DK2475635T3 - Fremgangsmåde til fremstilling af artemisinin-mellemprodukter - Google Patents

Fremgangsmåde til fremstilling af artemisinin-mellemprodukter Download PDF

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Publication number
DK2475635T3
DK2475635T3 DK10782673.7T DK10782673T DK2475635T3 DK 2475635 T3 DK2475635 T3 DK 2475635T3 DK 10782673 T DK10782673 T DK 10782673T DK 2475635 T3 DK2475635 T3 DK 2475635T3
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DK
Denmark
Prior art keywords
acid
compound
diimine
hydroxylamine
formula
Prior art date
Application number
DK10782673.7T
Other languages
English (en)
Inventor
Volker Kraft
Gerhard Kretzschmar
Kai Rossen
Original Assignee
Huvepharma Italia S R L
Priority date (The priority date 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 date listed.)
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Publication date
Application filed by Huvepharma Italia S R L filed Critical Huvepharma Italia S R L
Application granted granted Critical
Publication of DK2475635T3 publication Critical patent/DK2475635T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes

Claims (10)

1. Fremgangsmåde til fremstilling af en forbindelse med formlen I
hvor R1 er hydrogen eller ligekædet eller forgrenet alkyl, der har 1,2, 3, 4, 5 eller 6 carbonatomer eller cycloalkyl, der har 3, 4, 5, 6 eller 7 carbonatomer, omfattende at reagere en forbindelse med formlen III
med diimin, hvor diiminen genereres ud fra hydroxylamin og hydroxylamin-O-sulfonsyre i nærvær af en base, ud fra hydroxylamin-O-sulfonsyre i nærvær af en base, ud fra hydroxylamin og en eddikesyreester, ud fra hydrazin og hydrogenperoxid, eller ud fra syrekatalyseret decarboxylering af azodicarbo-xylat, kendetegnet ved, at det diastereomere forhold mellem råprodukterne af dia-stereomer I og diastereomer IV
er bedre end 90 % til 10 %.
2. Fremgangsmåde ifølge krav 1, hvor det diastereomere forhold er op til 99 %:1 %.
3. Fremgangsmåde ifølge et af kravene 1 eller 2, hvor den diastereomere renhed er øget til 100 % ved krystallisation.
4. Fremgangsmåde ifølge et af kravene 1 til 3, hvor diiminen fremstilles in situ.
5. Fremgangsmåde ifølge et af kravene 1 til 4, hvor diiminen genereres ud fra hydroxylamin og hydroxylamin-O-sulfonsyre i nærvær af en base.
6. Fremgangsmåde ifølge et af kravene 1 til 4, hvor diiminen genereres ud fra hydroxylamin-O-sulfonsyre i nærvær af en base.
7. Fremgangsmåde ifølge et af kravene 1 til 4, hvor diiminen genereres ud fra hydroxylamin og en eddikesyreester.
8. Fremgangsmåde ifølge et af kravene 1 til 4, hvor diiminen genereres ud fra hydrazin og hydrogenperoxid.
9. Fremgangsmåde ifølge et af kravene 1 til 4, hvor diiminen genereres ud fra syrekatalyseret decarboxylering af azodicarboxylat.
10. Fremgangsmåde ifølge et af kravene 1 til 9, yderligere omfattende at oxidere forbindelsen med formlen I til artemisinin II
DK10782673.7T 2009-09-11 2010-09-10 Fremgangsmåde til fremstilling af artemisinin-mellemprodukter DK2475635T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US24174409P 2009-09-11 2009-09-11
PCT/IB2010/002566 WO2011030223A2 (en) 2009-09-11 2010-09-10 Process for the production of artemisinin intermediates

Publications (1)

Publication Number Publication Date
DK2475635T3 true DK2475635T3 (da) 2017-07-03

Family

ID=43567786

Family Applications (1)

Application Number Title Priority Date Filing Date
DK10782673.7T DK2475635T3 (da) 2009-09-11 2010-09-10 Fremgangsmåde til fremstilling af artemisinin-mellemprodukter

Country Status (20)

