DE1263775B - Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes - Google Patents

Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes

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Publication number
DE1263775B
DE1263775B DEF41883A DEF0041883A DE1263775B DE 1263775 B DE1263775 B DE 1263775B DE F41883 A DEF41883 A DE F41883A DE F0041883 A DEF0041883 A DE F0041883A DE 1263775 B DE1263775 B DE 1263775B
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DE
Germany
Prior art keywords
tetraazapyrenes
substituted
preparation
general formula
tetraazapyren
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
DEF41883A
Other languages
German (de)
Inventor
Dr Marianne Bock
Dr Hans Pluempe
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.)
Bayer AG
Original Assignee
Bayer AG
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
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF41883A priority Critical patent/DE1263775B/en
Priority to DEF41884A priority patent/DE1265754B/en
Priority to FR3787A priority patent/FR1447183A/en
Priority to AT76365A priority patent/AT250982B/en
Priority to BE659016D priority patent/BE659016A/xx
Priority to NL6501197A priority patent/NL6501197A/xx
Priority to GB4020/65A priority patent/GB1022660A/en
Priority to FR15042A priority patent/FR4367M/fr
Publication of DE1263775B publication Critical patent/DE1263775B/en
Pending legal-status Critical Current

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    • 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
    • C07D487/06—Peri-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

Int. CL:Int. CL:

C07dC07d

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Deutsche Kl.: 12 ρ-10/10 German class: 12 ρ -10/10

Nummer: 1263 775Number: 1263 775

Aktenzeichen: F 41883IV d/12 ρFile number: F 41883IV d / 12 ρ

Anmeldetag: 31. Januar 1964Filing date: January 31, 1964

Auslegetag: 21. März 1968Open date: March 21, 1968

Gegenstand der Erfindung ist ein Verfahren zur Herstellung von neuen substituierten 1,3,6,8-Tetraazapyrenen der allgemeinen FormelThe invention relates to a process for the preparation of new substituted 1,3,6,8-tetraazapyrenes the general formula

worin R1 und R2 Alkylgruppen und R3 und R4. Wasserstoff- oder Halogenatome bedeuten, die sich durch eine ausgezeichnete Wirkung gegen pathogene Protozoen, besonders gegen Lamblien und Trichomonaden, auszeichnen. Im Gegensatz zu den oben bezeichneten Verbindungen besitzen das in 2,7-Stellung unsubstituierte, bereits von O. D i m r 0 t h und H. R ο ο s (Liebigs Annalen der Chemie, 456 [1927], S. 184 und 185) beschriebene 1,3,6,8-Tetraazapyren sowie dessen dort ebenfalls erwähntes Monochlorderivat nur eine ganz geringe Wirkung gegen einige Protozoenarten.wherein R 1 and R 2 are alkyl groups and R 3 and R 4 . Hydrogen or halogen atoms mean, which are characterized by an excellent effect against pathogenic protozoa, especially against lamblia and trichomonads. In contrast to the compounds referred to above, those which are unsubstituted in the 2,7-position and have already been described by O. D imr 0 th and H. R o o s (Liebigs Annalen der Chemie, 456 [1927], pp. 184 and 185) 1,3,6,8-Tetraazapyren and its monochlorine derivative, which is also mentioned there, only have a very slight effect against some species of protozoa.

Die erfindungsgemäß hergestellten Verbindungen wurden in Versuchen an der spontan mit Lamblia muris infizierten Maus getestet. Die Verabreichung der Substanzen erfolgt jeweils an fünf aufeinanderfolgenden Tagen mittels Schlundsonde. Am 7. Tag nach Behandlungsbeginn wurden die Tiere getötet und seziert. Zur Beurteilung einer Substanzwirkung wurde der Dünndarminhalt der Mäuse mikroskopisch auf Lamblia muris untersucht.The compounds prepared according to the invention were in experiments on the spontaneously with lamblia muris infected mouse. The substances are administered on five consecutive days Days by gavage. The animals were sacrificed on the 7th day after the start of treatment and dissected. The small intestine contents of the mice were examined microscopically to assess the effect of the substance examined for Lamblia muris.

