GB989455A - Cytosine derivatives and the manufacture thereof - Google Patents

Cytosine derivatives and the manufacture thereof

Info

Publication number
GB989455A
GB989455A GB1706363A GB1706363A GB989455A GB 989455 A GB989455 A GB 989455A GB 1706363 A GB1706363 A GB 1706363A GB 1706363 A GB1706363 A GB 1706363A GB 989455 A GB989455 A GB 989455A
Authority
GB
United Kingdom
Prior art keywords
fluoro
cytosine
deoxy
alpha
monoacyl
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.)
Expired
Application number
GB1706363A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB989455A publication Critical patent/GB989455A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 4-(N-monoacyl) -1-[31,51 - di - (O - aroyl) - 21 - deoxy - D - ribofuranosyl] - 5 - fluoro - cytosines, including their alpha and beta anomeric forms, and a process for their production comprising acylating 5-fluoro-cytosine, treating the resulting 4-(N-monoacyl) - 5 - fluoro - cytosine with a mercury salt, e.g. mercuric chloride or acetate, to form the corresponding monomercury salt, reacting the monomercury salt while suspended in an inert, water-immiscible, organic solvent with a 3,5-diaroyl - 2 - deoxy - D - ribofuranosyl halide to form a mixture containing the alpha and beta anomers of a 4-(N-monoacyl)-1-[31,51-di-(O-aroyl) - 21 - deoxy - D - ribofuranosyl] - 5 - fluoro-cytosine and, if desired, separating the alpha and/or beta anomer from the mixture. The preferred compounds are those in which the 4-monoacyl group is a 4-toluoyl, 4-acetyl or 4-pivaloyl group and the aroyl groups are p-toluoyl groups. Alpha and/or beta anomers of 1-(21-deoxy-D-ribofuranosyl) - 5 - fluoro - cytosine are prepared by alkaline hydrolysis of the alpha and/or beta anomer of a 4-(N - monoacyl) - 1 - [31,51 - di -(O-aroyl) - 21 - deoxy - D - ribofuranosyl] - 5 - fluoro-cytosine. Specification 989,456 is referred to.
GB1706363A 1962-05-01 1963-05-01 Cytosine derivatives and the manufacture thereof Expired GB989455A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US19143862A 1962-05-01 1962-05-01

Publications (1)

Publication Number Publication Date
GB989455A true GB989455A (en) 1965-04-22

Family

ID=22705512

Family Applications (3)

Application Number Title Priority Date Filing Date
GB5220264A Expired GB1002278A (en) 1962-05-01 1963-05-01 Cytidine derivatives and the preparation thereof
GB5220164A Expired GB989456A (en) 1962-05-01 1963-05-01 Cytosine derivatives and the preparation thereof
GB1706363A Expired GB989455A (en) 1962-05-01 1963-05-01 Cytosine derivatives and the manufacture thereof

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB5220264A Expired GB1002278A (en) 1962-05-01 1963-05-01 Cytidine derivatives and the preparation thereof
GB5220164A Expired GB989456A (en) 1962-05-01 1963-05-01 Cytosine derivatives and the preparation thereof

Country Status (6)

Country Link
BR (1) BR6348745D0 (en)
CH (1) CH421973A (en)
DK (1) DK115916B (en)
ES (1) ES287587A1 (en)
FR (1) FR1514917A (en)
GB (3) GB1002278A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110034490A1 (en) * 2009-08-07 2011-02-10 Dow Agrosciences Llc N1-acyl-5-fluoropyrimidinone derivatives
US9271497B2 (en) 2012-12-28 2016-03-01 Dow Agrosciences Llc 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one derivatives
US9321734B2 (en) 2012-12-28 2016-04-26 Dow Agrosciences Llc N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives
US9622474B2 (en) 2012-12-28 2017-04-18 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives
US9642368B2 (en) 2012-12-31 2017-05-09 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110034490A1 (en) * 2009-08-07 2011-02-10 Dow Agrosciences Llc N1-acyl-5-fluoropyrimidinone derivatives
US8470839B2 (en) * 2009-08-07 2013-06-25 Dow Agrosciences, Llc. N1-acyl-5-fluoropyrimidinone derivatives
US9271497B2 (en) 2012-12-28 2016-03-01 Dow Agrosciences Llc 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one derivatives
US9321734B2 (en) 2012-12-28 2016-04-26 Dow Agrosciences Llc N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives
US9622474B2 (en) 2012-12-28 2017-04-18 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives
US9840475B2 (en) 2012-12-28 2017-12-12 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives
US9908855B2 (en) 2012-12-28 2018-03-06 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives
US9642368B2 (en) 2012-12-31 2017-05-09 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
US10059703B2 (en) 2012-12-31 2018-08-28 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides

Also Published As

Publication number Publication date
GB1002278A (en) 1965-08-25
DK115916B (en) 1969-11-24
ES287587A1 (en) 1963-11-01
FR1514917A (en) 1968-03-01
CH421973A (en) 1966-10-15
GB989456A (en) 1965-04-22
BR6348745D0 (en) 1973-07-03

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