DD287263A5 - PROCESS FOR PREPARING 6- (PYRID-4-YL) -1,2,4-TRIAZOLO- [1,5-A] PYRIDINES - Google Patents
PROCESS FOR PREPARING 6- (PYRID-4-YL) -1,2,4-TRIAZOLO- [1,5-A] PYRIDINES Download PDFInfo
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- DD287263A5 DD287263A5 DD33215389A DD33215389A DD287263A5 DD 287263 A5 DD287263 A5 DD 287263A5 DD 33215389 A DD33215389 A DD 33215389A DD 33215389 A DD33215389 A DD 33215389A DD 287263 A5 DD287263 A5 DD 287263A5
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Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von * durch Umsetzung von 3-substituierten * mit Orthoestern, Estern, Cyancarbonsaeureestern, Saeurehalogeniden, Saeureanhydriden, Dicarbonsaeureanhydriden, Lactonen bzw. Phosgen oder Harnstoff. Die Verbindungen sind biologisch aktiv. Anwendungsgebiete der Erfindung sind die pharmazeutische und die agrochemische Industrie.{* * * Ester; Orthoester; Cyancarbonsaeureester; Saeurehalogenide; Saeureanhydride; Dicarbonsaeureanhydride; Lactone; Phosgen; Harnstoff}The invention relates to a process for the preparation of * by reaction of 3-substituted * with ortho esters, esters, Cyancarbonsaeureestern, Saheehalogeniden, Saeureanhydriden, Dicarbonsaeureanhydriden, lactones or phosgene or urea. The compounds are biologically active. Areas of application of the invention are the pharmaceutical and agrochemical industries. {* * * Esters; Orthoester; Cyancarbonsaeureester; halides; anhydrides; dicarboxylic acid; lactones; phosgene; Urea}
Description
Einige 1,2,4-Triazolo[1,5-a]pyridine sind bereits bekannt (T.Okamoto, M. Hirobe, Y.Tamai, E. Yabe, Chern. Pharm. Bull. 14,606 [1966]; K.T. Potts, H.R. Burton, J.Bhattacharyya, J- Org. Chem. 31,260 [1966]; K.Gewald, A.Schubert, G.Martin, J. f. prakt. Chemie317,561 [1975); H. Berner, H. Reinshagen, Monatshefte f. Chemie 106,1059 [1975); T.lkura, S.Suzne DD-PS 2905823 bzw. US-PS 202977; K.Kubo, N.ltoh, I.Sohzu, Y.lsomura, H.Honma, JP.PS 7905996C.A. 91,57007r (1979), JP-PS 8163983 [CA. 95, 203904b [19811; R.C. Phadke, D.W. Rangnekar, Syntghesis 1986,860).Some 1,2,4-triazolo [1,5-a] pyridines are already known (T.Okamoto, M. Hirobe, Y. Tamai, E. Yabe, Chern. Pharm. Bull. 14,606 [1966]; KT Potts, HR Burton, J.Bhattacharyya, J Org Chem 31, 260 [1966], K.Gewald, A. Schubert, G. Martin, J. f.pra, Chemie 377, 561 [1975]; H. Berner, H. Reinshagen, Monatshefte f. Chemistry 106, 1059 [1975]; T. lkura, S.Suzne DD-PS 2905823 and US-PS 202977; K. Kubo, N.ltoh, I.Sohzu, Y. solomura, H.Honma, JP.PS 7905996C.A. 91, 57007r (1979), Japanese Patent 8163983 [CA. 95, 203904b [19811; R.C. Phadke, D.W. Rangnekar, Syntghesis 1986, 860).
Beschrieben ist auch ihre Darstellung ausgehend von 1-Amino-2-imino-1,2-dihydro-pyridinen bzw. 1,2-Diamlnopyridiniumsalzen durch Cyclisierung mit Carbonsäuren bzw. Carbonsäurederivaten (T. Okamoto et al. J. Org. Chem. 31, 260 [1966]; T.lkura et al. DD-PS 2905823 bzw. US-PS 202977, JP-PS 8163983). 6-(Pyrid-4-yl)-1,2,4-triazolo-[1,5-a]pyridino sind bisher nicht bekannt.Also described is their preparation starting from 1-amino-2-imino-1,2-dihydro-pyridines or 1,2-diaminopyridinium salts by cyclization with carboxylic acids or carboxylic acid derivatives (T. Okamoto et al., J. Org. Chem , 260 [1966], T.lkura et al., DD-PS 2905823 and US-PS 202977, JP-PS 8163983). 6- (Pyrid-4-yl) -1,2,4-triazolo [1,5-a] pyridino are not yet known.
