GB1379410A - 1-beta-d-arabino-furanosyl-n4-alpha-aminoacylcytosines - Google Patents



Publication number
GB1379410A GB2065572A GB2065572A GB1379410A GB 1379410 A GB1379410 A GB 1379410A GB 2065572 A GB2065572 A GB 2065572A GB 2065572 A GB2065572 A GB 2065572A GB 1379410 A GB1379410 A GB 1379410A
United Kingdom
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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.)
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Upjohn Co
Original Assignee
Upjohn Co
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Priority to US15091871A priority Critical
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB1379410A publication Critical patent/GB1379410A/en
Application status is Expired legal-status Critical



    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals


1379410 1 - (# - D - arabino - furanosyl) - N<SP>4</SP>- α-aminoacylcyptosines UPJOHN CO 3 May 1972 [8 June 1971] 20655/72 Heading C2C Novel compounds I and their acid addition salts in which R 1 and R 2 are hydrogen or an acyl group having up to twenty-one C atoms, Y is hydrogen, halogen, C 1-4 alkyl, C 1-4 hydroxyalkyl or C 1-4 haloalkyl and R 3 is an α-aminoacyl group comprising a single α-amino acid or up to ten α-aminoacids linked as peptides are prepared by reaction of a 1-(3<SP>1</SP>-O- and/or 5-O- blocked - # - D - arabinofuranosyl) cytosine protonate with an appropriately protected α- aminoacid, peptide or polypeptide in the presence of a peptide-bond forming agent preferably dicylohexylcarbodiimide, tetra-ethyl pyrophosphite or carbonyldiimidazole. In the compounds prepared R 2 is hydrogen, R 1 is a carboxylic acyl group chosen from palmitoyl, benzoyl, toluoyl, chlorobenzoyl anisoyl, acetyl propionyl, butyryl tetradecyl, eicosyl trifluoroacetyl, ethoxyacetyl, phenylacetyl, adamantoyl or cyclohexanecarbonyl, Y is hydrogen, iodine, methyl or trifluoromethyl; the α-aminoacyl group comprises glycine and arginine or glycine and phenylalanine and a single α-amino acyl group attached to the 4-nitrogen of cytosine is valine, phenylalanine, arginine, lysine or serine. 5<SP>1</SP>-O-blocked-cytarabine starting compounds are prepared by protecting the 4-amino group with a #,#,#-trihaloethoxy carbonyl halide, substituting in the 5<SP>1</SP>-position and removing the blocking group. 3<SP>1</SP>,5<SP>1</SP>-O-blocked cytarabines are prepared by acylation, using two molar equivalents of acid anhydride or halide, of protonated cytarabine or by acylation of protonated 2,2<SP>1</SP>-cyclo-cytarabine. Compounds I are active against neo-plastic cells and viruses and are also immunosuppressants and they form with a carrier a pharmaceutical preparation which may be administered orally, parenterally or topically.
GB2065572A 1971-06-08 1972-05-03 1-beta-d-arabino-furanosyl-n4-alpha-aminoacylcytosines Expired GB1379410A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US15091871A true 1971-06-08 1971-06-08

Publications (1)

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GB1379410A true GB1379410A (en) 1975-01-02



Family Applications (1)

Application Number Title Priority Date Filing Date
GB2065572A Expired GB1379410A (en) 1971-06-08 1972-05-03 1-beta-d-arabino-furanosyl-n4-alpha-aminoacylcytosines

Country Status (4)

Country Link
JP (1) JPS5624000B1 (en)
DE (1) DE2227373A1 (en)
FR (1) FR2140526B1 (en)
GB (1) GB1379410A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1327358C (en) * 1987-11-17 1994-03-01 Morio Fujiu Fluoro cytidine derivatives

Also Published As

Publication number Publication date
JPS5624000B1 (en) 1981-06-03
FR2140526B1 (en) 1976-04-16
DE2227373A1 (en) 1972-12-28
FR2140526A1 (en) 1973-01-19

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee