76093-34-0

Usage

Uses

Used in Cardiovascular Applications:
(S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester is used as a therapeutic agent for the prevention and treatment of atherosclerotic degradation of arterial walls. Atherosclerosis is a chronic inflammatory disease characterized by the buildup of plaque in the arterial walls, leading to reduced blood flow and an increased risk of cardiovascular events such as heart attacks and strokes. This 1,4-dihydropyridine derivative may exert its beneficial effects through various mechanisms, including the modulation of vascular tone, inhibition of smooth muscle cell proliferation, and anti-inflammatory actions.
In the pharmaceutical industry, (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester may be further developed and optimized for its potential use in cardiovascular medications, targeting the prevention and treatment of atherosclerosis and related cardiovascular diseases. Its unique structure and stereochemistry may provide advantages over existing therapies, offering new opportunities for the management of cardiovascular health.

InChI:InChI=1/C16H16N2O6/c1-8-12(15(19)20)14(13(9(2)17-8)16(21)24-3)10-5-4-6-11(7-10)18(22)23/h4-7,14,17H,1-3H3,(H,19,20)/t14-/m0/s1

Upstream product

• 88712-56-5 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride 
• 75130-24-4 2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester 
• 76093-31-7 1-Ethoxymethyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester 
• 76093-31-7 1-Ethoxymethyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester 
• 74936-72-4 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 
• 102993-38-4 2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate 
• 21881-77-6 m-nifedipine 
• 99-61-6 3-nitro-benzaldehyde 
• 134028-03-8 C₁₆H₁₆N₂O₆*C₁₉H₂₂N₂O 
• 152253-24-2 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid mono-(2-methanesulfonyl-ethyl) ester 
• 152375-53-6 (4R)-1,4-dihydro-3-(2-cyanoethyl)oxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid 
• 76093-31-7 1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid 
• 152253-28-6 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-methanesulfonyl-ethyl) ester 5-methyl ester 
• 143167-32-2 2-cyanoethyl (R)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylate 

Downstream Products

• 195065-58-8 3-Iodopropyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylate 
• 195065-71-5 3-(3-pyridyl)propyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylate 
• 1404063-61-1 (4R)-3-(1-benzyl-3-methylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 104757-53-1 [14C]-Barnidipine hydrochloride 
• 55985-32-5 (-)-nicardipine 
• 55985-32-5 (+)-nicardipine 
• 104713-77-1 (3R)-1-benzyl-3-pyrrolidinyl methyl (4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 134028-04-9 (4S)-(+)-2-<4-(4-Benzhydryl-1-piperazinyl)phenyl>ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 89226-75-5 (-)-manidipine dihydrochloride 
• 77940-88-6 BAY 3629 
• 104757-54-2 (+)-(3'S,4S)-3-(1'-benzyl-3'-pyrrolidinyl) methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 104757-55-3 (3R)-1-benzyl-3-pyrrolidinyl methyl (4R)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 119065-61-1 (R,S)-Benidipine 
• 105979-17-7 benidipine 

Relevant academic research and scientific papers

Barnidipine hydrochloride compound and preparation method thereof

The invention discloses a barnidipine hydrochloride compound and a preparation method thereof. The preparation method comprises the following steps: (1) using 3-hydroxypropionitrile to react with diketene, to obtain an intermediate 1; (2) enabling the intermediate 1 to react with m-nitrobenzaldehyde and Beta-amino methyl crotonate, to obtain an intermediate 2; (3) enabling the intermediate 2 to behydrolyzed by strong base, to obtain an intermediate 3; (4) enabling the intermediate 3 to be resolved by chiral organic base, to obtain an intermediate 4; (5) enabling the intermediate 4 to react with thionyl chloride, (S)-1-benzyl-3-pyrrolidinol, and HCI ethanol solution, to obtain a crude product of barnidipine hydrochloride; and (6) performing ethyl alcohol pulping and refining, and ethyl alcohol recrystallization on the crude product of the barnidipine hydrochloride, to obtain the barnidipine hydrochloride.

