ZA200007070B - Artemisinin derivatives, method for the preparation thereof and pharmaceutical compositions containing the same. - Google Patents
Artemisinin derivatives, method for the preparation thereof and pharmaceutical compositions containing the same. Download PDFInfo
- Publication number
- ZA200007070B ZA200007070B ZA200007070A ZA200007070A ZA200007070B ZA 200007070 B ZA200007070 B ZA 200007070B ZA 200007070 A ZA200007070 A ZA 200007070A ZA 200007070 A ZA200007070 A ZA 200007070A ZA 200007070 B ZA200007070 B ZA 200007070B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- compounds
- substituted
- defined hereinabove
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 3
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical class 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 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 34
- 239000002253 acid Substances 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 3
- OZHGNMKFSCKBBG-UHFFFAOYSA-N 4-[[(4-bromophenyl)-cyanomethyl]-methylamino]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)N(C)C(C#N)C1=CC=C(Br)C=C1 OZHGNMKFSCKBBG-UHFFFAOYSA-N 0.000 claims 3
- -1 HydroXypropyl Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004957 naphthylene group Chemical group 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 238000007171 acid catalysis Methods 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 108091028072 EteRNA Proteins 0.000 claims 1
- 101100365689 Homo sapiens SHC1 gene Proteins 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 102100022340 SHC-transforming protein 1 Human genes 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000006882 induction of apoptosis Effects 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 235000009973 maize Nutrition 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000005561 phenanthryl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000005760 substituted naphthylene group Chemical group 0.000 claims 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98114788A CN1084333C (zh) | 1998-06-17 | 1998-06-17 | 新的青蒿素化合物,其制备方法以及含有它们的药物组合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200007070B true ZA200007070B (en) | 2001-10-18 |
Family
ID=5224325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200007070A ZA200007070B (en) | 1998-06-17 | 2000-11-30 | Artemisinin derivatives, method for the preparation thereof and pharmaceutical compositions containing the same. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6307068B1 (zh) |
| EP (1) | EP1086107A1 (zh) |
| JP (1) | JP2002518398A (zh) |
| CN (2) | CN1084333C (zh) |
| AU (1) | AU748798B2 (zh) |
| BR (1) | BR9911274A (zh) |
| CA (1) | CA2342990A1 (zh) |
| HK (1) | HK1036985A1 (zh) |
| HU (1) | HUP0102599A3 (zh) |
| NO (1) | NO20006257L (zh) |
| NZ (1) | NZ508388A (zh) |
| PL (1) | PL344984A1 (zh) |
| WO (1) | WO1999065914A1 (zh) |
| ZA (1) | ZA200007070B (zh) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0129215D0 (en) * | 2001-12-06 | 2002-01-23 | Ufc Ltd | Trioxane derivatives |
| JP2005516909A (ja) * | 2001-12-06 | 2005-06-09 | ユーエフシー リミテッド | トリオキサン誘導体 |
| WO2003048167A1 (en) * | 2001-12-06 | 2003-06-12 | Ufc Limited | Trioxane derivatives |
| WO2003103592A2 (en) * | 2002-06-06 | 2003-12-18 | University Of Washington | Covalent conjugates between artemisinin-related endoperoxides and iron-carrying proteins and methods of use |
| US20040058981A1 (en) * | 2002-06-06 | 2004-03-25 | University Of Washington | Methods of using artemisinin-like compounds to prevent or delay the appearance of cancer |
| US6677463B1 (en) * | 2002-12-10 | 2004-01-13 | Council Of Scientific And Industrial Research | Single pot conversion of artemisinin to artesunic acid |
| CN1327842C (zh) * | 2003-02-12 | 2007-07-25 | 沈恒 | 一种新型的抗肿瘤药物复方制备方法 |
| EP1753419B1 (en) | 2004-06-21 | 2014-01-15 | University of Mississippi | Anticancer and antiprotozoal dihydroartemisinin and dihydroartemisitene dimers with desirable chemical functionalities |
