UA75325C2 - Antiparasitic derivatives of artemisin (endoperoxides) - Google Patents
Antiparasitic derivatives of artemisin (endoperoxides) Download PDFInfo
- Publication number
- UA75325C2 UA75325C2 UA2001021049A UA2001021049A UA75325C2 UA 75325 C2 UA75325 C2 UA 75325C2 UA 2001021049 A UA2001021049 A UA 2001021049A UA 2001021049 A UA2001021049 A UA 2001021049A UA 75325 C2 UA75325 C2 UA 75325C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- general formula
- compound
- dihydroartemisinin
- compounds
- Prior art date
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- 230000002141 anti-parasite Effects 0.000 title claims description 3
- BLUAFEHZUWYNDE-XRNKLDBLSA-N chembl77 Chemical class C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4C31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-XRNKLDBLSA-N 0.000 title description 2
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 C-56 alkoxycarbonyl Chemical group 0.000 claims description 103
- 229960002521 artenimol Drugs 0.000 claims description 58
- 230000003993 interaction Effects 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- WOJATDXXHKRDIF-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-(4-morpholin-4-ylphenyl)propan-1-one;dihydrochloride Chemical group Cl.Cl.COC1=CC=CC=C1N1CCN(CCC(=O)C=2C=CC(=CC=2)N2CCOCC2)CC1 WOJATDXXHKRDIF-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 27
- 244000045947 parasite Species 0.000 abstract description 23
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- 201000010099 disease Diseases 0.000 abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 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 description 37
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- C07D—HETEROCYCLIC COMPOUNDS
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- 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
- C07D493/18—Bridged systems
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98305596 | 1998-07-14 | ||
| PCT/GB1999/002267 WO2000004024A1 (en) | 1998-07-14 | 1999-07-14 | Antiparasitic artemisinin derivatives (endoperoxides) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75325C2 true UA75325C2 (en) | 2006-04-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001021049A UA75325C2 (en) | 1998-07-14 | 1999-07-14 | Antiparasitic derivatives of artemisin (endoperoxides) |
Country Status (27)
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| EP (2) | EP1655302A3 (ru) |
| JP (1) | JP2002520416A (ru) |
| KR (1) | KR100640113B1 (ru) |
| CN (1) | CN1122035C (ru) |
| AT (1) | ATE314373T1 (ru) |
| AU (1) | AU765860B2 (ru) |
| BG (1) | BG105137A (ru) |
| BR (1) | BR9912810A (ru) |
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| HK (1) | HK1040709B (ru) |
| HU (1) | HUP0102851A3 (ru) |
| IL (1) | IL140402A0 (ru) |
| NO (1) | NO20010223L (ru) |
| NZ (1) | NZ509324A (ru) |
| PL (1) | PL345503A1 (ru) |
| PT (1) | PT1095042E (ru) |
| RU (1) | RU2236413C2 (ru) |
| SI (1) | SI1095042T1 (ru) |
| SK (1) | SK542001A3 (ru) |
| TR (1) | TR200100073T2 (ru) |
| UA (1) | UA75325C2 (ru) |
| WO (1) | WO2000004024A1 (ru) |
| YU (1) | YU2101A (ru) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2337119A1 (en) * | 1998-07-14 | 2000-01-27 | Richard K. Haynes | Antiparasitic artemisinin derivatives (endoperoxides) |
