EP0074091A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
2(1H)-pyridinones and preparation thereof
Assignee: STWB Inc
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Filing: 1982-09-02
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Granted: —
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Expires: 2002-09-02
Abstract
Abstract Novel 1-R,-3-Q-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones where R, is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or R is nitro and R" is hydroxy, are useful as cardiotonics. Also known compounds where R is hydrogen are useful as cardiotonics. Both novel and known compounds can be prepared by a novel process which comprises reacting 1-R I -1,2-dihydro-2-oxo-5-(3-R'-4-R"- phenyl)-6-R-nicotinonitrile, where R 1 and R are defined as above, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy with 85% phosphoric acid.
Inventors
- 👤 George Yohe Lesher
- 👤 Chester Joseph Opalka, Jr.
- 👤 Donald Frederick Page
- 👤 Ruthann Marie Mcgarry
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 10:05
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: 24
Claim 1
Independent Claim
65 words
A 1-R 1 -5-(3-R'-4R"-phenyl)-6-R-2 (lH) -pyridinone having the Formula I where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or R' is nitro and R" is hydroxy; or an acid-addition salt thereof when at least one of R' and R" is amino.
Claim 2
Dependent Claim
65 words
A 1-R 1 -5-(3-R'-4R"-phenyl)-6-R-2 (lH) -pyridinone having the Formula I where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or R' is nitro and R" is hydroxy; or an acid-addition salt thereof when at least one of R' and R" is amino.
Claim 3
Dependent Claim
36 words
A compound according to claim 1, where R1 is hydrogen, R is methyl or ethyl, R' is hydrogen, hydroxy or amino, and R" is hydroxy or hydrogen, the latter only when R' is other than hydrogen.
Claim 4
Dependent Claim
5 words
5-(3-Hydroxyphenyl)-6-methyl-2(lH)-pyridinone according to claim 2.
Claim 5
Dependent Claim
5 words
5-(3,4-Dihydroxyphenyl)-6-methyl-2(lH)-pyridinone according to claim 2.
Claim 6
Dependent Claim
9 words
5-(3-Amino-4-hydroxyphenyl)-6-methyl-2(lH)-pyridinone or acid-addition salt thereof according to claim 2.
Claim 7
Dependent Claim
161 words
A process for preparing a 1-R 1 -5-(3-R'-4-R"- phenyl)-6-R-2(lH)-pyridinone, where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is hydrogen or lower-alkyl; R' is hydrogen, hydroxy or amino and R" is hydrogen, hydroxy or amino, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy, or an acid addition salt thereof, which comprises reacting a 1-R 1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R 1 and R have the above meanings, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, or R' is nitro and R" is hydroxy or methoxy, with 85% phosphoric acid, if desired, reacting a compound obtained where R' and/or R" are respectively methoxy and/or nitro with a reagent capable of converting methoxy to hydroxy or with a reagent capable of converting nitro to amino, respectively, and, if desired, converting a free base obtained where R' and/or R" is amino to an acid-addition salt of said compound.
Claim 8
Dependent Claim
161 words
A process for preparing a 1-R 1 -5-(3-R'-4-R"- phenyl)-6-R-2(lH)-pyridinone, where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is hydrogen or lower-alkyl; R' is hydrogen, hydroxy or amino and R" is hydrogen, hydroxy or amino, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy, or an acid addition salt thereof, which comprises reacting a 1-R 1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R 1 and R have the above meanings, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, or R' is nitro and R" is hydroxy or methoxy, with 85% phosphoric acid, if desired, reacting a compound obtained where R' and/or R" are respectively methoxy and/or nitro with a reagent capable of converting methoxy to hydroxy or with a reagent capable of converting nitro to amino, respectively, and, if desired, converting a free base obtained where R' and/or R" is amino to an acid-addition salt of said compound.
Claim 9
Dependent Claim
121 words
A process for preparing a compound according to claim 1, which comprises reacting a :-R 1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R1 and R have the above meanings, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy or methoxy, with 85% phosphoric acid, if desired, reacting a compound obtained where R' and/or R" are respectively methoxy and/or nitro with a reagent capable of converting methoxy to hydroxy or with a reagent capable of converting nitro to amino, respectively and, if desired, converting a free base obtained where R' and/or R" is amino to an acid-addition salt of said compound.
Claim 10
Dependent Claim
55 words
A process according-to claim 6 or 7, in which in the nicotinonitrile, at least one of R' and R" is methoxy or R' is nitro and R" is methoxy so as to produce a 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(lH)-pyridinone, where at least one of R' and R" is hydroxy or R' is nitro and R" is hydroxy.
Claim 11
Dependent Claim
14 words
A process according to any one of claims 6-8, where the reactants are refluxed.
