HRP20171139T1 - Postupak za proizvodnju intermedijera artemisinina - Google Patents
Postupak za proizvodnju intermedijera artemisinina Download PDFInfo
- Publication number
- HRP20171139T1 HRP20171139T1 HRP20171139TT HRP20171139T HRP20171139T1 HR P20171139 T1 HRP20171139 T1 HR P20171139T1 HR P20171139T T HRP20171139T T HR P20171139TT HR P20171139 T HRP20171139 T HR P20171139T HR P20171139 T1 HRP20171139 T1 HR P20171139T1
- Authority
- HR
- Croatia
- Prior art keywords
- diimine
- hydroxylamine
- image
- base
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 10
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 title claims 2
- 229960004191 artemisinin Drugs 0.000 title claims 2
- 229930101531 artemisinin Natural products 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 8
- 229910000071 diazene Inorganic materials 0.000 claims 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 4
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000005604 azodicarboxylate group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000006114 decarboxylation reaction Methods 0.000 claims 2
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Tropical Medicine & Parasitology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (10)
1. Postupak za pripremanje spoja formule I
[image]
u kojoj R1 je vodik ili ravni ili razgranati alkil s 1, 2, 3, 4, 5 ili 6 ugljikovih atoma ili cikloalkil s 3, 4, 5, 6 ili 7 ugljikovih atoma, koji sadrži reakciju spoja formule III
[image]
s diiminom, pri čemu se diimin tvori iz hidroksilamina i hidroksilamin O-sulfonske kiseline u prisutnosti baze, od hidroksilamin-O-sulfonske kiseline u prisutnosti baze, iz hidroksilamina i estera octene kiseline, iz hidrazina i vodikovog peroksida, ili iz kiselinom katalizirane dekarboksilacije azodikarboksilata,
naznačen time, da je diastereomerni omjer sirovih proizvoda diastereomera I prema diastereomeru IV
[image]
bolji od 90% prema 10%.
2. Postupak prema zahtjevu 1 naznačen time da je diastereomerni omjer do 99%:1%.
3. Postupak prema bilo kojem od zahtjeva 1 ili 2, naznačen time da je diastereomerna čistoća kristalizacijom proširena do 100%.
4. Postupak prema bilo kojem od zahtjeva 1 do 3 naznačen time da se diimin priprema in situ.
5. Postupak prema bilo kojem od zahtjeva 1 do 4 naznačen time da se diimin tvori iz hidroksilamina i hidroksilamin O-sulfonske kiseline u prisutnosti baze.
6. Postupak prema bilo kojem od zahtjeva 1 do 4 naznačen time da se diimin tvori iz hidroksilamin O-sulfonske kiseline u prisutnosti baze.
7. Postupak prema bilo kojem od zahtjeva 1 do 4 naznačen time da se diimin tvori iz hidroksilamina i estera octene kiseline.
8. Postupak prema bilo kojem od zahtjeva 1 do 4 naznačen time da se diimin tvori iz hidrazina i vodikovog peroksida.
9. Postupak prema bilo kojem od zahtjeva 1 do 4 naznačen time da se diimin tvori iz kiselinom katalizirane dekarboksilacije azodikarboksilata.
