DE2427382A1 - 3-BENZYLPYRIDO SQUARE CLAMP ON 3.4 SQUARE CLAMP FOR -AS-TRIAZINE AND METHOD OF MANUFACTURING THEREOF - Google Patents

3-BENZYLPYRIDO SQUARE CLAMP ON 3.4 SQUARE CLAMP FOR -AS-TRIAZINE AND METHOD OF MANUFACTURING THEREOF

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Publication number
DE2427382A1
DE2427382A1 DE19742427382 DE2427382A DE2427382A1 DE 2427382 A1 DE2427382 A1 DE 2427382A1 DE 19742427382 DE19742427382 DE 19742427382 DE 2427382 A DE2427382 A DE 2427382A DE 2427382 A1 DE2427382 A1 DE 2427382A1
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DE
Germany
Prior art keywords
benzylpyrido
triazine
square clamp
washed
manufacturing
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
DE19742427382
Other languages
German (de)
Inventor
Allan V Bayless
Joseph E Gray
George C Wright
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.)
ATK Launch Systems LLC
Original Assignee
Morton Norwich Products Inc
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 Morton Norwich Products Inc filed Critical Morton Norwich Products Inc
Publication of DE2427382A1 publication Critical patent/DE2427382A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

deren Herstellungtheir manufacture

Die Erfindung betrifft 3-Benzylpyrido^5,4-e7~as-triazin und 1,2-Dihydro-3-benzylpyrido/3j4-e7-as~triazin-hydrochlorid. Dieae Verbindungen sind wirksame Antipllzmittel, die gegebenenfalls in Form pharmazeutischer Zubereitungen zur Bekämpfung von Pilzinfektionen angewandt werden können. Die Verbindungen können leicht entsprechend den folgenden Beispielen hergestellt werden.The invention relates to 3-benzylpyrido ^ 5,4-e7 ~ as-triazine and 1,2-Dihydro-3-benzylpyrido / 3j4-e7-as-triazine hydrochloride. Dieae Compounds are effective anti-fungal agents that may be used in Form of pharmaceutical preparations for combating fungal infections can be applied. The compounds can be easily prepared according to the following examples.

Beispiel 1example 1

1,2-Dihydro-3-benzylpyrido/3 t4-e7-ae-triagin-hydroclilorid1,2-dihydro-3-benzylpyrido / 3 t 4-e7-ae-triagine hydrochloride

A. Äthyl 3-(3-nitro-4-pyridyl)oarbazat-hydroohlorid A. Ethyl 3- (3-nitro-4-pyridyl) oarbazate hydrochloride

Zu einer Lösung von 91 g (0,57 Mol) 4~Chlor-3-nitropyridin in 600 ml Phenol wurden unter mechanischem Rühren bei 40 bis 5O0C. 62 g (0,60 Hol) Äthylcarbazat zugegeben. Die Reaktion war ca. 5 min lang exotherm, wobei die Temperatur auf 720C stieg. Die Eeaktionslösung wurde ^ /A h auf dem Dampfbad erhitzt, auf 35 bis 4O0C abgekühlt und zu 3,2 1 wasserfreiem Äther gegeben. Nach 10-minütigem Stehen bei Raumtemperatur wurde die überstehendeTo a solution of 91 g (0.57 mol) of 4 ~ chloro-3-nitropyridine in 600 ml of phenol 62 g (0.60 Hol) Äthylcarbazat were added under mechanical stirring at 40 to 5O 0 C.. The reaction was exothermic for about 5 minutes, the temperature rising to 72 ° C. The Eeaktionslösung was heated ^ / A h on the steam bath, cooled to 35 to 4O 0 C and added to 3.2 1 of anhydrous ether. After standing for 10 minutes at room temperature, the supernatant

