DE1185618B - Verfahren zur Herstellung des bakterizid wirksamen 4, 5-Dihydro-6-(5'-nitro-2'-furyl)-as-triazin-3(2H)-ons - Google Patents
Verfahren zur Herstellung des bakterizid wirksamen 4, 5-Dihydro-6-(5'-nitro-2'-furyl)-as-triazin-3(2H)-onsInfo
- Publication number
- DE1185618B DE1185618B DEN25196A DEN0025196A DE1185618B DE 1185618 B DE1185618 B DE 1185618B DE N25196 A DEN25196 A DE N25196A DE N0025196 A DEN0025196 A DE N0025196A DE 1185618 B DE1185618 B DE 1185618B
- Authority
- DE
- Germany
- Prior art keywords
- furyl
- dihydro
- triazin
- nitro
- preparation
- 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 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 5
- -1 furan compound Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229960001907 nitrofurazone Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 241000607142 Salmonella Species 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000223932 Eimeria tenella Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RKEARERKYHKVQD-UHFFFAOYSA-N 2-amino-1-(furan-2-yl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=CO1 RKEARERKYHKVQD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- ASGFZASPWLGLCV-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(O1)C=1CNC(NN=1)=O Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1CNC(NN=1)=O ASGFZASPWLGLCV-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000003113 dilution method Methods 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
- 239000003937 drug carrier Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- ZNFFBRRTNGXHIF-UHFFFAOYSA-N ethyl N-[2-(furan-2-yl)-2-oxoethyl]carbamate Chemical compound O1C(=CC=C1)C(=O)CNC(=O)OCC ZNFFBRRTNGXHIF-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US184490A US3138593A (en) | 1962-04-02 | 1962-04-02 | 4, 5-dihydro-6-(5-nitro-2-furyl)-as-triazinor pyridazin-3-(2h)-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1185618B true DE1185618B (de) | 1965-01-21 |
Family
ID=22677090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN25196A Pending DE1185618B (de) | 1962-04-02 | 1963-02-28 | Verfahren zur Herstellung des bakterizid wirksamen 4, 5-Dihydro-6-(5'-nitro-2'-furyl)-as-triazin-3(2H)-ons |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3138593A (en, 2012) |
| BE (1) | BE630438A (en, 2012) |
| CH (1) | CH417617A (en, 2012) |
| DE (1) | DE1185618B (en, 2012) |
| ES (1) | ES286659A1 (en, 2012) |
| FR (1) | FR2609M (en, 2012) |
| GB (1) | GB1005041A (en, 2012) |
| NL (1) | NL291027A (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 (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1518600A (fr) * | 1966-03-07 | 1968-03-29 | Procédé pour la fabrication industrielle de l'hydroxocobalamine | |
| US3506656A (en) * | 1966-10-22 | 1970-04-14 | Boehringer Mannheim Gmbh | Triazolo-tetrazolo-pyridazine derivatives |
| US3494921A (en) * | 1968-08-29 | 1970-02-10 | Dow Chemical Co | 1,4-disubstituted pyridazino(4,5-d) pyridazines |
| US3715356A (en) * | 1971-02-19 | 1973-02-06 | Pfizer | 1-phenyl-6-azacytosines as coccidiostats |
| BE793629A (fr) * | 1972-01-03 | 1973-07-03 | Upjohn Co | Nouveaux derives de benzodiazepines et leur preparation |
| DE2202745A1 (de) * | 1972-01-21 | 1973-07-26 | Boehringer Mannheim Gmbh | Nitrofuryl-triazolo eckige klammer auf 4,3-b eckige klammer zu-pyridazin-carbonsaeurederivate |
| DE2202744A1 (de) * | 1972-01-21 | 1973-07-26 | Boehringer Mannheim Gmbh | Nitrofuryl-triazolo eckige klammer auf 4,3-b eckige klammer zu-pyridazin-amide |
| US3879386A (en) * | 1973-06-22 | 1975-04-22 | Scott & Sons Co O M | Amino substituted 1,2,4-triazinones |
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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL104211C (en, 2012) * | 1958-02-28 |
-
0
- BE BE630438D patent/BE630438A/xx unknown
- NL NL291027D patent/NL291027A/xx unknown
-
1962
- 1962-04-02 US US184490A patent/US3138593A/en not_active Expired - Lifetime
-
1963
- 1963-02-28 DE DEN25196A patent/DE1185618B/de active Pending
- 1963-03-27 CH CH386363A patent/CH417617A/de unknown
- 1963-03-28 GB GB12287/63A patent/GB1005041A/en not_active Expired
- 1963-04-01 ES ES0286659A patent/ES286659A1/es not_active Expired
- 1963-04-02 FR FR930139A patent/FR2609M/fr active Active
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 |
|---|---|
| CH417617A (de) | 1966-07-31 |
| GB1005041A (en) | 1965-09-22 |
| US3138593A (en) | 1964-06-23 |
| FR2609M (fr) | 1964-06-22 |
| BE630438A (en, 2012) | |
| NL291027A (en, 2012) | |
| ES286659A1 (es) | 1963-08-16 |
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