DE1178438B - Verfahren zur Herstellung von bakterizid wirksamen, alkylierten 6-(5'-Nitro-2'-furyl)-as-triazin-3,5(4H)-dionen - Google Patents
Verfahren zur Herstellung von bakterizid wirksamen, alkylierten 6-(5'-Nitro-2'-furyl)-as-triazin-3,5(4H)-dionenInfo
- Publication number
- DE1178438B DE1178438B DEN22771A DEN0022771A DE1178438B DE 1178438 B DE1178438 B DE 1178438B DE N22771 A DEN22771 A DE N22771A DE N0022771 A DEN0022771 A DE N0022771A DE 1178438 B DE1178438 B DE 1178438B
- Authority
- DE
- Germany
- Prior art keywords
- furyl
- triazine
- nitro
- alkylated
- diones
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IXVPCJUAKDVYKX-UHFFFAOYSA-N 2-(furan-2-yl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=CO1 IXVPCJUAKDVYKX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- -1 alkyl semicarbazones Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- KMCMZQBYRXQEQH-UHFFFAOYSA-N 1-amino-1,3-dimethylurea Chemical compound CNC(=O)N(C)N KMCMZQBYRXQEQH-UHFFFAOYSA-N 0.000 description 1
- DOORGKNGFZOACY-UHFFFAOYSA-N 1-amino-1-methylurea Chemical compound CN(N)C(N)=O DOORGKNGFZOACY-UHFFFAOYSA-N 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- 241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 206010041925 Staphylococcal infections Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18448962A | 1962-04-02 | 1962-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1178438B true DE1178438B (de) | 1964-09-24 |
Family
ID=22677087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN22771A Pending DE1178438B (de) | 1962-04-02 | 1963-02-19 | Verfahren zur Herstellung von bakterizid wirksamen, alkylierten 6-(5'-Nitro-2'-furyl)-as-triazin-3,5(4H)-dionen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE630437A (en, 2012) |
| BR (1) | BR6348139D0 (en, 2012) |
| CH (1) | CH417616A (en, 2012) |
| DE (1) | DE1178438B (en, 2012) |
| ES (1) | ES286658A1 (en, 2012) |
| FR (1) | FR2510M (en, 2012) |
| GB (1) | GB1004287A (en, 2012) |
| NL (1) | NL291026A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235931B (de) * | 1965-02-26 | 1967-03-09 | Norwich Pharma Co | Verfahren zur Herstellung des antimikrobiell wirksamen 2-Methyl-6-(5-nitro-2-furyl)-3-thio-as-triazin-3, 5(4H)-dions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4125719A (en) * | 1977-08-01 | 1978-11-14 | Merck & Co., Inc. | 1,3,5-S-Hexahydrotrisubstituted triazines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT217463B (de) * | 1960-02-23 | 1961-10-10 | Norwich Pharma Co | Verfahren zur Herstellung des neuen 6-(5'-Nitro-2'-furyl)-azauracils |
-
0
- NL NL291026D patent/NL291026A/xx unknown
- BE BE630437D patent/BE630437A/xx unknown
-
1963
- 1963-02-19 DE DEN22771A patent/DE1178438B/de active Pending
- 1963-03-27 CH CH386263A patent/CH417616A/de unknown
- 1963-03-28 GB GB12285/63A patent/GB1004287A/en not_active Expired
- 1963-04-02 FR FR930137A patent/FR2510M/fr active Active
- 1963-04-02 ES ES286658A patent/ES286658A1/es not_active Expired
- 1963-04-02 BR BR14813963A patent/BR6348139D0/pt unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT217463B (de) * | 1960-02-23 | 1961-10-10 | Norwich Pharma Co | Verfahren zur Herstellung des neuen 6-(5'-Nitro-2'-furyl)-azauracils |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235931B (de) * | 1965-02-26 | 1967-03-09 | Norwich Pharma Co | Verfahren zur Herstellung des antimikrobiell wirksamen 2-Methyl-6-(5-nitro-2-furyl)-3-thio-as-triazin-3, 5(4H)-dions |
Also Published As
| Publication number | Publication date |
|---|---|
| ES286658A1 (es) | 1963-07-01 |
| GB1004287A (en) | 1965-09-15 |
| BE630437A (en, 2012) | |
| BR6348139D0 (pt) | 1973-07-03 |
| NL291026A (en, 2012) | |
| FR2510M (fr) | 1964-05-04 |
| CH417616A (de) | 1966-07-31 |
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