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WO1988004660A3 - Synthesis process and oxygen-containing heterocyclic products thereof - Google Patents

Synthesis process and oxygen-containing heterocyclic products thereof Download PDF

Info

Publication number
WO1988004660A3
WO1988004660A3 PCT/US1987/003330 US8703330W WO8804660A3 WO 1988004660 A3 WO1988004660 A3 WO 1988004660A3 US 8703330 W US8703330 W US 8703330W WO 8804660 A3 WO8804660 A3 WO 8804660A3
Authority
WO
WIPO (PCT)
Prior art keywords
oxygen
containing heterocyclic
synthesis process
heterocyclic products
products
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.)
Ceased
Application number
PCT/US1987/003330
Other languages
French (fr)
Other versions
WO1988004660A2 (en
Inventor
Mitchell A Avery
Clive Jennings-White
Wesley K M Chong
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SRI International Inc
Original Assignee
SRI International Inc
Stanford Research Institute
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by SRI International Inc, Stanford Research Institute filed Critical SRI International Inc
Priority to GB8818816A priority Critical patent/GB2218088B/en
Publication of WO1988004660A2 publication Critical patent/WO1988004660A2/en
Publication of WO1988004660A3 publication Critical patent/WO1988004660A3/en
Anticipated expiration legal-status Critical
Priority to SE9000377A priority patent/SE9000377L/en
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A process for synthesizing oxygen-containing analogs of the antimalarial agent known as quinghaosu or artemisinin, and in particular compounds of formulae (I) and (II). The process employs as a reactant a vinylsilane that is subjected to an ozonolysis/acidification step which closes the oxygen-containing ring structure. The various products are claimed as aspects of this invention as is their use as antimalarials.
PCT/US1987/003330 1986-12-18 1987-12-15 Synthesis process and oxygen-containing heterocyclic products thereof Ceased WO1988004660A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB8818816A GB2218088B (en) 1986-12-18 1987-12-15 Synthesis process and oxygen-containing heterocyclic products thereof
SE9000377A SE9000377L (en) 1986-12-18 1990-02-02 SYNTHETIC PROCEDURE AND ACID CONTENT HETEROCYCLIC PRODUCT THEREOF

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US94355586A 1986-12-18 1986-12-18
US943,555 1986-12-18
US10814587A 1987-10-13 1987-10-13
US10813887A 1987-10-13 1987-10-13
US108,138 1987-10-13
US108,145 1987-10-13

Publications (2)

Publication Number Publication Date
WO1988004660A2 WO1988004660A2 (en) 1988-06-30
WO1988004660A3 true WO1988004660A3 (en) 1988-08-11

Family

ID=27380423

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1987/003330 Ceased WO1988004660A2 (en) 1986-12-18 1987-12-15 Synthesis process and oxygen-containing heterocyclic products thereof

Country Status (7)

Country Link
EP (1) EP0346356A1 (en)
JP (1) JPH01501710A (en)
CH (1) CH679486A5 (en)
DE (1) DE3790698T1 (en)
GB (1) GB2218088B (en)
SE (2) SE8802906L (en)
WO (1) WO1988004660A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8807523D0 (en) * 1988-03-30 1988-05-05 Jefford C W 1,2,4-trioxanes related to arteannuin
US5216175A (en) * 1990-03-23 1993-06-01 Sri International Antimalarial analogs of artemisinin
TW198722B (en) * 1990-05-07 1993-01-21 Hoechst Ag
JPH07500325A (en) * 1991-10-14 1995-01-12 ザ ユニバーシティ オブ シドニー Cyclic peroxyacetal compound
US6160004A (en) * 1997-12-30 2000-12-12 Hauser, Inc. C-10 carbon-substituted artemisinin-like trioxane compounds having antimalarial, antiproliferative and antitumor activities
EP0974593A1 (en) * 1998-07-14 2000-01-26 The Hong Kong University of Science & Technology Artemisinin derivatives as antiparasitic agents

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, volume 102, no. 9, 04 March 1985, (Columbus, Ohio, US), X. Luo et al.: "Detection of metabolites of Qing Hao Sau in nanomolar quantities: DADF-esters of dihyaroQing Hao Sau and its epoxy analog. The chamistry of drugs. V.", see page 12, abstract 72313b, & Heterocycles 1984, 22(11), 2559-62 *
Chemical Abstracts, volume 105, no. 3, 21 July 1986, (Columbus, Ohio, US), P. Yu et al.: "Analogs of Qing Hao Su (artemisinin, arteannuin). IV. Synthesis of derivatives of Qing Hao Su containing halogen, nitrogen, and sulfur heteroatoms", see page 658, abstract 24454p, & Yaoxue Xuebao 1985, 20(5), 357-65 *
Chemical Abstracts, volume 97, no. 11, 13 September 1982, (Columbus, Ohio, US). Y. Li et al.: "Studies on artemisinine analogs. I. Sythesis of ethers, carboxylates and carbonates of dihydroartemisinine", see page 768, abstract 92245n, & Yaoxue Xuebao 1981, 16(6), 429-39 *

Also Published As

Publication number Publication date
JPH01501710A (en) 1989-06-15
GB2218088B (en) 1991-07-10
SE8802906D0 (en) 1988-08-16
DE3790698T1 (en) 1988-12-08
EP0346356A1 (en) 1989-12-20
SE8802906L (en) 1988-08-16
SE9000377D0 (en) 1990-02-02
CH679486A5 (en) 1992-02-28
WO1988004660A2 (en) 1988-06-30
GB8818816D0 (en) 1988-10-05
SE9000377L (en) 1991-08-03
GB2218088A (en) 1989-11-08

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