Es ist das Ziel der Erfindung, neue biologisch aktive und als Zwischenprodukte nutzbare 1,2,4-Triazolo|1,5-a)pyridine herzustellen, wobei von gut zugänglichen Ausgangsprodukten ausgegangen werden soll.It is the object of the invention to produce novel biologically active 1,2,4-triazolo | 1,5-a) pyridines which can be used as intermediates, starting from easily accessible starting materials.
darzustellen.display.
werden, indem Verbindungen der Formel Ilbe prepared by compounds of the formula II
(V. Hagen et al., DD 263769), In denen X die oben angegebene Bedeutung hat mit einem Orthoester, Ester, Cyancarbonsäureester,(V. Hagen et al., DD 263769), in which X has the abovementioned meaning with an orthoester, ester, cyano-carboxylic acid ester,
herzustellen, wobei gut zugängliche Ausgangsstoffe eingesetzt werden.produce, with readily available starting materials are used.
anorganischen oder organischen Säuren dargestellt werden können, sind biologisch aktiv. Insbesondere wurden positivinotrope und vasodilatatorische Wirkungen gafunden.inorganic or organic acids can be represented, are biologically active. In particular, positive inotropic and vasodilatory effects were found.
die Herstellung weiterer biologisch aktiver Verbindungen.the preparation of other biologically active compounds.
entsprechenden pharmazeutischen Verabreichungsformen.corresponding pharmaceutical administration forms.
8-Cyan-6-(pyrld-4-yl)-1,2,4-trlazolo[1,5-a)pyrldln8-cyano-6- (pyrld-4-yl) -1,2,4-trlazolo [1,5-a) pyrldln
1g(4,73mmol) 1-Amino-3-cyan-2-lmino-5-(pyrid-4-yl)-1,2-dihydro-pyridin werden mit 16ml Orthoameisensäuretriethylesterund 5ml Ameisensäure 5h am Rückfluß gekocht. Es wird mit Aktivkohle versetzt, filtriert, neutralisiert, abgesaugt und aus1 g (4.73 mmol) of 1-amino-3-cyano-2-imino-5- (pyrid-4-yl) -1,2-dihydro-pyridine are refluxed with 16 ml of triethyl orthoformate and 5 ml of formic acid for 5 h. It is mixed with activated charcoal, filtered, neutralized, filtered with suction and off
C12H7N6 (221,2)C 12 H 7 N 6 (221.2)
8-Carbamoyl-6-(pyrld-4-yl)-1,2,4-trlozolo[1,5-a]pyrldln8-carbamoyl-6- (pyrld-4-yl) -1,2,4-trlozolo [1,5-a] pyrldln
2g (8,7mmol) 1-Amino-3-carbamoyl-2-imino-5-(pyrid-4-yl)-1,2-dihydro-pyridin werden in 50ml Eisessig 1 h mit 30ml2 g (8.7 mmol) of 1-amino-3-carbamoyl-2-imino-5- (pyrid-4-yl) -1,2-dihydro-pyridine are dissolved in 50 ml of glacial acetic acid for 1 h with 30 ml
verdünnter HCI-Lösung gelöst, durch Alkalisieren mit wäßriger NHj-Lösung gefällt, abgei lugt und getrocknet.Dissolved dilute HCl solution, precipitated by alkalization with aqueous NHj solution, abgei peeps and dried.
C12H9N6O, (239,2)C 12 H 9 N 6 O, (239.2)
e-CyaivZ-ovanmethyl-e-lpyrlcM-yn-i^-trlrzoloH.B-alpyrldlne-CyaivZ-ovanmethyl-e-lpyrlcM-yn-i ^ -trlrzoloH.B-alpyrldln
2,11 gdOmmol) i-Amino-S-cyan^-imino-S-fpyrid^-ylM^-dihydro-pyridin werden mit4mlCyanesslgsMureethylester 1 h in 80ml Methylglykol am Rückfluß gekocht. Es wird mit Aktivkohle versetzt, filtriert, abgekühlt, Wasser hinzugefügt, über Nacht im Kühlschrank stehengelassen und abgesaugt.2.11 gdOmmol) of i-amino-S-cyano-imino-S-fpyridyl-1-methyl-dihydro-pyridine are refluxed with 4 ml of cyanogenethylmethyl ester in 80 ml of methyl glycol. It is mixed with activated charcoal, filtered, cooled, added water, allowed to stand overnight in the refrigerator and vacuumed.
