JP2010539122A - 生物学的に活性のある化合物のインビボ生物活性の増加 - Google Patents
生物学的に活性のある化合物のインビボ生物活性の増加 Download PDFInfo
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- 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 claims description 42
- 229960002521 artenimol Drugs 0.000 claims description 25
- 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 description 25
- 229930016266 dihydroartemisinin Natural products 0.000 claims description 25
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- 241000124008 Mammalia Species 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
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- 206010062016 Immunosuppression Diseases 0.000 claims description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical group CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- ROJKPKOYARNFNB-UHFFFAOYSA-N Propyl pentanoate Chemical group CCCCC(=O)OCCC ROJKPKOYARNFNB-UHFFFAOYSA-N 0.000 claims description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
- JXTHNDFMNIQAHM-UHFFFAOYSA-M dichloroacetate Chemical group [O-]C(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-M 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 208000016097 disease of metabolism Diseases 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- 230000001773 anti-convulsant effect Effects 0.000 claims description 3
- 208000000291 Nematode infections Diseases 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- ZQGMLVQZBIKKMP-NNWCWBAJSA-N deoxyartemisinin Chemical compound C([C@](O1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C ZQGMLVQZBIKKMP-NNWCWBAJSA-N 0.000 claims 1
- ZQGMLVQZBIKKMP-UHFFFAOYSA-N desoxyartemisinin Natural products O1C(O2)(C)CCC3C(C)CCC4C32C1OC(=O)C4C ZQGMLVQZBIKKMP-UHFFFAOYSA-N 0.000 claims 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 229940079593 drug Drugs 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
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- 239000002904 solvent Substances 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
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- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
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- 238000010168 coupling process Methods 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 5
- LSEFXLGTUCVBPE-UHFFFAOYSA-N 1h-imidazol-2-ylcarbamic acid Chemical compound OC(=O)NC1=NC=CN1 LSEFXLGTUCVBPE-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 230000015556 catabolic process Effects 0.000 description 3
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- BOQMASYCUFVXCR-LHJKONGQSA-N deoxoartemisinin Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC[C@@H]4C BOQMASYCUFVXCR-LHJKONGQSA-N 0.000 description 3
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- 239000007788 liquid Substances 0.000 description 3
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- PIYNUZCGMLCXKJ-UHFFFAOYSA-N 1,4-dioxane-2,6-dione Chemical compound O=C1COCC(=O)O1 PIYNUZCGMLCXKJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- BJDCWCLMFKKGEE-KDTBHNEXSA-N Dihydroartemisinin (DHA) 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-KDTBHNEXSA-N 0.000 description 2
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- 230000009286 beneficial effect Effects 0.000 description 2
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- 230000000975 bioactive effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000006013 carbendazim Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- -1 convex Chemical compound 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
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- 230000009466 transformation Effects 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KSAPYRIVHFAQGR-UHFFFAOYSA-N 1-sulfanylbenzimidazole Chemical class C1=CC=C2N(S)C=NC2=C1 KSAPYRIVHFAQGR-UHFFFAOYSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- ZUSLEOOZAITYGH-UHFFFAOYSA-N 2-(aminomethyl)-3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=C(CN)C(C(C)(C)C)=C1 ZUSLEOOZAITYGH-UHFFFAOYSA-N 0.000 description 1
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical class C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 1
- PJFVQKKKKWEEIF-UHFFFAOYSA-N 4-(chloromethyl)heptane Chemical compound CCCC(CCl)CCC PJFVQKKKKWEEIF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 0 CC1(*)C(CCCC2CC3)[C@]22OOC3(C)O[C@@]2OC1* Chemical compound CC1(*)C(CCCC2CC3)[C@]22OOC3(C)O[C@@]2OC1* 0.000 description 1
