ES2466319T3 - Compuestos contra la malaria con base diespiro-1,2,4-trioxolano - Google Patents
Compuestos contra la malaria con base diespiro-1,2,4-trioxolano Download PDFInfo
- Publication number
- ES2466319T3 ES2466319T3 ES08845311.3T ES08845311T ES2466319T3 ES 2466319 T3 ES2466319 T3 ES 2466319T3 ES 08845311 T ES08845311 T ES 08845311T ES 2466319 T3 ES2466319 T3 ES 2466319T3
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- Prior art keywords
- trioxolane
- cis
- mmol
- adamantane
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 54
- 230000000078 anti-malarial effect Effects 0.000 title description 8
- RZYIPLSVRHWROD-UHFFFAOYSA-N 1,2,4-trioxolane Chemical compound C1OCOO1 RZYIPLSVRHWROD-UHFFFAOYSA-N 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
- 201000004792 malaria Diseases 0.000 claims description 74
- MAAKQSASDHJHIR-UHFFFAOYSA-N trioxolane Chemical compound C1COOO1 MAAKQSASDHJHIR-UHFFFAOYSA-N 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 67
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 59
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 27
- 229940079593 drug Drugs 0.000 claims description 25
- -1 camphorrate Chemical compound 0.000 claims description 22
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 201000004409 schistosomiasis Diseases 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003937 drug carrier Substances 0.000 claims description 7
- DUMMLBFJPQGNSA-BTJKTKAUSA-N (z)-but-2-enedioic acid;decane Chemical compound OC(=O)\C=C/C(O)=O.CCCCCCCCCC DUMMLBFJPQGNSA-BTJKTKAUSA-N 0.000 claims description 6
- 238000002648 combination therapy Methods 0.000 claims description 6
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
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- 229920000615 alginic acid Polymers 0.000 claims description 3
- PFGGIURFPXPANK-UHFFFAOYSA-N decane;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCC PFGGIURFPXPANK-UHFFFAOYSA-N 0.000 claims description 3
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- DUMMLBFJPQGNSA-WLHGVMLRSA-N (e)-but-2-enedioic acid;decane Chemical compound OC(=O)\C=C\C(O)=O.CCCCCCCCCC DUMMLBFJPQGNSA-WLHGVMLRSA-N 0.000 claims description 2
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- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 2
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- NNKBTSMMVOYXPX-UHFFFAOYSA-N C(C(O)C(O)C(=O)O)(=O)O.CCCCCCCCCC Chemical compound C(C(O)C(O)C(=O)O)(=O)O.CCCCCCCCCC NNKBTSMMVOYXPX-UHFFFAOYSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
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- 229910019142 PO4 Inorganic materials 0.000 claims description 2
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- 229940072056 alginate Drugs 0.000 claims description 2
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 2
- 229940009098 aspartate Drugs 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 2
- 229940001468 citrate Drugs 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229940075930 picrate Drugs 0.000 claims description 2
- 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 description 2
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims description 2
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- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 1
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- A61P33/12—Schistosomicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C07D323/02—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
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 |
| US930606 | 2007-10-31 | ||
| PCT/US2008/081579 WO2009058859A2 (en) | 2007-10-31 | 2008-10-29 | Dispiro 1,2,4-trioxolane antimalarials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2466319T3 true ES2466319T3 (es) | 2014-06-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08845311.3T Active ES2466319T3 (es) | 2007-10-31 | 2008-10-29 | Compuestos contra la malaria con base diespiro-1,2,4-trioxolano |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8067620B2 (enExample) |
| EP (1) | EP2203457B1 (enExample) |
| JP (1) | JP5559057B2 (enExample) |
| KR (1) | KR101588468B1 (enExample) |
| CN (1) | CN101842377B (enExample) |
| AU (1) | AU2008318819C1 (enExample) |
| BR (1) | BRPI0818121B8 (enExample) |
| CA (1) | CA2702256C (enExample) |
| CY (1) | CY1115148T1 (enExample) |
| DK (1) | DK2203457T3 (enExample) |
| ES (1) | ES2466319T3 (enExample) |
| HR (1) | HRP20140435T1 (enExample) |
| MX (1) | MX2010004601A (enExample) |
| PL (1) | PL2203457T3 (enExample) |
| PT (1) | PT2203457E (enExample) |
| RU (1) | RU2493159C2 (enExample) |
| SI (1) | SI2203457T1 (enExample) |
| UA (1) | UA99742C2 (enExample) |
| WO (1) | WO2009058859A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067620B2 (en) * | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
| CN103429607B (zh) | 2011-01-31 | 2016-02-17 | 百时美施贵宝公司 | 具有hiv成熟抑制活性的c-17和c-3经修饰的三萜系化合物 |
| CA2874295A1 (en) * | 2012-06-13 | 2013-12-19 | Medizinische Universitat Wien | Amidophenoxypropanolamines |
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| EP3526214A1 (en) | 2016-10-13 | 2019-08-21 | MMV Medicines for Malaria Venture | New anti-malarial agent |
| EP3309156A1 (en) | 2016-10-13 | 2018-04-18 | MMV Medicines for Malaria Venture | New anti-malarial agents |
| US11246854B2 (en) | 2017-05-16 | 2022-02-15 | 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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| US8067620B2 (en) | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
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| JP2011502131A (ja) | 2011-01-20 |
| UA99742C2 (en) | 2012-09-25 |
| PL2203457T3 (pl) | 2014-08-29 |
| MX2010004601A (es) | 2010-05-27 |
| CA2702256C (en) | 2017-09-26 |
| WO2009058859A2 (en) | 2009-05-07 |
| RU2010121919A (ru) | 2011-12-10 |
| DK2203457T3 (da) | 2014-05-12 |
| BRPI0818121A2 (pt) | 2015-11-17 |
| AU2008318819A1 (en) | 2009-05-07 |
| AU2008318819B2 (en) | 2013-11-21 |
| US20080125411A1 (en) | 2008-05-29 |
| KR101588468B1 (ko) | 2016-01-25 |
| HK1147092A1 (en) | 2011-07-29 |
| JP5559057B2 (ja) | 2014-07-23 |
| CY1115148T1 (el) | 2016-12-14 |
| KR20100087199A (ko) | 2010-08-03 |
| CN101842377B (zh) | 2015-07-01 |
| RU2493159C2 (ru) | 2013-09-20 |
| BRPI0818121B8 (pt) | 2021-05-25 |
| SI2203457T1 (sl) | 2014-06-30 |
| AU2008318819C1 (en) | 2014-04-24 |
| BRPI0818121B1 (pt) | 2020-12-08 |
| EP2203457A2 (en) | 2010-07-07 |
| PT2203457E (pt) | 2014-06-06 |
| HRP20140435T1 (hr) | 2014-06-20 |
| WO2009058859A3 (en) | 2009-06-18 |
| CA2702256A1 (en) | 2009-05-07 |
| CN101842377A (zh) | 2010-09-22 |
| EP2203457B1 (en) | 2014-03-05 |
| US8067620B2 (en) | 2011-11-29 |
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