Verfahren zur Herstellung von neuen
substituierten 1,3,6,8-TetraazapyrenenMethod of making new
substituted 1,3,6,8-tetraazapyrenes

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,

5090 Leverkusen5090 Leverkusen

Als Erfinder benannt:Named as inventor:

Dr. Hans Plumpe,Dr. Hans Plump,

Dr. Marianne Bock, 5600 Wuppertal-ElberfeldDr. Marianne Bock, 5600 Wuppertal-Elberfeld

Die Ergebnisse der Teste sind in den nachstehenden Tabellen zusammengefaßt. Zum Vergleich wurden die unter den entsprechenden Versuchsbedingungen mit 1 -Diäthylamino-3-[6'-chlor-2'-methoxy-acridinyl-(9')-amino]-propan-2-ol-dihydrochlorid und 1-(/J-Hydroxyäthyl) - 2 - methyl - 5 - nitroimidazol gewonnenen Daten eingetragen, deren Wirkung auf die Lamblien-Infektion des Menschen literaturbekannt ist.The results of the tests are summarized in the tables below. For comparison were under the corresponding test conditions with 1-diethylamino-3- [6'-chloro-2'-methoxy-acridinyl- (9 ') -amino] -propan-2-ol dihydrochloride and 1 - (/ J-hydroxyethyl) - 2 - methyl - 5 - nitroimidazole entered data, their effect on the lamblia infection of man is known from literature.

Der in den Tabellen für jedes Präparat angegebene therapeutische Index errechnet sich aus dem Verhältnis der minimal wirksamen zur maximal verträglichen Dosis. Aus einer Gegenüberstellung dieser im Tierversuch erhaltenen Werte ergibt sich die Überlegenheit der erfindungsgemäß hergestellten Verbindungen über die bekannten Präparate.The therapeutic index given in the tables for each preparation is calculated from the ratio the minimally effective to the maximally tolerated dose. From a comparison of these in The values obtained in animal experiments show the superiority of the compounds prepared according to the invention about the known preparations.

Substanzsubstance mg/kg
5 χ per osmg / kg
5 χ per os Positive Tiere
GesamtzahlPositive animals
Total number Unbehandelte
Kontrolltiere
" positive Tiere
GesamtzahlUntreated
Control animals
"positive animals
Total number % Reduktion
der Infektion
durch Behandlung% Reduction
the infection
through treatment Bewertung*)Valuation*) 2,7-Dimethyl-1,3,6,8-tetra-2,7-dimethyl-1,3,6,8-tetra- 10001000 0/20/2 4/44/4 100100 W-toxischW-toxic azapyrenazapyren 500500 0/40/4 5/55/5 100100 WW. 250250 0/30/3 5/55/5 100100 WW. 100100 0/260/26 35/4035/40 100100 WW. 5050 0/380/38 35/4035/40 100100 WW. 2525th 1/471/47 49/5449/54 9898 WW. 1010 9/449/44 44/4844/48 7878 W-SW-S 55 16/2416/24 22/2422/24 2828 S-ΦS-Φ

Therapeutischer Index 1Therapeutic index 1

*) Die Bewertung ergibt sich aus der errechneten Reduktion:
0 bis 25% = ohne Wirkung = (·) *) The evaluation results from the calculated reduction:
0 to 25% = no effect = (·)

100100

26 bis 75%
76 bis 100%26 to 75%
76 to 100%

geringe Wirkung = S
Wirkung = Wlittle effect = S
Effect = W

809 519/640809 519/640

Fortsetzungcontinuation

Substanzsubstance mg/kg
5 χ per psmg / kg
5 χ per ps Positive Tiere
GesamtzahlPositive animals
Total number Unbehandelte
Kontroll tiere
positive Tiere
GesamtzahlUntreated
Control animals
positive animals
Total number % Reduktion
der Infektion
durch Behandlung% Reduction
the infection
through treatment Bewertung*)Valuation*) 2,7-Diäthyl-l,3,6,8-tetra-2,7-diethyl-1,3,6,8-tetra- 500500 tox. Dosistox. dose azapyrenazapyren 250250 0/70/7 7/87/8 100100 WW. 100100 0/40/4 5/65/6 100100 WW. 5050 0«0 « 9/109/10 100100 WW. 2525th 0/40/4 4/44/4 100100 WW. 1010 3/43/4 4/44/4 2525th S-ΦS-Φ

