DE1273535B - 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene - Google Patents
1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethyleneInfo
- Publication number
- DE1273535B DE1273535B DEB66565A DEB0066565A DE1273535B DE 1273535 B DE1273535 B DE 1273535B DE B66565 A DEB66565 A DE B66565A DE B0066565 A DEB0066565 A DE B0066565A DE 1273535 B DE1273535 B DE 1273535B
- Authority
- DE
- Germany
- Prior art keywords
- ethylene
- aminopyridazyl
- nitrofuryl
- vol
- formula
- 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
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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- B24B33/00—Honing machines or devices; Accessories therefor
- B24B33/08—Honing tools
- B24B33/082—Honing tools having only one honing stone
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES 'MJTSSIb PATENTAMTFEDERAL REPUBLIC OF GERMANY GERMAN 'MJTSSIb PATENTAMT
Int. CV:Int. CV:
Deutsche KL:German KL:
Nummer: Aktenzeichen: Anmeldetag: Auslegetag:Number: File number: Filing date: Display date:
C07dC07d
A61kA61k
12 ρ-10/01 12 ρ -10/01
30 h-2/3630 h-2/36
P 12 73 535.2-44 (B 66565)P 12 73 535.2-44 (B 66565)
28. März 1962March 28, 1962
25. Juli 1968July 25, 1968
Die Erfindung betrifft das neue l-[5-Nitrofuryl-(2)]-.2 - [6 - aminopyridazyl - (3)] - äthylen der Formel (I)The invention relates to the new 1- [5-nitrofuryl- (2)] -. 2- [6 - aminopyridazyl - (3)] - ethylene of the formula (I)
O2NO 2 N
CH = CHCH = CH
2N -CJ- CH = CH —4 V- NH2 2 N -CJ-CH = CH -4 V-NH 2
N-N (I) jN-N (I) j
und seine Herstellung.and its manufacture.
Es wurde gefunden, daß diese Verbindung hervorragende germistatische Eigenschaften aufweist. Im Vergleich zu bekannten Nitrofuranderivaten ergibt sich insbesondere eine verbesserte Wirksamkeit gegenüber Staphylococcus aureus, Escherichia coli und Streptococcus aureus.It has been found that this compound has excellent germistatic properties. in the Compared to known nitrofuran derivatives, there is in particular an improved effectiveness against Staphylococcus aureus, Escherichia coli and Streptococcus aureus.
Die Herstellung dieser Verbindung erfolgt in an sich bekannter Weise dadurch, daß man 5-Nitrofurfurol-mit B-Methyl-o-acetamino-pyridazin kondensiert und die erhaltene 6-Acetylamino-Verbindung hydrolisiert.This compound is prepared in a manner known per se by reacting 5-nitrofurfurol with B-methyl-o-acetaminopyridazine condensed and hydrolyzing the obtained 6-acetylamino compound.
Die überlegene germistatische Wirkung des neuen Nitrofuranderivats 1 - [5 - Nitrofuryl -(2)] - 2 - [6-aminopyridazyl-(3)]-äthylen (HB 115) wurde im Vergleich zu den als Handelspräparaten bekannten Verbindungen 5 - Nitrofurfurol - semicarbazon (A), N - (5 - Nitro-2-furfuryliden)-3-amino-oxazolidon-(2)(B), N-(5-Nitro - 2 - furfuryliden) -1 - amino - hydantoin (C) und 5 - Nitro - 2 - furfuryl - methyläther (D) durchgeführt.The superior germistatic effect of the new nitrofuran derivative 1 - [5 - nitrofuryl - (2)] - 2 - [6-aminopyridazyl- (3)] - ethylene (HB 115) was compared to the compounds known as commercial preparations 5 - nitrofurfurol - semicarbazon (A), N - (5 - nitro-2-furfurylidene) -3-amino-oxazolidone- (2) (B), N- (5-nitro-2-furfurylidene) -1-amino-hydantoin (C) and 5 - nitro - 2 - furfuryl - methyl ether (D) carried out.