CuHeNe (260,3)C u H e N e (260.3)
Ausbeute: 1,8g (69,2% d. Theorie); Schmb.: 290-2970C (Zers.)Yield: 1.8 g (69.2% of theory); Schmb.: 290-297 0 C (Zers.)
e-Carbamoyl^-cyanmethyl-B-fpyrid^-ylM^-triazolor.i.S-alpyrldine-carbamoyl ^ -cyanmethyl B fpyrid ^ ^ -ylM -triazolor.i.S-alpyrldin
0,5g (2,2mmol) 1-Amino-3-carbamoyl-2-imino-5-(pyrid-4-yl)-1,2-dihydro-pyridin werden mit 1 ml Cyanessigsäureethylester in 25ml Butanol 1 h am Rückfluß gekocht. Es wird abgekühlt und aus viel Methylglykol umkristallisiert.0.5 g (2.2 mmol) of 1-amino-3-carbamoyl-2-imino-5- (pyrid-4-yl) -1,2-dihydro-pyridine are refluxed with 1 ml of ethyl cyanoacetate in 25 ml of butanol for 1 h , It is cooled and recrystallized from much methylene glycol.
C14H10N6O1 (278,3)C 14 H 10 N 6 O 1 (278.3)
Ausbeute: 0,4g (65,3% d. Theorie); Schmb.: > 3100C (Zers.)Yield: 0.4 g (65.3% of theory); Schmb .:> 310 0 C (Zers.)
2-(2-Carboxy-ethyl)-8-cyan-6-(pyrld-4-yl)-1,2,4-trlazolo[1,5-a]pyrldln2- (2-carboxy-ethyl) -8-cyano-6- (pyrld-4-yl) -1,2,4-trlazolo [1,5-a] pyrldln
0,5g (2,4mmol) 1-Amino-3-cyan-2-imino-5-(pyrid-4-yl)-1,2-dihydro-pyridin werden mit 1 g Bernsteinsäureanhydrid in 3ml Eisessig 0,5 h art. Rückfluß gekocht. Es wird abgekühlt, mit Wasser versetzt, abgesaugt und aus DMF unter Zusatz von Aktivkohle umkristallisiert.0.5 g (2.4 mmol) of 1-amino-3-cyano-2-imino-5- (pyrid-4-yl) -1,2-dihydro-pyridine are treated with 1 g of succinic anhydride in 3 ml of glacial acetic acid for 0.5 h art , Reflux cooked. It is cooled, mixed with water, filtered off and recrystallized from DMF with addition of activated carbon.
C16H11N6O2 (293,3)C 16 H 11 N 6 O 2 (293.3)
Ausbeute: 0,49g (69,6% d. Theorie); Schmb.: 248-2540CYield: 0.49 g (69.6% of theory); Shear: 248-254 0 C
2-(3-Acetoxy-propyl)-8-carbamoyl-e-(pyrld-4-yl)-1,2,4-trlazolo(1,5-a]pyrldln 2,3g (lOmmol) 1-Amino-3-carbamoyl-2-imino-5-(pyrid-4-yl)-1,2-dihydro-pyridin werden mit 10ml γ-Butyrolacton in 10ml Eisessig 3 h am Rückfluß gekocht. Es wird 1 ml Acetanhydrid hinzugefügt, für weitere 0,5h gekocht, mit Aktivkohle versetzt, filtriert, neutralisiert, abgesaugt und aus EtH ->nol umkristallisiert.2- (3-Acetoxy-propyl) -8-carbamoyl-e- (pyrld-4-yl) -1,2,4-triazole (1,5-a] pyridine-2,3g (10mmol) 1-amino-3 -carbamoyl-2-imino-5- (pyrid-4-yl) -1,2-dihydro-pyridine are refluxed with 10 ml of γ-butyrolactone in 10 ml of glacial acetic acid for 3 hours, 1 ml of acetic anhydride is added, for another 0, Cooked 5h, mixed with charcoal, filtered, neutralized, filtered off with suction and recrystallized from EtH -> nol.