Therapeutischer Index 1 :10Therapeutic index 1: 10

2,7-Diäthyl-4-chlor-1,3,6,8-tetraazapyren 2,7-diethyl-4-chloro-1,3,6,8-tetraazapyren

l-Diäthylamino-3-[6'-chlor-2'-methoxyacridinyl-(9')-amino]-propan-2-oldihydrochlorid 1-Diethylamino-3- [6'-chloro-2'-methoxyacridinyl- (9 ') -amino] -propane-2-aleneihydrochloride

l-(/?-Hydroxyäthyl)-2-methyl-5-nitroimidazol l - (/? - Hydroxyethyl) -2-methyl-5-nitroimidazole

Therapeutischer Index 1:10 *) Die Bewertung ergibt sich aus der errechneten Reduktion:Therapeutic index 1:10 *) The evaluation results from the calculated reduction:

0 bis 25% = ohne Wirkung = Θ
26 bis 75% = geringe Wirkung = S
76 bis 100% = Wirkung = W0 to 25% = no effect = Θ
26 to 75% = little effect = p
76 to 100% = effect = W

10001000 0/40/4 10/1010/10 100100 WW. 500500 0/40/4 10/1010/10 0/120/12 8/128/12 100100 WW. 250250 1/61/6 ■ 17/17■ 17/17 0/130/13 12/1612/16 0/30/3 2/42/4 8282 WW. 100100 1/21/2 7/77/7 7/177/17 13/1613/16 4/84/8 8/98/9 50-50- SS. Therapeutischer Index < 1:10Therapeutic index <1:10 8/88/8 7/87/8 6/86/8 8/98/9 500500 Therapeutischer Index 1:5Therapeutic index 1: 5 tox. Dosistox. dose 250250 25002500 100100 WW. 100100 10001000 100100 WW. 5050 500500 7070 SS. 2525th 250250 ΦΦ ΦΦ 100100 vertr. Dosistolerated dose ■ —■ - vertr. Dosistolerated dose 100100 WW. 4444 SS. 1616 ΦΦ

Bezüglich des 2,7 -Diäthyl-1,3,6,8 - tetraazapyrens ist festzustellen, daß dessen chemotherapeutischer Indexwert 1:10 zwar gleich demjenigen von l-(/?-Hydroxyäthyl)-2-methyl-5-nitroimidazol ist, seine an der Maus noch wirksame Dosis aber mit 25 mg/kg absolut gesehen zehnmal geringer ist als diejenige von 1 - (ß - Hydroxyäthyl) - 2 - methyl - 5 - nitro - imidazol mit 250 mg/kg. Das genannte Verfahrensprodukt istWith regard to 2,7-diethyl-1,3,6,8-tetraazapyrene, it can be stated that its chemotherapeutic index value 1:10 is equal to that of 1- (/? - hydroxyethyl) -2-methyl-5-nitroimidazole, his the dose still effective in the mouse, however, at 25 mg / kg in absolute terms, is ten times lower than that of 1 - (ß - hydroxyethyl) - 2 - methyl - 5 - nitro - imidazole at 250 mg / kg. The process product mentioned is

in der R1, R2, R3 und R4 die oben angegebene Bedeutung besitzen, mit Eisen(III)-chlorid, Wasserstoffperoxyd oder einem Alkalichromat oder -bichromat dehydriert. '·in which R 1 , R 2 , R 3 and R 4 have the meaning given above, dehydrogenated with iron (III) chloride, hydrogen peroxide or an alkali chromate or bichromate. '·