10. Postupak prema bilo kojem od zahtjeva 1 do 9, naznačen time da nadalje sadrži oksidaciju spoja formule I do artemisinina II
[image]
.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24174409P | 2009-09-11 | 2009-09-11 | |
| EP10782673.7A EP2475635B1 (en) | 2009-09-11 | 2010-09-10 | Process for the production of artemisinin intermediates |
| PCT/IB2010/002566 WO2011030223A2 (en) | 2009-09-11 | 2010-09-10 | Process for the production of artemisinin intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171139T1 true HRP20171139T1 (hr) | 2017-10-06 |
Family
ID=43567786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171139TT HRP20171139T1 (hr) | 2009-09-11 | 2017-07-24 | Postupak za proizvodnju intermedijera artemisinina |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8334392B2 (hr) |
| EP (1) | EP2475635B1 (hr) |
| JP (1) | JP5711745B2 (hr) |
| KR (1) | KR20120065395A (hr) |
| CN (1) | CN102612507B (hr) |
| AU (2) | AU2010293907B2 (hr) |
| BR (1) | BR112012005345A2 (hr) |
| CA (1) | CA2773007C (hr) |
| DK (1) | DK2475635T3 (hr) |
| EA (1) | EA021061B1 (hr) |
| ES (1) | ES2634940T3 (hr) |
| HR (1) | HRP20171139T1 (hr) |
| HU (1) | HUE035319T2 (hr) |
| IL (2) | IL218483A (hr) |
| LT (1) | LT2475635T (hr) |
| MX (1) | MX2012003001A (hr) |
| MY (1) | MY155952A (hr) |
| PT (1) | PT2475635T (hr) |
| SI (1) | SI2475635T1 (hr) |
| WO (1) | WO2011030223A2 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9150535B2 (en) | 2011-08-29 | 2015-10-06 | 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)
| 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 (hr) | 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 (hr) | 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 |
-
2010
- 2010-09-10 JP JP2012528468A patent/JP5711745B2/ja not_active Expired - Fee Related
- 2010-09-10 EP EP10782673.7A patent/EP2475635B1/en active Active
- 2010-09-10 CA CA2773007A patent/CA2773007C/en not_active Expired - Fee Related
- 2010-09-10 US US12/879,241 patent/US8334392B2/en not_active Expired - Fee Related
- 2010-09-10 ES ES10782673.7T patent/ES2634940T3/es active Active
- 2010-09-10 EA EA201270409A patent/EA021061B1/ru not_active IP Right Cessation
- 2010-09-10 LT LTEP10782673.7T patent/LT2475635T/lt unknown
- 2010-09-10 HU HUE10782673A patent/HUE035319T2/en unknown
- 2010-09-10 MY MYPI2012001020A patent/MY155952A/en unknown
- 2010-09-10 DK DK10782673.7T patent/DK2475635T3/en active
- 2010-09-10 WO PCT/IB2010/002566 patent/WO2011030223A2/en active Application Filing
- 2010-09-10 PT PT107826737T patent/PT2475635T/pt unknown
- 2010-09-10 BR BR112012005345A patent/BR112012005345A2/pt not_active IP Right Cessation
- 2010-09-10 KR KR1020127009209A patent/KR20120065395A/ko not_active Application Discontinuation
- 2010-09-10 CN CN201080051228.3A patent/CN102612507B/zh not_active Expired - Fee Related
- 2010-09-10 AU AU2010293907A patent/AU2010293907B2/en not_active Ceased
- 2010-09-10 MX MX2012003001A patent/MX2012003001A/es active IP Right Grant
- 2010-09-10 SI SI201031499T patent/SI2475635T1/sl unknown
-
2012
- 2012-03-05 IL IL218483A patent/IL218483A/en not_active IP Right Cessation
-
2016
- 2016-06-02 AU AU2016203676A patent/AU2016203676A1/en not_active Abandoned
- 2016-06-20 IL IL246336A patent/IL246336A0/en unknown
-
2017
- 2017-07-24 HR HRP20171139TT patent/HRP20171139T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2016203676A1 (en) | 2016-06-16 |
| LT2475635T (lt) | 2017-07-25 |
| JP5711745B2 (ja) | 2015-05-07 |
| IL218483A0 (en) | 2012-04-30 |
| AU2010293907B2 (en) | 2016-03-03 |
| WO2011030223A3 (en) | 2011-05-19 |
| EP2475635B1 (en) | 2017-04-26 |
| AU2010293907A1 (en) | 2012-04-26 |
| HUE035319T2 (en) | 2018-05-02 |
| CN102612507B (zh) | 2015-04-22 |
| US8334392B2 (en) | 2012-12-18 |
| ES2634940T3 (es) | 2017-09-29 |
| JP2013504557A (ja) | 2013-02-07 |
| WO2011030223A2 (en) | 2011-03-17 |
| US20110230669A1 (en) | 2011-09-22 |
| IL218483A (en) | 2016-07-31 |
| PT2475635T (pt) | 2017-07-10 |
| EA201270409A1 (ru) | 2012-12-28 |
| SI2475635T1 (sl) | 2017-08-31 |
| EP2475635A2 (en) | 2012-07-18 |
| DK2475635T3 (en) | 2017-07-03 |
| IL246336A0 (en) | 2016-08-31 |
| BR112012005345A2 (pt) | 2016-03-22 |
| CA2773007A1 (en) | 2011-03-17 |
| CA2773007C (en) | 2017-04-25 |
| MY155952A (en) | 2015-12-31 |
| MX2012003001A (es) | 2012-07-17 |
| CN102612507A (zh) | 2012-07-25 |
| EA021061B1 (ru) | 2015-03-31 |
| KR20120065395A (ko) | 2012-06-20 |
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