US4264603A
Expired / Lapsed
US
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5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridine-3-amines, their use as cardiotonics and their preparation
Assignee: Sanofi SA
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Filing: 1980-03-17
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Granted: 1981-04-28
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Expires: 2000-03-17
Abstract
Abstract 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridin-3-amines or pharmaceutically-acceptable acid-addition salts thereof, which are useful as cardiotonics, are prepared by reacting a 2-halo-5-PY-6-Q-nicotinonitrile with 1-R-hydrazine, where R is hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl or lower-alkoxyalkyl, 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. Also shown are cardiotonic compositions and method for increasing cardiac contractility using said compounds or salts.
Inventors
- 👤 George Y. Lesher
- 👤 Monte D. Gruett
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:52
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/53; A; A61; A61P; A61P9/00; A61P9/04; C07D213/46; C07D213/50; C07D213/60; C07D213/78; C07D213/79; C07D213/80; C07D213/84; C07D213/85; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
71 words
A 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridin-3-amine having the formula ##STR4## where R is hydrogen, lower-alkyl, lower-hydroxyalkyl having from two to six carbon atoms, 2,3-dihydroxypropyl or lower-alkoxyalkyl having from three to six carbon atoms, 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 where lower-alkyl, all occurrences other than specifically defined above, contains from one to six carbon atoms, or pharmaceutically-acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
71 words
A 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridin-3-amine having the formula ##STR4## where R is hydrogen, lower-alkyl, lower-hydroxyalkyl having from two to six carbon atoms, 2,3-dihydroxypropyl or lower-alkoxyalkyl having from three to six carbon atoms, 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 where lower-alkyl, all occurrences other than specifically defined above, contains from one to six carbon atoms, or pharmaceutically-acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 where R is hydrogen.
Claim 4
Dependent Claim
10 words
A compound according to claim 1 where R is methyl.
Claim 5
Dependent Claim
10 words
A compound according to claim 1 where R is 2-hydroxyethyl.
Claim 6
Dependent Claim
12 words
A compound according to claim 1 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 7
Dependent Claim
12 words
A compound according to claim 1 where Q is hydrogen or methyl.
Claim 8
Dependent Claim
7 words
3-Amino-5-(4-pyridinyl)-1H-pyrazolo [3,4-b]pyridine-1-ethanol or pharmaceutically-acceptable acid-addition salt thereof.
Claim 9
Dependent Claim
7 words
3-Amino-5-(4-pyridinyl)-1H-pyrazolo [3,4-b]pyridine-1-ethanol or pharmaceutically-acceptable acid-addition salt thereof.
Claim 10
Dependent Claim
96 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 for increasing cardiac contractility of a cardiotonic 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridine-3-amine or pharmaceutically-acceptable acid-addition salt thereof, where R is hydrogen, lower-alkyl, lower-hydroxyalkyl having from two to six carbon atoms, 2,3-dihydroxypropyl or lower-alkoxyalkyl having from three to six carbon atoms, 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 where lower-alkyl, all occurrences other than specifically defined above, contains from one to six carbon atoms.
Claim 11
Dependent Claim
96 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 for increasing cardiac contractility of a cardiotonic 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridine-3-amine or pharmaceutically-acceptable acid-addition salt thereof, where R is hydrogen, lower-alkyl, lower-hydroxyalkyl having from two to six carbon atoms, 2,3-dihydroxypropyl or lower-alkoxyalkyl having from three to six carbon atoms, 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 where lower-alkyl, all occurrences other than specifically defined above, contains from one to six carbon atoms.
Claim 12
Dependent Claim
17 words
A composition according to claim 8, where the active component is 3-amino-5-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-1-ethanol or pharmaceutically-acceptable acid-addition salt thereof.
Claim 13
Independent Claim
103 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 for increasing cardiac contractility of a cardiotonic 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridin-3-amine or pharmaceutically-acceptable acid-addition salt thereof, where R is hydrogen, lower-alkyl, lower-hydroxyalkyl having from two to six carbon atoms, 2,3-dihydroxypropyl or lower-alkoxyalkyl having from three to six carbon atoms, 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 where lower-alkyl, all occurrences not specifically defined above, contains from one to six carbon atoms.
Claim 14
Independent Claim
103 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 for increasing cardiac contractility of a cardiotonic 1-R-5-PY-6-Q-1H-pyrazolo[3,4-b]pyridin-3-amine or pharmaceutically-acceptable acid-addition salt thereof, where R is hydrogen, lower-alkyl, lower-hydroxyalkyl having from two to six carbon atoms, 2,3-dihydroxypropyl or lower-alkoxyalkyl having from three to six carbon atoms, 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 where lower-alkyl, all occurrences not specifically defined above, contains from one to six carbon atoms.
Claim 15
Dependent Claim
16 words
The method according to claim 10 where the cardiotonic is 3-amino-5-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-1-ethanol or pharmaceutically-acceptable acid-addition salt thereof.
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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) | 1984-04-27 | 1984-10-27 | 1985-04-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-27 | 1988-10-27 | 1989-04-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-27 | 1992-10-27 | 1993-04-28 | $7700.00 | Window Closed / Lapsed |