62760-69-4

Upstream product

• 87191-97-7 3-<(2-Nitrophenyl)methylene>-2,4(3H,5H)-furandione 
• 141-97-9 ethyl acetoacetate 
• 552-89-6 2-nitro-benzaldehyde 
• 62759-85-7 4,4-Diethoxy-2-[1-(2-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 62760-68-3 diethyl 2-methyl-4-(2-nitrophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 10495-09-7 ethyl 4,4-diethoxyacetoacetate 
• 62759-86-8 diethyl 2-methyl-4-(2-nitrophenyl)-6-diethoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 62760-22-9 diethyl 2-methyl-4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate 

Downstream Products

• 518313-16-1 2-Methyl-4-(2-nitrosophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridin-3-carbonsaeureethylester 
• 502770-35-6 2-Methyl-4-(2-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridin-3-carbonsaeureethylester 

Relevant academic research and scientific papers

3-(Nitrobenzylidene)-2,4(3H,5H)-furandiones in the Hantzsch pyridine synthesis, part 1.: A new approach to furo[3,4-b]pyridines

The nitrobenzylidenefurandiones 7 react with acetoacetic ester (8) and ammonium acetate or 3-aminocrotonic esters (9a, b) and 2-aminopent-2-en-4-on (9c), respectively heating in acetic acid to yield the tetrahydrofuro[3,4-b] pyridines 10. The dehydrogenation of 10 using nitric acid or activated manganese dioxide leads to the dihydrofuro[3,4-b]pyridines 12. When the reaction is carried out with the tetronic acid derivatives 7 and the enaminocarbonyl compounds 9 at 30°C in tert-butanol the hexahydro-7a-hydroxyfuro[3,4-b]pyridines 11 are obtained. Treating the N,O-acetales 11 with acetic anhydride in pyridine affords the annulated lactones 10.

Studies on nilvadipine. I. Synthesis and structure-activity relationships of 1,4-dihydropyridines containing novel substituents at the 2-position

The synthesis of new 1,4-dihydropyridine derivatives containing novel substituent at the 2-position of the nucleus via the key intermediate 2-formyl-1,4-dihydropyridines (X), is described. The aldehydes (X) were prepared by hydrolysis of the acetals (IX) which were obtained from aryl aldehyde (V) and alkyl 4,4-dialkoxyacetoacetate (VI) by the Knoevenagel reaction and treatment with alkyl 3-aminocrotonate (VIII) according to the modified Hantzsch method. The formyl group of the aldehydes (X) was reactive enough to be converted to a variety of functional groups such as hydroxymethyl, cyano, substituted iminomethyl, carbamoyl, semicarbazone, substituted vinyl, ethynyl, and so on. In all of the novel compounds we prepared, 2-hydroxymethyl- and 2-cyano-1,4-dihydropyridines (IV and XXII) were found to possess potent activities in preliminary biological evaluations on hypotension in normotensive rats and on an increase in coronary blood flow in pentobarbital-anesthetized dogs. Optimization research in order to obtain a more potent compound was accomplished in the 2-hydroxymethyl- and 2-cyano-1,4-dihydropyridine series. We selected isopropyl 2-cyano-3-methoxycarbonyl-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridin e-5-carboxylate (XXIIj) as a candidate compound for further biological evaluation studies. Fortunately, XXIIj (nilvadipine) has been accepted in clinical use for the treatment of hypertension.

1,4-Dihydropyridine derivatives, and pharmaceutical method of the same

1,4-dihydropyridine derivatives of the general formula STR1 having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.

6-Acyloryalkyl-1,4-dihydropyridine derivatives and a method of effecting vasodilation therewith

This invention relates to 1,4-dihydropyridine derivatives. More particularly, it relates to new 1,4-dihydropyridine derivatives thereof which have vasodilating and anti-hypertensive activity, to processes for the preparation thereof, and to pharmaceutical composition comprising the same for therapeutical treatment in cardiovascular diseases and hypertension in human being.