Preparation of 5-(hydroxy- and/or aminophenyl-6-lower-alkyl)-2(1

Details Preparation of 5-(hydroxy- and/or aminophenyl-6-lower-alkyl)-2(1 Preparation of 5-(hydroxy- and/or aminophenyl-6-lower-alkyl)-2(1

1984-04-02

1986-07-08

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546301, 546288, C07D21176

Patent

active

045994234

ABSTRACT:
Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.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.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.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.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.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.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone, where R.sub.1 and R are defined as above for II, R' is hydrogen, hydroxy or amino and R" is hydroxy or hydrogen, at least one of R' and R" being hydroxy, or where R' is nitro and R" is hydroxy.

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