JP2011502131A5 - - Google Patents
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- JP2011502131A5 JP2011502131A5 JP2010531331A JP2010531331A JP2011502131A5 JP 2011502131 A5 JP2011502131 A5 JP 2011502131A5 JP 2010531331 A JP2010531331 A JP 2010531331A JP 2010531331 A JP2010531331 A JP 2010531331A JP 2011502131 A5 JP2011502131 A5 JP 2011502131A5
- Authority
- JP
- Japan
- Prior art keywords
- trioxolane
- dispiro
- administered
- scheduled
- malaria
- 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.)
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- RZYIPLSVRHWROD-UHFFFAOYSA-N 1,2,4-trioxolane Chemical compound C1OCOO1 RZYIPLSVRHWROD-UHFFFAOYSA-N 0.000 claims 20
- MAAKQSASDHJHIR-UHFFFAOYSA-N trioxolane Chemical compound C1COOO1 MAAKQSASDHJHIR-UHFFFAOYSA-N 0.000 claims 8
- 201000004792 malaria Diseases 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- NAUWDMTWMDTGJV-UHFFFAOYSA-N CS(O)(=O)=O.CCCCCCCCCC Chemical compound CS(O)(=O)=O.CCCCCCCCCC NAUWDMTWMDTGJV-UHFFFAOYSA-N 0.000 claims 2
- -1 digluconate Chemical compound 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrugs Drugs 0.000 claims 2
- 201000004409 schistosomiasis Diseases 0.000 claims 2
- 229940080296 2-naphthalenesulfonate Drugs 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 claims 1
- 229940009098 Aspartate Drugs 0.000 claims 1
- 229940050390 Benzoate Drugs 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 claims 1
- 229940001468 Citrate Drugs 0.000 claims 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N DL-aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N Glycerol 3-phosphate Chemical compound OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N Pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 claims 1
- 229920002230 Pectic acid Polymers 0.000 claims 1
- 229950010765 Pivalate Drugs 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N Pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- 229940072056 alginate Drugs 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 239000003430 antimalarial agent Substances 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 229940077388 benzenesulfonate Drugs 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- MIOPJNTWMNEORI-UHFFFAOYSA-M camphorsulfonate anion Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-M 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M caproate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims 1
- 238000002648 combination therapy Methods 0.000 claims 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- SUMDYPCJJOFFON-UHFFFAOYSA-M isethionate Chemical compound OCCS([O-])(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-M 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 230000003287 optical Effects 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M palmitate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229940075930 picrate Drugs 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 229940086735 succinate Drugs 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