Geeignete Ausgangsstoffe sind z. B. die Dihydrochloride oder die Hexachlorostannate der substituierten l,8-Dihydro-l,3,6,8-tetraazapyrene, welche sich besonders gut in wäßriger Lösung oder. Suspension mit den genannten Oxydationsmitteln bei Temperaturen zwischen 0 und 1000C dehydrieren lassen. Schon während der Zugabe der wäßrigen Lösung des Oxydationsmittels scheidet sich das freie substituierte 1,3,6,8-Tetraazapyren aus der Lösung ab, da es weit daher leichter applizierbar als die bekannte Vergleichssubstanz, zumal auch das Verfahrensprodukt schon in ziemlich großer Dosis verabreicht werden muß.Suitable starting materials are, for. B. the dihydrochloride or the hexachlorostannate of the substituted l, 8-dihydro-l, 3,6,8-tetraazapyrene, which is particularly good in aqueous solution or. Can dehydrate with the aforementioned oxidizing agents at temperatures between 0 and 100 0 C suspension. Already during the addition of the aqueous solution of the oxidizing agent, the free substituted 1,3,6,8-tetraazapyrene separates from the solution, since it is therefore far easier to apply than the known comparison substance, especially since the process product is already administered in a fairly large dose got to.

Man erhält die substituierten 1,3,6,8-Tetraazapyrene der allgemeinen Formel I, indem man.in an sich bekannter Weise ein Salz eines substituierten 1,8-Dihydro-l,3,6,8-tetraazapyrens der allgemeinen FormelThe substituted 1,3,6,8-tetraazapyrenes of the general formula I are obtained by using a method known per se Way, a salt of a substituted 1,8-dihydro-1,3,6,8-tetraazapyrene the general formula

IIII

weniger basisch ist als seine entsprechende Dihydroverbindung und in verdünnter wäßriger Lösung keine löslichen Salze zu bilden vermag.
Die nach Absaugen und Auswaschen mit Wasser sowie Methanol oder Äthanol schon ziemlich rein anfallenden Reaktionsprodukte lassen sich durch Umkristallisieren aus geeigneten Lösungsmitteln, wie Toluol, Tetrachloräthan, Äthoxyäthanol, Äthylenglykol oder Dimethylformamid, weiter reinigen und fallen als mehr oder weniger stark gelbgefärbte kristalline und beständige Verbindungen an.is less basic than its corresponding dihydro compound and cannot form soluble salts in dilute aqueous solution.
The reaction products, which are already fairly pure after suctioning off and washing with water and methanol or ethanol, can be further purified by recrystallization from suitable solvents such as toluene, tetrachloroethane, ethoxyethanol, ethylene glycol or dimethylformamide, and are obtained as more or less yellow-colored crystalline and stable compounds .

Die als Ausgangsstoffe verwendeten Salze von substituierten l,8-Dihydro-l,3,6,8-tetraazapyrenen der all-The salts of substituted l, 8-dihydro-l, 3,6,8-tetraazapyrenes of the all-

gemeinen Formel II werden in an sich bekannter Weise durch Reduktion von !,S-B
naphthalinen der Formelcommon formula II are in a manner known per se by reducing!, SB
naphthalenes of the formula

O2N
R, CNHO 2 N
R, CNH

NHC — R1
NO,NHC - R 1
NO,

IOIO

mit Reduktionsmitteln, ζ. Β. Zinn(II)-chlorid, erhalten.with reducing agents, ζ. Β. Tin (II) chloride.

Beispiel 1example 1

1515th

570 Gewichtsteile 2,7 - Dimethyl - 1,8 - dihydro-1,3,6,8 - tetraazapyren - hexachlorostannat werden in 5700 Volumteilen Warser heiß gelöst und bei 50 bis 6O0C eine Lösung von 149 Gewichtsteilen Natriumbichromatdihydrat in 1500 Volumteilen Wasser zugegeben. Man läßt kurze Zeit stehen und saugt den gebildeten Niederschlag ab. Das abgesaugte Rohprodukt wird mehrmals mit Wasser, schließlich mit Methanol gewaschen und getrocknet. Nach Umkristallisieren aus Toluol erhält man das 2,7-Dimethyl-1,3,6,8-teträazapyren in Form gelber Nadeln, die im geschlossenen Schmelzpunktröhrchen bei 31Γ C unter Sublimation schmelzen; Ausbeute: 210 bis 220 Gewichtsteile = 90% der Theorie.570 parts by weight of 2,7 - dimethyl - hexachlorostannate are dissolved hot in 5700 parts by volume Warser and added at 50 to 6O 0 C, a solution of 149 parts by weight Natriumbichromatdihydrat 1500 parts by volume of water - 1,8 - dihydro-1,3,6,8 - tetraazapyren . It is left to stand for a short time and the precipitate formed is filtered off with suction. The crude product filtered off with suction is washed several times with water and finally with methanol and dried. After recrystallization from toluene, 2,7-dimethyl-1,3,6,8-teträazapyren is obtained in the form of yellow needles which melt in a closed melting point tube at 31 ° C. with sublimation; Yield: 210 to 220 parts by weight = 90% of theory.