| DE60307239D1 (de) * | 2002-03-08 | 2006-09-14 | Bayer Healthcare Ag | Artemisininderivate (endoperoxide) mit wirkung gegen parasiten |
| DE102004027871B3 (de) | 2004-06-08 | 2006-03-16 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von 10α-[4'-(S,S-Dioxothiomorpholin-1'-yl)]-10-desoxo-10-dihydroartemisinin |
| EP1714967A1 (en) * | 2005-04-22 | 2006-10-25 | Bayer HealthCare AG | Antiparasitic artemisinin derivatives |
| US8431611B2 (en) | 2006-10-20 | 2013-04-30 | Johns Hopkins University | Artemisinin derivatives |
| US8193376B2 (en) | 2007-01-01 | 2012-06-05 | Bioderm Research | Artemisinin derivatives with natural amino acids, peptides, and amino sugars for the treatment of infection and topical condition in mammals |
| GB0720967D0 (en) * | 2007-10-25 | 2007-12-05 | Protophama Ltd | Anti-material pharmaceutical composition |
| CA2719365C (en) * | 2008-04-29 | 2017-03-07 | Novartis Ag | Spiro-indole derivatives for the treatment of parasitic diseases |
| ES2390046T3 (es) * | 2009-04-23 | 2012-11-06 | Londonpharma Ltd. | Formulación de pulverización sublingual que comprende dihidroartemesinina |
| US8815942B2 (en) | 2010-10-20 | 2014-08-26 | The Royal Institution For The Advancement Of Learning/Mcgill University | Combination therapy and uses thereof for treatment and prevention of parasitic infection and disease |
| RU2466133C1 (ru) * | 2011-06-24 | 2012-11-10 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Трициклические органические монопероксиды и способ их получения |
| US9675582B2 (en) | 2011-10-25 | 2017-06-13 | U.S. Phytotherapy, Inc. | Alternative ACT with natural botanical active GRAS ingredients for treatment and prevention of the Zika virus |
| US9358261B2 (en) | 2011-10-25 | 2016-06-07 | U.S. Phytotherapy, Inc. | Additional artemisinin and berberine compositions and methods of making |
| US9011892B2 (en) | 2011-10-25 | 2015-04-21 | U.S. Phytotherapy, Inc. | Artemisinin with berberine compositions and methods of making |
| WO2013157005A1 (en) * | 2012-04-18 | 2013-10-24 | The Hong Kong University Of Science And Technology | Methods and compositions for treating viral infections |
| JP5994059B2 (ja) * | 2012-09-05 | 2016-09-21 | 国立大学法人東京農工大学 | 抗マラリア活性を有するアザアルテミシニン誘導体及びその製造方法 |
| WO2014070673A1 (en) * | 2012-10-29 | 2014-05-08 | University Of Rochester | Artemisinin derivatives, methods for their preparation and their use as antimalarial agents |
| WO2015041722A1 (en) | 2013-09-17 | 2015-03-26 | Kryptonite Group, Ltd | Enhanced artemisinin-based combination therapy for treating parasitic mediated disease |
| USD729631S1 (en) | 2013-10-03 | 2015-05-19 | Gk Packaging, Inc. | Bottle |
| USD730736S1 (en) | 2013-10-03 | 2015-06-02 | Gk Packaging, Inc. | Bottle |
| USD729632S1 (en) | 2013-10-03 | 2015-05-19 | Gk Packaging, Inc. | Bottle |
| USD726543S1 (en) | 2013-11-04 | 2015-04-14 | Gk Packaging, Inc. | Bottle |
| USD727160S1 (en) | 2013-11-04 | 2015-04-21 | Gk Packaging, Inc. | Bottle |
| USD726544S1 (en) | 2013-11-04 | 2015-04-14 | Gk Packaging, Inc. | Bottle |
| USD726545S1 (en) | 2013-11-04 | 2015-04-14 | Gk Packaging, Inc. | Bottle |
| CN103664982A (zh) * | 2013-12-06 | 2014-03-26 | 湖南科源生物制品有限公司 | 青蒿素类似物及其制备方法 |
| CN103896960A (zh) * | 2014-01-14 | 2014-07-02 | 李学强 | 一种高效、绿色的青蒿砜制备方法 |
