JP2004535436A5 - - Google Patents
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- Publication number
- JP2004535436A5 JP2004535436A5 JP2003507080A JP2003507080A JP2004535436A5 JP 2004535436 A5 JP2004535436 A5 JP 2004535436A5 JP 2003507080 A JP2003507080 A JP 2003507080A JP 2003507080 A JP2003507080 A JP 2003507080A JP 2004535436 A5 JP2004535436 A5 JP 2004535436A5
- Authority
- JP
- Japan
- Prior art keywords
- trioxolane
- substituted
- spiro
- dispiro
- group
- 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.)
- Granted
Links
- 125000003003 spiro group Chemical group 0.000 claims 18
- RZYIPLSVRHWROD-UHFFFAOYSA-N 1,2,4-trioxolane Chemical compound C1OCOO1 RZYIPLSVRHWROD-UHFFFAOYSA-N 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 9
- 125000002723 alicyclic group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000004434 sulfur atom Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 201000004792 malaria Diseases 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 150000002596 lactones Chemical class 0.000 claims 3
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
- -1 N-substituted piperidyl Chemical group 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000002923 oximes Chemical class 0.000 claims 2
- 201000004409 schistosomiasis Diseases 0.000 claims 2
- 150000007659 semicarbazones Chemical class 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- 150000003457 sulfones Chemical class 0.000 claims 2
- MAAKQSASDHJHIR-UHFFFAOYSA-N trioxolane Chemical compound C1COOO1 MAAKQSASDHJHIR-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- VJMNBTXNKDIRQB-UHFFFAOYSA-N trioxole Chemical compound O1OC=CO1 VJMNBTXNKDIRQB-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/886,666 US6486199B1 (en) | 2001-06-21 | 2001-06-21 | Spiro and dispiro 1,2,4-trioxolane antimalarials |
| PCT/US2002/019767 WO2003000676A1 (en) | 2001-06-21 | 2002-06-21 | 1,2,4-trioxolane antimalarials |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004535436A JP2004535436A (ja) | 2004-11-25 |
| JP2004535436A5 true JP2004535436A5 (enExample) | 2005-09-29 |
| JP4303585B2 JP4303585B2 (ja) | 2009-07-29 |
Family
ID=25389491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003507080A Expired - Fee Related JP4303585B2 (ja) | 2001-06-21 | 2002-06-21 | １，２，４−トリオキソラン抗マラリア物質 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6486199B1 (enExample) |
| EP (1) | EP1414813B1 (enExample) |
| JP (1) | JP4303585B2 (enExample) |
| KR (1) | KR100759144B1 (enExample) |
| CN (1) | CN1545508B (enExample) |
| AT (1) | ATE339411T1 (enExample) |
| AU (1) | AU2002327183B2 (enExample) |
| BR (1) | BRPI0210549B8 (enExample) |
| CA (1) | CA2451006C (enExample) |
| CY (1) | CY1106214T1 (enExample) |
| DE (1) | DE60214733T8 (enExample) |
| DK (1) | DK1414813T3 (enExample) |
| ES (1) | ES2271323T3 (enExample) |
| HU (1) | HUP0400246A3 (enExample) |
| IL (1) | IL159474A0 (enExample) |
| MX (1) | MXPA03011915A (enExample) |
| NO (1) | NO20035721L (enExample) |
| PL (1) | PL226418B1 (enExample) |
| PT (1) | PT1414813E (enExample) |
| RU (1) | RU2271357C2 (enExample) |
| SI (1) | SI1414813T1 (enExample) |
| UA (1) | UA78709C2 (enExample) |
| WO (1) | WO2003000676A1 (enExample) |
| YU (1) | YU100703A (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE536887T1 (de) * | 2002-06-06 | 2011-12-15 | Univ Washington | Kovalente konjugate zwischen mit artemisinin verwandten endoperoxiden und eisentragenden proteinen und anwendungsverfahren |
| US20080125441A1 (en) * | 2002-06-21 | 2008-05-29 | Medicines For Malaria Venture Mmv | Spiro and dispiro 1,2,4-trioxolane antimalarials |
| US7371778B2 (en) * | 2002-06-21 | 2008-05-13 | Medicines For Malaria Venture Mmv | Spiro and dispiro 1,2,4-trioxolane antimalarials |
| US6906205B2 (en) * | 2002-06-21 | 2005-06-14 | Medicines For Malaria Venture Mmv | Spiro and dispiro 1,2,4-trioxolane antimalarials |
| US6825230B2 (en) * | 2002-06-21 | 2004-11-30 | Medicines For Malaria Venture Mmv | Spiro and dispiro 1,2,4-trixolane antimalarials |