409881/1234409881/1234

- 2 - 1A-44 560- 2 - 1A-44 560

Lösung dekantiert und der entstehende amorphe Feststoff zweimal mit wasserfreiem Äther- gewaschen. Der Peststoff wurde mit 500 ml Isopropanol behandelt. Beim Verreiben unter Erhitzen auf dean Dampfbad erhielt man einen hellgelben kristallinen Feststoff. Beim ungefähr 10-minütigen Abkühlen im Eisbad wurde das anfängliche Produkt gesammelt, gut mit Isopropanol und Äther gewaschen und im Vakuumexsikkator über Nacht getrocknet. Ausbeute 55 g (37 $)· Das Produkt wurde aus 700 ml Äthanol umkristallisiert, Fp 203-204°. Ausbeute 40 g. Q fi N The solution is decanted and the amorphous solid formed is washed twice with anhydrous ether. The pesticide was treated with 500 ml of isopropanol. Trituration with heating on the steam bath gave a pale yellow crystalline solid. Upon cooling in the ice bath for about 10 minutes, the initial product was collected, washed well with isopropanol and ether, and dried in the vacuum desiccator overnight. Yield 55 g ($ 37). The product was recrystallized from 700 ml of ethanol, mp 203-204 °. Yield 40g. Q fi N

Anal. Berechnet für C8H10N4O4-HGl: 36,58 4,22 21,33Anal. Calculated for C 8 H 10 N 4 O 4 -HGl: 36.58 4.22 21.33

Gefunden: 36,70 4,22 21,65Found: 36.70 4.22 21.65

B. 4-Kydrazin—3-nitröpyridin-~hydroohlorid B. 4-Kydrazine-3-nitro pyridine hydrochloride

Eine Lösung von 87 g (0,33 Mol) von A. in 520 ml konz. HCl wurde 23 h auf einem Dampfbad zur Trockene erhitzt. Der gelbe Feststoff wurde mit 200 ml Äthanol aufgeschlämmt, 20 min unter Rückfluß erhitzt und heiß filtriert. Der rote kristalline Feststoff wurde mit 100 ml Isopropanol und 200 ml Äther gewaschen und getrocknet. Fp 219-221° (Zers.). Ausbeute 39 g (56 ^).A solution of 87 g (0.33 mol) of A. in 520 ml of conc. HCl was heated to dryness on a steam bath for 23 h. The yellow solid was slurried with 200 ml of ethanol, 20 min under Heated to reflux and filtered hot. The red crystalline solid was washed with 100 ml of isopropanol and 200 ml of ether and dried. Mp 219-221 ° (dec.). Yield 39 g (56 ^).

Das rohe Produkt wurde aus 1050 ml Methanol umkristallisiert, mit fünf mal 20 ml Methanol und 250 ml Äther gewaschen und getrocknet. Fp 225-227° (Zers.). Ausbeute 24 g (38The crude product was recrystallized from 1050 ml of methanol, washed five times with 20 ml of methanol and 250 ml of ether and dried. Mp 225-227 ° (dec.). Yield 24 g (38

C HC H

Anal. Berechnet für C5H6N4O2.HCl: 31,51 3,70Anal. Calculated for C 5 H 6 N 4 O 2 .HCl: 31.51 3.70

Gefunden: 31,60 3,80Found: 31.60 3.80

C. ^-Amino-4-hydrazinopyridin-hydrochlorid C. ^ -Amino-4-hydrazinopyridine hydrochloride

22 g (0,12 Mol) B. wurden in 170 ml Äthanol auf ge schlämmt, mit 1,4 g 5 i> Pd/C (50 i> Feuchtigkeit) behandelt und unter einem Druck von 3,52kg/cm (50 psig) hydriert. Die VTasseratoffaufnahme betrug 13,62 kg (30 Va) in 4 h. Das Eeduktionsgemisch wurde 2 h abgekühlt land filtriert. Das Produkt und der Katalysator wurden mit drei mal 10 ml Isopropanol und Äther gewaschen und getrocknet. Fp 217 bis22 g (0.12 mol) of B. was slurried in 170 ml of ethanol, treated with 1.4 g of 5 i> Pd / C (50 i> moisture) and pressurized under a pressure of 3.52 kg / cm (50 psig ) hydrogenated. The V-water uptake was 13.62 kg (30 Va) in 4 hours. The reduction mixture was cooled and filtered for 2 hours. The product and the catalyst were washed three times with 10 ml of isopropanol and ether and dried. Fp 217 to

409881/1234409881/1234

NN ClCl 6060 2929 ,40, 40 18,18 5050 2929 ,66, 66 16,16,

- 3 - ■ 1A-44 560- 3 - ■ 1A-44 560

218° (Zers.). Ausbeute 17g (92 $).218 ° (dec.). Yield 17g ( $ 92).

