DE1273535B - 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene - Google Patents

1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene

Info

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
Application number
DEB66565A
Other languages
German (de)
Inventor
Dr Med Johann Daniel Achelis
Dr Phil Herbert Berger
Dr Phil Erich Haack
Dr Med Wolfgang Voemel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to NL121061D priority Critical patent/NL121061C/xx
Priority to NL290715D priority patent/NL290715A/xx
Priority to BE630163D priority patent/BE630163A/xx
Application filed by Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Priority to DE19621545607 priority patent/DE1545607A1/en
Priority to DEB66565A priority patent/DE1273535B/en
Priority to GB11064/63A priority patent/GB966832A/en
Priority to FI55963A priority patent/FI43880C/en
Priority to CH379863A priority patent/CH455828A/en
Priority to LU43422D priority patent/LU43422A1/xx
Priority to FR929433A priority patent/FR1375010A/en
Priority to SE334763A priority patent/SE315596B/xx
Priority to DK142163A priority patent/DK123528B/en
Priority to FR939444A priority patent/FR2660M/en
Priority to FR939445A priority patent/FR3284M/en
Priority to FR949604A priority patent/FR84814E/en
Priority to MY6700139A priority patent/MY6700139A/en
Publication of DE1273535B publication Critical patent/DE1273535B/en
Pending legal-status Critical Current

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

AUSLEGESCHRIFTEDITORIAL

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

Absolut germistatische Minimal-Absolutely germistatic minimal HB 115HB 115 conzentration inconcentration in BB. j.g/ml fürj.g / ml for DD. KeimartType of germ 11 AA. CC. StreptococcusStreptococcus 0,0620.062 88th —- pyogenes,pyogenes, 0,0080.008 44th 0,250.25 44th —- Aronson Aronson 44th 88th 6464 88th —- Escherichia coli .Escherichia coli. 128128 256256 Proteus vulgaris.Proteus vulgaris. 22 6464 —- PseudomonasPseudomonas 128128 256256 aeruginosa ...aeruginosa ... 1616 —- 128128 MicrosporumMicrosporum —- —- gypseum gypseum TrichophytonTrichophyton 1616 —- 128128 mentagro-mentagro- —- —- phytes phytes

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

Substanzsubstance Orale GabeOral administration Intraperitoneale GabeIntraperitoneal administration HB 115HB 115 720720 540540 AA. 230230 162162 BB. 12801280 500500 CC. 250250 215215 DD. 430430 —-

!09 587/558! 09 587/558

Beispielexample

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)

Patentansprüche:Patent claims: 1. l-[5-Nitrofuryl-(2)]-2-[6-aminopyridazyl-(3)]-äthylen der Formel (I)1. 1- [5-Nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] ethylene of formula (I) O2NO 2 N CH = CHCH = CH NH,NH, N-NN-N 2. Verfahren zur Herstellung von l-[5-Nitrofur yl - (2)] - 2 - [6 - aminopyridazyl - (3)] - äthylen der FormelI, dadurch gekennzeichnet, daß man in an sich bekannter Weise 5-Nitrofurfurol mit 3-Methyl-6-acetaminopyridazin kondensiert und die erhaltene 6-Acetylaminoverbindung hydrolysiert. __^ 2. Process for the preparation of l- [5-nitrofur yl - (2)] - 2 - [6 - aminopyridazyl - (3)] - ethylene of Formula I, characterized in that 5-nitrofurfurol is used in a manner known per se condensed with 3-methyl-6-acetaminopyridazine and hydrolyzed the 6-acetylamino compound obtained. __ ^ In Betracht gezogene Druckschriften:
E1 d e r f i e 1 d, R. C, »Heterocyclic Compounds«,Considered publications:
E1 derfie 1 d, R. C, "Heterocyclic Compounds", Bd. 6, New York, 1957, S. 111;
»Journal of the American Chemical Society«, Bd. 77,Vol. 6, New York, 1957, p. 111;
"Journal of the American Chemical Society", vol. 77, 1955, S. 2333/2334.1955, pp. 2333/2334. 809 557/558 7.68 Q Bundesdruckerei Berlin809 557/558 7.68 Q Bundesdruckerei Berlin
DEB66565A 1962-03-28 1962-03-28 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene Pending DE1273535B (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
NL121061D NL121061C (en) 1962-03-28
NL290715D NL290715A (en) 1962-03-28
BE630163D BE630163A (en) 1962-03-28
DE19621545607 DE1545607A1 (en) 1962-03-28 1962-03-28 Process for the preparation of new 5-nitrofuran derivatives
DEB66565A DE1273535B (en) 1962-03-28 1962-03-28 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene
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
FR929433A FR1375010A (en) 1962-03-28 1963-03-27 Process for the preparation of novel 5-nitrofuran derivatives
SE334763A SE315596B (en) 1962-03-28 1963-03-27
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
DEB66565A Pending DE1273535B (en) 1962-03-28 1962-03-28 1- [5-nitrofuryl- (2)] - 2- [6-aminopyridazyl- (3)] -ethylene
DE19621545607 Pending DE1545607A1 (en) 1962-03-28 1962-03-28 Process for the preparation of new 5-nitrofuran derivatives

Family Applications After (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) DE1273535B (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)

* Cited by examiner, † Cited by third party
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
FR3284M (en) 1965-05-03
FI43880C (en) 1971-07-12
FR1375010A (en) 1964-10-16
NL290715A (en)
GB966832A (en) 1964-08-19
DE1545607A1 (en) 1969-12-04
FR2660M (en) 1964-07-15
FR84814E (en) 1965-04-23
CH455828A (en) 1968-05-15
NL121061C (en)
BE630163A (en)
SE315596B (en) 1969-10-06
MY6700139A (en) 1967-12-31
DK123528B (en) 1972-07-03
LU43422A1 (en) 1963-05-27
FI43880B (en) 1971-03-31

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