Country Link
US (1) US8334392B2 (da)
EP (1) EP2475635B1 (da)
JP (1) JP5711745B2 (da)
KR (1) KR20120065395A (da)
CN (1) CN102612507B (da)
AU (2) AU2010293907B2 (da)
BR (1) BR112012005345A2 (da)
CA (1) CA2773007C (da)
DK (1) DK2475635T3 (da)
EA (1) EA021061B1 (da)
ES (1) ES2634940T3 (da)
HR (1) HRP20171139T1 (da)
HU (1) HUE035319T2 (da)
IL (2) IL218483A (da)
LT (1) LT2475635T (da)
MX (1) MX2012003001A (da)
MY (1) MY155952A (da)
PT (1) PT2475635T (da)
SI (1) SI2475635T1 (da)
WO (1) WO2011030223A2 (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013030247A1 (en) 2011-08-29 2013-03-07 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Method and device for the synthesis of artemisinin
EP2565197A1 (en) 2011-08-29 2013-03-06 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Method and device for the synthesis of artemisinin
EP2660234A1 (en) * 2012-05-02 2013-11-06 Sanofi Process for the production of artemisinin intermediates
CN103087074A (zh) * 2012-12-14 2013-05-08 湖南科源生物制品有限公司 一种青蒿素的半合成方法
CN103755550B (zh) * 2013-11-28 2016-03-02 湖南科源生物制品有限公司 一种二氢青蒿酸的合成方法
CN112538010B (zh) * 2019-09-20 2023-08-11 凯特立斯（深圳）科技有限公司 一种青蒿素类化合物合成关键中间体的制备方法
DE102020120218A1 (de) 2020-07-31 2022-02-03 KBHB Consult GmbH Gegen das ribosomale Protein rpL35/uL29 gerichtete Moleküle zur Verwendung in der Behandlung von Erkrankungen, insbesondere Epidermolysis bullosa (EB)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4992561A (en) 1990-05-11 1991-02-12 The United States Of America As Represented By The Secretary Of The Army Simple conversion of artemisinic acid into artemisinin
IN184682B (da) 1995-12-29 2000-09-23 Council Scient Ind Res
JP3148136B2 (ja) 1996-12-26 2001-03-19 高砂香料工業株式会社 新規なキラルジホスフィン化合物、その製造中間体、該ジホス フィン化合物を配位子とする遷移金属錯体並びに該錯体を含む 不斉水素化触媒
US5995084A (en) * 1997-01-17 1999-11-30 Tritech Microelectronics, Ltd. Touchpad pen-input and mouse controller
IN188174B (da) 1997-03-17 2002-08-31 Council Scient Ind Res
JP3549390B2 (ja) 1998-03-23 2004-08-04 高砂香料工業株式会社 ルテニウム−ホスフィン錯体及びその製造方法
US20060270863A1 (en) 2005-05-27 2006-11-30 Amyris Biotechnologies Conversion of amorpha-4,11-diene to artemisinin and artemisinin precursors
CN1900081A (zh) * 2005-07-22 2007-01-24 中国科学院上海药物研究所 水溶性青蒿素衍生物、制法、药物组合物及用途
WO2009088404A1 (en) * 2007-12-30 2009-07-16 Amyris Biotechnologies, Inc. Processes for the preparation of artemisinin an its precursors

Also Published As

Publication number Publication date
EA201270409A1 (ru) 2012-12-28
AU2010293907A1 (en) 2012-04-26
CN102612507B (zh) 2015-04-22
MY155952A (en) 2015-12-31
KR20120065395A (ko) 2012-06-20
IL218483A0 (en) 2012-04-30
LT2475635T (lt) 2017-07-25
PT2475635T (pt) 2017-07-10
BR112012005345A2 (pt) 2016-03-22
SI2475635T1 (sl) 2017-08-31
JP2013504557A (ja) 2013-02-07
AU2016203676A1 (en) 2016-06-16
JP5711745B2 (ja) 2015-05-07
EP2475635A2 (en) 2012-07-18
EA021061B1 (ru) 2015-03-31
WO2011030223A3 (en) 2011-05-19
US8334392B2 (en) 2012-12-18
EP2475635B1 (en) 2017-04-26
CA2773007C (en) 2017-04-25
AU2010293907B2 (en) 2016-03-03
US20110230669A1 (en) 2011-09-22
HRP20171139T1 (hr) 2017-10-06
CN102612507A (zh) 2012-07-25
CA2773007A1 (en) 2011-03-17
WO2011030223A2 (en) 2011-03-17
HUE035319T2 (en) 2018-05-02
IL218483A (en) 2016-07-31
MX2012003001A (es) 2012-07-17
ES2634940T3 (es) 2017-09-29
IL246336A0 (en) 2016-08-31

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