Claim 12
Dependent Claim
91 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-Rl-5-(3-R'-4-R"- phenyl)-6-R-2(lH)-pyridinone of the Formula I (herein) where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy; or a pharmaceutically acceptable acid-addition salt thereof when at least one of R' and R" is amino.
Claim 13
Dependent Claim
91 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-Rl-5-(3-R'-4-R"- phenyl)-6-R-2(lH)-pyridinone of the Formula I (herein) where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy; or a pharmaceutically acceptable acid-addition salt thereof when at least one of R' and R" is amino.
Claim 14
Dependent Claim
161 words
A process for preparing a 1-R 1 -5-(3-R'-4-R"- phenyl)-6-R-2(lH)-pyridinone, where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is hydrogen or lower-alkyl; R' is hydrogen, hydroxy or amino and R" is hydrogen, hydroxy or amino, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy, or an acid addition salt thereof, characterized by reacting a 1-R 1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R 1 and R have the above meanings, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, or R' is nitro and R" is hydroxy or methoxy, with 85% phosphoric acid, if desired, reacting a compound obtained where R' and/or R" are respectively methoxy and/or nitro with a reagent capable of converting methoxy to hydroxy or with a reagent capable of converting nitro to amino, respectively, and, if desired, converting a free base obtained where R' and/or R" is amino to an acid-addition salt of said compound.
Claim 15
Dependent Claim
161 words
A process for preparing a 1-R 1 -5-(3-R'-4-R"- phenyl)-6-R-2(lH)-pyridinone, where R 1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is hydrogen or lower-alkyl; R' is hydrogen, hydroxy or amino and R" is hydrogen, hydroxy or amino, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy, or an acid addition salt thereof, characterized by reacting a 1-R 1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R 1 and R have the above meanings, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, or R' is nitro and R" is hydroxy or methoxy, with 85% phosphoric acid, if desired, reacting a compound obtained where R' and/or R" are respectively methoxy and/or nitro with a reagent capable of converting methoxy to hydroxy or with a reagent capable of converting nitro to amino, respectively, and, if desired, converting a free base obtained where R' and/or R" is amino to an acid-addition salt of said compound.
Claim 16
Dependent Claim
14 words
A process according to claim 1, characterized by the fact that R is lower-alkyl.
Claim 17
Dependent Claim
78 words
A process according to claim 2, characterized by the fact that in the compound prepared R1 is hydrogen, R is methyl or ethyl, R' is hydrogen, hydroxy or amino, and R" is hydroxy or hydrogen, the latter only when R' is other than hydrogen, and in the nicotinonitrile R 1 is hydrogen, R is methyl or ethyl, R' is hydrogen, methoxy or amino and R" is methoxy or hydrogen, at least one of R' and R" being methoxy.
Claim 18
Dependent Claim
58 words
A process according to claim 1 or 2, characterized by the fact that in the nicotinonitrile, at least one of R' and R" is methoxy or R' is nitro and R" is methoxy so as to produce a 1-R 1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone, where at least one of R' and R" is hydroxy or R' is.hitro and R" is hydroxy.
Claim 19
Dependent Claim
19 words
A process according to any one of the preceding claims, characterized by the fact that the reactants are refluxed.
Claim 20
Dependent Claim
16 words
A process according to any one of claims 1-4, characterized by using 1,2-dihydro-5-(4-methoxyphenyl-6-methyl-2-oxonicotinonitrile to produce 5-(4-hydroxyphenyl)-6-methyl-2(lH)-pyridinone.
Claim 21
Dependent Claim
16 words
A process according to any one of claims 1-4, characterized by using 1,2-dihydro-5-(3-methoxyphenyl)-6-methyl-2-oxonicotinonitrile to produce 5-(3-hydroxyphenyl)-6-methyl-2(lH)-pyridinone.
Claim 22
Dependent Claim
16 words
A process according to any one of claims 1-4, characterized by using 1,2-dihydro-5-(3,4-dimethoxyphenyl)-6-methyl-2-oxonicotinonitrile to produce 5-(3,,4-dihydroxyphenyl)-6-methyl-2(lH)-pyridinone.
Claim 23
Dependent Claim
16 words
A process according to any one of claims 1-4, characterized by using 1,2-dihydro-5-(4-methoxy-3-nitrophenyl)-6-methyl-2-oxonicotinonitrile to produce 5-(4-hydroxy-3-nitrophenyl)-6-methyl-2(lH)-pyridinone.
Claim 24
Dependent Claim
16 words
A process according to any one of claims 1-4, characterized by using 5-(3-amino-4-methoxyphenyl)-1,2-dihydro-6-methyl-2-oxonicotinonitrile to produce 5-(3-amino-4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone.
References Cited (Backward Citations)
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