- ZDPHROOEEOARMN-UHFFFAOYSA-M undecanoate Chemical compound CCCCCCCCCCC([O-])=O ZDPHROOEEOARMN-UHFFFAOYSA-M 0.000 claims 1
- JAEQOSKUYPMJAT-UHFFFAOYSA-N COCCN1CCOCC1 Chemical compound COCCN1CCOCC1 JAEQOSKUYPMJAT-UHFFFAOYSA-N 0.000 description 1
Claims (17)
- OZ439、OZ461、OZ462、OZ466、OZ482、OZ493、OZ499、OZ527、OZ537、OZ539、OZ543、OZ545、OZ555、OZ571及びOZ572からなる群より選択される、請求項1記載のジスピロ1,2,4−トリオキソラン。
- 前記ジスピロ1,2,4−トリオキソランがシス−アダマンタン−2−スピロ−3′−8′−〔4′−〔2′−(4′−モルホリニル)エトキシ〕フェニル〕−1′,2′,4′−トリオキサスピロ〔4.5〕デカンメシレートである、請求項1〜2のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- 請求項1〜3のいずれか1項に記載のジスピロ1,2,4−トリオキソランを含む医薬組成物及び薬学的に許容される担体。
- 医薬品としての使用のための、請求項1〜4のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- マラリアの発症を低減する又はマラリアを治療するための、請求項1〜3のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランがマラリアへの暴露前又は後に投与される予定の、請求項6記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランが、約1〜100mg/kg/日の用量範囲で投与される予定の、請求項6〜7のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランが単回用量で投与される予定の、請求項5記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランが、約0.5〜5.0mg/kgの投与範囲で投与される予定の、請求項9記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランが、約0.1〜1000mg/kg/日の用量範囲で2回以上投与される予定の、請求項5〜8のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- 塩が、酢酸塩、アジピン酸塩、アルギン酸塩、クエン酸塩、アスパラギン酸塩、安息香酸塩、ベンゼンスルホン酸塩、重硫酸塩、酪酸塩、ショウノウ酸塩、ショウノウスルホン酸塩、ジグルコン酸塩、グリセロリン酸塩、半硫酸塩、ヘプタン酸塩、ヘキサン酸塩、フマル酸塩、塩酸塩、臭化水素酸塩、ヨウ化水素酸塩、2−ヒドロキシエタンスルホネート(イソチオン酸塩)、乳酸塩、マレイン酸塩、メタンスルホン酸塩、ニコチン酸塩、2−ナフタレンスルホネート、シュウ酸塩、パルミチン酸塩、ペクチン酸塩、過硫酸塩、3−フェニルプロピオネート、ピクリン酸塩、ピバル酸塩、プロピオン酸塩、コハク酸塩、酒石酸塩、チオシアン酸塩、リン酸塩、グルタミン酸塩、重炭酸塩、p−トルエンスルホン酸塩及びウンデカン酸塩からなる群より選択される、請求項5〜11のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- 前記ジスピロ1,2,4−トリオキソランがシス−アダマンタン−2−スピロ−3′−8′−〔4′−〔2′−(4′−モルホリニル)エトキシ〕フェニル〕−1′,2′,4′−トリオキサスピロ〔4.5〕デカンメシレートである、請求項5〜12のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランが、併用療法の一部として別の抗マラリア剤とともに投与される予定の、請求項5〜13のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- トリオキソランが経口投与される予定の、請求項5〜14のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
- マラリアの予防又は治療のための組成物を製造する方法であって、マラリア予防又はマラリア治療有効量のジスピロ1,2,4−トリオキソラン、そのプロドラッグ及び光学異性体と薬学的に許容される担体とを混合することを含み、前記トリオキソランが、請求項1〜3のいずれか1項に記載のジスピロ1,2,4−トリオキソランである、方法。
- 住血吸虫症の発生を低減する又は住血吸虫症を治療するための、請求項1〜3のいずれか1項に記載のジスピロ1,2,4−トリオキソラン。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/930,606 US8067620B2 (en) | 2005-05-04 | 2007-10-31 | Dispiro 1,2,4-trioxolane antimalarials |
US11/930,606 | 2007-10-31 | ||
PCT/US2008/081579 WO2009058859A2 (en) | 2007-10-31 | 2008-10-29 | Dispiro 1,2,4-trioxolane antimalarials |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2011502131A JP2011502131A (ja) | 2011-01-20 |
JP2011502131A5 true JP2011502131A5 (ja) | 2011-12-15 |
JP5559057B2 JP5559057B2 (ja) | 2014-07-23 |
Family
ID=40228026
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010531331A Active JP5559057B2 (ja) | 2007-10-31 | 2008-10-29 | ジスピロ1,2,4−トリオキソラン抗マラリア剤 |
Country Status (20)
Country | Link |
---|---|
US (1) | US8067620B2 (ja) |
EP (1) | EP2203457B1 (ja) |
JP (1) | JP5559057B2 (ja) |
KR (1) | KR101588468B1 (ja) |
CN (1) | CN101842377B (ja) |
