JP2005529938A5 - - Google Patents
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- Publication number
- JP2005529938A5 JP2005529938A5 JP2004510709A JP2004510709A JP2005529938A5 JP 2005529938 A5 JP2005529938 A5 JP 2005529938A5 JP 2004510709 A JP2004510709 A JP 2004510709A JP 2004510709 A JP2004510709 A JP 2004510709A JP 2005529938 A5 JP2005529938 A5 JP 2005529938A5
- Authority
- JP
- Japan
- Prior art keywords
- sesquiterpene
- composition
- free radical
- iron
- endoperoxide
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- 229930004725 sesquiterpene Natural products 0.000 claims 16
- -1 sesquiterpene alcohols Chemical class 0.000 claims 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 14
- 150000003254 radicals Chemical class 0.000 claims 13
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 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 claims 7
- 229960004191 artemisinin Drugs 0.000 claims 7
- 229930101531 artemisinin Natural products 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- 229910052742 iron Inorganic materials 0.000 claims 7
- 229960000981 artemether Drugs 0.000 claims 5
- SXYIRMFQILZOAM-HVNFFKDJSA-N dihydroartemisinin methyl ether Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OC)O[C@H]4[C@]32OO[C@@]1(C)O4 SXYIRMFQILZOAM-HVNFFKDJSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229960002521 artenimol Drugs 0.000 claims 4
- BJDCWCLMFKKGEE-ISOSDAIHSA-N artenimol Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-ISOSDAIHSA-N 0.000 claims 4
- 229930016266 dihydroartemisinin Natural products 0.000 claims 4
- 230000003834 intracellular effect Effects 0.000 claims 4
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 150000004354 sesquiterpene derivatives Chemical class 0.000 claims 3
- 229930009674 sesquiterpene lactone Natural products 0.000 claims 3
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 claims 3
- WNDUPUMWHYAJOR-SADXPQEKSA-K (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+) Chemical compound [Fe+3].OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WNDUPUMWHYAJOR-SADXPQEKSA-K 0.000 claims 2
- RLSFDUAUKXKPCZ-UITAMQMPSA-N (z)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one Chemical compound C1CN(C(=NN=2)C(F)(F)F)C=2CN1C(=O)\C=C(/N)CC1=CC(F)=C(F)C=C1F RLSFDUAUKXKPCZ-UITAMQMPSA-N 0.000 claims 2
- FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 claims 2
- 229920002307 Dextran Polymers 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000001888 Peptone Substances 0.000 claims 2
- 108010080698 Peptones Proteins 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- LRTRTVPZZJAADL-DAHZFVMQSA-N arteflene Chemical compound C(/[C@@]1(C)[C@@H]2C[C@H](OO1)[C@@H](C(C2)=O)C)=C/C1=CC=C(C(F)(F)F)C=C1C(F)(F)F LRTRTVPZZJAADL-DAHZFVMQSA-N 0.000 claims 2
- 229950010777 arteflene Drugs 0.000 claims 2
- 229960002970 artemotil Drugs 0.000 claims 2
- NLYNIRQVMRLPIQ-XQLAAWPRSA-N artemotil Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OCC)O[C@H]4[C@]32OO[C@@]1(C)O4 NLYNIRQVMRLPIQ-XQLAAWPRSA-N 0.000 claims 2
- FIHJKUPKCHIPAT-AHIGJZGOSA-N artesunate Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@@H](OC(=O)CCC(O)=O)[C@@H]4C FIHJKUPKCHIPAT-AHIGJZGOSA-N 0.000 claims 2
- 229960004991 artesunate Drugs 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 108010045676 holotransferrin Proteins 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- 229940074445 iron sorbitex Drugs 0.000 claims 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims 2
