85633-96-1

Usage

Uses

4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutanoic acid is a useful research chemical.

InChI:InChI=1/C11H10ClNO5/c1-6(4-10(14)15)11(16)7-2-3-8(12)9(5-7)13(17)18/h2-3,5-6H,4H2,1H3,(H,14,15)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 53012-96-7 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile 
• 52240-25-2 4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid 

Downstream Products

• 1338058-47-1 ethyl 4-(4-(benzylamino)-3-nitrophenyl)-3-methyl-4-oxo-butanoate 
• 85634-10-2 5-methyl-6-(3'-amino-4'ethylamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone 
• 85634-12-4 5-methyl-6-(3'-amino-4'-isopropylamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone 

Relevant academic research and scientific papers

Synthesis of novel pyridazinonylbenzotriazoles

4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl- 4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12(a-i).

Synthesis of novel Pyridazinonylbenzotriazoles

4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12(a-i).

CRYSTALLINE PIMOBENDAN, PROCESS FOR THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION AND USE

The invention relates to a pharmaceutical composition containing pimobendan as an active ingredient. The invention also relates to a crystalline form of pimobendan, as well as to a combination of said crystalline form with at least one other therapeutically active ingredient. Moreover, the invention relates to uses of said crystalline form, as well as to a pharmaceutical composition containing it. Finally, the invention relates to a process for preparing a crystalline form of pimobendan.

Synthesis and biological activities of meribendan and related heterocyclic benzimidazolo-pyridazinones

The synthesis of a new heterocyclic benzimidazolo-pyridazinones is described.The new compounds were evaluated as inotropic agents with 'calcium-sensitizing' effects. 5-Methyl-6--2,3,4,5-tetrahydro-pyridazin-3-one hydrochloride (meribendan) turned out to be the most interesting compound and was chosen for development as a positive inotrope. benzimidazole / calcium sensivity / cardiotonics / inotropes / phosphodiesterase / papillary muscle / pyridazinone