Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
  • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
  • C07D495/18—Bridged systems
• • 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
  • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
• • 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
• • 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
  • A61P31/04—Antibacterial agents
• • 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
• • 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
  • A61P35/00—Antineoplastic agents
  • A61P35/04—Antineoplastic agents specific for metastasis
• • 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

Definitions

• R is NH-R 2 residue and R 2 is selected from H, or alkyl, cycloalkyl or aryl groups free or containing one of a variety of functional groups such as COOH, OH or NH 2 or derivatives thereof are prepared by reacting the ketone dimer from dihydroxy acetone with NH 2 ⁇ R2 (where R 2 is the appropriate substituent) and sodium cyanoborohydride or sodium triacetoxyborohydride, followed by purification of the reaction mixture to separate the purified amine.
• R is R4 residue and where R 3 is an alkyl, cycloalkyl or aryl residue with acidic functional group (such as COOH), a sulfate (SO 3 H), a phosphate (PO 3 H 2 ) ester, or basic functionality (such as primary, secondary or tertiary amine) and R 4 is H; OR where R 3 is H and R 4 is an alkyl, cycloalkyl or aryl residue with acidic or basic functionality; OR where R 4 is H and R 3 is an ester or carbamate residue, such residue might be containing functional groups such as COOH, OH, amino, or sugar moiety, are prepared by reacting the ketone dimer from dihydroxy acetone with the proper nucleophile or by first reducing the ketone dimer with sodium borohydride followed by reacting the resulting alcohol with the proper reagent to produce the desired product.
• acidic functional group such as COOH
• SO 3 H sulfate
• PO 3 H 2 phosphate
• R 5 is N-OR-) residue and R] is selected from H, or alkyl, cycloalkyl or aryl groups free or containing one of a variety of functional groups such as COOH, OH or NH or derivatives thereof are prepared by reacting the ketone dimer of dihydroxy acetone and dihydroartemisitene with NH 2 ⁇ ° ⁇ R 1 (where Ri is the appropriate substituent) under basic conditions followed by purification of the reaction mixture to separate the purified oxime.
• R is H 0-R 3 -CH 2 -C-CH 2 - , or -CH 2 -C-CH 2 - , or -CH 2 -C-CH 2 - N-ORi NH-R 2 R 4 where R 1 is H or alkyl, cycloalkyl or aryl moiety, free or containing one of a variety of functional groups such as COOH, OH, NH or derivatives thereof; where R 2 is H or alkyl, cycloalkyl or aryl moiety, free or containing one of a variety of functional groups such as COOH, OH, NH or derivatives thereof; where R 3 is an alkyl, cycloalkyl or aryl residue with acidic functional group such as COOH, a sulfate (SO 3 H), a phosphate (PO 3 H 2 ) ester or basic functionality (such as primary, secondary or tertiary amine) and R 4 is H; OR where R 3 is H and R 4 is an alkyl
• the dosage unit for a particular patient can be readily determined by the medical practitioner in accordance with the techniques known in the medical arts.
• the compounds of this invention have been prepared by reaction of dihydroartemisinin or dihydroartemisitene with dihydroxy acetone to produce the dimeric ketone under acidic conditions (borontrifluoride etherate) in dry ether followed by subsequent functionalization of the purified ketone dimer to produce the desired product.

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (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)
• General Chemical & Material Sciences (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Tropical Medicine & Parasitology (AREA)
• Oncology (AREA)
• Communicable Diseases (AREA)
• Epidemiology (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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• 2005
  • 2005-06-21 CA CA2570961A patent/CA2570961C/en not_active Expired - Fee Related
  • 2005-06-21 EP EP05762351.4A patent/EP1753419B1/en not_active Expired - Lifetime
  • 2005-06-21 AU AU2005258005A patent/AU2005258005B2/en not_active Ceased
  • 2005-06-21 MX MXPA06015060A patent/MXPA06015060A/es active IP Right Grant
  • 2005-06-21 US US11/570,652 patent/US7842720B2/en not_active Expired - Fee Related
  • 2005-06-21 JP JP2007518185A patent/JP5140416B2/ja not_active Expired - Fee Related
  • 2005-06-21 WO PCT/US2005/021826 patent/WO2006002105A1/en not_active Ceased

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