283A2 (en) 2023-03-01
CN115956127A (zh) 2023-04-11
JP2023523585A (ja) 2023-06-06
EP4139468A1 (en) 2023-03-01
WO2021214278A3 (en) 2021-12-02
US20230183177A1 (en) 2023-06-15
CN115916746A (zh) 2023-04-04
WO2021214278A2 (en) 2021-10-28
KR20230005242A (ko) 2023-01-09
US20230159452A1 (en) 2023-05-25

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