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

1-beta-d-arabino-furanosyl-n4-alpha-aminoacylcytosines

Info

Publication number
GB1379410A
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
Authority
GB
United Kingdom
Prior art keywords
sp
lt
gt
α
hydrogen
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
GB2065572A
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.)
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
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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • 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

Abstract

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)

Publication Number Publication Date
GB1379410A true GB1379410A (en) 1975-01-02

Family

ID=22536544

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