JPWO2021214278A5 - - Google Patents
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- JPWO2021214278A5 JPWO2021214278A5 JP2022564288A JP2022564288A JPWO2021214278A5 JP WO2021214278 A5 JPWO2021214278 A5 JP WO2021214278A5 JP 2022564288 A JP2022564288 A JP 2022564288A JP 2022564288 A JP2022564288 A JP 2022564288A JP WO2021214278 A5 JPWO2021214278 A5 JP WO2021214278A5
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- compound
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- saturated
- heterocyclic
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- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 2
- 229930194542 Keto Natural products 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Claims (1)
［式中、
Ｚ基は、単結合または二重結合を介して複素式環に結合し、－ＯＨおよび＝Ｏから選択され；
ｎは０又は１～４の整数であり；
Ｒ１及びＲ２は、互いに独立して、Ｈ又は１～６個の炭素原子を有する直鎖又は分枝状の飽和又は不飽和の炭化水素基を表し；
Ｒ３及びＲ４は、互いに独立して、Ｈ、１～６個の炭素原子を有する直鎖もしくは分枝状の飽和もしくは不飽和の炭化水素基を表し；又は、それらが結合している窒素原子と一緒に、飽和もしくは不飽和の、非芳香族もしくは芳香族の、１以上の環ヘテロ原子を有する４～７員環基を形成する］
以下の工程を含む方法：
１）一般式Ｉの非酸化の複素環式α－アミノアミド化合物：
［式中、Ｚ、ｎ及びＲ１～Ｒ４は、上記の定義と同じ意味を有する］
を、酸化触媒と接触させることによって、式Ｉの化合物中の複素環式α－アミノアミド基を酸化する、特に式Ｉの化合物のそのα－メチレン基において複素環式アミノ残基にケト基またはヒドロキシル基を導入する工程；又は、
上記で定義した式Ｉの化合物の電気化学的な（アノード）酸化を行う工程；
及び、
２）任意に、式ＩＩの化合物を単離する工程。 A process for preparing an oxidized heterocyclic α-amino amide compound of general formula II comprising:
[Wherein,
The Z group is attached to the heterocycle through a single or double bond and is selected from -OH and =O;
n is 0 or an integer from 1 to 4;
R 1 and R 2 , independently of each other, represent H or a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms;
R 3 and R 4 each independently represent H, a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms; or together with the nitrogen atom to which they are attached, form a saturated or unsaturated, non-aromatic or aromatic, 4- to 7-membered ring group having one or more ring heteroatoms.
A method comprising the steps of:
1) Non-oxidized heterocyclic α-aminoamide compounds of general formula I:
[wherein Z, n and R 1 to R 4 have the same meanings as defined above]
with an oxidation catalyst, thereby introducing a keto or hydroxyl group into the heterocyclic amino residue of the compound of formula I, particularly at its α-methylene group; or
carrying out the electrochemical (anodic) oxidation of a compound of formula I as defined above;
as well as,
2) optionally isolating the compound of formula II.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20171351 | 2020-04-24 | ||
| EP20171351.8 | 2020-04-24 | ||
| EP20172908.4 | 2020-05-05 | ||
| EP20172908 | 2020-05-05 | ||
| EP20199842.4 | 2020-10-02 | ||
| EP20199842 | 2020-10-02 | ||
| EP20213425.0 | 2020-12-11 | ||
| EP20213425 | 2020-12-11 | ||
| PCT/EP2021/060639 WO2021214278A2 (en) | 2020-04-24 | 2021-04-23 | Regioselective oxidation of heterocyclic alpha-amino amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2023523585A JP2023523585A (en) | 2023-06-06 |
| JPWO2021214278A5 true JPWO2021214278A5 (en) | 2024-05-02 |
Family
ID=75562771
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022564282A Pending JP2023522406A (en) | 2020-04-24 | 2021-04-23 | Enantioselective chemoenzymatic synthesis of optically active aminoamide compounds |
| JP2022564288A Pending JP2023523585A (en) | 2020-04-24 | 2021-04-23 | Regioselective oxidation of heterocyclic α-aminoamides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022564282A Pending JP2023522406A (en) | 2020-04-24 | 2021-04-23 | Enantioselective chemoenzymatic synthesis of optically active aminoamide compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20230183177A1 (en) |
