GB1427304A - 1,2,4-triazole-3-carboxamides as antiviral agents - Google Patents
1,2,4-triazole-3-carboxamides as antiviral agentsInfo
- 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
Links
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical class NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 title abstract 4
- 239000003443 antiviral agent Substances 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- GUQHFZFTGHNVDG-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carbonitrile Chemical compound N#CC1=NC=NN1 GUQHFZFTGHNVDG-UHFFFAOYSA-N 0.000 abstract 1
- VYJPYFZLFQUVFZ-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carbothioamide Chemical compound NC(=S)C1=NC=NN1 VYJPYFZLFQUVFZ-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 102100036286 Purine nucleoside phosphorylase Human genes 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- QMPFMODFBNEYJH-UHFFFAOYSA-N methyl 1h-1,2,4-triazole-5-carboxylate Chemical compound COC(=O)C1=NC=NN1 QMPFMODFBNEYJH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- RPMBQFASZSFPQD-UHFFFAOYSA-N n'-amino-1-cyanomethanimidamide Chemical compound NNC(=N)C#N RPMBQFASZSFPQD-UHFFFAOYSA-N 0.000 abstract 1
- 108010009099 nucleoside phosphorylase Proteins 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- CGHGUMDRADFZLN-UHFFFAOYSA-M sodium 1H-1,2,4-triazole-5-carbonylazanide Chemical compound [Na+].N1N=C(N=C1)C(=O)[NH-] CGHGUMDRADFZLN-UHFFFAOYSA-M 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
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)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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.
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)
| 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 |
| AU548977B2 (en) * | 1980-04-23 | 1986-01-09 | Wellcome Foundation Limited, The | Method for the preparation of deazapurine nucleosides |
| 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 |
| WO2009028573A1 (en) | 2007-08-27 | 2009-03-05 | National University Corporation Nagoya University | Use of ribavirin in blood coagulation disorder |
| EP2198870A4 (en) | 2007-08-27 | 2011-08-03 | Univ Nagoya Nat Univ Corp | ACTIVATOR FOR BLOOD COAGULATION FACTOR VII PROMOTER AND USE THEREOF |
-
1974
- 1974-01-01 AR AR252737A patent/AR205339A1/en active
- 1974-03-11 GB GB1078374A patent/GB1427304A/en not_active Expired
- 1974-03-11 IE IE00506/74A patent/IE38987B1/en unknown
- 1974-03-11 NO NO740841A patent/NO138376C/en unknown
- 1974-03-11 IL IL44394A patent/IL44394A0/en unknown
- 1974-03-11 FR FR7408233A patent/FR2221138B1/fr not_active Expired
- 1974-03-12 LU LU69626A patent/LU69626A1/xx unknown
- 1974-03-12 BE BE141915A patent/BE812191A/en unknown
- 1974-03-12 CH CH343674A patent/CH602785A5/xx not_active IP Right Cessation
- 1974-03-12 ES ES424201A patent/ES424201A1/en not_active Expired
- 1974-03-12 JP JP49028432A patent/JPS5836960B2/en not_active Expired
- 1974-03-12 ZA ZA00741610A patent/ZA741610B/en unknown
- 1974-03-12 NL NL7403289A patent/NL7403289A/xx not_active Application Discontinuation
- 1974-03-12 PH PH15614A patent/PH12043A/en unknown
- 1974-03-12 DE DE2411823A patent/DE2411823A1/en active Pending
-
1975
- 1975-12-03 FR FR7537057A patent/FR2289520A1/en active Granted
-
1977
- 1977-08-29 IL IL52848A patent/IL52848A0/en unknown
-
1983
- 1983-04-21 JP JP58069292A patent/JPS5915886B2/en not_active Expired
-
1985
- 1985-11-19 BE BE0/215891A patent/BE903675Q/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO740841L (en) | 1974-09-13 |
| JPS58219115A (en) | 1983-12-20 |
| IL52848A0 (en) | 1977-10-31 |
| JPS5836960B2 (en) | 1983-08-12 |
| NO138376B (en) | 1978-05-16 |
| BE903675Q (en) | 1986-05-20 |
| JPS5915886B2 (en) | 1984-04-12 |
| AR205339A1 (en) | 1976-04-30 |
| DE2411823A1 (en) | 1974-09-26 |
| IE38987L (en) | 1974-09-12 |
| FR2221138A1 (en) | 1974-10-11 |
| BE812191A (en) | 1974-07-01 |
| LU69626A1 (en) | 1974-08-06 |
| CH602785A5 (en) | 1978-08-15 |
| FR2289520A1 (en) | 1976-05-28 |
| IL44394A0 (en) | 1974-06-30 |
| IE38987B1 (en) | 1978-07-05 |
| JPS5029720A (en) | 1975-03-25 |
| FR2221138B1 (en) | 1978-07-28 |
| PH12043A (en) | 1978-10-18 |
| FR2289520B1 (en) | 1978-05-12 |
| AU6670874A (en) | 1975-09-18 |
| NL7403289A (en) | 1974-09-16 |
| ES424201A1 (en) | 1976-05-01 |
| NO138376C (en) | 1978-08-23 |
| ZA741610B (en) | 1975-02-26 |
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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 |