US4312875A
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5-(Pyridinyl)-6-(lower-alkyl)-2(1H)-pyridinones, 1,2-dihydro-2-oxo-5-(pyridinyl)-6-(lower-alkyl)nicotinic acids and lower-alkyl esters thereof, and cardiotonic use thereof
Assignee: Sanofi SA
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Filing: 1980-11-06
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Granted: 1982-01-26
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Expires: 2000-11-06
Abstract
Abstract 1-R 1 -6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones or 1-R 1 -1,2-dihydro-2-oxo-6-(lower-alkyl)-5-(pyridinyl)nicotinic acids or lower-alkyl esters thereof or pharmaceutically-acceptable acid-addition or cationic salts thereof are useful as cardiotonic agents, where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. These compounds are prepared by hydrolyzing the corresponding 3-cyano compounds to produce the corresponding 3-carboxylic acids and then either by decarboxylating or esterifying the acids.
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 20:24
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: 27
Claim 1
Independent Claim
43 words
A 1-R 1 -5-PY-6-R-2(1H)-pyridinone having the formula ##STR3## where R 1 is hydrogen, R is methyl or ethyl and PY if 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substitutents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 2
Dependent Claim
43 words
A 1-R 1 -5-PY-6-R-2(1H)-pyridinone having the formula ##STR3## where R 1 is hydrogen, R is methyl or ethyl and PY if 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substitutents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 where PY is 4-pyridinyl.
Claim 4
Dependent Claim
6 words
6-Methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 5
Dependent Claim
6 words
6-Methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 6
Dependent Claim
6 words
6-Ethyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 7
Dependent Claim
6 words
6-Ethyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 8
Dependent Claim
53 words
A 1-R 1 -1,2-dihydro-5-PY-2-oxo-6-R-nicotonic acid or lower-alkyl ester thereof having the formula ##STR4## where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen or lower-alkyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 9
Dependent Claim
53 words
A 1-R 1 -1,2-dihydro-5-PY-2-oxo-6-R-nicotonic acid or lower-alkyl ester thereof having the formula ##STR4## where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen or lower-alkyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 10
Dependent Claim
10 words
A compound according to claim 5 where R' is hydrogen.
Claim 11
Dependent Claim
10 words
A compound according to claim 5 where R' is lower-alkyl.
Claim 12
Dependent Claim
12 words
A compound according to claim 5 wherein PY is 4-pyridinyl or 3-pyridinyl.
Claim 13
Dependent Claim
7 words
1,2-Dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinic acid or pharmaceutically-acceptable acid-addition salt thereof.
Claim 14
Dependent Claim
7 words
1,2-Dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinic acid or pharmaceutically-acceptable acid-addition salt thereof.
Claim 15
Dependent Claim
67 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, a cardiotonically-effective amount of a 1-R 1 -5-PY-6-R-2(1H)-pyridinone having the formula ##STR5## where R 1 is hydrogen, R is methyl or ethyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 16
Dependent Claim
67 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, a cardiotonically-effective amount of a 1-R 1 -5-PY-6-R-2(1H)-pyridinone having the formula ##STR5## where R 1 is hydrogen, R is methyl or ethyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 17
Dependent Claim
17 words
A composition according to claim 10 where the active component is 6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 18
Dependent Claim
17 words
A composition according to claim 10 where the active component is 6-ethyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 19
Independent Claim
76 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 a patient a cardiotonically-effective amount of a 1-R 1 -5-PY-6-R-2(1H)-pyridinone having the formula ##STR6## where R 1 is hydrogen, R is methyl or ethyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substitutents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 20
Independent Claim
76 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 a patient a cardiotonically-effective amount of a 1-R 1 -5-PY-6-R-2(1H)-pyridinone having the formula ##STR6## where R 1 is hydrogen, R is methyl or ethyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substitutents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 21
Dependent Claim
12 words
The method according to claim 13 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 22
Dependent Claim
77 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, a cardiotonically-effective amount of a 1-R 1 -1,2-dihydro-2-oxo-5-PY-6-R-nicotinic acid or lower-alkyl ester thereof having the formula ##STR7## where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen or lower-alkyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 23
Dependent Claim
77 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, a cardiotonically-effective amount of a 1-R 1 -1,2-dihydro-2-oxo-5-PY-6-R-nicotinic acid or lower-alkyl ester thereof having the formula ##STR7## where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen or lower-alkyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 24
Dependent Claim
18 words
A composition according to claim 15 where the active component is 1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinic acid or pharmaceutically-acceptable acid-addition salt thereof.
Claim 25
Independent Claim
85 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 a cardiotonically-effective amount of a 1-R 1 -1,2-dihydro-2-oxo-5-PY-6-R-nicotinic acid or lower-alkyl ester thereof having the formula ##STR8## where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen or lower-alkyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 26
Independent Claim
85 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 a cardiotonically-effective amount of a 1-R 1 -1,2-dihydro-2-oxo-5-PY-6-R-nicotinic acid or lower-alkyl ester thereof having the formula ##STR8## where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen or lower-alkyl and PY is 4-, 3- or 2-pyridinyl or 4-, 3- or 2-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition or cationic salt thereof.
Claim 27
Dependent Claim
12 words
The method according to claim 17 where PY is 4-pyridinyl or 3-pyridinyl.
References Cited (Backward Citations)
US4004012A
Cited
US4072746A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-25 | 1985-07-27 | 1986-01-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-25 | 1989-07-27 | 1990-01-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-25 | 1993-07-27 | 1994-01-26 | $7700.00 | Window Closed / Lapsed |