DE1470348A1 - Verfahren zur Herstellung neuer 5-Nitrofuryl-Verbindungen - Google Patents
Verfahren zur Herstellung neuer 5-Nitrofuryl-VerbindungenInfo
- Publication number
- DE1470348A1 DE1470348A1 DE19631470348 DE1470348A DE1470348A1 DE 1470348 A1 DE1470348 A1 DE 1470348A1 DE 19631470348 DE19631470348 DE 19631470348 DE 1470348 A DE1470348 A DE 1470348A DE 1470348 A1 DE1470348 A1 DE 1470348A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- group
- nitrofuryl
- hydroxymethyl
- oxadiazole
- 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 7
- -1 5-nitrofuryl compounds Chemical class 0.000 title description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 13
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical class N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002240 furans Chemical class 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
- 239000003960 organic solvent Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3895262 | 1962-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1470348A1 true DE1470348A1 (de) | 1969-05-29 |
Family
ID=12539520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631470348 Pending DE1470348A1 (de) | 1962-09-11 | 1963-09-10 | Verfahren zur Herstellung neuer 5-Nitrofuryl-Verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3303188A (enExample) |
| CH (1) | CH420172A (enExample) |
| DE (1) | DE1470348A1 (enExample) |
| FR (1) | FR1572123A (enExample) |
| GB (1) | GB1048266A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1470351A1 (de) * | 1962-10-15 | 1969-05-29 | Toyama Kagaku Kogyo Kabushiki | Verfahren zur Herstellung neuer Nitrofuranderivate |
| US3493565A (en) * | 1966-03-14 | 1970-02-03 | Squibb & Sons Inc | 3-amino-5-(nitrofuryl)-1,2,4-oxadiazole derivatives |
| USD570697S1 (en) * | 2007-08-29 | 2008-06-10 | Richard Norman Zach Wagner | Water bottle |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146232A (en) * | 1962-09-17 | 1964-08-25 | Saikachi Haruo | 5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process |
-
1963
- 1963-09-04 GB GB34904/63A patent/GB1048266A/en not_active Expired
- 1963-09-06 US US307021A patent/US3303188A/en not_active Expired - Lifetime
- 1963-09-10 DE DE19631470348 patent/DE1470348A1/de active Pending
- 1963-09-11 CH CH1124063A patent/CH420172A/de unknown
- 1963-09-11 FR FR1572123D patent/FR1572123A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1572123A (enExample) | 1969-06-27 |
| GB1048266A (en) | 1966-11-16 |
| CH420172A (de) | 1966-09-15 |
| US3303188A (en) | 1967-02-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1795344B2 (de) | Verfahren zur herstellung von 3-aminoisothiazolen | |
| DE1620515A1 (de) | Verfahren zur Herstellung neuer 5-Nitrofuryl-Verbindungen | |
| DE2166270C3 (de) | Nicotinoylaminoäthansulfonyl-2amino-thiazol | |
| DE1263743B (de) | Verfahren zur Herstellung von substituierten Acetamiden | |
| DE2105112A1 (de) | Chinoxahn di Noxide und ihre Verwendung in einem pharmazeutischen Gemisch | |
| DE1620161B2 (de) | 1,3,4-Oxadiazolderivate, Verfahren zu deren Herstellung und insektizide Mittel | |
| DE2162917C3 (enExample) | ||
| DE1670967C3 (de) | 3-Imino-l,2-benzisothiazolin-salze und Verfahren zu ihrer Herstellung | |
| AT222115B (de) | Verfahren zur Herstellung von neuen, substituierten Pyrrolidonen | |
| DE1966132B2 (de) | 7-Chlor-2-hydroxy-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin | |
| AT154905B (de) | Verfahren zur Darstellung organischer Quecksilberverbindungen. | |
| DE1112521B (de) | Verfahren zur Herstellung der 1, 2, 5-Thiadiazol-3, 4-dicarbonsaeure und ihrer Derivate | |
| DE1670936C3 (de) | 3-Carbonsäureamido-chinoxalin-di-Nojdde-0,4), ein Verfahren zu ihrer Herstellung und diese enthaltende antibakterielle Mittel | |
| AT227707B (de) | Verfahren zur Herstellung von neuen Chinazolinonderivaten | |
| DE1643784C (de) | Biologisch wirksame Isothiocyanate und Verfahren zu deren Herstellung | |
| AT251585B (de) | Verfahren zur Herstellung von neuen 6,7-Dihydro-5H-pyrrolo-[3,4-d]-pyrimidinen | |
| DE1217958B (de) | Verfahren zur Herstellung von 11, 12-Dihydro-6H-dibenzo[b, f]-[1, 4] thiazocinen | |
| DE1958238C (de) | l-Oxy-S^-dibrom-ö-halogen-thiochromanone | |
| DE1670598C3 (de) | Neue Cephalosporine und Verfahren zu ihrer Herstellung | |
| CH460017A (de) | Verfahren zur Herstellung neuer Nitrothiazolverbindungen | |
| AT214442B (de) | Verfahren zur Herstellung von neuen p-Benzochinon-bis-hydrazonen | |
| DE1795350C3 (de) | Pyrimldlnylthiophosphorsäureester, Verfahren zu ihrer Herstellung und diese enthaltende Mittel | |
| AT317246B (de) | Verfahren zur Herstellung von neuen Schwermetall-Komplexsalzen von trisubstituierten Dithiocarbamoylhydrazinen | |
| DE185601C (enExample) | ||
| AT293393B (de) | Verfahren zur Herstellung von Benzodiazepin-2-onen bzw. von Salzen hievon |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |