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YU15195A - PROCEDURE FOR OBTAINING 2-BETA-D-RIBOFURANOSYLSELENAZOLE-4-CARBOXIAMIDE - Google Patents

PROCEDURE FOR OBTAINING 2-BETA-D-RIBOFURANOSYLSELENAZOLE-4-CARBOXIAMIDE

Info

Publication number
YU15195A
YU15195A YU15195A YU15195A YU15195A YU 15195 A YU15195 A YU 15195A YU 15195 A YU15195 A YU 15195A YU 15195 A YU15195 A YU 15195A YU 15195 A YU15195 A YU 15195A
Authority
YU
Yugoslavia
Prior art keywords
beta
ribofuranosylselenazole
selenazofurine
anhydro
synthesis
Prior art date
Application number
YU15195A
Other languages
Serbo-Croatian (sh)
Other versions
YU49442B (en
Inventor
Vjera dr. Pejanović
Jadranka Vojimirović
Original Assignee
Ad Icn Jugoslavija
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 Ad Icn Jugoslavija filed Critical Ad Icn Jugoslavija
Priority to YU15195A priority Critical patent/YU49442B/en
Priority to US08/603,106 priority patent/US5907036A/en
Priority to AU52980/96A priority patent/AU5298096A/en
Priority to PCT/US1996/002512 priority patent/WO1996026212A1/en
Priority to EP96909514A priority patent/EP0804447A1/en
Priority to SK1202-97A priority patent/SK120297A3/en
Publication of YU15195A publication Critical patent/YU15195A/en
Publication of YU49442B publication Critical patent/YU49442B/en

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  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cilj pronalaska je dobijanje, na nov način, 2-beta-D-ribofuranozilselenazol-4-karboksiamida (selenazofurina) za koji je utvrđena značajna antitumorska aktivnost kod životinja i širok spektar antiviralne aktivnosti na ćelijskim kulturama. Postupkom prema pronalasku je opisan nov put sinteze etil 2-beta-D-ribofuranozilselenazol-4-karboksilata, intermedijera u sintezi selenazofurina, iz metil-2,5-anhidro-D-alonimidata, čime se obezbeđuje ekonomičniji postupak i znatno veći prinos finalnog proizvoda - selenazofurina. Postupak se sastoji u sintezi metil-2,5-anhidro-D-alonimidata, koji se dobija baznom metanolizom 2,3-anhidro-3,4,6-tri-O-benzoil-beta-D-alononitrila, a koji sa gasovitim vodonik selenidom daje 2,5-anhidro-D-alonselenoamid, koji se ne izoluje nego in situ reaguje sa etil-alfa-bromopiruvatom dajući etil-2-beta-D-ribofuranozilselenazol-4-karboksilat koji amonolizom prelazi u 2-beta-D-ribofuranozilselenazol-4-karboksiamid-selenazofurin.The aim of the invention is to provide, in a novel way, 2-beta-D-ribofuranosylselenazole-4-carboxamide (selenazofurine), which has been shown to have significant antitumor activity in animals and a wide range of antiviral activity on cell cultures. The process of the invention describes a novel route for the synthesis of ethyl 2-beta-D-ribofuranosylselenazole-4-carboxylate, an intermediate in the synthesis of selenazofurine from methyl-2,5-anhydro-D-alonimidate, thereby providing a more economical process and a significantly higher yield of the final product - selenazofurine. The process consists in the synthesis of methyl-2,5-anhydro-D-alonimidate, obtained by basic methanolysis of 2,3-anhydro-3,4,6-tri-O-benzoyl-beta-D-alononitrile, which is gaseous hydrogen selenide gives 2,5-anhydro-D-allonselenoamide, which is not isolated but reacted in situ with ethyl alpha-bromopyruvate to give ethyl 2-beta-D-ribofuranosylselenazole-4-carboxylate which by ammonolysis is converted to 2-beta-D -ribofuranosylselenazole-4-carboxamide-selenazofurine.

YU15195A 1995-02-17 1995-03-07 PROCESS FOR OBTAINING 2-β-D-RIBOFURANOSYLSELENOAZOLE-4-CARBOXYLAMIDE YU49442B (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
YU15195A YU49442B (en) 1995-03-07 1995-03-07 PROCESS FOR OBTAINING 2-β-D-RIBOFURANOSYLSELENOAZOLE-4-CARBOXYLAMIDE
US08/603,106 US5907036A (en) 1995-02-17 1996-02-20 Procedures for obtaining ribo-C-nucleosides
AU52980/96A AU5298096A (en) 1995-02-17 1996-02-20 Procedures for obtaining ribo-c-nucleosides
PCT/US1996/002512 WO1996026212A1 (en) 1995-02-17 1996-02-20 Procedures for obtaining ribo-c-nucleosides
EP96909514A EP0804447A1 (en) 1995-03-07 1996-02-20 Procedures for obtaining ribo-c-nucleosides
SK1202-97A SK120297A3 (en) 1995-03-07 1996-02-20 Procedures for obtaining ribo-c-nucleosides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
YU15195A YU49442B (en) 1995-03-07 1995-03-07 PROCESS FOR OBTAINING 2-β-D-RIBOFURANOSYLSELENOAZOLE-4-CARBOXYLAMIDE

Publications (2)

Publication Number Publication Date
YU15195A true YU15195A (en) 1998-07-10
YU49442B YU49442B (en) 2006-03-03

Family

ID=25548578

Family Applications (1)

Application Number Title Priority Date Filing Date
YU15195A YU49442B (en) 1995-02-17 1995-03-07 PROCESS FOR OBTAINING 2-β-D-RIBOFURANOSYLSELENOAZOLE-4-CARBOXYLAMIDE

Country Status (3)

Country Link
EP (1) EP0804447A1 (en)
SK (1) SK120297A3 (en)
YU (1) YU49442B (en)

Also Published As

Publication number Publication date
YU49442B (en) 2006-03-03
SK120297A3 (en) 1998-01-14
EP0804447A1 (en) 1997-11-05

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