HRP20040927A2 - Antiparasitic artemisinin derivatives (endoperoxides) - Google Patents
Antiparasitic artemisinin derivatives (endoperoxides)Info
- Publication number
- HRP20040927A2 HRP20040927A2 HR20040927A HRP20040927A HRP20040927A2 HR P20040927 A2 HRP20040927 A2 HR P20040927A2 HR 20040927 A HR20040927 A HR 20040927A HR P20040927 A HRP20040927 A HR P20040927A HR P20040927 A2 HRP20040927 A2 HR P20040927A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- alkyl
- hydrogen atom
- optionally substituted
- aryl
- Prior art date
Links
- 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 title claims description 17
- 230000002141 anti-parasite Effects 0.000 title 1
- 239000003096 antiparasitic agent Substances 0.000 title 1
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 24
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- 125000001424 substituent group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 11
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 231100000316 potential neurotoxicity Toxicity 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005494 pyridonyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229930183339 qinghaosu Natural products 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 208000026775 severe diarrhea Diseases 0.000 description 1
- 230000036301 sexual development Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 230000005002 sporogony Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 239000000892 thaumatin Substances 0.000 description 1
- 235000010436 thaumatin Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
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
- C07D493/18—Bridged 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
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02005233 | 2002-03-08 | ||
| PCT/EP2003/001839 WO2003076446A1 (en) | 2002-03-08 | 2003-02-24 | Antiparasitic artemisinin derivatives (endoperoxides) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040927A2 true HRP20040927A2 (en) | 2005-06-30 |
Family
ID=27798779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040927A HRP20040927A2 (en) | 2002-03-08 | 2004-10-06 | Antiparasitic artemisinin derivatives (endoperoxides) |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20050119232A1 (es) |
| EP (1) | EP1485389B1 (es) |
| JP (1) | JP2005526073A (es) |
| KR (1) | KR20040104493A (es) |
| CN (1) | CN1649874A (es) |
| AR (1) | AR038842A1 (es) |
| AT (1) | ATE334987T1 (es) |
| AU (1) | AU2003215584A1 (es) |
| BR (1) | BR0308291A (es) |
| CA (1) | CA2478600A1 (es) |
| DE (1) | DE60307239D1 (es) |
| HR (1) | HRP20040927A2 (es) |
| IL (1) | IL163870A0 (es) |
| MX (1) | MXPA04008638A (es) |
| NZ (1) | NZ535084A (es) |
| PL (1) | PL372341A1 (es) |
| RU (1) | RU2004130284A (es) |
| TW (1) | TW200400964A (es) |
| WO (1) | WO2003076446A1 (es) |
| YU (1) | YU79304A (es) |
| ZA (1) | ZA200407102B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US8013011B2 (en) * | 2005-10-20 | 2011-09-06 | Epipharm Gmbh | Treatment and prevention of benign pigmented moles (naevi) using artemisinine and the derivatives thereof |
| US8431611B2 (en) | 2006-10-20 | 2013-04-30 | Johns Hopkins University | Artemisinin derivatives |
| EP2219643B1 (en) * | 2007-11-15 | 2012-05-16 | Novartis AG | Anthelmintic paste comprising praziquantel, a macrolide lactone, cyclodextrin and a thickener |
