131741-08-7

Basic information

• Product Name: Simendan
• Synonyms: 2-[[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]hydrazinylidene]propanedinitrile;((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono)propanedinitrile;simendan;simendan R--[4-(1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl] hydrozono]-propanedinitrile;R-(-)-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl hydrozono-propanedinitrile;LEVOFLUOROCARBOXYLICACID;2-[[4-(6-keto-4-methyl-4,5-dihydro-1H-pyridazin-3-yl)phenyl]hydrazono]malononitrile;Propanedinitrile,2-[2-[4-(1,4,5,6-tetrahydro-4-Methyl-6-oxo-3-pyridazinyl)phenyl]hydrazinylidene]-
• CAS NO: 131741-08-7
• Molecular Formula: C₁₄H₁₂N₆O
• Molecular Weight: 280.28
• Mol File: 131741-08-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.33 g/cm³
• Refractive Index: 1.673
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), THF (Slightly, Sonicated)
• PKA: 6.12±0.10(Predicted)
• CAS DataBase Reference: Simendan(CAS DataBase Reference)
• NIST Chemistry Reference: Simendan(131741-08-7)
• EPA Substance Registry System: Simendan(131741-08-7)

Safety Data

• Hazardous Substances Data: 131741-08-7(Hazardous Substances Data)

Usage

Uses

Simendan is the racemic mixture of Levosimendan (L378000) which is a positive inotropic agent with vasodilating activity.

InChI:InChI=1/C14H12N6O/c1-9-6-13(21)19-20-14(9)10-2-4-11(5-3-10)17-18-12(7-15)8-16/h2-5,9,17H,6H2,1H3,(H,19,21)/t9-/m0/s1

Synthetic route

6-(4-aminophenyl)-5-methylpyridazine-3(2H)-one (52240-11-6) → (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]-propanedinitrile (131741-08-7)

Conditions	Yield
	97%

malononitrile (109-77-3) + 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone (36725-28-7) → (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]-propanedinitrile (131741-08-7)

Conditions	Yield
With sodium nitrite
With sodium nitrite

piperazine (110-85-0) + (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]-propanedinitrile (131741-08-7) → 2-imino-N'-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)-2-(piperazin-1-yl)acetohydrazonoyl cyanide

Conditions	Yield
In ethanol at 80℃; for 17.5h;	76%

(-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]-propanedinitrile (131741-08-7) → levosimendan (141505-33-1) + (+)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]propanedinitrile

Conditions	Yield
1-propanol, poly(vinylpyrrolidone), Tris/Tricine buffer, pH 7.4;

water ethanol (180330-54-5) + (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]-propanedinitrile (131741-08-7) + methyl iodide (74-88-4) → 6-[4-(1,1-dicyanomethylidene-N-methylhydrazino)phenyl]-4,5-dihydro-5-methylpyridazin-3(2H)one (131741-28-1)

Conditions	Yield
With potassium carbonate In acetone

Upstream product

• 109-77-3 malononitrile 
• 36725-28-7 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 52240-11-6 6-(4-aminophenyl)-5-methylpyridazine-3(2H)-one 

Downstream Products

• 131741-28-1 6-[4-(1,1-dicyanomethylidene-N-methylhydrazino)phenyl]-4,5-dihydro-5-methylpyridazin-3(2H)one 
• 141505-33-1 levosimendan 
• 144238-75-5 (+)-{[4-(1,4,5,5-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono}propanedinitrile 

Related news

Improved survival with Simendan (cas 131741-08-7) after experimental myocardial infarction in rats07/22/2019

This study compared the effects of simendan, a calcium sensitizer, with those of milrinone and enalapril on survival of rats with healed myocardial infarction. Seven days after ligation-induced myocardial infarction, the rats were randomized to control, milrinone, enalapril, or simendan groups. ...detailed

Relevant articles and documents

Method for obtaining pure enantiomers of a pyridazinone derivative

The present invention relates to a method for preparing optically active enantiomers of [[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]-hydrazono]propanedinitrile (I), particularly (-) enantiomer of (I). Furthermore, the invention relates to a novel crystalline polymorphic form of the (-) enantiomer.

Novel pyridazinone compounds, compositions thereof and method of use

New heterocyclic compounds of formula I STR1 in which Het means one of following groups; STR2 wherein R11, R13 and R14 mean independently hydrogen, hydroxymethyl or lower alkyl group, Z means S, O or NH; A means valency bond, --CH=CH--, or --CH2 --CH2 --group; R1 and R2 independently means nitro, cyano, halogen, amino, carboxamido, aryl, aroyl, pyridyl, alkoxycarbonyl, acyl or one of following groups; STR3 wherein R6 means hydrogen or lower alkyl group, R8 means lower alkyl, R7 means cyano or COOR10, wherein R10 means hydrogen or lower alkyl or R1 and R2 together form a substituted or unsubstituted 5 or 6 membered ring which may contain 1 or 2 heteroatom N; R3, R4, and R5 mean independently hydrogen, hydroxy or lower alkyl group; Y means N or CH. The compounds may be used in the treatment of congestive heart failure.