US4294837A
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1,3-Dihydro-6-(pyridinyl)-2H-imidazo[4,5-b]pyridin-2-ones and -imidazo[4,5-b]pyridine-2-thiones and their cardiotonic use
Assignee: Sanofi SA
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Filing: 1980-03-28
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Granted: 1981-10-13
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Expires: 2000-03-28
Abstract
Abstract 1,3-Dihydro-1-R 1 -3-R 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 1 and R 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 1 and R 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 3 NH-3-R 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 3 NH-3-R 1 NH-5-PY-6-Q-pyridines and other intermediates used in said processes.
Inventors
- 👤 George Y. Lesher
- 👤 Chester J. Opalka, Jr.
- 👤 Donald F. Page
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:01
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/61; C07D213/72; C07D213/73; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
89 words
A 1,3-dihydro-1-R 1 -3-R 3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or -2-thione having the formula ##STR5## where Z is O or S, Q is hydrogen or lower-alkyl, R 1 and R 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 1 or R 3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
89 words
A 1,3-dihydro-1-R 1 -3-R 3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or -2-thione having the formula ##STR5## where Z is O or S, Q is hydrogen or lower-alkyl, R 1 and R 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 1 or R 3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
12 words
A compound according to claim 1 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 4
Dependent Claim
13 words
A compound according to claim 1 where Q is hydrogen, methyl or ethyl.
Claim 5
Dependent Claim
10 words
A compound according to claim 1 where Z is O.
Claim 6
Dependent Claim
19 words
A compound according to claim 1 where R 3 is hydrogen when R 1 is methyl, ethyl or 2-hydroxyethyl.
Claim 7
Dependent Claim
19 words
A compound according to claim 1 where R 1 is hydrogen when R 3 is methyl, ethyl or 2-hydroxyethyl.
Claim 8
Dependent Claim
25 words
A compound according to claim 1 where R 1 is hydrogen, R 3 is 2-hydroxyethyl, PY is 4-pyridinyl and Q is hydrogen, methyl or ethyl.
Claim 9
Dependent Claim
6 words
1,3-Dihydro-3-(2-hydroxyethyl)-6-(4-pyridinyl)-2H-imidazo[4,5-b]pyridin-2-one or pharmaceutically-acceptable acid-addition salt thereof.
Claim 10
Dependent Claim
6 words
1,3-Dihydro-3-(2-hydroxyethyl)-6-(4-pyridinyl)-2H-imidazo[4,5-b]pyridin-2-one or pharmaceutically-acceptable acid-addition salt thereof.
Claim 11
Dependent Claim
110 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, an effective amount of a cardiotonic 1,3-dihydro-1-R 1 -3-R 3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or -2-thione or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, Q is hydrogen or lower-alkyl, R 1 and R 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 1 or R 3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 12
Dependent Claim
110 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, an effective amount of a cardiotonic 1,3-dihydro-1-R 1 -3-R 3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or -2-thione or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, Q is hydrogen or lower-alkyl, R 1 and R 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 1 or R 3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 13
Dependent Claim
17 words
A composition according to claim 9 where the active component is 1,3-dihydro-3-(2-hydroxyethyl)-6-(4-pyridinyl)-2H-imidazo[4,5-b]pyridin-2-one or pharmaceutically-acceptable acid-addition salt thereof.
Claim 14
Independent Claim
118 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering orally or parenterally in a solid or liquid dosage form to such patient an effective amount of the cardiotonic 1,3-dihydro-1-R 1 -3-R 3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or -2-thione or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, Q is hydrogen or lower-alkyl, R 1 and R 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 1 or R 3 being hydrogen, and PY or 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 15
Independent Claim
118 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering orally or parenterally in a solid or liquid dosage form to such patient an effective amount of the cardiotonic 1,3-dihydro-1-R 1 -3-R 3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-one or -2-thione or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, Q is hydrogen or lower-alkyl, R 1 and R 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 1 or R 3 being hydrogen, and PY or 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 16
Dependent Claim
16 words
The method according to claim 11 where the cardiotonic is 1,3-dihydro-3-(2-hydroxyethyl)-6-(4-pyridinyl)-2H-imidazo[4,5-b]pyridin-2-one or pharmaceutically-acceptable acid-addition salt thereof.
References Cited (Backward Citations)
US4152434A
Cited
US4195088A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-12 | 1985-04-13 | 1985-10-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-12 | 1989-04-13 | 1989-10-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-12 | 1993-04-13 | 1993-10-13 | $7700.00 | Window Closed / Lapsed |