Dieses Verfahren wurde wiederholt, wobei man insgesamt 34 g Produkt plus Katalysator erhielt. Das rohe Produkt (34 g) wurde aus 1,7 1 Methanol:H20 (19:1) umkristallisiert, mit 170 ml Methanol und 300 ml Äther gewaschen und getrocknet. Pp 223-225° (Zers.). Ausbeute 23 g (61 °/°). This procedure was repeated, giving a total of 34 grams of product plus catalyst. The crude product (34 g) was recrystallized from 1.7 l of methanol: H 2 O (19: 1), washed with 170 ml of methanol and 300 ml of ether and dried. Pp 223-225 ° (dec.). Yield 23 g (61 ° / °).

C H NC H N

Anal. Berechnet für C5H8N41HCl:" 37,39 5,65 34,89Anal. Calculated for C 5 H 8 N 41 HCl: "37.39 5.65 34.89

Gefunden: 37,14 5,58 34,72Found: 37.14 5.58 34.72

D· 1,2-Dihydro-3-benzylpyrido/3,4-e7~as-triazin-hydrochlorid D 1,2-dihydro-3-benzylpyrido / 3,4-e7 ~ as-triazine hydrochloride

Ein Gemisch von 35,4 g (0,22 Mol) C. und 60 g (0,44 Mol) Phenylessigsäure wurde 2 h in einem Bad von 130 bis 135°C erhitzt. Es wurde dann abgekühlt und mit einem Gemisch von 350 ml Chloroform und 400 ml Wasser gewaschen. Die wäßrige Sohicht wurde dreimal mit 300 ml Chloroform gewaschen und zur Trockene unter Vakuum eingedampft. Das entstehende rote öl wurde in 400 ml abs. Äthanol gelost. Der entstehende Niederschlag'wurde abfiltriert und mit Äthanol und dann mit Äther gewaschen. Ausbeute 30 g, Pp 268-270° (Zers.).A mixture of 35.4 g (0.22 mol) of C. and 60 g (0.44 mol) of phenylacetic acid was heated in a bath at 130 to 135 ° C. for 2 hours. It was then cooled and washed with a mixture of 350 ml of chloroform and 400 ml of water. The watery layer was washed three times with 300 ml of chloroform and taken to dryness Evaporated in vacuo. The resulting red oil was in 400 ml of abs. Dissolved ethanol. The resulting precipitate was filtered off and washed with ethanol and then with ether. Yield 30 g, pp 268-270 ° (dec.).

Dieses Produkt wurde aus wasserfreiem Methanol umkristallisiert. Pp 265-275° (Zers.). CHNThis product was recrystallized from anhydrous methanol. Pp 265-275 ° (dec.). CHN

Anal. Berechnet für C13H12N41HCl: 59,88 5,03 21,49Anal. Calculated for C 13 H 12 N 41 HCl: 59.88 5.03 21.49

Gefunden: 59,77 4,96 21,57Found: 59.77 4.96 21.57

Beispiel 2Example 2

3-Benzylpyrido/3,4-37-as-triazin3-benzylpyrido / 3,4-37-as-triazine

Zu einer Lösung von 20 g (0,077 Mol) der Verbindung des Beispiels 1 in 400 ml Vaeser und 100 ml Äthanol wurde eine Lösung von 6,5 g (0,077 Mol) NaHCO5 in 50 ml Wasser gegeben. Dann wurden 60 g Mangandioxid zugegeben und das Reaktionsgemisch IV2 h gerührt. Das Reaktionsgemisch wurde filtriert und der Rückstand A solution of 6.5 g (0.077 mol) of NaHCO 5 in 50 ml of water was added to a solution of 20 g (0.077 mol) of the compound from Example 1 in 400 ml of Vaeser and 100 ml of ethanol. Then 60 g of manganese dioxide were added and the reaction mixture was stirred for IV2 h. The reaction mixture was filtered and the residue