Die Prüfung der Substanzen wurde im üblichen Reihenverdünnungstest mit flüssigem Nährmedium durchgeführt. Zur Gewinnung einer breiteren Basis der Beurteilung und im Hinblick auf die Abhängigkeit der Hemmwerte von der Stärke der Keim-Einsaat wurden bei jeder Keimart 3 bis 5 verschiedene Kulturverdünnungen angesetzt. Die Nitrofuranverbindungen wurden mit Hilfe lösungsvermittelnder organischer Lösungsmittel in wäßrige Lösung gebracht. Bei jedem einzelnen Versuch wurde durch parallellaufende Kontrollverdünnungsreihen eine germistatische Eigenwirkung der organischen Lösungsmittel ausgeschlossen. Diese Kontrollverdünnungsreihen enthielten dieselben Lösungsmittelkonzentrationen wie die eigentlichen Versuchsreihen, jedoch keine Nitrofuranverbindüngen. Die in den Tabellen genannte germistatische Minimalkonzentration ist die niedrigste Konzentration der geprüften Verbindungen, die jeweils das Bakterien- bzw. Pilzwachstum vollständig unterdrückte. The substances were tested in the usual serial dilution test with liquid nutrient medium carried out. To gain a broader base of assessment and in terms of addiction the inhibition values on the strength of the germination were 3 to 5 different culture dilutions for each germ type scheduled. The nitrofuran compounds became organic with the aid of solubilizing agents Solvent brought into aqueous solution. In each individual experiment, serial control dilutions were run in parallel a germistatic intrinsic effect of the organic solvents is excluded. These control dilution series contained the same Solvent concentrations like the actual test series, but no nitrofuran compounds. The germistatic minimum concentration given in the tables is the lowest concentration of the compounds tested, each of which completely suppressed bacterial or fungal growth.
l-[5-Nitrofuryl-(2)]-2-[6-aminopyridazyl-(3)]-äthylen 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] ethylene
Anmelder:Applicant:
C. F. Boehringer & Soehne G. m. b. H., 6800 MannheimC. F. Boehringer & Soehne G. m. B. H., 6800 Mannheim
Als Erfinder benannt:Named as inventor:
Dr. phil. Herbert Berger, 8961 Sulzberg-Ried; Dr. phil. Erich Haack, Dr. med. Johann Daniel Achelis, 6900 Heidelberg; Dr. med. Wolfgang Vömel, 6800 MannheimDr. phil. Herbert Berger, 8961 Sulzberg-Ried; Dr. phil. Erich Haack, Dr. med. Johann Daniel Achelis, 6900 Heidelberg; Dr. med. Wolfgang Vömel, 6800 Mannheim
Die Toxizität wurde als LD 50 (mg/kg) bei der Maus bestimmt:The toxicity was expressed as LD 50 (mg / kg) in the mouse certainly:
KeimartType of germ
Staphylococcus
aureus Staphylococcus
aureus
Absolut germistatische Minimalkonzentration in μ^ΐηΐ fürAbsolute germistatic minimum concentration in μ ^ ΐηΐ for
HB 115HB 115
0,1250.125
!09 587/558! 09 587/558
1,51 g 3 - Methyl - 6 - acetaminopyridazin erhitzt man mit 1,41 g 5-Nitrofurfurol, 10 ml Acetanhydrid und 10 ml Eisessig 3 Stunden auf 1600C (Badtemperatur). Dann dampft man im Vakuum zur Trockene ein, nimmt den Rückstand mit Wasser auf, neutralisiert mit Natriumbicarbonat und saugt ab. Der Niederschlag wird 5mal mit je 15 ml Dioxan ausgekocht. Beim Abkühlen der vereinigten Dioxanextrakte erhält man 0,65 g Kristalle vom Fp. 290 bis 292° C (Zersetzung); aus der eingeengten Mutterlauge werden weitere 0,5 g vom Fp. 290 bis 291°C erhalten. Nach Umkristallisation aus Pyridin schmilzt das l-[5-Nitrofuryl - (2)] - 2 - [6 - acetaminopyridazyl - (3)] - äthylen bei 292° C.1.51 g of 3-methyl-6-acetaminopyridazine are heated with 1.41 g of 5-nitrofurfurol, 10 ml of acetic anhydride and 10 ml of glacial acetic acid at 160 ° C. (bath temperature) for 3 hours. Then it is evaporated to dryness in a vacuum, the residue is taken up in water, neutralized with sodium bicarbonate and filtered off with suction. The precipitate is boiled 5 times with 15 ml of dioxane each time. On cooling the combined dioxane extracts, 0.65 g of crystals with a melting point of 290 ° to 292 ° C. (decomposition) are obtained; A further 0.5 g with a melting point of 290 ° to 291 ° C. are obtained from the concentrated mother liquor. After recrystallization from pyridine, the l- [5-nitrofuryl - (2)] - 2 - [6 - acetaminopyridazyl - (3)] - ethylene melts at 292 ° C.
