EA200000350A1 - METHOD OF OBTAINING 3-ARYLOXY, 4-ARYLFURAN-2-ONES, USEFUL AS A CYCLOOXYGENASE-2 INHIBITORS - Google Patents

METHOD OF OBTAINING 3-ARYLOXY, 4-ARYLFURAN-2-ONES, USEFUL AS A CYCLOOXYGENASE-2 INHIBITORS

Info

Publication number
EA200000350A1
EA200000350A1 EA200000350A EA200000350A EA200000350A1 EA 200000350 A1 EA200000350 A1 EA 200000350A1 EA 200000350 A EA200000350 A EA 200000350A EA 200000350 A EA200000350 A EA 200000350A EA 200000350 A1 EA200000350 A1 EA 200000350A1
Authority
EA
Eurasian Patent Office
Prior art keywords
useful
obtaining
cyclooxygenase
inhibitors
ones
Prior art date
Application number
EA200000350A
Other languages
Russian (ru)
Other versions
EA002690B1 (en
Inventor
Ченг Й. Чен
Роберт Д. Ларсен
Луши Тан
Original Assignee
Мерк Энд Ко., Инк.
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
Priority claimed from GBGB9815805.8A external-priority patent/GB9815805D0/en
Application filed by Мерк Энд Ко., Инк. filed Critical Мерк Энд Ко., Инк.
Publication of EA200000350A1 publication Critical patent/EA200000350A1/en
Publication of EA002690B1 publication Critical patent/EA002690B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Описан способ получения 3-арил, 4-арилоксифуран-5-онов, которые являются полезными в качестве ингибиторов циклооксигеназы-2 (COX-2). Такие соединения являются полезными в качестве противовоспалительных агентов. Способ направлен на асимметричный синтез, который включает: получение тризамещенных производных стирола реакцией Хорнера-Ведсворта-Эммонса с последующим в одном сосуде трифторметилированием аллилового спирта; получение α-гидроксикетона с использованием асимметричного дигидроксилирования Шарплесса и окисления Сверна; эстерификацию α-гидроксикетона феноксиуксусной кислотой и конденсацию Дайкмана полученного в результате сложного эфира.Международная заявка была опубликована вместе с отчетом о международном поиске.A method for producing 3-aryl, 4-aryloxyfuran-5-ones, which are useful as inhibitors of cyclooxygenase-2 (COX-2), is described. Such compounds are useful as anti-inflammatory agents. The method is aimed at asymmetric synthesis, which includes: obtaining trisubstituted derivatives of styrene by the Horner-Westsworth-Emmons reaction followed by trifluoromethylation of allyl alcohol in one vessel; obtaining α-hydroxyketone using asymmetric Sharpless dihydroxylation and Swern oxidation; esterification of α-hydroxyketone with phenoxyacetic acid and Dyckman condensation of the resulting ester. The international application was published together with an international search report.

EA200000350A 1997-09-24 1998-09-21 Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhibitors of cox-2 EA002690B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6069497P 1997-09-24 1997-09-24
GBGB9815805.8A GB9815805D0 (en) 1998-07-21 1998-07-21 Chemical process
PCT/US1998/019642 WO1999015513A1 (en) 1997-09-24 1998-09-21 Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhibitors of cox-2

Publications (2)

Publication Number Publication Date
EA200000350A1 true EA200000350A1 (en) 2000-10-30
EA002690B1 EA002690B1 (en) 2002-08-29

Family

ID=26314074

Family Applications (1)

Application Number Title Priority Date Filing Date
EA200000350A EA002690B1 (en) 1997-09-24 1998-09-21 Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhibitors of cox-2

Country Status (7)

Country Link
EP (1) EP1017687A4 (en)
JP (1) JP3516658B2 (en)
CN (1) CN1271352A (en)
AU (1) AU2247599A (en)
EA (1) EA002690B1 (en)
SK (1) SK4202000A3 (en)
WO (1) WO1999015513A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2001232175B2 (en) 2000-03-03 2005-07-07 Pfizer Products Inc. Pyrazole ether derivatives as anti-inflammatory/analgesic agents
HUP0302068A3 (en) 2000-07-20 2005-05-30 Lauras As Use of cox-2 inhibitors for treating or preventing immunodeficiency and pharmaceutical compositions containing them

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5352832A (en) * 1992-12-18 1994-10-04 Schering Corporation Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates
US5393790A (en) * 1994-02-10 1995-02-28 G.D. Searle & Co. Substituted spiro compounds for the treatment of inflammation
UA57002C2 (en) * 1995-10-13 2003-06-16 Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі. (methylsulfonyl)phenyl-2-(5n)-furanon derivative, a pharmaceutical composition and a method for treatment
US5789413A (en) * 1996-02-01 1998-08-04 Merck Frosst Canada, Inc. Alkylated styrenes as prodrugs to COX-2 inhibitors

Also Published As

Publication number Publication date
EP1017687A1 (en) 2000-07-12
JP2001517661A (en) 2001-10-09
WO1999015513A1 (en) 1999-04-01
SK4202000A3 (en) 2000-10-09
AU2247599A (en) 1999-04-12
EP1017687A4 (en) 2001-10-31
JP3516658B2 (en) 2004-04-05
EA002690B1 (en) 2002-08-29
CN1271352A (en) 2000-10-25

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Legal Events

Date Code Title Description
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ BY KZ KG MD TJ TM RU