409881/123A409881 / 123A

- 4 - 1A-44 560- 4 - 1A-44 560

mit Chloroform gewaschen 'tis die Waschflüssigkeiten farblos waren (300 ml). Die Chloroformschicht wurde mit Wasser gewaschen, durch wasserfreies MgSO. filtriert und schnell zur Trockene eingedampft. Ausbeute 16 g (94 #)f Pp 76-78,5°washed with chloroform until the wash liquids were colorless (300 ml). The chloroform layer was washed with water by anhydrous MgSO. filtered and quickly evaporated to dryness. Yield 16 g (94 #) f Pp from 76 to 78.5 °

Anal. Berechnet für CAnal. Calculated for C

CC. 2525th HH 5454 2525th NN C13H10N4: C 13 H 10 N 4 : 70,70 2020th 4,4, 5353 2525th ,21, 21 Gefunden:Found: 70,70 4,4, ,23, 23

Die erfindungsgemäßen Verbindungen sind wirksame Antipilzmittel. Sie sind in geringen Konzentrationen im Stande, das Wachstum von pathogenen Pilzen, wie Candida albicans und Microeporum canis zu hemmen. Diese Fähigkeit der erfindungsgemäßen Verbindungen ist in der folgenden Tabelle angegeben, die bei üblichen in vitro Versuchen zur Bestimmung der Antipilzaktivität erhalten worden sind unter Anwendung von Sabouraud's Dextrose Agar als Medium, das das Pilzwachstum trägt und Messung der Hemmung dieses Wachstums in Millimeter über einen Zeitraum von acht Tagen.The compounds of the invention are effective antifungal agents. In low concentrations they are able to do that Growth of pathogenic fungi such as candida albicans and Inhibit Microeporum canis. This ability of the invention Compounds is given in the following table, the in usual in vitro tests for the determination of the antifungal activity have been obtained using Sabouraud's Dextrose Agar as a medium supporting fungal growth and measurement of the Inhibition of this growth in millimeters over a period of eight days.

+ Kon^;. in
mcg/ml + Kon ^ ;. in
mcg / ml 0 der Hemmzone
nach Tagen 0 of the inhibition zone
after days in ιin ι mmmm 5252 Verbindunglink 20002000 C. albicans
2 4 6 8C. albicans
2 4 6 8 M
4M.
4th 1010 Beispiel 1example 1 18601860 35 33 32 3135 33 32 31 5252 . oanis
6 8. oanis
6 8 Beispiel 2Example 2 33 33 33 3233 33 33 32 1818th 5252 1010

+ Das Träger-Verdünnungsmittel für die Verbindung in diesem Versuch ist 50 #iges Äthanol, das keine Antipilzwirkung besitzt. + The carrier diluent for the compound in this experiment is 50 # ethanol, which has no antifungal activity.

Eine bemerkenswerte Eigenschaft der erfindungegemäßen Verbindungen ist, daß sie nioht zu Hautreizungen führen. Wenn sie täglich in Form einer Suspension mit Konzentrationen bis zu 4 # in einem Träger, wie wäßriger Methylcellulose, aufgebracht werden, wird keine Hautreizung über einen Zeitraum von 3 Tagen beobachtet.A remarkable property of the compounds according to the invention is that they do not cause skin irritation. If you applied daily in the form of a suspension with concentrations up to 4 # in a carrier such as aqueous methyl cellulose, no skin irritation is observed over a period of 3 days.

409881/12409881/12

- 5 - 1A-44 560- 5 - 1A-44 560

Zur Erleichterung der Verabreichung der erfindungsgemäßen Verbindungen können sie in verschiedenen pharmazeutischen Formen, wie als Salben, Lösungen, Suspensionen, Pulver und Sprays zubereitet werden unter Verwendung im Handel erhältlicher und üblicherweise angewandter Exoipientien, mit denen sie verträglich sind.To facilitate the administration of the invention They can take them in various pharmaceutical forms, such as ointments, solutions, suspensions, powders and compounds Sprays are prepared using commercially available and commonly used exoipients with which they are compatible.

