101328-84-1

Basic information

• Product Name: (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methyl-
• Synonyms: (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methyl-;3(2H)-Pyridazinone, 6-(4-aMinophenyl)-4,5-dihydro-5-Methyl-, (5S)-;(S)-6-(4-aMinophenyl)-5-Methyl-4,5-dihydropyridazin-3(2H)-one
• CAS NO: 101328-84-1
• Molecular Formula: C₁₁H₁₃N₃O
• Molecular Weight: 203.24042
• Mol File: 101328-84-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methyl-(101328-84-1)
• EPA Substance Registry System: (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methyl-(101328-84-1)

Safety Data

• Hazardous Substances Data: 101328-84-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methylis used as a key intermediate in the synthesis of Dextrosimendan (D299550), an isomer and impurity of Levosimendan (L378000). Levosimendan is a bioactive enantiomer of Simendan (S466000) and possesses positive inotropic and vasodilating activities, making it a valuable compound in the development of cardiovascular medications.
In the synthesis process, (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methylcontributes to the formation of the desired pharmacological agents, which can be further optimized for their therapeutic properties. Its role as an intermediate highlights the importance of (S)-3(2h)-Pyridazinone, 6-(4-Aminophenyl)-4,5-Dihydro-5-Methyl- in the advancement of novel drug candidates for the treatment of various medical conditions, particularly those related to cardiovascular health.

Upstream product

• 36725-28-7 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 50583-51-2 O,O′-di-p-anisoyl-D-tartaric acid 
• 139052-01-0 (S)-4-(4-Acetylamino-phenyl)-3-methyl-4-oxo-butyric acid 
• 103-84-4 Acetanilid 
• 139052-03-2 3-(p-Acetamidobenzoyl)-crotonsaeure 
• 616-02-4 citraconic acid anhydride 
• 139128-27-1 N-[4-((S)-4-Methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-acetamide 
• 81937-39-5 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester 
• 63514-63-6 N-(4-(2-bromopropionyl)phenyl)acetamide 
• 16960-49-9 N-(4-propionylphenyl)acetamide 
• 1260774-44-4 (-)-6-(4-aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone di-p-anisoyl-D-tartrate 
• 50583-51-2 (2R,3R)-2,3-bis[(4-methoxyphenyl)carbonyloxy]butanedioic acid 
• 132298-10-3 N-[4-((R)-2-Chloro-propionyl)-phenyl]-acetamide 
• 132298-12-5 2-[(R)-2-(4-Amino-phenyl)-1-methyl-2-oxo-ethyl]-malonic acid benzyl ester methyl ester 

Downstream Products

• 141505-33-1 levosimendan 
• 1221499-63-3 (R)-(-)-6-[4-(2-pyridinylmethylene)amino]phenyl-5-methyl-4,5-dihydro-3(2H)-pyridazinone 
• 1221499-65-5 (R)-(-)-6-[4-(2-furanylmethylene)amino]phenyl-5-methyl-4,5-dihydro-3(2H)-pyridazinone 
• 1221499-60-0 C₁₈H₁₆ClN₃O 
• 1221499-56-4 C₁₈H₁₆N₄O₃ 
• 1221499-55-3 C₁₈H₁₆N₄O₃ 
• 1221499-61-1 C₂₁H₂₃N₃O₄ 
• 1221499-58-6 C₁₈H₁₇N₃O₂ 
• 1221499-59-7 C₁₈H₁₇N₃O₂ 
• 1221499-62-2 C₁₈H₁₅Cl₂N₃O 
• 1221499-57-5 C₁₈H₁₇N₃O₃ 
• 112065-88-0 (S)-(+)-6-<4-(3-bromopropionamido)phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone 
• 36725-28-7 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 36725-28-7 OR-1855 

Relevant articles and documents

Carbene-catalyzed enantioselective annulation of dinucleophilic hydrazones and bromoenals for access to aryl-dihydropyridazinones and related drugs

4,5-Dihydropyridazinones bearing an aryl substituent at the C6-position are important motifs in drug molecules. Herein, we developed an efficient protocol to access aryl-dihydropyridazinone moleculesviacarbene-catalyzed asymmetric annulation between dinuc

Preparation method of important intermediate of levosimendan

The invention belongs to the field, of synthesis of intermediates and relates to (R)- 6 - (4 -aminophenyl) - 5 - methyl - 444455-dihydropyridazine - 3333337. acetamide N - (4 - obtained by hydrolyzing)-methylpropionyl, phenyl, acetamide, in N - (4 - (3 - (-propionyl phenyl) - 2 - acetamide as starting material) and then chemical resolution.) yields high-purity,methylpropionyl (R)- N - (4 - (3 - (phenyl) - 2 - acetamide.). The present invention is very suitable for industrial production) by chemically resolving the high yield; dimethylamino,methylpropionyl-methaneanoyl-benzenesulfonamido (R)- N - (4 - (3 - phenylacetamido) obtained by hydrolyzing the intermediates with formaldehyde) dimethylamine. yields a high yield, yields a high yield of intermediate. The present invention relates to a, process for, producing high-chiral purified p-methyl propionylphenyl phenylacetonitrile.

DIHYDROPYRIDAZINONES SUBSTITUTED WITH PHENYLUREAS

Compounds of formula (I) which are nicotinamide phosphoribosyltransferase (NAMPT) inhibitors and their use for the treatment of hyperproloferative diseases and/or disorders responsive to induction of cell death.

PROCESS FOR PREPARING LEVOSIMENDAN AND INTERMEDIATES FOR USE IN THE PROCESS

In an embodiment, the present invention provides a process for preparing (-)-6-(4- aminophenyl)-5-methylpyridazin-3-(2H)-one, which process comprises: a) reacting racemic 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone of formula (Il) with a chiral tartaric acid derivative to obtain a diastereomeric salt of (-)-6-(4- aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone and the chiral tartaric acid derivative; and b) reacting the diastereomeric salt with a base to obtain (-)-6-(4- aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone. The (-)-6-(4-aminophenyl)-4,5- dihydro-5-methyl-3-(2H)-pyridazinone may be used to prepare levosimendan.

Synthesis and anti-congestive heart failure activity of novel levosimendan analogues

A series of levosimendan analogues were designed and synthesized, employing the Friedel-Crafts reaction, hydrolysis, and cyclization from the key intermediate compound R(-)-6-(4-aminophenyl)-5-methyl-4, 5-dihydro-3(2H)- pyridazinone, which was obtained from the starting material, acetanilide. These compounds, except 1b, exhibited potent anti-congestive heart failure activities, especially the compounds 1e and 1k, which showed more effective action than levosimendan. Springer Science+Business Media, LLC 2010.

Studies on agents with vasodilator and β-blocking activities. V. Synthesis and pharmacological activity of the optical isomers of TZC-5665

Synthesis of the four optical isomers of TZC-5665 (1), a candidate for the treatment of congestive heart failure, was achieved by the reaction of chiral diaminopyridazinone (2) with chiral glycidyl ether (3). The hypotensive and β-blocking activities of 1 and its optical isomers were examined when given intravenously into anesthetized rats. Furthermore these compounds were evaluated for inhibitory activity on cAMP phosphodiesterase III. Among the four optical isomers, R(A),S(B)-one (1c) possessed the essential activities of TZC-5665 (1).