52600-60-9

Usage

Uses

Used in Pharmaceutical Industry:
5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXAMIDE is used as an active pharmaceutical ingredient for its antifungal and antibacterial properties, targeting a range of microbial infections. Its unique structure allows it to disrupt the normal functions of fungi and bacteria, thereby inhibiting their growth and proliferation.
Used in Neurodegenerative Disease Treatment:
In the field of neurology, 5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXAMIDE is being investigated as a potential therapeutic agent for neurodegenerative diseases. Its specific mechanism of action is still under research, but it may offer neuroprotective effects or modulate pathways implicated in the progression of such diseases.
Used as a Key Intermediate in Drug Synthesis:
5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXAMIDE is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its chemical structure can be modified to create new drugs with improved efficacy, safety, or pharmacokinetic profiles, contributing to the advancement of medicinal chemistry.
Used in Drug Development Research:
In the research and development sector, 5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXAMIDE serves as a valuable compound for exploring new drug candidates. Its versatile chemical properties make it an attractive starting point for the design and synthesis of novel therapeutic agents targeting a variety of medical conditions.

InChI:InChI=1/C9H10N2O3/c1-4-6(5(2)12)3-7(8(10)13)9(14)11-4/h3H,1-2H3,(H2,10,13)(H,11,14)

Upstream product

• 52600-53-0 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinonitrile 
• 18856-72-9 3-dimethylaminomethylenepentane-2,4-dione 
• 107-91-5 cyanoacetic acid amide 
• 108-13-4 malonodiamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 123-54-6 acetylacetone 
• 33884-41-2 ethoxylideneacetylacetone 

Downstream Products

• 5220-65-5 5-acetyl-6-methyl-2(1H)-pyridinone 
• 88302-06-1 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of substituted nicotinamides from enamines derived from N,N-dimethylformamide dimethyl acetal

Reactions of 1,3-dicarbonyl compounds with N,N-dimethylformamide dimethyl acetal followed by malonamide in the presence of sodium hydride give 5,6-disubstituted 1,2-dihydro-2-oxopyridine-3-carboxamides 3a-e, whereas reactions of the intermediate enamines with cyanothioacetamide or cyanoacetamide in the presence of piperidine give 4,5-disubstituted 1,2-dihydro-2-thioxopyridine-3-carboxamides 6a-c and 1,2-dihydro-2-oxopyridine-3-carboxamides 6d-h.

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

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.

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-(4-Thiazolyl)-6-alkyl-2(1H)-pyridinones and their cardiotonic use

3-Q-4-R2 -5-(2-Q'-5-R3 -4-thiazolyl)-6-R1 -2(1H)-pyridinones (I), where R1 is alkyl having from one to four carbon atoms, R2 is hydrogen or methyl, R3 is hydrogen or alkyl having from one to three carbon atoms, Q is amino, carbamyl, carboxy, cyano or hydrogen, and Q' is alkyl having from one to four carbon atoms, amino or R4 NH where R4 is alkyl having from one to four carbon atoms, or acid-addition salts thereof where at least one of Q and Q' is amino or Q' is R4 NH, are useful as cardiotonics (I where Q is amino, cyano or hydrogen) and/or as intermediates (I where Q is cyano, carbamyl or carboxy). Also shown as intermediates are 1,2-dihydro-4-R2 -5-[R3 CH(Br)CO]-6-R1 -2-oxo-3-pyridinecarbonitriles (II), and, also, processes for preparing I and II.

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.

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