| USD740125S1 (en) | 2014-03-26 | 2015-10-06 | Gk Packaging, Inc. | Bottle |
| USD740677S1 (en) | 2014-03-26 | 2015-10-13 | Gk Packaging, Inc. | Bottle |
| USD742748S1 (en) | 2014-06-13 | 2015-11-10 | Gk Packaging, Inc. | Bottle |
| USD753503S1 (en) | 2014-09-25 | 2016-04-12 | Gk Packaging, Inc. | Bottle |
| USD753502S1 (en) | 2014-09-25 | 2016-04-12 | Gk Packaging, Inc. | Bottle |
| USD746145S1 (en) | 2014-12-04 | 2015-12-29 | GK Packaging, Inc | Bottle |
| USD784820S1 (en) | 2015-02-05 | 2017-04-25 | Gk Packaging, Inc. | Bottle |
| CN105198898A (zh) * | 2015-09-23 | 2015-12-30 | 山东大学（威海） | 一种用于预防和/或治疗癌症的化合物 |
| USD807190S1 (en) | 2015-10-13 | 2018-01-09 | Gk Packaging, Inc. | Bottle |
| USD784821S1 (en) | 2015-10-13 | 2017-04-25 | Gk Packaging, Inc. | Bottle |
| USD774914S1 (en) | 2015-10-13 | 2016-12-27 | Gk Packaging, Inc. | Bottle |
| USD806555S1 (en) | 2017-03-15 | 2018-01-02 | Gk Packaging, Inc. | Bottle |
| IL269390B (en) | 2017-03-20 | 2022-08-01 | Broad Inst Inc | Preparations and methods for the treatment of parasitic diseases |
| USD825342S1 (en) | 2017-06-02 | 2018-08-14 | Gk Packaging, Inc. | Bottle |
| WO2019180708A1 (en) * | 2018-03-22 | 2019-09-26 | Hadasit Medical Research Services And Development Ltd. | Methods and synergic compositions for treating viral infections |
| USD908011S1 (en) | 2019-04-30 | 2021-01-19 | Gk Packaging, Inc. | Bottle |
| CN110448552B (zh) * | 2019-08-23 | 2023-05-12 | 西南大学 | 二氢青蒿素衍生物在制备抗疟药物中的应用 |
| CN110483547B (zh) * | 2019-08-28 | 2022-08-16 | 西南大学 | 二氢青蒿素的简单酚类偶联物、合成方法及应用 |
| CN110642869B (zh) * | 2019-09-26 | 2022-03-15 | 西南大学 | 二氢青蒿素的硫醚、亚砜与砜衍生物及其应用 |
| USD883798S1 (en) | 2019-09-30 | 2020-05-12 | Gk Packaging, Inc. | Bottle |
| CN114276365B (zh) * | 2021-12-30 | 2023-06-13 | 威胜生物医药(苏州)股份有限公司 | 一种蒿甲醚杂质脱水双氢青蒿素的制备方法 |
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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 |
| US5225427A (en) | 1988-10-04 | 1993-07-06 | Hoechst Aktiengesellschaft | 10-substituted ether derivatives of dihydroartemisinin, process for their preparation and their use as antiprotozoal agents |
| CN1028294C (zh) | 1989-12-21 | 1995-04-26 | 中国科学院上海药物研究所 | 一类含氮青蒿素衍生物的合成 |
| TW198722B (ru) | 1990-05-07 | 1993-01-21 | Hoechst Ag | |
| US5225562A (en) * | 1990-08-10 | 1993-07-06 | Mcchesney James D | Method of preparing (+)-deoxoartemisinin and selected analogues of (+)-deoxoartemisinin |
| WO1993008195A1 (en) * | 1991-10-14 | 1993-04-29 | The University Of Sydney | Cyclic peroxyacetal compounds |
| JPH05203550A (ja) * | 1992-01-24 | 1993-08-10 | Shimadzu Corp | 界面強度測定方法及びその測定装置 |
| CN1049435C (zh) * | 1994-11-09 | 2000-02-16 | 中国科学院上海药物研究所 | 含苯基和杂环基的青蒿素衍生物及其制备方法 |
| WO1997008182A1 (en) * | 1995-08-24 | 1997-03-06 | Merck & Co., Inc. | Process for the preparation of imidazolyl macrolide immunosuppressants |
| US6160004A (en) | 1997-12-30 | 2000-12-12 | Hauser, Inc. | C-10 carbon-substituted artemisinin-like trioxane compounds having antimalarial, antiproliferative and antitumor activities |
| CA2337119A1 (en) * | 1998-07-14 | 2000-01-27 | Richard K. Haynes | Antiparasitic artemisinin derivatives (endoperoxides) |
| US6649647B1 (en) | 1998-07-14 | 2003-11-18 | Richard Haynes | Trioxane derivatives |
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