- 235000019319 peptone Nutrition 0.000 claims 2
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 claims 2
- XNSAINXGIQZQOO-SRVKXCTJSA-N protirelin Chemical compound NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-SRVKXCTJSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000003826 tablet Substances 0.000 claims 2
- ZITFTYGHYGPDAV-UHFFFAOYSA-L 2-aminoacetic acid;iron(2+);sulfate Chemical compound [H+].[Fe+2].NCC([O-])=O.[O-]S([O-])(=O)=O ZITFTYGHYGPDAV-UHFFFAOYSA-L 0.000 claims 1
- UQSASSBWRKBREL-UHFFFAOYSA-K 2-hydroxyethyl(trimethyl)azanium;iron(3+);2-oxidopropane-1,2,3-tricarboxylate;trihydrate Chemical group O.O.O.[Fe+3].C[N+](C)(C)CCO.[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O UQSASSBWRKBREL-UHFFFAOYSA-K 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 102000008857 Ferritin Human genes 0.000 claims 1
- 238000008416 Ferritin Methods 0.000 claims 1
- 108050000784 Ferritin Proteins 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 claims 1
- 230000002354 daily effect Effects 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 230000003203 everyday effect Effects 0.000 claims 1
- 229950003601 ferrocholinate Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38692802P | 2002-06-06 | 2002-06-06 | |
| PCT/US2003/017791 WO2003103588A2 (en) | 2002-06-06 | 2003-06-06 | Methods of using artemisinin-like compounds to prevent or delay the appearance of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529938A JP2005529938A (ja) | 2005-10-06 |
| JP2005529938A5 true JP2005529938A5 (https=) | 2006-06-22 |
Family
ID=29736235
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004510713A Expired - Fee Related JP4440768B2 (ja) | 2002-06-06 | 2003-06-06 | アルテミシニン関連エンドペルオキシダーゼと鉄保有タンパク質と間の共有結合コンジュゲート、および使用方法 |
| JP2004510709A Pending JP2005529938A (ja) | 2002-06-06 | 2003-06-06 | 癌の発症を予防または遅延するためのアルテミシニン様化合物を使用する方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004510713A Expired - Fee Related JP4440768B2 (ja) | 2002-06-06 | 2003-06-06 | アルテミシニン関連エンドペルオキシダーゼと鉄保有タンパク質と間の共有結合コンジュゲート、および使用方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20040058981A1 (https=) |
| EP (2) | EP1553935A4 (https=) |
| JP (2) | JP4440768B2 (https=) |
| CN (3) | CN1668293A (https=) |
| AU (2) | AU2003243418B2 (https=) |
| BR (2) | BR0312685A (https=) |
| CA (2) | CA2488347A1 (https=) |
| NZ (2) | NZ537114A (https=) |
| RU (2) | RU2004139090A (https=) |
| WO (1) | WO2003103588A2 (https=) |
| ZA (1) | ZA200500023B (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3257509A1 (en) * | 2003-02-12 | 2017-12-20 | Georgetown University | Use of artemisinin and related compounds for treating anorectal squamous cell cancer induced by human papilloma virus |
| US8394365B2 (en) | 2003-09-17 | 2013-03-12 | Nektar Therapeutics | Multi-arm polymer prodrugs |
| ES2629696T3 (es) * | 2003-09-17 | 2017-08-14 | Nektar Therapeutics | Profármacos poliméricos multibrazo |
| CN1255106C (zh) * | 2003-09-26 | 2006-05-10 | 李国桥 | 复方青蒿素 |
| US20050096369A1 (en) * | 2003-11-04 | 2005-05-05 | Hoang Ba X. | Compositions and methods for treating cellular proliferation disorders |
| EP1686982A4 (en) * | 2003-11-19 | 2007-03-21 | Vecta Ltd | METHODS AND COMPOSITIONS FOR THE TREATMENT OF DISEASES ASSOCIATED WITH HELICOBACTER PYLORI USING COMPOUNDS CONTAINING ENDOPEROXIDE BRIDGE |
| CN1311832C (zh) * | 2005-01-12 | 2007-04-25 | 四川科伦药业股份有限公司 | 溴代二氢青蒿素的医药用途 |
