C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/295, 260/264
C07D 401/04 (2006.01) C07D 213/04 (2006.01) C07D 213/55 (2006.01)
Patent
CA 1166254
ABSTRACT OF THE DISCLOSURE 2-R-4-R'-6-py-3(2H)-pyridazinones (I)or salts thereof, which are useful as intermediates and some as cardiotonics, are prepared by reacting di-(lower-alkyl) hydroxy[2-oxo-2-PY-ethyl]propanedioate (II) with a hydrazine salt of the formula RNHNH2.nHXAn (III) to produce lower- alkyl 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylate (Ia where R' is lower-carbalkoxy) and reacting Ia with hydrazine hydrate or anhydrous hydrazine to produce 2,3-dihydro-2-R-3- oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (Ib where R' is aminocarbamyl), where PY is 4- or 3-pyridinyl or 4- or 3- pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, R' is carbamyl, carboxy, aminocarbamyl or lower-carbalkoxy, n is 1 or 2, x is 1, 2 or 3, and An is an anion of a strong inorganic acid or an organic sulfonic acid. Also shown are: the prep- aration of II from PY-COCH3 (IV), the conversion of Ia to Ib (Id where R' is carboxy), and the use of 2-R-4-R"-6-PY- 3(2H)-pyridazinones (I where R is lower-alkyl or lower- hydroxyalkyl and R" is carbamyl, aminocarbamyl or lower- carbalkoxy) as cardiotonic agents. Other intermediates are shown.
376317
Dickinson William B.
Lesher George Y.
Fetherstonhaugh & Co.
Sterling Drug Inc.
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