| CN1814601A (zh) * | 2005-02-04 | 2006-08-09 | 中国科学院上海药物研究所 | 具有免疫抑制作用的青蒿素衍生物及药物组合物 |
| FR2899586B1 (fr) | 2006-04-11 | 2008-06-20 | Sanofi Aventis Sa | Dimeres de derives d'artemisinine, leur preparation et leur application en therapeutique |
| ITMI20071915A1 (it) * | 2007-10-04 | 2009-04-05 | Lachifarma Srl Lab Chimico Far | Derivati dell'artemisinina per il trattamento del melanoma |
| GB0720967D0 (en) * | 2007-10-25 | 2007-12-05 | Protophama Ltd | Anti-material pharmaceutical composition |
| GB2469791B (en) * | 2009-04-23 | 2011-12-14 | Londonpharma Ltd | Transmucosal formulation of compounds providing dihydroartemesinin for use in the treatment of neoplastic disease |
| US8815942B2 (en) | 2010-10-20 | 2014-08-26 | The Royal Institution For The Advancement Of Learning/Mcgill University | Combination therapy and uses thereof for treatment and prevention of parasitic infection and disease |
| CN103570738B (zh) * | 2012-08-07 | 2016-04-13 | 中国科学院上海生命科学研究院 | 新型青蒿素衍生物及其制法和应用 |
| EP3450549B1 (en) | 2012-10-29 | 2020-09-30 | University Of Rochester | Artemisinin derivatives, methods for their preparation and their use as antimalarial agents |
| CN117695222B (zh) * | 2024-02-06 | 2024-04-26 | 山东百奥生物医药有限公司 | 一种用于改善皮肤问题的青蒿素壬二酸酯-聚乙二醇二胺胶束及制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4916204A (en) * | 1987-07-31 | 1990-04-10 | Massachusetts Institute Of Technology | Pure polyanhydride from dicarboxylic acid and coupling agent |
| CN1049435A (zh) * | 1990-08-16 | 1991-02-20 | 中国对外贸易运输总公司 | 电传线路自动转换开关 |
| US5219880A (en) * | 1991-03-29 | 1993-06-15 | Dermatologic Research Corporation | Treatment of viral tumors and hemorrhoids with artemisinin and derivatives |
| CN1038416C (zh) * | 1992-12-04 | 1998-05-20 | 中国科学院上海药物研究所 | 新型青蒿素衍生物及其制备方法 |
| CN1049435C (zh) * | 1994-11-09 | 2000-02-16 | 中国科学院上海药物研究所 | 含苯基和杂环基的青蒿素衍生物及其制备方法 |
| US5578637A (en) * | 1995-05-03 | 1996-11-26 | University Of Washington | Methods of inhibition or killing cancer cells using an endoperoxide |
| US5677468A (en) | 1995-06-29 | 1997-10-14 | Hauser, Inc. | Artemisinin dimer compounds having anticancer activity |
-
1998
- 1998-06-17 CN CN98114788A patent/CN1084333C/zh not_active Expired - Fee Related
-
1999
- 1999-06-09 NZ NZ508388A patent/NZ508388A/en unknown
- 1999-06-09 CN CN99807416A patent/CN1111162C/zh not_active Expired - Fee Related
- 1999-06-09 US US09/719,767 patent/US6307068B1/en not_active Expired - Fee Related
- 1999-06-09 CA CA002342990A patent/CA2342990A1/fr not_active Abandoned
- 1999-06-09 JP JP2000554739A patent/JP2002518398A/ja active Pending
- 1999-06-09 HU HU0102599A patent/HUP0102599A3/hu unknown
- 1999-06-09 WO PCT/FR1999/001359 patent/WO1999065914A1/fr not_active Application Discontinuation
- 1999-06-09 AU AU40474/99A patent/AU748798B2/en not_active Ceased
- 1999-06-09 PL PL99344984A patent/PL344984A1/xx not_active Application Discontinuation
- 1999-06-09 BR BR9911274-4A patent/BR9911274A/pt not_active IP Right Cessation
- 1999-06-09 EP EP99923702A patent/EP1086107A1/fr not_active Withdrawn
-
2000
- 2000-11-30 ZA ZA200007070A patent/ZA200007070B/en unknown
- 2000-12-08 NO NO20006257A patent/NO20006257L/no not_active Application Discontinuation
-
2001
- 2001-11-12 HK HK01107929A patent/HK1036985A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20006257L (no) | 2001-02-19 |
| BR9911274A (pt) | 2001-10-23 |
| HUP0102599A3 (en) | 2003-03-28 |
| NO20006257D0 (no) | 2000-12-08 |
| CN1111162C (zh) | 2003-06-11 |
| JP2002518398A (ja) | 2002-06-25 |
| CN1305482A (zh) | 2001-07-25 |
| AU748798B2 (en) | 2002-06-13 |
| PL344984A1 (en) | 2001-11-19 |
| HUP0102599A2 (hu) | 2001-11-28 |
| WO1999065914A1 (fr) | 1999-12-23 |
| AU4047499A (en) | 2000-01-05 |
| HK1036985A1 (en) | 2002-01-25 |
| CN1239097A (zh) | 1999-12-22 |
| US6307068B1 (en) | 2001-10-23 |
| NZ508388A (en) | 2003-07-25 |
| CA2342990A1 (fr) | 1999-12-23 |
| EP1086107A1 (fr) | 2001-03-28 |
| CN1084333C (zh) | 2002-05-08 |
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