- IWISTPMZHKGPOX-KIWJVMNNSA-N CCOC(C)(CCC1CCC2)O[C@H]3OCC(C)C2[C@]13O Chemical compound CCOC(C)(CCC1CCC2)O[C@H]3OCC(C)C2[C@]13O IWISTPMZHKGPOX-KIWJVMNNSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
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- 101710088194 Dehydrogenase Proteins 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical group CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 108010022394 Threonine synthase Proteins 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
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- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
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- GYOZYWVXFNDGLU-XLPZGREQSA-N dTMP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 GYOZYWVXFNDGLU-XLPZGREQSA-N 0.000 description 1
- JSRLJPSBLDHEIO-SHYZEUOFSA-N dUMP Chemical compound O1[C@H](COP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(=O)NC(=O)C=C1 JSRLJPSBLDHEIO-SHYZEUOFSA-N 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
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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
- C07D493/20—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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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
- A61P33/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Tropical Medicine & Parasitology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
(I)
で示されるアルテミシニン誘導体を含む化合物である。
ブチレートは、特に、ヒスタミンアンタゴニストである。
プロピルペンタノエートは、バルプロ酸、エピリム、コンヴレックス、エウレケン(eurekene)、ラバゼン(labazene)、セレニカ、オルフィリル(orfiril)、バレリンなどの別名でも知られている。
[ここで、少なくとも1つのR1またはR2が、本発明の生物学的に活性な分子であるという条件下で、R1およびR2は、Hであるか、または、本発明の生物学的に活性な分子である]の一般的合成
Claims (40)
- 生物活性をもつ化合物が、スルフィド(-S-)、エーテル(-O-)、エステル(-OCO-)またはアミン(-N-)結合を介して、アルテミシニン誘導体に共有的に結合する請求項1に記載の化合物。
- 生物活性をもつ化合物が、1位においてアルテミシニン誘導体に共有的に結合する請求項1または2に記載の化合物。
- 生物活性をもつ化合物が、2位においてアルテミシニン誘導体に共有的に結合する請求項1または2に記載の化合物。
- アルテミシニン誘導体が、ジヒドロアルテミシニン、無水ジヒドロアルテミシニンおよびデオキシアルテミシニンから選ばれる化合物から誘導される請求項1〜4のいずれかに記載の化合物。
- 生物活性をもつ化合物が、N-(1H-ベンズイミダゾール-2-イル)カルバミン酸メチルである請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、メトキシ酢酸である請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、2,2-ジクロロアセテートである請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、5-フルオロ-1H-ピリミジン-2,4-ジオンである請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、アセテートである請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、イソブチレートである請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、ブチレートである請求項1〜5のいずれかに記載の化合物。
- 生物活性をもつ化合物が、プロピルペンタノエートである請求項1〜5のいずれかに記載の化合物。
- 請求項1〜22または25〜28のいずれかに記載の生物活性をもつ化合物の生物活性を増加させるために、請求項1〜19のいずれかに記載のアルテミシニン誘導体を、1または2位において、スルフィド(-S-)、エーテル(-O-)、エステル(-OCO-)またはアミン(-N-)結合を介して、該生物活性をもつ化合物に共有的に結合させることを含む、請求項1〜22または25〜28のいずれかに記載の化合物を得るための方法。
- 請求項1〜22または25〜28のいずれかに記載の化合物の生物活性を増加させるための、請求項1〜28のいずれかに記載のアルテミシニン誘導体の使用。
- 医薬として用いるための請求項1〜22または25〜28のいずれかに記載の化合物。
- 治療を必要とする哺乳類の治療用医薬の製造のための、請求項1〜22または25〜28のいずれかに記載の化合物の使用。
- 線虫感染を患っている哺乳類の治療用医薬の製造のための請求項1〜6、14または15のいずれかに記載の化合物の使用。
- 免疫抑制を必要とする哺乳類の治療用医薬の製造のための請求項1〜5、7または16のいずれかに記載の化合物の使用。
- 代謝性疾患を患っている哺乳類の治療用医薬の製造のための請求項1〜5、8または17のいずれかに記載の化合物の使用。
- 免疫抑制を必要とする代謝性疾患を患っているか、またはガンを患っている哺乳類の治療用医薬の製造のための請求項1〜5、9または18のいずれかに記載の化合物の使用。
- ヒリヒリする痛みを患っている哺乳類の治療用医薬の製造のための請求項1〜5、10または19のいずれかに記載の化合物の使用。
- ガンを患っている哺乳類の治療用医薬の製造のための請求項1〜5、11または20のいずれかに記載の化合物の使用。
- 免疫抑制を必要とする哺乳類の治療用医薬の製造のための請求項1〜5、12または21のいずれかに記載の化合物の使用。
- 抗けいれん活性を必要とする哺乳類の治療用医薬の製造のための請求項1〜5、13または22のいずれかに記載の化合物の使用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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PCT/EP2007/007868 WO2009033494A1 (en) | 2007-09-10 | 2007-09-10 | 1- or 2-substituted artemisinin derivatives for increasing the in vivo biological activity of biologically active compounds |
PCT/EP2008/007556 WO2009033706A1 (en) | 2007-09-10 | 2008-09-10 | Increasing the in vivo biological activity of biologically active compounds |
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JP2010539122A true JP2010539122A (ja) | 2010-12-16 |
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JP2010524406A Pending JP2010539122A (ja) | 2007-09-10 | 2008-09-10 | 生物学的に活性のある化合物のインビボ生物活性の増加 |
Country Status (8)
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US (1) | US8692003B2 (ja) |
JP (1) | JP2010539122A (ja) |
KR (1) | KR20100059958A (ja) |
CN (1) | CN101855226A (ja) |
CA (1) | CA2698973C (ja) |
EA (1) | EA018238B1 (ja) |