1 g dieser Acetylverbindung hydrolysiert man 1 Stunde bei 1100C mit 30 ml 5n-Salzsäure; die ursprüngliche Suspension wandelt sich nach wenigen Minuten in eine klare Lösung um, welche nach einiger Zeit — noch in der Hitze — ein Kristallisat ausscheidet. Man läßt erkalten und kühlt im Eisbad, saugt ab und kristallisiert aus 50 ml Wasser unter Zusatz von Aktivkohle und 2,5 ml konzentrierter Salzsäure um. Ausbeute: 0,75 g l-[5-Nitrofuryl-(2)]- - [6 - aminopyridazyl - (3)] - äthylen in Form des Hydrochlorids vom Fp. 2900C.1 g of this acetyl compound is hydrolyzed for 1 hour at 110 ° C. with 30 ml of 5N hydrochloric acid; the original suspension turns into a clear solution after a few minutes, which after a while - still in the heat - precipitates a crystallizate. It is allowed to cool and then cooled in an ice bath, filtered off with suction and recrystallized from 50 ml of water with the addition of activated charcoal and 2.5 ml of concentrated hydrochloric acid. . Yield: 0.75 g of l- [5-Nitrofuryl- (2)] - - [6 - aminopyridazyl - (3)] - ethylene of the hydrochloride of melting in the form of 290 0 C.
Claims (2)
E1 d e r f i e 1 d, R. C, »Heterocyclic Compounds«,Considered publications:
E1 derfie 1 d, R. C, "Heterocyclic Compounds",
»Journal of the American Chemical Society«, Bd. 77,Vol. 6, New York, 1957, p. 111;
"Journal of the American Chemical Society", vol. 77,
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE630163D BE630163A (en) | 1962-03-28 | ||
NL290715D NL290715A (en) | 1962-03-28 | ||
NL121061D NL121061C (en) | 1962-03-28 | ||
DEB66565A DE1273535B (en) | 1962-03-28 | 1962-03-28 | 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene |
DE19621545607 DE1545607A1 (en) | 1962-03-28 | 1962-03-28 | Process for the preparation of new 5-nitrofuran derivatives |
GB11064/63A GB966832A (en) | 1962-03-28 | 1963-03-20 | New nitrofuran derivatives |
CH379863A CH455828A (en) | 1962-03-28 | 1963-03-26 | Process for the preparation of new 5-nitrofuran derivatives |
FI55963A FI43880C (en) | 1962-03-28 | 1963-03-26 | Method for preparing 5-nitrofuran derivatives that inhibit bacterial growth |
LU43422D LU43422A1 (en) | 1962-03-28 | 1963-03-26 | |
SE334763A SE315596B (en) | 1962-03-28 | 1963-03-27 | |
FR929433A FR1375010A (en) | 1962-03-28 | 1963-03-27 | Process for the preparation of novel 5-nitrofuran derivatives |
DK142163A DK123528B (en) | 1962-03-28 | 1963-03-28 | Process for the preparation of 5-nitrofuran derivatives or their quaternary ammonium salts or N-oxides. |
FR939444A FR2660M (en) | 1962-03-28 | 1963-06-26 | New drug consisting of or based on 1- (5-nitro-2-furyl) -2- (6-amino-3-pyridazyl) -ethylene and its salts. |
FR939445A FR3284M (en) | 1962-03-28 | 1963-06-26 | New drug consisting of or based on 1- (5-nitro-2-furyl) -2- [5-amino-2- (1,3,4-thiadiazolyl)] - ethylene. |
FR949604A FR84814E (en) | 1962-03-28 | 1963-10-04 | Process for the preparation of novel 5-nitrofuran derivatives |
MY6700139A MY6700139A (en) | 1962-03-28 | 1967-12-31 | New nitrofuran derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB66565A DE1273535B (en) | 1962-03-28 | 1962-03-28 | 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene |
DEB0083025 | 1962-03-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1273535B true DE1273535B (en) | 1968-07-25 |
Family
ID=25966202
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19621545607 Pending DE1545607A1 (en) | 1962-03-28 | 1962-03-28 | Process for the preparation of new 5-nitrofuran derivatives |
DEB66565A Pending DE1273535B (en) | 1962-03-28 | 1962-03-28 | 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19621545607 Pending DE1545607A1 (en) | 1962-03-28 | 1962-03-28 | Process for the preparation of new 5-nitrofuran derivatives |
Country Status (11)
Country | Link |
---|---|
BE (1) | BE630163A (en) |
CH (1) | CH455828A (en) |
DE (2) | DE1545607A1 (en) |
DK (1) | DK123528B (en) |
FI (1) | FI43880C (en) |
FR (4) | FR1375010A (en) |
GB (1) | GB966832A (en) |
LU (1) | LU43422A1 (en) |
MY (1) | MY6700139A (en) |
NL (2) | NL290715A (en) |
SE (1) | SE315596B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3359262A (en) * | 1963-03-16 | 1967-12-19 | Dainippon Pharmaceutical Co | 2-[2-(5-nitrofuryl)-vinyl]-pyrimidines |
CH473142A (en) * | 1964-06-11 | 1969-05-31 | Ciba Geigy | Process for the production of new pyridazines |
US3337541A (en) * | 1964-12-28 | 1967-08-22 | Fujisawa Pharmacentical Co Ltd | 5-[2-(5-nitro-2-furyl) vinyl]-1, 3, 4-oxadiazole derivatives |
NL128591C (en) * | 1965-07-02 | |||
US3464982A (en) * | 1965-09-01 | 1969-09-02 | Dainippon Pharmaceutical Co | (2 - (5 - nitro - 2 - furyl) - vinyl) - pyrimidine derivative and process for the preparation thereof |
US3505346A (en) * | 1966-12-01 | 1970-04-07 | American Cyanamid Co | Novel 2,5-disubstituted thiazole carboxaldehyde and derivatives of the same |
JPS511631B2 (en) * | 1973-03-23 | 1976-01-19 |
-
0
- BE BE630163D patent/BE630163A/xx unknown
- NL NL121061D patent/NL121061C/xx active
- NL NL290715D patent/NL290715A/xx unknown
-
1962
- 1962-03-28 DE DE19621545607 patent/DE1545607A1/en active Pending
- 1962-03-28 DE DEB66565A patent/DE1273535B/en active Pending
-
1963
- 1963-03-20 GB GB11064/63A patent/GB966832A/en not_active Expired
- 1963-03-26 CH CH379863A patent/CH455828A/en unknown
- 1963-03-26 LU LU43422D patent/LU43422A1/xx unknown
- 1963-03-26 FI FI55963A patent/FI43880C/en active
- 1963-03-27 SE SE334763A patent/SE315596B/xx unknown
- 1963-03-27 FR FR929433A patent/FR1375010A/en not_active Expired
- 1963-03-28 DK DK142163A patent/DK123528B/en unknown
- 1963-06-26 FR FR939444A patent/FR2660M/en active Active
- 1963-06-26 FR FR939445A patent/FR3284M/en active Active
- 1963-10-04 FR FR949604A patent/FR84814E/en not_active Expired
-
1967
- 1967-12-31 MY MY6700139A patent/MY6700139A/en unknown
Non-Patent Citations (1)
Title |
---|
None * |
Also Published As
Publication number | Publication date |
---|---|
SE315596B (en) | 1969-10-06 |
NL121061C (en) | |
BE630163A (en) | |
FI43880B (en) | 1971-03-31 |
FI43880C (en) | 1971-07-12 |
FR3284M (en) | 1965-05-03 |
CH455828A (en) | 1968-05-15 |
FR84814E (en) | 1965-04-23 |
MY6700139A (en) | 1967-12-31 |
NL290715A (en) | |
DE1545607A1 (en) | 1969-12-04 |
DK123528B (en) | 1972-07-03 |
LU43422A1 (en) | 1963-05-27 |
GB966832A (en) | 1964-08-19 |
FR1375010A (en) | 1964-10-16 |
FR2660M (en) | 1964-07-15 |
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