Patent US4736128A successfully refreshed from Google Patents.
US4465686A
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5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones, their cardiotonic use and preparation
Assignee: STWB Inc
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Filing: 1982-04-26
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Granted: 1984-08-14
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Expires: 2002-04-26
Abstract
Abstract Disclosed and claimed is the cardiotonic use of 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R 1 , R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R 1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R 1 and R are defined as above for II, R' is hydrogen, hydroxy, methoxy or amino and R" is hydroxy, methoxy or hydrogen, preferably at least one of R' and R" being methoxy, or where R' is nitro and R" is hydrogen or methoxy, preferably methoxy, with 85% phosphoric acid to produce 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone.
Inventors
- 👤 George Y. Lesher
- 👤 Chester J. Opalka, Jr.
- 👤 Donald F. Page
- 👤 Ruthann M. McGarry
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 06:30
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/72; C07D213/73; C07D213/78; C07D213/81; C07D213/82; C07D213/84; C07D213/85
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
57 words
A 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone having the formula ##STR3## where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl, and, R' and R" are each hydrogen or hydroxy, at least one of R' or R" being hydroxy, or where R' is amino or nitro when R" is hydroxy, or an acid-addition salt thereof where R' is amino.
Claim 2
Dependent Claim
57 words
A 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone having the formula ##STR3## where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl, and, R' and R" are each hydrogen or hydroxy, at least one of R' or R" being hydroxy, or where R' is amino or nitro when R" is hydroxy, or an acid-addition salt thereof where R' is amino.
Claim 3
Dependent Claim
26 words
A compound according to claim 1 where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen, hydroxy or amino, and R" is hydroxy.
Claim 4
Dependent Claim
5 words
5-(4-Hydroxyphenyl)-6-methyl-2(1H)-pyridinone according to claim 2.
Claim 5
Dependent Claim
5 words
5-(3-Hydroxyphenyl)-6-methyl-2(1H)-pyridinone according to claim 2.
Claim 6
Dependent Claim
5 words
5-(3,4-Dihydroxyphenyl)-6-methyl-2(1H)-pyridinone according to claim 2.
Claim 7
Dependent Claim
9 words
5-(3-Amino-4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone or acid-addition salt thereof according to claim 2.
Claim 8
Dependent Claim
5 words
5-(4-Hydroxy-3-nitrophenyl)-6-methyl-2(1H)-pyridinone according to claim 1.
Claim 9
Dependent Claim
82 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically acceptable carrier and, as the active component thereof, a cardiotonically effective amount of 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone of the formula ##STR4## where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. R is lower-alkyl, and, R' and R" are each hydrogen or hydroxy, at least one of R' and R" being hydroxy or where R' is amino or nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salt thereof where R' is amino.
Claim 10
Dependent Claim
82 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically acceptable carrier and, as the active component thereof, a cardiotonically effective amount of 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone of the formula ##STR4## where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. R is lower-alkyl, and, R' and R" are each hydrogen or hydroxy, at least one of R' and R" being hydroxy or where R' is amino or nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salt thereof where R' is amino.
Claim 11
Dependent Claim
26 words
A composition according to claim 8 where R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen, hydroxy or amino and R" is hydroxy.
Claim 12
Dependent Claim
12 words
A composition according to claim 9 where the active component is 5-(4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone.
Claim 13
Dependent Claim
12 words
A composition according to claim 9 where the active component is 5-(3-hydroxyphenyl)-6-methyl-2(1H)-pyridinone.
Claim 14
Dependent Claim
12 words
A composition according to claim 9 where the active component is 5-(3,4-dihydroxyphenyl)-6-methyl-2(1H)-pyridinone.
Claim 15
Dependent Claim
12 words
A composition according to claim 9 where the active component is 5-(3-amino-4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone.
Claim 16
Dependent Claim
12 words
A composition according to claim 8 where the active component is 5-(3-nitro-4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone.
Claim 17
Dependent Claim
40 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 cardiotonic composition according to claim 8 where R also is hydrogen.
Claim 18
Dependent Claim
29 words
The method according to claim 15 where Q is hydrogen, R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen, hydroxy or amino and R" is hydroxy.
Claim 19
Dependent Claim
12 words
The method according to claim 16 where the active component is 5-(4-hydroxyphenyl)-6-methyl-2(1H)pyridinone.
Claim 20
Dependent Claim
17 words
The method according to claim 16 where the active component is 5-(3-amino-4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof.
Claim 21
Dependent Claim
12 words
The method according to claim 16 where the active component is 5-(3,4-dihydroxyphenyl)-6-methyl-2(1H)-pyridinone.
References Cited (Backward Citations)
CA865757A
Cited
US3655679A
Cited
US3703582A
Cited
US3718743A
Cited
US3853896A
Cited
US4065290A
Cited
US4004012A
Cited
US4072746A
Cited
US4297362A
Cited
US4313951A
Cited
US4302462A
Cited
GB2070606A
Cited
US4276293A
Cited
US4312875A
Cited
EP0074091A2
Cited
US4431651A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-08-14 | 1988-02-13 | 1988-08-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-14 | 1992-02-13 | 1992-08-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-14 | 1996-02-13 | 1996-08-14 | $7700.00 | Window Closed / Lapsed |