AU (1) | AU2008318819C1 (ja) |
BR (1) | BRPI0818121B8 (ja) |
CA (1) | CA2702256C (ja) |
CY (1) | CY1115148T1 (ja) |
DK (1) | DK2203457T3 (ja) |
ES (1) | ES2466319T3 (ja) |
HK (1) | HK1147092A1 (ja) |
HR (1) | HRP20140435T1 (ja) |
MX (1) | MX2010004601A (ja) |
PL (1) | PL2203457T3 (ja) |
PT (1) | PT2203457E (ja) |
RU (1) | RU2493159C2 (ja) |
SI (1) | SI2203457T1 (ja) |
UA (1) | UA99742C2 (ja) |
WO (1) | WO2009058859A2 (ja) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US8067620B2 (en) | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
PT2670765T (pt) | 2011-01-31 | 2018-01-08 | Viiv Healthcare Uk No 4 Ltd | Triterpenoides modificados em c-17 e c-3 com atividade inibidora da maturação do vih |
KR20150024329A (ko) * | 2012-06-13 | 2015-03-06 | 메디치니쉐 유니베르지테트 빈 | 아미도페녹시프로판올아민 |
EP3104857A4 (en) * | 2014-02-14 | 2017-10-11 | The Regents of The University of California | Cyclic peroxides as prodrugs for selective delivery of agents |
EP3309156A1 (en) | 2016-10-13 | 2018-04-18 | MMV Medicines for Malaria Venture | New anti-malarial agents |
JP2019530712A (ja) | 2016-10-13 | 2019-10-24 | エムエムヴィ メディシンズ フォア マラリア ヴェンチャーMmv Medicines For Malaria Venture | 新規抗マラリア薬 |
WO2018213220A1 (en) * | 2017-05-16 | 2018-11-22 | The Johns Hopkins University | Ozonides for treating or preventing virus infections |
US11072594B2 (en) | 2017-06-27 | 2021-07-27 | The Regents Of The University Of California | Trioxolane agents |
CN110878069A (zh) * | 2019-12-09 | 2020-03-13 | 南京杰运医药科技有限公司 | 一种4-吗琳基-2-乙基哌嗪的制备方法 |
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US20080125441A1 (en) * | 2002-06-21 | 2008-05-29 | 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 |
US8067620B2 (en) * | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
WO2006123314A2 (en) * | 2005-05-18 | 2006-11-23 | Ranbaxy Laboratories Limited | Stable dosage forms of spiro and dispiro 1,2,4-trioxolane antimalarials |
-
2007
- 2007-10-31 US US11/930,606 patent/US8067620B2/en active Active
-
2008
- 2008-10-29 EP EP08845311.3A patent/EP2203457B1/en active Active
- 2008-10-29 AU AU2008318819A patent/AU2008318819C1/en not_active Ceased
- 2008-10-29 BR BRPI0818121A patent/BRPI0818121B8/pt active IP Right Grant
- 2008-10-29 UA UAA201005157A patent/UA99742C2/ru unknown
- 2008-10-29 RU RU2010121919/04A patent/RU2493159C2/ru active
- 2008-10-29 KR KR1020107012029A patent/KR101588468B1/ko active IP Right Grant
- 2008-10-29 ES ES08845311.3T patent/ES2466319T3/es active Active
- 2008-10-29 MX MX2010004601A patent/MX2010004601A/es active IP Right Grant
- 2008-10-29 SI SI200831204T patent/SI2203457T1/sl unknown
- 2008-10-29 WO PCT/US2008/081579 patent/WO2009058859A2/en active Application Filing
- 2008-10-29 PL PL08845311T patent/PL2203457T3/pl unknown
- 2008-10-29 JP JP2010531331A patent/JP5559057B2/ja active Active
- 2008-10-29 CN CN200880114154.6A patent/CN101842377B/zh active Active
- 2008-10-29 DK DK08845311.3T patent/DK2203457T3/da active
- 2008-10-29 PT PT88453113T patent/PT2203457E/pt unknown
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