| FR2862304A1 (fr) | 2003-11-14 | 2005-05-20 | Centre Nat Rech Scient | Molecules duales racemiques ou achirales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques |
| WO2006010362A1 (de) * | 2004-07-23 | 2006-02-02 | Justus-Liebig-Universität Giessen | Aminoadamantan-derivate, verfahren zu ihrer herstellung und ihre verwendung |
| US20060040761A1 (en) * | 2004-08-23 | 2006-02-23 | Sam-Kyu Shin | Scale mark mat for putting practice |
| US8067620B2 (en) * | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
| US20090042821A1 (en) | 2005-05-18 | 2009-02-12 | Arno Appavoo Enose | Stable dosage forms of spiro and dispiro 1,2,4-trioxolane antimalarials |
| WO2007036947A1 (en) * | 2005-09-30 | 2007-04-05 | Ipca Laboratories Limited | Delayed release anti-malarial composition |
| EP1934194B1 (en) | 2005-10-04 | 2010-04-14 | The Director General, Defence Research & Development Organisation | Anti-malarial compound isolated from gomphostemma niveum |
| US20070231300A1 (en) * | 2006-03-28 | 2007-10-04 | Washington, University Of | Covalent conjugates between endoperoxides and transferrin and lactoferrin receptor-binding agents |
| EP2007723A2 (en) | 2006-04-11 | 2008-12-31 | Novartis AG | Organic compounds |
| AP2525A (en) * | 2006-05-17 | 2012-12-05 | Ranbaxy Lab Ltd | Antimarial therapy using a combination of synthetic artemisinin derivative and bisquinoline derivative |
| WO2007138435A2 (en) * | 2006-05-24 | 2007-12-06 | Ranbaxy Laboratories Limited | A process for the preparation of dispiro 1,2,4-trioxolane antimalarials (oz277) |
| FR2902100A1 (fr) * | 2006-06-13 | 2007-12-14 | Sanofi Aventis Sa | Molecules duales contenant un derive peroxydique, leur synthese et leurs applications en therapeutique |
| GB0619333D0 (en) * | 2006-09-30 | 2006-11-08 | Univ Liverpool | Dispiro tetraoxane compounds |
| WO2008046109A2 (en) * | 2006-10-13 | 2008-04-17 | University Of Washington | Conjugates of artemisinin-related endoperoxides and hydrazone derivatives for the treatment of cancer |
| FR2924343A1 (fr) * | 2007-12-04 | 2009-06-05 | Palumed Sa | Nouvelles utilisations therapeutiques de molecules duales contenant un derive peroxydique. |
| JP5587776B2 (ja) | 2008-07-01 | 2014-09-10 | 国立大学法人 岡山大学 | 新規抗住血吸虫剤 |
| WO2010011684A2 (en) | 2008-07-21 | 2010-01-28 | The Regents Of The University Of California | Prodrug and fluoregenic compositions and methods for using the same |
| JP2014522856A (ja) | 2011-07-14 | 2014-09-08 | ランバクシー ラボラトリーズ リミテッド | アルテロランおよびピペラキンの安定した投与形態物 |
| WO2015123595A1 (en) | 2014-02-14 | 2015-08-20 | The Regents Of The University Of California | Cyclic peroxides as prodrugs for selective delivery of agents |
| AU2015370911B2 (en) | 2014-12-23 | 2020-07-09 | Bergenbio Asa | Inhibitors of Akt kinase |
| RU2601315C1 (ru) * | 2015-06-10 | 2016-11-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ получения пентаоксаспироалканов |
| WO2019005977A1 (en) * | 2017-06-27 | 2019-01-03 | The Regents Of The University Of California | Trioxolane agents |
| CN108424371B (zh) * | 2018-01-19 | 2021-07-16 | 北京理工大学 | 2-(4-氨基环己基)-乙酸乙酯的制备方法 |
| US20210386814A1 (en) * | 2020-05-20 | 2021-12-16 | Amanuel Tesfazion | Methods and compound for the treatment of malaria |
| JP7630193B2 (ja) * | 2021-02-01 | 2025-02-17 | 西湖大学 | １，２，４，５－テトラオキサン化合物の標的化送達及びその使用 |
| CN117085004A (zh) * | 2023-09-27 | 2023-11-21 | 赣南师范大学 | 一种2,6-二苯亚甲基环己酮类似物在制备抗血吸虫药物中的应用 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3621062A (en) | 1966-10-25 | 1971-11-16 | Sterling Drug Inc | 2-(8-cyclohexyloctanoyl or 7-cyclohexylheptanoyl)-1-naphthol |
| US3673222A (en) | 1969-11-26 | 1972-06-27 | Sydney Archer | 2-(8-cyclohexyloctyl or 7-cyclohexylheptyl)-1,4-naphthoquinone and process for preparation and use thereof |
| US3682991A (en) | 1970-10-19 | 1972-08-08 | Sterling Drug Inc | 3,3,5-trimethylcyclohexyl-alkyl-carboxylic acids |
| SU1421743A1 (ru) * | 1987-02-18 | 1988-09-07 | Физико-химический институт им.А.В.Богатского | Способ получени 11-нитро-12- @ (2-метокси)-этокси @ -бензо-9-краун-3 |
| US4916204A (en) | 1987-07-31 | 1990-04-10 | Massachusetts Institute Of Technology | Pure polyanhydride from dicarboxylic acid and coupling agent |