| 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 |
| CN102010422B (zh) * | 2010-11-23 | 2014-11-26 | 沈阳药科大学 | 含有胍基的青蒿素类衍生物及其应用 |
| US8232417B1 (en) | 2010-12-01 | 2012-07-31 | Bioderm Research | Artemisinin derivatives with natural amino acids, peptides, and amino sugars for skin imperfections and infection in mammals |
| CN103183682B (zh) * | 2011-12-31 | 2015-10-14 | 沈阳药科大学 | C-10位脲基取代的青蒿素衍生物及其制备方法和用途 |
| WO2013157005A1 (en) * | 2012-04-18 | 2013-10-24 | The Hong Kong University Of Science And Technology | Methods and compositions for treating viral infections |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995003311A1 (fr) * | 1993-07-19 | 1995-02-02 | Xuande Luo | Derives de qinghaosu utilises pour lutter contre le sida |
| CA2337119A1 (en) * | 1998-07-14 | 2000-01-27 | Richard K. Haynes | Antiparasitic artemisinin derivatives (endoperoxides) |
| EP0974594A1 (en) * | 1998-07-14 | 2000-01-26 | The Hong Kong University of Science & Technology | Artemisinin derivatives as anti-infective agent |
-
2003
- 2003-02-24 DE DE60307239T patent/DE60307239D1/de not_active Expired - Lifetime
- 2003-02-24 MX MXPA04008638A patent/MXPA04008638A/es unknown
- 2003-02-24 WO PCT/EP2003/001839 patent/WO2003076446A1/en active IP Right Grant
- 2003-02-24 KR KR10-2004-7013999A patent/KR20040104493A/ko not_active Application Discontinuation
- 2003-02-24 EP EP03743815A patent/EP1485389B1/en not_active Expired - Lifetime
- 2003-02-24 PL PL03372341A patent/PL372341A1/xx not_active Application Discontinuation
- 2003-02-24 NZ NZ535084A patent/NZ535084A/en unknown
- 2003-02-24 AU AU2003215584A patent/AU2003215584A1/en not_active Abandoned
- 2003-02-24 US US10/506,926 patent/US20050119232A1/en not_active Abandoned
- 2003-02-24 JP JP2003574662A patent/JP2005526073A/ja active Pending
- 2003-02-24 YU YU79304A patent/YU79304A/sh unknown
- 2003-02-24 BR BR0308291-1A patent/BR0308291A/pt not_active IP Right Cessation
- 2003-02-24 CN CNA038095998A patent/CN1649874A/zh active Pending
- 2003-02-24 IL IL16387003A patent/IL163870A0/xx unknown
- 2003-02-24 RU RU2004130284/04A patent/RU2004130284A/ru not_active Application Discontinuation
- 2003-02-24 AT AT03743815T patent/ATE334987T1/de not_active IP Right Cessation
- 2003-02-24 CA CA002478600A patent/CA2478600A1/en not_active Abandoned
- 2003-02-26 AR ARP030100629A patent/AR038842A1/es unknown
- 2003-03-07 TW TW092104875A patent/TW200400964A/zh unknown
-
2004
- 2004-09-06 ZA ZA200407102A patent/ZA200407102B/en unknown
- 2004-10-06 HR HR20040927A patent/HRP20040927A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200407102B (en) | 2005-09-06 |
| WO2003076446A8 (en) | 2004-10-07 |
| US20050119232A1 (en) | 2005-06-02 |
| JP2005526073A (ja) | 2005-09-02 |
| BR0308291A (pt) | 2005-01-11 |
| YU79304A (sh) | 2006-08-17 |
| CN1649874A (zh) | 2005-08-03 |
| RU2004130284A (ru) | 2005-05-10 |
| MXPA04008638A (es) | 2005-04-19 |
| AR038842A1 (es) | 2005-01-26 |
| AU2003215584A1 (en) | 2003-09-22 |
| WO2003076446A1 (en) | 2003-09-18 |
| IL163870A0 (en) | 2005-12-18 |
| EP1485389A1 (en) | 2004-12-15 |
| ATE334987T1 (de) | 2006-08-15 |
| PL372341A1 (en) | 2005-07-11 |
| CA2478600A1 (en) | 2003-09-18 |
| NZ535084A (en) | 2006-05-26 |
| DE60307239D1 (de) | 2006-09-14 |
| EP1485389B1 (en) | 2006-08-02 |
| KR20040104493A (ko) | 2004-12-10 |
| TW200400964A (en) | 2004-01-16 |
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| ODBC | Application rejected |