| US20060270863A1 (en) * | 2005-05-27 | 2006-11-30 | Amyris Biotechnologies | Conversion of amorpha-4,11-diene to artemisinin and artemisinin precursors |
| JP5119155B2 (ja) * | 2005-10-20 | 2013-01-16 | エピフアルマ・アクチエンゲゼルシヤフト | アルテミシニン及びその誘導体を使用する良性色素性ホクロ（母斑）の処置及び予防 |
| US7671067B2 (en) * | 2006-02-09 | 2010-03-02 | Enzon Pharmaceuticals, Inc. | Treatment of non-hodgkin's lymphomas with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamtothecin |
| US7462627B2 (en) * | 2006-02-09 | 2008-12-09 | Enzon Pharmaceuticals, Inc. | Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers |
| US20070231300A1 (en) * | 2006-03-28 | 2007-10-04 | Washington, University Of | Covalent conjugates between endoperoxides and transferrin and lactoferrin receptor-binding agents |
| WO2008046109A2 (en) * | 2006-10-13 | 2008-04-17 | University Of Washington | Conjugates of artemisinin-related endoperoxides and hydrazone derivatives for the treatment of cancer |
| CN101583380B (zh) | 2006-11-30 | 2013-07-10 | 尼克塔治疗公司 | 用于制备聚合物轭合物的方法 |
| WO2008098178A2 (en) * | 2007-02-09 | 2008-08-14 | Enzon Pharmaceuticals, Inc. | Treatment of resistant or refractory cancers with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
| CN106986926A (zh) * | 2008-01-30 | 2017-07-28 | 皮里斯股份公司 | 具有对人c‑met受体酪氨酸激酶的亲和性的泪脂质运载蛋白的突变蛋白及其获得方法 |
| CN101323569B (zh) * | 2008-07-24 | 2011-01-26 | 上海交通大学 | 倍半萜青蒿萜酯ae及其提取纯化方法 |
| KR101671537B1 (ko) | 2008-08-11 | 2016-11-01 | 넥타르 테라퓨틱스 | 다분지형 중합체 알카노에이트 컨쥬게이트 |
| TW201010732A (en) * | 2008-08-29 | 2010-03-16 | Enzon Pharmaceuticals Inc | Method of treating RAS associated cancer |
| HUE047352T2 (hu) | 2008-09-23 | 2020-04-28 | Nektar Therapeutics | Eljárás ütemezett beadásra kamptotecin elõgyógyszerekkel (például PEG-ironotekánnal) |
| CA2738807A1 (en) * | 2008-10-21 | 2010-04-29 | Enzon Pharmaceuticals, Inc. | Treatment of neuroblastoma with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
| GB2469791B (en) * | 2009-04-23 | 2011-12-14 | Londonpharma Ltd | Transmucosal formulation of compounds providing dihydroartemesinin for use in the treatment of neoplastic disease |
| NZ595469A (en) * | 2009-04-23 | 2013-10-25 | Londonpharma Ltd | Sublingual spray formulation comprising dihydroartemesinin |
| JP5624735B2 (ja) | 2009-07-22 | 2014-11-12 | 国立大学法人岡山大学 | フィルター |
| CN102399142B (zh) * | 2010-09-14 | 2014-09-24 | 华北制药集团新药研究开发有限责任公司 | 一类倍半萜酯化合物及其制备方法和用途 |
| WO2012088422A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of taxane-based compounds |
| US10894087B2 (en) | 2010-12-22 | 2021-01-19 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds |
| CN102727522B (zh) * | 2011-04-08 | 2013-09-25 | 石雁羽 | 由溴代双氢青蒿素和Fe2+剂组成的复方双释胶囊制剂 |
| CN103845360A (zh) * | 2012-11-29 | 2014-06-11 | 昆明制药集团股份有限公司 | 含蒿甲醚的药物组合物、制剂及其用途 |
| CN103405779B (zh) * | 2013-07-18 | 2015-09-30 | 江苏省血吸虫病防治研究所 | 一种预防血吸虫感染长效青蒿琥酯药物及其制备方法 |
| GB201800736D0 (en) * | 2018-01-17 | 2018-02-28 | St Georges Hospital Medical School | Combination therapy for treatment of leukemia |
| CN109908137B (zh) * | 2019-03-11 | 2022-02-18 | 江苏省人民医院（南京医科大学第一附属医院） | 青蒿素在杀伤乳腺癌干细胞的药物中的应用 |
| CN114983999A (zh) * | 2022-06-09 | 2022-09-02 | 四川大学 | 一种青蒿素及其衍生物的新用途、验证方法 |
Family Cites Families (16)
| 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 |
| FR2630329B1 (fr) * | 1988-04-20 | 1991-07-05 | Merieux Inst | Conjugues macromoleculaires d'hemoglobine, leur procede de preparation et leurs applications |
