GB1376437A - Nucleoside derivatives and the preparation thereof - Google Patents

Nucleoside derivatives and the preparation thereof

Info

Publication number
GB1376437A
GB1376437A GB5442671A GB5442671A GB1376437A GB 1376437 A GB1376437 A GB 1376437A GB 5442671 A GB5442671 A GB 5442671A GB 5442671 A GB5442671 A GB 5442671A GB 1376437 A GB1376437 A GB 1376437A
Authority
GB
United Kingdom
Prior art keywords
pentofuranosyl
thio
azauracils
azauracil
alkanoyloxy
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
GB5442671A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB1376437A publication Critical patent/GB1376437A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07H19/12—Triazine 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

1376437 1-(#-D-pentofuranosyl)-2-thiouracils and -2-thio-6-azauracils UPJOHN CO 23 Nov 1971 [21 Dec 1970] 54426/71 Heading C2C Novel 1-(2- or 3-dioxy-#-D-pentofuranosyl)- 2-thiouracils and 1-#-D-pentofuranosyl- 2-thio-6-azauracils (other than 1-#-D-ribofuranosyl- and 1-#-D-(2,3,5-tri-O-benzoyl)- ribofuranocyl-2-thio-6-azauracils) of general Formula I where M is hydrogen, a C 1-4 alkyl, C 1-3 hydroxyalkyl, C 2-5 alkoxymethyl or alkanoic acid esters of hydroxyalkyl having a total of 3 to 6 C atoms, X is =CH- or =N-, Y is hydroxy, C 1-4 alkanoyloxy or C 7-8 aroyl and Z, Z<SP>a</SP>, Z<SP>b</SP> and Z<SP>c</SP> are hydrogen, hydroxyl, C 1-4 alkanoyloxy or C 7-8 aroyloxy provided that at least one but no more than two are selected from hydroxyl, alkanoyloxy and aroyloxy are prepared by reacting a (2,5<SP>1</SP>-anhydro-1-#-D-pentofuranosyl) uracil or -6-azauracil nucleoside having the substituents M, Z, Z<SP>a</SP>, Z<SP>b</SP> and Z<SP>c</SP> desired in the product with methanol in the presence of an alkali metal alkoxide to produce the corresponding 1-#-D-pentofuranosyl-2-O-methyluracil or 2-O-methyl-6-azauracil respectively and treating the latter with hydrogen sulphide to obtain the 2-thiouracil or 2-thio-6-azauracil respectively. Compounds of Formula I impede replication of viruses and neoplastic cells and form with a carrier a pharmaceutical composition which may be administered orally or parenterally or by infusing into the nuleu containing the virus or neoplastic cells.
GB5442671A 1970-12-21 1971-11-23 Nucleoside derivatives and the preparation thereof Expired GB1376437A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10042370A 1970-12-21 1970-12-21

Publications (1)

Publication Number Publication Date
GB1376437A true GB1376437A (en) 1974-12-04

Family

ID=22279694

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5442671A Expired GB1376437A (en) 1970-12-21 1971-11-23 Nucleoside derivatives and the preparation thereof

Country Status (5)

Country Link
BE (1) BE777053A (en)
DE (1) DE2162616A1 (en)
FR (1) FR2118956B1 (en)
GB (1) GB1376437A (en)
NL (1) NL7117347A (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3463850A (en) * 1967-01-03 1969-08-26 Merck & Co Inc Arabinofuranosyl 2-thiopyrimidines and pharmaceutical compositions thereof
DE1795357A1 (en) * 1968-09-18 1972-01-05 Schering Ag 2-thio-pyrimidine nucleoside
FR2066931A2 (en) * 1970-10-30 1971-08-13 Schering Ag 2-thio -6-aza-uridine derivs

Also Published As

Publication number Publication date
NL7117347A (en) 1972-06-23
FR2118956B1 (en) 1975-10-10
DE2162616A1 (en) 1972-07-13
BE777053A (en) 1972-06-21
FR2118956A1 (en) 1972-08-04

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Legal Events

Date Code Title Description
PS Patent sealed
49S Specification amended (sect. 9/1949)
SPA Amended specification published
PCNP Patent ceased through non-payment of renewal fee