Production of imidazo[4,5-b]pyridin-2-ones or thiones
AssigneeSterling Drug Inc.
InventorsGeorge Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
Life of this patent
Estimating the term…
Loading patent…
AssigneeSterling Drug Inc.
InventorsGeorge Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
Estimating the term…
1,3-Dihydro-1-R.sub.1 -3-R.sub.3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones or pharmaceutically-acceptable acid-addition salts thereof, which are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, R.sub.1 and R.sub.3 are each hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 and R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, are prepared by reacting a 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine with urea or carbonyldiimidazole to produce said -2-one or with an alkali metal xanthate, thiourea or thiocarbonyldiimidazole to produce said -2-thione. Also shown and claimed are cardiotonic compositions and a method for increasing cardiac contractility using said cardiotonic agents. Also shown are processes for preparing said intermediate 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridines and other intermediates used in said processes.
The process which comprises reacting 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine with urea or carbonyldiimidazole to produce 1,3-dihydro-1-R.sub.1 -3-R.sub.3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or with an alkali metal xanthate, thiourea or thiocarbonyldiimidazole to produce 1,3-dihydro-1-R.sub.1 -3-R.sub.3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridine-2-thione, where Q is hydrogen or lower-alkyl, R.sub.1 and R.sub.3 each are hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene having at least two carbon atoms between its connecting linkages and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 or R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Dependencies are inferred from the claim text.