US4297360A
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5-(Pyridinyl)pyridine-2,3-diamines, preparation thereof and their cardiotonic use
Assignee: Sanofi SA
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Filing: 1980-03-28
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Granted: 1981-10-27
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Expires: 2000-03-28
Abstract
Abstract 2-R 3 RN-3-R 1 R'N-5-PY-6-Q-pyridines (I) or pharmaceutically-acceptable acid-addition salts thereof are useful as intermediates in the preparation of 1- or 3-substituted-1,3-dihydro-5-Q-6-PY-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones and also as intermediates for preparing 1- or 3-substituted-5-Q-6-PY-3H(or 1H)-imidazo[4,5-b]pyridines, where R 1 , R 3 , R, R', PY and Q are defined hereinbelow. Also shown are processes for preparing I and the following intermediates used therein: 2-halo-3-nitro-5-PY-6-Q-pyridines (III), 2-R 3 RN-3-nitro-5-PY-6-Q-pyridines (V), 2-halo-5-PY-6-Q-pyridines (VII), 2-R 3 RN-5-PY-6-Q-pyridines (VIII) and 2-R 3 RN-3-halo-5-PY-6-Q-pyridines (IX) or salts thereof. Certain embodiments of II and VIII also are useful as cardiotonics and are shown as active components of cardiac compositions and methods for increasing cardiac contractility.
Inventors
- 👤 George Y. Lesher
- 👤 Chester J. Opalka, Jr.
- 👤 Donald F. Page
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:53
CPC Classifications
C; C07; C07D; C07D333/00; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/84; C07D213/85; A; A61; A61P; A61P9/00; A61P9/04; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07D213/61; C07D213/62; C07D213/63; C07D213/64; C07D213/72; C07D213/73; C07D213/74; C07D213/75; C07D213/76; C07D213/77; C07D213/79; C07D213/80; C07D213/81; C07D213/82
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
75 words
A 2-R 3 RN-3-R 1 RN-5-PY-6-Q-pyridine having the formula ##STR4## or pharmaceutically-acceptable acid-addition salt thereof, where Q, R and R' are each hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and, 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 linkgages and NB is di-(lower-alkyl)amino or 4-morpholinyl.
Claim 2
Dependent Claim
75 words
A 2-R 3 RN-3-R 1 RN-5-PY-6-Q-pyridine having the formula ##STR4## or pharmaceutically-acceptable acid-addition salt thereof, where Q, R and R' are each hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and, 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 linkgages and NB is di-(lower-alkyl)amino or 4-morpholinyl.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 where Q is hydrogen, methyl or ethyl.
Claim 4
Dependent Claim
12 words
A compound according to claim 1 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 5
Dependent Claim
37 words
A compound according to claim 1 wherein R and R' are each hydrogen when one of R 1 or R 3 is hydrogen and the other of R 1 or R 3 is methyl, ethyl or 2-hydroxyethyl.
Claim 6
Dependent Claim
28 words
A compound according to claim 1 where R 1 and R' are each hydrogen when R 3 is methyl or ethyl and R is hydrogen, methyl or ethyl.
Claim 7
Dependent Claim
34 words
A 2-halo-3-nitro-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where halo is bromo or chloro, Q is hydrogen or lower-alkyl and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 8
Dependent Claim
34 words
A 2-halo-3-nitro-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where halo is bromo or chloro, Q is hydrogen or lower-alkyl and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 9
Dependent Claim
64 words
A 2-R 3 RN-3-nitro-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q and R are each hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R 3 is 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.
Claim 10
Dependent Claim
64 words
A 2-R 3 RN-3-nitro-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q and R are each hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R 3 is 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.
Claim 11
Dependent Claim
34 words
A 2-halo-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where halo is bromo or chloro, Q is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 12
Dependent Claim
34 words
A 2-halo-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where halo is bromo or chloro, Q is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 13
Dependent Claim
62 words
A 2-R 3 RN-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where R and Q are each lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R 3 is 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.
Claim 14
Dependent Claim
62 words
A 2-R 3 RN-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where R and Q are each lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R 3 is 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.
Claim 15
Dependent Claim
70 words
A 2-R 3 RN-3-halo-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where R and Q are each hydrogen or lower-alkyl, halo is bromo, chloro or iodo, Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R 3 is 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.
Claim 16
Dependent Claim
70 words
A 2-R 3 RN-3-halo-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where R and Q are each hydrogen or lower-alkyl, halo is bromo, chloro or iodo, Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R 3 is 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.
Claim 17
Dependent Claim
63 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-NRR-3-NR'R'-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and NRR and NR'R' are each amino, lower-alkylamino or di-(lower-alkyl)amino.
Claim 18
Dependent Claim
63 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-NRR-3-NR'R'-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and NRR and NR'R' are each amino, lower-alkylamino or di-(lower-alkyl)amino.
Claim 19
Independent Claim
71 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-NRR-3-NR'R'-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and NRR and NR'R' are each amino, lower-alkylamino or di-(lower-alkyl)amino.
Claim 20
Independent Claim
71 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-NRR-3-NR'R'-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and NRR and NR'R' are each amino, lower-alkylamino or di-(lower-alkyl)amino.
Claim 21
Dependent Claim
57 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-amino(or monomethylamino or dimethylamino)-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 22
Dependent Claim
57 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-amino(or monomethylamino or dimethylamino)-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 23
Independent Claim
65 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-amino(or monomethylamino or dimethylamino)-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 24
Independent Claim
65 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-amino(or monomethylamino or dimethylamino)-5-PY-6-Q-pyridine or pharmaceutically-acceptable acid-addition salt thereof, where Q is hydrogen or lower-alkyl and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-26 | 1985-04-27 | 1985-10-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-26 | 1989-04-27 | 1989-10-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-26 | 1993-04-27 | 1993-10-27 | $7700.00 | Window Closed / Lapsed |