PatentansprücheClaims

409881/1234409881/1234

Claims (3)

PatentansprüoheClaims 1. I12-Dihydro-3-benzylpyrido^5,4-e7~as-triazin.1. I 1 2-Dihydro-3-benzylpyrido ^ 5,4-e7 ~ as-triazine. 2. 1, 2-Dihydro-3-"benzylpyrido-/5 f 4-ej7-as-t riazin-hydro ohlorid.2. 1,2-Dihydro-3- "benzylpyrido- / 5 f 4-ej7-as-triazine hydrochloride. 3. 3-Benzylpyrido/3,4-e7-as-triazin.3. 3-Benzylpyrido / 3,4-e7-as-triazine. Verfahren zur Herstellung von 1,2-Dihydro~3-benzylpyrido-Process for the preparation of 1,2-dihydro ~ 3-benzylpyrido- ae-triazin-hydrochlorid, dadurch gekennzeichnet, daß man 3-Amino-4-hydrazinpyridin-hydrochlorid tunsetzt mit Phenylessigsäure.ae-triazine hydrochloride, characterized in that 3-amino-4-hydrazine pyridine hydrochloride is used does set with phenylacetic acid. 5· Verfahren zur Herstellung von 3-Eenzylpyrido/3,4-e7-astriazin, dadurch g ekennze iohnet, daß man 1 f2-Dihydro-3-l3enzylpyrido/3\ 4-e7-as-triazin-hydrochlorid mit Mangandioxid oxidiert.5. Process for the preparation of 3-eenzylpyrido / 3,4-e7-astriazine, characterized in that 1 f 2-dihydro-3-l3enzylpyrido / 3 \ 4-e7-as-triazine hydrochloride is oxidized with manganese dioxide. 409881/1234409881/1234 6 2XXI6 2XXI
DE19742427382 1973-06-06 1974-06-06 3-BENZYLPYRIDO SQUARE CLAMP ON 3.4 SQUARE CLAMP FOR -AS-TRIAZINE AND METHOD OF MANUFACTURING THEREOF Pending DE2427382A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US367500A US3883526A (en) 1973-06-06 1973-06-06 3-Benzylpyrido {8 3,4-e{9 -as-triazine and 1,2-dihydro-3-benzylpyrido{8 3,4-e{9 -as-triazine hydrochloride

Publications (1)

Publication Number Publication Date
DE2427382A1 true DE2427382A1 (en) 1975-01-02

Family

ID=23447426

Family Applications (1)

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DE19742427382 Pending DE2427382A1 (en) 1973-06-06 1974-06-06 3-BENZYLPYRIDO SQUARE CLAMP ON 3.4 SQUARE CLAMP FOR -AS-TRIAZINE AND METHOD OF MANUFACTURING THEREOF

Country Status (13)

Country Link
US (1) US3883526A (en)
JP (1) JPS5019772A (en)
AU (1) AU473797B2 (en)
BE (1) BE816006A (en)
CH (1) CH591479A5 (en)
DE (1) DE2427382A1 (en)
DK (1) DK302274A (en)
FR (1) FR2232322B1 (en)
GB (1) GB1391900A (en)
IL (1) IL44304A (en)
NL (1) NL7403598A (en)
SE (1) SE7405655L (en)
ZA (1) ZA741277B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE409863B (en) * 1975-08-01 1979-09-10 Egyt Gyogyszervegyeszeti Gyar ANALOGICAL PROCEDURE FOR THE PREPARATION OF PYRIDO (3,4-E) -AS-TRIAZINE DERIVATIVES
DE3064301D1 (en) * 1979-10-18 1983-08-25 Interox Chemicals Ltd Magnesium salts of peroxycarboxylic acids, processes for their preparation and their use as bleaching agents in washing compositions, and processes
JPS6336085A (en) * 1986-07-30 1988-02-16 Taiko Kikai Kogyo Kk Screw type vacuum pump

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3597427A (en) * 1969-01-13 1971-08-03 American Cyanamid Co 1,2-dihydropyrido(3,4-e)-as-triazines

Also Published As

Publication number Publication date
FR2232322B1 (en) 1977-09-09
AU6884674A (en) 1975-11-13
GB1391900A (en) 1975-04-23
SE7405655L (en) 1974-12-09
AU473797B2 (en) 1976-07-01
CH591479A5 (en) 1977-09-15
IL44304A (en) 1977-05-31
ZA741277B (en) 1975-10-29
US3883526A (en) 1975-05-13
DK302274A (en) 1975-02-03
BE816006A (en) 1974-12-06
IL44304A0 (en) 1974-05-16
NL7403598A (en) 1974-12-10
FR2232322A1 (en) 1975-01-03
JPS5019772A (en) 1975-03-01

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