GB1427304A - 1,2,4-triazole-3-carboxamides as antiviral agents - Google Patents

1,2,4-triazole-3-carboxamides as antiviral agents

Info

Publication number
GB1427304A
GB1427304A GB1078374A GB1078374A GB1427304A GB 1427304 A GB1427304 A GB 1427304A GB 1078374 A GB1078374 A GB 1078374A GB 1078374 A GB1078374 A GB 1078374A GB 1427304 A GB1427304 A GB 1427304A
Authority
GB
United Kingdom
Prior art keywords
triazole
carboxamide
yield
prepared
march
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
GB1078374A
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.)
Valeant Pharmaceuticals International Inc USA
Original Assignee
ICN Pharmaceuticals Inc
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 claimed from US340332A external-priority patent/US3927216A/en
Application filed by ICN Pharmaceuticals Inc filed Critical ICN Pharmaceuticals Inc
Publication of GB1427304A publication Critical patent/GB1427304A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • C07H19/056—Triazole or tetrazole radicals
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • C12P19/38—Nucleosides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Zoology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Oncology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)

Abstract

1427304 1,2,4 - Triazole - 3 - carboxamide and derivatives thereof ICN PHARMACEUTICALS Inc 11 March 1974 [12 March 1973] 10783/74 Heading C2C [Also in Division A5] 1 - # - D - Ribofuranosyl - 1,2,4 - triazole - 3- carboxamide is prepared by heating methyl 1,2,4 - triazole carboxylate with aqueous ammonia to yield 1,2,4 - triazole - 3 - carboxamide which is then reacted with the enzyme nucleoside phosphorylase to yield the desired product. The semihydrate of 1,2,4-triazole-3-carboxamide sodium salt is prepared by reacting the 1,2,4- triazole-3-carboxamide with sodium hydroxide. 1,2,4 - Triazole - 3 - thiocarboxamide is prepared by treating a mixture of triethyl orthoformate and 1-cyanoformimidic acid hydrazide with a solution of dioxane saturated with anhydrous hydrogen chloride to yield 3-cyano- 1,2,4-triazole which is then reacted with ethanol, triethylamine and hydrogen sulphide gas to yield the desired product.
GB1078374A 1973-03-12 1974-03-11 1,2,4-triazole-3-carboxamides as antiviral agents Expired GB1427304A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US340332A US3927216A (en) 1971-06-01 1973-03-12 1,2,4-Triazol E-3-carboxamides for inhibiting virus infections

Publications (1)

Publication Number Publication Date
GB1427304A true GB1427304A (en) 1976-03-10

Family

ID=23332899

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1078374A Expired GB1427304A (en) 1973-03-12 1974-03-11 1,2,4-triazole-3-carboxamides as antiviral agents

Country Status (15)

Country Link
JP (2) JPS5836960B2 (en)
AR (1) AR205339A1 (en)
BE (2) BE812191A (en)
CH (1) CH602785A5 (en)
DE (1) DE2411823A1 (en)
ES (1) ES424201A1 (en)
FR (2) FR2221138B1 (en)
GB (1) GB1427304A (en)
IE (1) IE38987B1 (en)
IL (2) IL44394A0 (en)
LU (1) LU69626A1 (en)
NL (1) NL7403289A (en)
NO (1) NO138376C (en)
PH (1) PH12043A (en)
ZA (1) ZA741610B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2940654A1 (en) * 1979-10-06 1981-04-16 Bayer Ag, 5090 Leverkusen DIMERES KETEN OF 1,2 ,, - TRIAZOL-3-CARBONIC ACID
EP0034481B1 (en) * 1980-02-14 1984-05-30 Grigg, Ronald Ernest 2-methyl-5-thiazole-methylamine and carboxamide derivatives
HU185928B (en) * 1980-04-23 1985-04-28 Wellcome Found Process for preparing 4-substituted-1beta-d-ribofuranosyl-1h-imidazo/4,5-c/pyridines
JPS57146593A (en) * 1981-03-09 1982-09-10 Ajinomoto Co Inc Preparation of ribofuranosyltriazole derivative
BE902199A (en) * 1984-10-29 1985-07-31 Vira Tek Inc METHOD OF MEDICAL TREATMENT OF VIRAL DISEASES USING 1-BETA-D-RIBOFURANNOSYL-1, 2,4-TRIAZOLE-3-CARBOXAMIDE.
JPS62165096A (en) * 1986-01-14 1987-07-21 Hitachi Ltd Oil supplying device
WO2009028575A1 (en) 2007-08-27 2009-03-05 National University Corporation Nagoya University Activator for blood coagulation factor vii promoter and utilization of the same
WO2009028573A1 (en) 2007-08-27 2009-03-05 National University Corporation Nagoya University Use of ribavirin in blood coagulation disorder

Also Published As

Publication number Publication date
AR205339A1 (en) 1976-04-30
FR2221138A1 (en) 1974-10-11
CH602785A5 (en) 1978-08-15
ZA741610B (en) 1975-02-26
IL52848A0 (en) 1977-10-31
IE38987B1 (en) 1978-07-05
JPS5029720A (en) 1975-03-25
FR2289520A1 (en) 1976-05-28
ES424201A1 (en) 1976-05-01
AU6670874A (en) 1975-09-18
NL7403289A (en) 1974-09-16
LU69626A1 (en) 1974-08-06
JPS5915886B2 (en) 1984-04-12
NO740841L (en) 1974-09-13
PH12043A (en) 1978-10-18
BE903675Q (en) 1986-05-20
DE2411823A1 (en) 1974-09-26
JPS5836960B2 (en) 1983-08-12
NO138376B (en) 1978-05-16
NO138376C (en) 1978-08-23
IL44394A0 (en) 1974-06-30
JPS58219115A (en) 1983-12-20
FR2221138B1 (en) 1978-07-28
BE812191A (en) 1974-07-01
IE38987L (en) 1974-09-12
FR2289520B1 (en) 1978-05-12

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee
728C Application made for restoration (sect. 28/1977)
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
728A Order made restoring the patent (sect. 28/1977)
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee