88302-06-1

Basic information

• Product Name: RARECHEM AL BO 1862
• Synonyms: RARECHEM AL BO 1862;3-PYRIDINECARBOXYLIC ACID, 5-ACETYL-1,2-DIHYDRO-6-METHYL-2-OXO-;5-ACETYL-1,2-DIHYDRO-6-METHYL-2-OXO-3-PYRIDINECARBOXYLIC ACID;5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXYLIC ACID;AKOS VGYB0001124;5-acetyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarboxylic acid(SALTDATA: FREE);5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid;5-acetyl-2-keto-6-methyl-1H-pyridine-3-carboxylic acid
• CAS NO: 88302-06-1
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.17
• Mol File: 88302-06-1.mol

Chemical Properties

• Boiling Point: 415.352°C at 760 mmHg
• Flash Point: 204.998°C
• Appearance: /
• Density: 1.364g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: RARECHEM AL BO 1862(CAS DataBase Reference)
• NIST Chemistry Reference: RARECHEM AL BO 1862(88302-06-1)
• EPA Substance Registry System: RARECHEM AL BO 1862(88302-06-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 88302-06-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
RARECHEM AL BO 1862 is used as a catalyst in chemical reactions for its ability to accelerate processes and improve efficiency.
Used in Advanced Material Production:
RARECHEM AL BO 1862 is used as a component in the production of advanced materials, contributing to the development of innovative and high-performance products.
Used in Materials Science:
RARECHEM AL BO 1862 is utilized in materials science for its unique properties, which can enhance the performance and characteristics of various materials.
Used in Chemical Engineering:
RARECHEM AL BO 1862 is employed in chemical engineering to facilitate the design and optimization of chemical processes and systems.

InChI:InChI=1/C9H9NO4/c1-4-6(5(2)11)3-7(9(13)14)8(12)10-4/h3H,1-2H3,(H,10,12)(H,13,14)

Upstream product

• 71407-96-0 methyl 5-acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate 
• 18856-72-9 3-dimethylaminomethylenepentane-2,4-dione 
• 33884-41-2 ethoxylideneacetylacetone 
• 52600-60-9 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carboxamide 
• 52600-53-0 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinonitrile 

Downstream Products

• 136117-46-9 5-acetyl-3-bromo-6-methyl-2(1H)-pyridinone 
• 58405-00-8 5-acetyl-3-chloro-6-methyl-2(1H)-pyridinone 
• 5220-65-5 5-acetyl-6-methyl-2(1H)-pyridinone 

Relevant articles and documents

Synthesis and pharmacological characterization of functionalized 2-pyridones structurally related to the cardiotonic agent milrinone

A new class of cardiotonic agents characterized by a 2-pyridone structure was synthesized. Appropriate sym-2-dimethylaminomethylene-1,3-diones reacted with methylcyanoacetate to afford the desired compounds. These derivatives were evaluated for their ability in inducing cardiotonic response on guinea pig isolated myocardial preparations. Compound 8b increased atrial contractility to an extent which is significantly higher than that of milrinone, the parent drug used as a reference compound. The pharmacological characterization and the docking studies performed on 8b highlighted its selective mechanism of action via type 3 PDE (PDE3) inhibition.

Imidazo[1,2-a]pyridines. Synthesis and inotropic activity of new 5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinone derivatives

A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinones was synthesized and evaluated for positive inotropic activity. 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-3- pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a]pyridin-2-yl)-6-methyl-2(1H)- pyridinone (3a) was the most potent (i.v. ED50 11 μg/kg) in this seris. E-1020 is presently under development for the treatment of congestive heart failure.

Novel alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones

This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.

5-Acyl-2-(1H)-pyridinones

Novel 5-acyl-2-(1H)pyridinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-penta

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles.V. Synthesis of 5-Acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles and 1,2,5,6,7,8-Hexahydro-2,5-dioxo-3-quinolinecarboxamides

The reaction of open-chain sym-2-dimethylaminomethylene-1,3-diones Ia-d with sodium cyanoacetamide gave, generally in good yields, 6-substituted 5-acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles IIa-d, whereas cyclohexane sym-2-dimethylaminomethylene-1,3-diones Ie-h afforded in general a mixture of 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarbonitriles and 5,6,7,8-tetrahydro-2,5-dioxo-2H-1-benzopyran-3-carboxamides, the latter being isolated in two cases.The reaction of Ie-h with cyanoacetamide in refluxing anhydrous ethanol gave 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarboxamides IIIe-h in excellent yields, whereas Ia-d did not react with the exception of Ia which afforded in good yield 3-pyridinecarboxamide IIIa.Other 3-pyridinecarboxamides were obtained by partial hydrolysis of nitriles IIb,d. 3-Pyridine and 3-quinoline carboxamides were hydrolyzed in satisfactory yields with hydrochloric acid to the corresponding carboxylic acids, which were decarboxylated in good yields to 5-acyl-2(1H)-pyridinones and 7,8-dihydro-2,5-(1H,6H)-quinolinediones, respectively, by reflux in quinoline containing a catalytic amount of copper powder.

5-Alkyl-1,6-naphthyridin-2(1H)-ones and cardiotonic use thereof

1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic ag

5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use

4-R2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III), Q is CN) or corresponding 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

Certain 2-(1H)-pyridinones cardiotonic compositions containing same and method of using same

1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic ag

Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone

4-R2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III, Q is CN) or corresponding 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.