Beispiel 2Example 2

309 Gewichtsteile 2,7 - Dimethyl - 1,8 - dihydro-1,3,6,8 - tetraazapyren - dihydrochlorid werden in 4500 Volumteilen Wasser heiß gelöst und bei Raumtemperatur 810 Gewichtsteile Eisen(III)-chlorid-hexahydrat, gelöst in 3000 Volumteilen Wasser, hinzugegeben. Nach 15 Minuten wird das ausgefallene Reaktionsprodukt abgesaugt, mit Wasser und Methanol gewaschen und getrocknet. Nach Umkristallisieren aus Toluol erhält man 2,7-Dimethyl-l,3,6,8-tetraazapyren in Form gelber Nadeln; F. 311°C (Sublimation); Ausbeute: 190 bis 200 g = 80 bis 85% der Theorie.309 parts by weight 2,7 - dimethyl - 1,8 - dihydro-1,3,6,8 - tetraazapyren - dihydrochloride are in 4500 parts by volume of hot water and 810 parts by weight of iron (III) chloride hexahydrate at room temperature, dissolved in 3000 parts by volume of water, added. After 15 minutes the precipitated Sucked off the reaction product, washed with water and methanol and dried. After recrystallization 2,7-dimethyl-1,3,6,8-tetraazapyren in the form of yellow needles is obtained from toluene; Mp 311 ° C (sublimation); Yield: 190 to 200 g = 80 to 85% of theory.

In analoger Weise erhält man aus den Salzen der entsprechenden 1,8-Dihydroverbindungen der allgemeinen Formel II folgende Derivate des 1,3,6,8-Tetraazapyrens: In an analogous manner, the salts of the corresponding 1,8-dihydro compounds give the general Formula II the following derivatives of 1,3,6,8-tetraazapyrene:

2,7-Diäthyl-l,3,6,8-tetraazapyren,2,7-diethyl-1,3,6,8-tetraazapyren,

gelbbraune Kristalle; F. 238°C, 2,7-Di-n-propyl-1,3,6,8-tetraazapyren,yellow-brown crystals; Mp 238 ° C, 2,7-di-n-propyl-1,3,6,8-tetraazapyren,

gelbbraune Kristalle; F. 2110C, 2,7-Dimethyl-4-chlor-l,3,6,8-tetraazapyren,yellow-brown crystals; F. 211 0 C, 2,7-dimethyl-4-chloro-l, 3,6,8-tetraazapyren,

gelbbraune Kristalle; F. 2700C (Zersetzung), 2,7-Dimethyl-4-brom-l,3,6,8-tetraazapyren,yellow-brown crystals; F. 270 0 C (decomposition), 2,7-dimethyl-4-bromo-1, 3,6,8-tetraazapyren,

gelbe Kristalle; F. 2300C (Zersetzung), 2,7-Dimethyl-4,9-dichlor-1,3,6,8-tetraazapyren, gelbe Kristalle; F. 2600C (Zersetzung).yellow crystals; F. 230 0 C (decomposition), 2,7-dimethyl-4,9-dichloro-1,3,6,8-tetraazapyren, yellow crystals; F. 260 0 C (decomposition).

