115344-47-3

Basic information

• Product Name: SIGUAZODAN
• Synonyms: SIGUAZODAN;SK AND F-94836;SKF 94836;N-CYANO-N'-METHYL-N''-[4-(1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-3-PYRIDAZINYL)PHENYL]GUANIDINE;N-Cyano-Nmethyl-Nⅱ-[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]guanidine;Siguazodan, N-Cyano-Nμ-methyl-N-[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]guanidine;Siguazodan (SKF 94836);[4R,(-)]-4,5-Dihydro-3-[4-[[(cyanoimino)(methylamino)methyl]amino]phenyl]-4-methylpyridazin-6(1H)-one
• CAS NO: 115344-47-3
• Molecular Formula: C₁₄H₁₆N₆O
• Molecular Weight: 284.32
• Product Categories: Cyclic Nucleotide related
• Mol File: 115344-47-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 268-268.9 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: 1.31g/cm³
• Refractive Index: 1.655
• Storage Temp.: 2-8°C
• Solubility: DMSO: >5 mg/mL, freely soluble
• PKA: 13.71±0.60(Predicted)
• CAS DataBase Reference: SIGUAZODAN(CAS DataBase Reference)
• NIST Chemistry Reference: SIGUAZODAN(115344-47-3)
• EPA Substance Registry System: SIGUAZODAN(115344-47-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 115344-47-3(Hazardous Substances Data)

Usage

Uses

Siguazodan is a selective phosphodiesterase PDE III inhibitor and a potent inotropic agent.

Biological Activity

Phosphodiesterase inhibitor, selective for PDE3 (IC 50 = 117 nM).

InChI:InChI=1/C14H16N6O/c1-9-7-12(21)19-20-13(9)10-3-5-11(6-4-10)18-14(16-2)17-8-15/h3-6,9H,7H2,1-2H3,(H,19,21)(H2,16,17,18)

Upstream product

• 36725-27-6 SKF 93741 
• 36725-28-7 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 103-84-4 Acetanilid 
• 120757-13-3 4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride 
• 120757-14-4 3-(4-acetamidobenzoyl)-4-(N-piperidinyl)butanoic acid 
• 81937-39-5 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester 
• 120757-15-5 4-(4-Amino-phenyl)-4-oxo-3-piperidin-1-ylmethyl-butyric acid methyl ester 
• 120757-17-7 methyl 3-(4-acetaminobenzoyl)butyrate 
• 120757-16-6 3-(4-Acetylamino-benzoyl)-but-3-enoic acid methyl ester 
• 81112-08-5 N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide 
• 5473-15-4 4-(4-acetamidophenyl)-4-oxobutanoic acid 
• 79463-77-7 N-cyanodiphenylcarbonimidate 
• 74-89-5 methylamine 
• 99591-85-2 6-<4-(N'-cyano-S-methylisothioureido)phenyl>-5-methyl-4,5-dihydropyridazin-3(2H)-one 

Relevant articles and documents

6-(substituted phenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-ones of medicinal interest. The synthesis of SK&F 94836 and SK&F 95654

Two synthetic routes to the dihydropyridazinone-cyanoguanidine 4 (SK&F 94836) are described, both proceeding via the anilino compound 6. An efficient synthesis of the dihydropyridazinone-pyridone 5 (SK&F 95654) is reported. This synthesis proceeds via the fluoro-keto-acid 24, with subsequent displacement of the fluoro substituent by 4-pyridone. The surprising effectiveness of water as a solvent in this reaction has been highlighted.