Inotropic Activities of Imidazopyridines

Barraclough, P.; Black, J.W.; Cambridge, D.; Gerskowitch, V.P.; Hull, Robert; Lyer, Ramachandran; King, W. R.; Kneen, Clare O.; Nobbs, M. S.; Shah, Gita P.; Smith, S.; Vine, S. J.; Whiting, M. V.

doi:10.1002/ardp.19903230811

Archiv der Pharmazie

1990

DOI: 10.1002/ardp.19903230811

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Inotropic Activities of Imidazopyridines

P. Barraclough

J.W. Black

D. Cambridge

et al.

Abstract: A series of 2-substituted 1H-imidazo[4,5-b]pyridines and the isomeric 1H-imidazo[4,5-c]pyridine derivatives has been prepared and evaluated as inotropic agents. The 1H-imidazo-[4,5-b] derivatives were found to be consistently more potent than their isomers in the [4,5-c] series in isolated guinea pig papillary muscle preparations. Structure-activity relationships and the species-dependence of inotropic potencies are discussed.

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Cited by 8 publications

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Inotropic Polyazapentalene Sulmazole Analogues

Barraclough¹,

Black²,

Cambridge³

et al. 1992

Archiv der Pharmazie

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Aryl substituted 1H-imidazo[1,2-a]imidazole 8, imidazo[2,1-b]thiazole 9, 1,4-dihydroimidazo[4,5-d]imidazole 11, and 1(2),4-dihydroimidazo[4,5-c]pyrazoles 12-17 have been prepared. An X-ray crystallographic study confirmed the structure of 8 and showed this analogue to exist as the 1H-tautomer. These heterocycles were evaluated as inotropic agents and analogues 12, 15, and 17 found to display inotropic properties which were less potent in vitro, but more potent in vivo, than those of sulmazole. Structure-activity relationships are discussed.

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Inotropic Polyazapentalene Sulmazole Analogues

Barraclough¹,

Black²,

Cambridge³

et al. 1992

Archiv der Pharmazie

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Nitroketenaminal, 10.Mit. Synthese von 5‐Methyl‐ und 5‐Phenyl‐Sulmazol. Nitroketeneaminals, X: Synthesis of 5‐Methyl‐ and 5‐Phenyl‐sulmazol

Troschütz

Lückel

1992

Archiv der Pharmazie

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Hemmstoffe der Phosphodiesterase stellen ein neuartiges Therapieprinzip in der Behandlung der Herzinsuftiziens da?). Sulmazol (SC)~).~), ein Wirkstoff aus dieser G~p p e , wirkt positiv inotrop, indem er die Phosphodiesterase 111 am Herzen hemmt6). Als Imidazo [4,5-b]pyridin rnit 2,3-Diamino-Partialstruktur wird 5c aus 2,3-Diaminopyridin (lc) und der Benzoesiiuiure (3) aufgebaut7).Die Herstellung von im Pyridinring substituierten Derivaten des S u l m a z~l s~)~~)~~~) , Verbindungen rnit ahnlichem pharmakologischen Wirkprofil, war aufwendig, da die benotigten 2,3-Diaminopyridine nur durch mehrstufige Synthese zugkglich sind"). Dies war fur uns Ausgangspunkt, die beiden nach unserer Methode aus 2-Nitroethen-1,l-diamin und den P-Aminovinylketonen 4-Amino-3-buten-2-on und 3-dimethy lamino-1 -phenyl-2-propen-1 -on gut zuganglichen 2-Amino-3-nitropyridine la bzw. der Verschiebungswert fiir die Methylsulfoxidgruppe 6 = 2.84 ppm; er ist gegeniiber der Methylthiogruppe in 4a (6 = 2.57 ppm) um A6 = 0,27 ppm zu tieferem Feld verschoben, was gut rnit Literaturdaten iiberein~timmt'~) (entsprechend die 'H-NMR-Verschiebungswerte von 5b bei 6 = 2.85 ppm und von 4b bei 6 = 2.59 ppm).Aufgrund der Tautomerie des Imidazolringes konnen Imidazo [4,5-b]pyridine in der 1H-und/oder 3H-F0rm'~) vorliegen.

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ChemInform Abstract: Inotropic Activities of Imidazopyridines.

et al. 1990

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Inotropic Activities of Imidazopyridines

Cited by 8 publications

References 9 publications

Inotropic Polyazapentalene Sulmazole Analogues

Inotropic Polyazapentalene Sulmazole Analogues

Nitroketenaminal, 10.Mit. Synthese von 5‐Methyl‐ und 5‐Phenyl‐Sulmazol. Nitroketeneaminals, X: Synthesis of 5‐Methyl‐ and 5‐Phenyl‐sulmazol

ChemInform Abstract: Inotropic Activities of Imidazopyridines.

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