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von neuen substituierten 1,3,6,8-Tetraazapyrenen, dadurch gekennzeichnet, daß man in an sich bekannter Weise ein Salz eines substituierten 1,8-Dihydro-1,3,6,8-tetraazapyrens der allgemeinen FormelProcess for the preparation of new substituted 1,3,6,8-tetraazapyrenes, characterized in that that a salt of a substituted 1,8-dihydro-1,3,6,8-tetraazapyrene is used in a manner known per se the general formula R3 R 3 worin R1 und R2 Alkylgruppen und R3 und R4 Wasserstoff- oder Halogenatome bedeuten, mit Eisen(III)-chlorid, Wasserstoffperoxyd oder einem Alkalichromat oder -bichromat dehydriert und die erhaltene Verbindung der allgemeinen Formelwherein R 1 and R 2 are alkyl groups and R 3 and R 4 are hydrogen or halogen atoms, dehydrogenated with iron (III) chloride, hydrogen peroxide or an alkali chromate or bichromate, and the resulting compound of the general formula isoliert.isolated. In Betracht gezogene Druckschriften: Liebigs Annalen der Chemie, 456 (1927), S. 177 ff.Considered publications: Liebigs Annalen der Chemie, 456 (1927), p. 177 ff.
DEF41883A 1964-01-31 1964-01-31 Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes Pending DE1263775B (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DEF41883A DE1263775B (en) 1964-01-31 1964-01-31 Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes
DEF41884A DE1265754B (en) 1964-01-31 1964-01-31 Process for the preparation of salts of substituted 1, 8-dihydro-1, 3, 6, 8-tetraazapyrenes
FR3787A FR1447183A (en) 1964-01-31 1965-01-27 Process for the production of substituted 1, 8-dihydro-1, 3, 6, 8-tetraazapyrenes and substituted 1, 3, 6, 8-tetraazapyrenes
AT76365A AT250982B (en) 1964-01-31 1965-01-28 Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes
BE659016D BE659016A (en) 1964-01-31 1965-01-29
NL6501197A NL6501197A (en) 1964-01-31 1965-01-29
GB4020/65A GB1022660A (en) 1964-01-31 1965-01-29 Substituted 1,8-dihydro-1,3,6,8-tetra-azapyrenes and dehydrogenation products thereof
FR15042A FR4367M (en) 1964-01-31 1965-04-28

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF41883A DE1263775B (en) 1964-01-31 1964-01-31 Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes
DEF41884A DE1265754B (en) 1964-01-31 1964-01-31 Process for the preparation of salts of substituted 1, 8-dihydro-1, 3, 6, 8-tetraazapyrenes

Publications (1)

Publication Number Publication Date
DE1263775B true DE1263775B (en) 1968-03-21

Family

ID=25976125

Family Applications (2)

Application Number Title Priority Date Filing Date
DEF41884A Pending DE1265754B (en) 1964-01-31 1964-01-31 Process for the preparation of salts of substituted 1, 8-dihydro-1, 3, 6, 8-tetraazapyrenes
DEF41883A Pending DE1263775B (en) 1964-01-31 1964-01-31 Process for the preparation of new substituted 1, 3, 6, 8-tetraazapyrenes

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DEF41884A Pending DE1265754B (en) 1964-01-31 1964-01-31 Process for the preparation of salts of substituted 1, 8-dihydro-1, 3, 6, 8-tetraazapyrenes

Country Status (5)

Country Link
BE (1) BE659016A (en)
DE (2) DE1265754B (en)
FR (2) FR1447183A (en)
GB (1) GB1022660A (en)
NL (1) NL6501197A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2675804A1 (en) * 2011-02-18 2013-12-25 Basf Se Tetraazapyrene compounds and their use as n-type semiconductors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2561506C1 (en) * 2014-04-04 2015-08-27 Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук METHOD OF OBTAINING 2,7-DIALKYL-2,3a,5a,7,8a,10a-HEXAAZAPERHYDROPYRENES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1005520B (en) * 1953-07-18 1957-04-04 Hoechst Ag Process for the preparation of derivatives of naphthophenazine

Non-Patent Citations (1)

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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2675804A1 (en) * 2011-02-18 2013-12-25 Basf Se Tetraazapyrene compounds and their use as n-type semiconductors
EP2675804A4 (en) * 2011-02-18 2014-07-16 Basf Se Tetraazapyrene compounds and their use as n-type semiconductors
US8901300B2 (en) 2011-02-18 2014-12-02 Basf Se Tetraazapyrene compounds and their use as N-type semiconductors

Also Published As

Publication number Publication date
BE659016A (en) 1965-07-29
FR4367M (en) 1966-08-22
NL6501197A (en) 1965-08-02
DE1265754B (en) 1968-04-11
FR1447183A (en) 1966-07-29
GB1022660A (en) 1966-03-16

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