Production of imidazo[4,5-b]pyridin-2-ones or thiones

Details Production of imidazo[4,5-b]pyridin-2-ones or thiones Production of imidazo[4,5-b]pyridin-2-ones or thiones

1981-02-20

1982-01-05

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

546256, 546257, C07D47104, C07D41314, C07D40114

Patent

active

043095372

ABSTRACT:
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.

REFERENCES:
Baldwin et al., Jour. of Medicinal Chemistry, vol. 20, pp. 1189-1193 (1977).

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