Patent US4276293A successfully refreshed from Google Patents.
US4276293A
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Compositions and their preparation
Assignee: Sanofi SA
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Filing: 1980-03-28
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Granted: 1981-06-30
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Expires: 2000-03-28
Abstract
Abstract 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridines (I) or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridines (IA) or pharmaceutically-acceptable acid-addition salts thereof, where Q and R 2 are each 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 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, which are useful as cardiotonics, are prepared by reacting 2-R 3 NH-3-R 1 NH-5-PY-6-Q-pyridine (II) with a tri-(lower-alkyl) ortho-(lower-alkanoate). Also shown are: the use of I or IA or salts in cardiotonic compositions and a method for increasing cardiac contractility; and, the preparation of the intermediates II, as well as intermediates used to prepare II.
Inventors
- 👤 George Y. Lesher
- 👤 Chester J. Opalka, Jr.
- 👤 Donald F. Page
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:37
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/76; C07D213/77; A; A61; A61P; A61P9/00; A61P9/04; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07D213/61; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
84 words
A 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridine having formula I or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine having formula IA ##STR3## where Q and R 2 are each 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, 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
84 words
A 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridine having formula I or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine having formula IA ##STR3## where Q and R 2 are each 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, 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
18 words
A compound according to claim 1 where R 1 or R 3 is hydrogen, methyl, ethyl or 2-hydroxyethyl.
Claim 4
Dependent Claim
12 words
A compound according to claim 1 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 5
Dependent Claim
13 words
A compound according to claim 1 where Q is hydrogen, methyl or ethyl.
Claim 6
Dependent Claim
14 words
A compound according to claim 1 where R 2 is hydrogen, methyl or ethyl.
Claim 7
Dependent Claim
64 words
The process which comprises reacting 2-R 3 NH-3-R 1 NH-5-PY-6-Q-pyridine with a tri-(lower-alkyl) ortho(lower-alkanoate) to produce when R 1 is hydrogen 2-R 2 -3-R 3 -3H-imidazo[4,5-b]pyridine or when R 3 is hydrogen 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine, where PY, R 1 , R 2 , R 3 and Q have the meanings given in claim 1 for the compound of formula I or IA.
Claim 8
Dependent Claim
22 words
The process according to claim 6 where trimethyl or triethyl orthoformate is used to produce the product where R 2 is hydrogen.
Claim 9
Dependent Claim
22 words
The process according to claim 6 where trimethyl or triethyl orthoacetate is used to produce the product where R 2 is methyl.
Claim 10
Dependent Claim
102 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 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridine or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q and R 2 are each 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, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 11
Dependent Claim
102 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 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridine or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q and R 2 are each 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, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 12
Independent Claim
101 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 a cardiotonic 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridine or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q and R 2 are each hydrogen or 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, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 13
Independent Claim
101 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 a cardiotonic 2-R 2 -3-R 3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridine or 1-R 1 -2-R 2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q and R 2 are each hydrogen or 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, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
References Cited (Backward Citations)
No citation records indexed.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-06-29 | 1984-12-29 | 1985-06-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-29 | 1988-12-29 | 1989-06-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-29 | 1992-12-29 | 1993-06-30 | $7700.00 | Window Closed / Lapsed |