| EP (2) | EP4139468A1 (en) |
| JP (2) | JP2023522406A (en) |
| KR (2) | KR20230005242A (en) |
| CN (2) | CN115956127A (en) |
| WO (2) | WO2021214283A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114717582B (en) * | 2022-04-08 | 2023-09-19 | 云南大学 | Method for preparing theophylline derivatives by green electrochemical coupling |
Family Cites Families (19)
| 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 (en) | 1999-07-09 | 2001-01-11 | Basf Ag | Immobilized lipase |
| NL1013348C2 (en) | 1999-10-20 | 2001-04-23 | Univ Eindhoven Tech | Periodate preparation by electrolytic oxidation of iodate, comprises use of lithium iodate as electrolyte and electrode comprising lead, lead alloy or electrically conducting diamond |
| DE10019373A1 (en) | 2000-04-18 | 2001-10-31 | Pfreundt Gmbh & Co Kg | Device for controling machine part has three accelerometers mounted on machine part so that they detect acceleration of machine part in three mutually perpendicular directions. |
| DE10019380A1 (en) | 2000-04-19 | 2001-10-25 | Basf Ag | Process for the production of covalently bound biologically active substances on polyurethane foams and use of the supported polyurethane foams for chiral syntheses |
| DE10258652A1 (en) | 2002-12-13 | 2004-06-24 | Degussa Ag | Electrolytic manufacture of inorganic peroxygen compound, e.g. perhalogen acids, involves anodically oxidizing inorganic halogen compound in aqueous solution using anode with doped diamond coating |
| 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 |
| EP1863761A1 (en) * | 2005-03-10 | 2007-12-12 | 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 |
| CN102260721A (en) * | 2010-05-31 | 2011-11-30 | 尚科生物医药（上海）有限公司 | Process for preparing (S)-2-aminobutanamide by using enzyme method |
| KR101698709B1 (en) * | 2011-06-07 | 2017-01-20 | 미쯔비시 레이온 가부시끼가이샤 | Improved nitrile hydratase |
| CN104450657B (en) * | 2014-11-06 | 2017-10-03 | 浙江大学 | Nitrile hydratase and its encoding gene and application |
| FR3053363B1 (en) * | 2016-06-30 | 2021-04-09 | Herakles | ELECTROLYTIC SYSTEM FOR THE SYNTHESIS OF SODIUM PERCHLORATE WITH ANODE WITH EXTERNAL SURFACE IN DIAMOND DOPED WITH BORON |
| CN106544336A (en) * | 2016-12-06 | 2017-03-29 | 江南大学 | A kind of nitrile hydratase improved by aliphatic dintrile regioselectivity |
| CN111757940B (en) * | 2017-11-14 | 2023-11-07 | 哥伦比亚有限公司 | Microbiological method for producing amides |
| CN108660131B (en) * | 2018-04-27 | 2020-07-21 | 浙江工业大学 | Preparation method of immobilized nitrile hydratase and (S) -N-ethylpyrrolidine-2-formamide |
-
2021
- 2021-04-23 CN CN202180044986.0A patent/CN115956127A/en active Pending
- 2021-04-23 JP JP2022564282A patent/JP2023522406A/en active Pending
- 2021-04-23 US US17/996,863 patent/US20230183177A1/en active Pending
- 2021-04-23 EP EP21719679.9A patent/EP4139468A1/en active Pending
- 2021-04-23 CN CN202180044663.1A patent/CN115916746A/en active Pending
- 2021-04-23 WO PCT/EP2021/060648 patent/WO2021214283A1/en unknown
- 2021-04-23 EP EP21720491.6A patent/EP4139283A2/en active Pending
- 2021-04-23 WO PCT/EP2021/060639 patent/WO2021214278A2/en active Search and Examination
- 2021-04-23 KR KR1020227040534A patent/KR20230005242A/en active Search and Examination
- 2021-04-23 US US17/996,844 patent/US20230159452A1/en active Pending
- 2021-04-23 KR KR1020227040535A patent/KR20230005243A/en active Search and Examination
- 2021-04-23 JP JP2022564288A patent/JP2023523585A/en active Pending
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