| US4816478A (en) | 1987-08-24 | 1989-03-28 | Thornfeldt Carl R | Treatment of acquired immunodeficiency syndrome |
| US5053342A (en) | 1987-12-24 | 1991-10-01 | Litmus Concepts, Inc. | Fecal occult blood test reagents |
| US5559145A (en) | 1988-06-01 | 1996-09-24 | Oxaco S.A. | 1,2,4-trioxane derivatives |
| US5270344A (en) | 1988-06-24 | 1993-12-14 | Stephen Herman | Method of treating a systemic disorder using trioxolane and diperoxide compounds |
| JP2867529B2 (ja) | 1990-01-22 | 1999-03-08 | 三菱電機株式会社 | 投写型表示装置 |
| US5216175A (en) | 1990-03-23 | 1993-06-01 | Sri International | Antimalarial analogs of artemisinin |
| US5219880A (en) | 1991-03-29 | 1993-06-15 | Dermatologic Research Corporation | Treatment of viral tumors and hemorrhoids with artemisinin and derivatives |
| DE4125201C1 (enExample) * | 1991-07-30 | 1992-10-01 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung Ev, 8000 Muenchen, De | |
| US5510356A (en) | 1991-10-03 | 1996-04-23 | University Of Nebraska Board Of Regents | Bisquinolines and processes for their production and use to treat malaria |
| US5171676A (en) | 1991-10-31 | 1992-12-15 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Method of introducing hydroxyl groups into artemisinin and its derivatives |
| US5430148A (en) | 1992-03-31 | 1995-07-04 | Agouron Pharmaceuticals, Inc. | Antiproliferative quinazolines |
| BR9306816A (pt) | 1992-07-28 | 1998-12-08 | Procter & Gamble | Composição farmaceutica para uso tópico contendo um polímero catiônico reticulado e um eter alcoxilado |
| US5721209A (en) | 1995-02-03 | 1998-02-24 | The Regents Of The University Of California | Iron chelator and inhibitor of iron-mediated oxidant injury |
| US5780675A (en) | 1995-04-28 | 1998-07-14 | The University Of New Mexico | Deoxygossylic compounds |
| US5578637A (en) | 1995-05-03 | 1996-11-26 | University Of Washington | Methods of inhibition or killing cancer cells using an endoperoxide |
| US5672624A (en) | 1995-11-22 | 1997-09-30 | The Johns Hopkins University | Endoperoxides useful as antiparasitic agents |
| US5817692A (en) | 1995-11-22 | 1998-10-06 | The Johns Hopkins University | Endoperoxides useful as antiparasitic agents |
| US5932591A (en) | 1996-12-02 | 1999-08-03 | Johns Hopkins University | C3 substituted trioxanes useful as antiparasitic drugs |
-
2001
- 2001-06-21 US US09/886,666 patent/US6486199B1/en not_active Expired - Lifetime
-
2002
- 2002-06-21 PL PL367158A patent/PL226418B1/pl unknown
- 2002-06-21 HU HU0400246A patent/HUP0400246A3/hu unknown
- 2002-06-21 AU AU2002327183A patent/AU2002327183B2/en not_active Expired
- 2002-06-21 RU RU2004101409/04A patent/RU2271357C2/ru active
- 2002-06-21 JP JP2003507080A patent/JP4303585B2/ja not_active Expired - Fee Related
- 2002-06-21 YU YU100703A patent/YU100703A/sh unknown
- 2002-06-21 MX MXPA03011915A patent/MXPA03011915A/es active IP Right Grant
- 2002-06-21 BR BR0210549-7 patent/BRPI0210549B8/pt not_active IP Right Cessation
- 2002-06-21 PT PT02763208T patent/PT1414813E/pt unknown
- 2002-06-21 WO PCT/US2002/019767 patent/WO2003000676A1/en not_active Ceased
- 2002-06-21 KR KR1020037016719A patent/KR100759144B1/ko not_active Expired - Lifetime
- 2002-06-21 SI SI200230411T patent/SI1414813T1/sl unknown
- 2002-06-21 ES ES02763208T patent/ES2271323T3/es not_active Expired - Lifetime
- 2002-06-21 DE DE60214733T patent/DE60214733T8/de active Active
- 2002-06-21 AT AT02763208T patent/ATE339411T1/de not_active IP Right Cessation
- 2002-06-21 CA CA2451006A patent/CA2451006C/en not_active Expired - Lifetime
- 2002-06-21 DK DK02763208T patent/DK1414813T3/da active
- 2002-06-21 EP EP02763208A patent/EP1414813B1/en not_active Expired - Lifetime
- 2002-06-21 IL IL15947402A patent/IL159474A0/xx active IP Right Grant
- 2002-06-21 UA UA2004010426A patent/UA78709C2/uk unknown
- 2002-06-21 CN CN028164539A patent/CN1545508B/zh not_active Expired - Lifetime
-
2003
- 2003-12-19 NO NO20035721A patent/NO20035721L/no not_active Application Discontinuation
-
2006
- 2006-10-23 CY CY20061101517T patent/CY1106214T1/el unknown
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