C17H17N6O2 (339,4)C 17 H 17 N 6 O 2 (339.4)
Ausbeute: 1,75g (51,6% d. Theorie); Schmb.: 183-187"CYield: 1.75 g (51.6% of theory); Schmb.: 183-187 "C
e-Cyan^-oxo-e-ipyrld^-yll^-dlhydro-i^-trloazolon.B-al-pyridln-hydrat 423md, (2mmol) 1-Amino-3-cyan-2-imino-5-(pyrid-4-yl)-1,2-dihydro-pyridin werden in 8ml Dioxan suspendiert, mit0,4ml Triethylamin versetzt und bei Zugabe von 3,5mmol COCI2 in Toluen bei 0-50C 15min gerührt. Es wird 4 Tage stehengelassen, mit etwas Wasser versetzt, abgesaugt, in Ethanol unter Zusatz von etwas 6N NH3-Lösung aufgenommen, mit 6N HCI-Lösung neutralisiert und abgesaugt.e-cyano -oxo-e-ipyrld ^ -yl ^ -dlhydro-i ^ -trloazolone.B-al-pyridine hydrate 423md, (2mmol) 1-amino-3-cyano-2-imino-5- (pyrid -4-yl) -1,2-dihydro-pyridine are suspended in 8 ml of dioxane, admixed with 0.4 ml of triethylamine and stirred with addition of 3.5 mmol COCI 2 in toluene at 0-5 0 C for 15 min. It is allowed to stand for 4 days, mixed with a little water, filtered off, taken up in ethanol with the addition of some 6N NH 3 solution, neutralized with 6N HCl solution and filtered with suction.
C12H8N6O2 (235,2)C 12 H 8 N 6 O 2 (235.2)
Ausbeute: 60mg (11,9% d. Theorie); Schmb.: >320°C (Zers.)Yield: 60 mg (11.9% of theory); Shear:> 320 ° C (decomp.)
Testung auf biologische WirkungTesting for biological effect
Isolierter, spontanaktiver Vorhof des MeerschweinchensIsolated, spontaneously active guinea pig atrium
Für die Versuche wurden männliche Meerschweinchen mit einer Körpermasse von 400-50Og verwendet. Am isolierten, spontanaktiven Vorhof erfolgte nach einer 60 min währenden Adaptationszeit der Organpräparate in bei 320C temperierter carbogendurchperlter Tyrodelösung die Untersuchung der Beeinflussung von Inotropie und Frequenz unter Einwirkung der 6-(Pyrid-4-yl)-1,2,4-trlazolo-[1,5-a]pyridine. So wurde beispielsweise bei Gabe der Verbindung ν .η Beispiel 6 in oiner Konzentration von 10~4mol/l eine 23%ige Steigerung dor Inotropie gefunden.For the experiments male guinea pigs with a body mass of 400-50Og were used. The isolated, spontaneously active atrium was examined after 60 minutes of adaptation of the organ preparations in a temperature controlled at 32 0 C carboxylated Tyrodelösung the influence of inotropy and frequency under the action of 6- (pyrid-4-yl) -1,2,4-trlazolo - pyridine [1,5-a]. Thus, a 23% increase was inotropy dor example, upon administration of the compound in Example 6 ν .η oiner concentration of 10 ~ 4 mol / l found.
Claims (3)
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DD33215389A DD287263A5 (en) | 1989-08-29 | 1989-08-29 | PROCESS FOR PREPARING 6- (PYRID-4-YL) -1,2,4-TRIAZOLO- [1,5-A] PYRIDINES |
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DD33215389A DD287263A5 (en) | 1989-08-29 | 1989-08-29 | PROCESS FOR PREPARING 6- (PYRID-4-YL) -1,2,4-TRIAZOLO- [1,5-A] PYRIDINES |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009068482A1 (en) * | 2007-11-27 | 2009-06-04 | Cellzome Limited | Amino triazoles as pi3k inhibitors |
US8153651B2 (en) | 2007-11-13 | 2012-04-10 | Evotec Ag | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
US8883820B2 (en) | 2006-08-30 | 2014-11-11 | Cellzome Ltd. | Triazole derivatives as kinase inhibitors |
-
1989
- 1989-08-29 DD DD33215389A patent/DD287263A5/en not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8883820B2 (en) | 2006-08-30 | 2014-11-11 | Cellzome Ltd. | Triazole derivatives as kinase inhibitors |
US8153651B2 (en) | 2007-11-13 | 2012-04-10 | Evotec Ag | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
WO2009068482A1 (en) * | 2007-11-27 | 2009-06-04 | Cellzome Limited | Amino triazoles as pi3k inhibitors |
CN101952285A (en) * | 2007-11-27 | 2011-01-19 | 塞尔卓姆有限公司 | Amino triazoles as PI3K inhibitors |
US8865699B2 (en) | 2007-11-27 | 2014-10-21 | Cellzome Ltd. | Amino triazoles as PI3K inhibitors |
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