WO (2) | WO2009033494A1 (ja) |
ZA (1) | ZA201001825B (ja) |
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EP2289554A1 (en) * | 2009-07-31 | 2011-03-02 | Dafra Pharma N.V. | Compositions comprising thalidomide and artemisinin for the treatment of cancer |
WO2012017004A1 (en) * | 2010-08-03 | 2012-02-09 | Dafra Pharma N.V. | Novel artemisinin-like derivatives with cytotoxic and anti-angiogenic properties |
WO2014023081A1 (zh) * | 2012-08-07 | 2014-02-13 | 中国科学院上海生命科学研究院 | 青嵩素衍生物及其制法和应用 |
CN106456600B (zh) * | 2014-04-28 | 2020-08-04 | 埃皮法姆股份公司 | 使用青蒿素及其衍生物治疗或预防脂溢性角化病 |
CN108653272B (zh) * | 2017-03-31 | 2022-09-20 | 中国科学院上海药物研究所 | 青蒿素类衍生物在制备用于治疗炎症性肠病的药物中的用途 |
CN110078748A (zh) * | 2019-05-08 | 2019-08-02 | 云白药征武科技(上海)有限公司 | 双-(10-去氧双氢青蒿素)-间苯三酚缀合物的制备方法和应用 |
CN111362964B (zh) * | 2020-03-19 | 2022-03-08 | 中国人民解放军陆军军医大学 | 青蒿琥酯的琥珀酯化衍生物及其制备方法和药物中的用途 |
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EP0362730A1 (en) * | 1988-10-04 | 1990-04-11 | Hoechst Aktiengesellschaft | Artemisinin derivatives, processes for their preparation and their use as antiprotozoal agents |
EP0974354A1 (en) * | 1998-07-14 | 2000-01-26 | The Hong Kong University of Science & Technology | Artemisinin derivatives |
WO2000004026A1 (en) * | 1998-07-14 | 2000-01-27 | The Hong Kong University Of Science & Technology | Trioxane derivatives |
JP2001521894A (ja) * | 1997-11-03 | 2001-11-13 | メファ・アクチェンゲゼルシャフト | アルテミニシニン及び/又はアルテミシニン誘導体を含有する製薬学的活性組成物 |
WO2003022855A1 (fr) * | 2001-09-07 | 2003-03-20 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Tert-butoxy-dihydro-artemisinine, sa production et composition pharmaceutique la contenant |
EP1604992B1 (de) * | 2004-06-08 | 2009-08-05 | Saltigo GmbH | Verfahren zur Herstellung von 10alpha-[4'-(S-S-Dioxothothiomorpholin-1'-yl)]-10-Deoxo-10-Dihydroartemisinin |
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US6156790A (en) * | 1997-12-30 | 2000-12-05 | Hauser, Inc. | C-10 carbon-substituted artemisinin-like trioxane compounds having antimalarial, antiproliferative and antitumor activities |
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2007
- 2007-09-10 WO PCT/EP2007/007868 patent/WO2009033494A1/en active Application Filing
-
2008
- 2008-09-10 JP JP2010524406A patent/JP2010539122A/ja active Pending
- 2008-09-10 EA EA201070352A patent/EA018238B1/ru not_active IP Right Cessation
- 2008-09-10 WO PCT/EP2008/007556 patent/WO2009033706A1/en active Application Filing
- 2008-09-10 CN CN200880115197A patent/CN101855226A/zh active Pending
- 2008-09-10 KR KR1020107007587A patent/KR20100059958A/ko not_active Application Discontinuation
- 2008-09-10 US US12/677,186 patent/US8692003B2/en not_active Expired - Fee Related
- 2008-09-10 CA CA2698973A patent/CA2698973C/en not_active Expired - Fee Related
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2010
- 2010-03-15 ZA ZA2010/01825A patent/ZA201001825B/en unknown
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EP0362730A1 (en) * | 1988-10-04 | 1990-04-11 | Hoechst Aktiengesellschaft | Artemisinin derivatives, processes for their preparation and their use as antiprotozoal agents |
JP2001521894A (ja) * | 1997-11-03 | 2001-11-13 | メファ・アクチェンゲゼルシャフト | アルテミニシニン及び/又はアルテミシニン誘導体を含有する製薬学的活性組成物 |
EP0974354A1 (en) * | 1998-07-14 | 2000-01-26 | The Hong Kong University of Science & Technology | Artemisinin derivatives |
WO2000004026A1 (en) * | 1998-07-14 | 2000-01-27 | The Hong Kong University Of Science & Technology | Trioxane derivatives |
WO2003022855A1 (fr) * | 2001-09-07 | 2003-03-20 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Tert-butoxy-dihydro-artemisinine, sa production et composition pharmaceutique la contenant |
EP1604992B1 (de) * | 2004-06-08 | 2009-08-05 | Saltigo GmbH | Verfahren zur Herstellung von 10alpha-[4'-(S-S-Dioxothothiomorpholin-1'-yl)]-10-Deoxo-10-Dihydroartemisinin |
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Also Published As
Publication number | Publication date |
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EA201070352A1 (ru) | 2010-10-29 |
WO2009033706A1 (en) | 2009-03-19 |
ZA201001825B (en) | 2011-05-25 |
US8692003B2 (en) | 2014-04-08 |
KR20100059958A (ko) | 2010-06-04 |
WO2009033494A1 (en) | 2009-03-19 |
CA2698973C (en) | 2015-11-17 |
CA2698973A1 (en) | 2009-03-19 |
US20100286393A1 (en) | 2010-11-11 |
EA018238B1 (ru) | 2013-06-28 |
CN101855226A (zh) | 2010-10-06 |
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