| RU2098407C1 (ru) * | 1989-09-27 | 1997-12-10 | Рон-Пуленк Рорер С.А. | Способ получения пероксиацетальлактонового соединения (варианты) и лактон |
| US5681811A (en) * | 1993-05-10 | 1997-10-28 | Protein Delivery, Inc. | Conjugation-stabilized therapeutic agent compositions, delivery and diagnostic formulations comprising same, and method of making and using the same |
| US5472684A (en) * | 1993-06-02 | 1995-12-05 | Colgate Palmolive Company | Oral compositions for plaque and gingivitis |
| 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 |
| US5869310A (en) * | 1996-06-03 | 1999-02-09 | Promega Corporation | Isolated agarase enzyme from flavobacterium sp. strain NR19, cloned genes therefor, and expression thereof in transformed host cells |
| US6160004A (en) * | 1997-12-30 | 2000-12-12 | Hauser, Inc. | C-10 carbon-substituted artemisinin-like trioxane compounds having antimalarial, antiproliferative and antitumor activities |
| CN1084333C (zh) * | 1998-06-17 | 2002-05-08 | 中国科学院上海药物研究所 | 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 |
| US6127405A (en) * | 1998-07-10 | 2000-10-03 | Council Of Scientific And Industrial Research | Method for the use of alpha arteether as an anti-bacterial and anti-fungal agent |
| US6297272B1 (en) * | 1999-01-12 | 2001-10-02 | Hauser, Inc. | Artemisinin analogs having antimalarial antiproliferative and antitumor activities and chemoselective methods of making the same |
| IN191696B (https=) * | 1999-02-12 | 2003-12-20 | Council Scient Ind Res | |
| GB9916012D0 (en) * | 1999-07-09 | 1999-09-08 | Ufc Limited | Peroxide-based antimalarial compounds |
| JP2002128784A (ja) * | 2000-10-25 | 2002-05-09 | Japan Science & Technology Corp | 細胞侵入型励起一重項酸素発生化合物および該化合物を含む薬剤類 |
| US7101842B2 (en) * | 2001-05-16 | 2006-09-05 | Faulk Pharmaceuticals, Inc. | Targeted delivery of drugs for the treatment of parasitic infections |
-
2003
- 2003-06-06 CN CNA038167972A patent/CN1668293A/zh active Pending
- 2003-06-06 CA CA002488347A patent/CA2488347A1/en not_active Abandoned
- 2003-06-06 RU RU2004139090/14A patent/RU2004139090A/ru unknown
- 2003-06-06 AU AU2003243418A patent/AU2003243418B2/en not_active Ceased
- 2003-06-06 RU RU2004139096/15A patent/RU2325156C2/ru not_active IP Right Cessation
- 2003-06-06 JP JP2004510713A patent/JP4440768B2/ja not_active Expired - Fee Related
- 2003-06-06 EP EP03757363A patent/EP1553935A4/en not_active Withdrawn
- 2003-06-06 CN CN201010165713A patent/CN101843904A/zh active Pending
- 2003-06-06 JP JP2004510709A patent/JP2005529938A/ja active Pending
- 2003-06-06 BR BR0312685-4A patent/BR0312685A/pt not_active IP Right Cessation
- 2003-06-06 NZ NZ537114A patent/NZ537114A/en not_active IP Right Cessation
- 2003-06-06 WO PCT/US2003/017791 patent/WO2003103588A2/en not_active Ceased
- 2003-06-06 CA CA002488360A patent/CA2488360A1/en not_active Abandoned
- 2003-06-06 EP EP03757380A patent/EP1531851B1/en not_active Expired - Lifetime
- 2003-06-06 CN CNB038167956A patent/CN1313145C/zh not_active Expired - Fee Related
- 2003-06-06 NZ NZ537113A patent/NZ537113A/en unknown
- 2003-06-06 AU AU2003251405A patent/AU2003251405A1/en not_active Abandoned
- 2003-06-06 BR BR0311627-1A patent/BR0311627A/pt not_active IP Right Cessation
- 2003-06-06 US US10/457,079 patent/US20040058981A1/en not_active Abandoned
-
2005
- 2005-01-03 ZA ZA200500023A patent/ZA200500023B/en unknown
-
2007
- 2007-11-30 US US11/948,560 patent/US20080119542A1/en not_active Abandoned
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