Process for synthesis of hydrochloric acid ramiah of lercanidipine (by machine translation)

The invention discloses a process for synthesizing hydrochloric acid ramiah of lercanidipine, its synthesis process comprises the following steps : (1) 3 -? Hydroxy-propionitrile (I) and (II) reaction of ketene dimer, to obtain compound (VI) ; (2) compound (III) with (VI) reaction between formaldehyde nitrobenzene, to obtain compound (VII) ; (3) compound (VII) with β-amino-crotonic acid ethyl ester (IV) reaction, to obtain compound (VIII) ; (4) by strong alkali hydrolysis of compound (VIII), to obtain compound (IX) ; (5) compound (IX) using chiral organic alkali splitting, to obtain compound (X) ;? (6) compound (X) with benzyl quick (V) reaction, to obtain compound (XI) ; (7) a solution of compound (XI) by adding hydrogen chloride, hydrochloric acid ramiah horizontal (XII) can be obtained. Synthetic process of this invention has the following several advantages : (1) mild reaction conditions, each step the product is easy to separate, purification, controllable quality ; (2) higher yield for each step, the used original helping material is easy to obtain, the total cost is low ; (3) do not need to be too column, is suitable for industrial production. (by machine translation)

1,4-dihydropyridine-3,5-dicarboxylate Derivatives And Preparation And Use Thereof

The present invention relates to a 1,4-dihydropyridine-3,5-dicarboxylate compound of general compound (I), a process for preparing the same, a use thereof for the manufacture of a medicament for treating and/or preventing kidney injury, cardiovascular diseases and/or endocrine diseases, as well as a pharmaceutical composition and a pharmaceutical formulation containing said compounds, wherein the definitions of R1, R2, R3, R4, R5, R6, R7, R8, m, n1, n2, p and q are the same as those defined in the description.

1,4-DIHYDROPYRIDINE -3,5-DICARBOXYLATE DERIVATIVES, PREPARATION METHODS AND USES THEREOF

The present invention relates to a 1,4-dihydropyridine-3,5-dicarboxylate compound of general compound (I), a process for preparing the same, a use thereof for the manufacture of a medicament for treating and/or preventing kidney injury, cardiovascular diseases and/or endocrine diseases, as well as a pharmaceutical composition and a pharmaceutical formulation containing said compounds, wherein the definitions of R1, R2, R3, R4, R5, R6, R7, R8, m, n1, n2, p and q are the same as those defined in the description.

Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

An efficient total synthesis of (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in high optical purities is reported. The useful step is the resolution of racemic 2, 6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid by using commercially available Cinchona alkaloids cinchonidine and quinidine as the resolving agents. Under the optimum conditions, the optical purities for R- and S-enantiomers are extremely high (ee >99.5%). The further dihydropyridine receptor binding activity assay shows that the S-enantiomer is more potent than R-enantiomer both in rat cardiac (approximately 19 times) and cerebral cortex membrane (12 times).

Optically active 1,4-hydropyridine compounds

Optically active 1,4-dihydropyridine derivatives represented by general formula (I), process for preparing compounds (Ic) (in general formula (I) , R1 is a lower alkyl group), process for preparing compounds represented by general formula (II)

Optically-active dihydropyridines via lipase-catalyzed enantioselective hydrolysis

Several prochiral esters of 1,4-dihydropyridines were enantioselectively hydrolyzed by Pseudomonas lipases (AK, P-30, and K-10) and Candida cylindracea lipase (OF-360). The stereochemical preferences of the lipase P-30 and K-10 were found to be always 4-P

Synthesis of Optically Pure 1,4-Dihydropyridine Derivatives by Means of Diastereoisomeric Separation of the Hantzsch Intermediates Bearing (R)-1-Phenylethylamino Group

Hantzsch intermediates, which were obtained by Michael addition reaction of benzylideneacetoacetates with the enamino esters bearing (R)-1-phenylethylamino group as a chiral auxiliary, were separated into two diastereoisomeric mixtures.Each of them underw

1,4-dihydropyridine derivatives

1,4-dihydropyridine derivatives and optically active 1,4-dihydropyridine derivatives with the following formula, having vasodilating activity based on calcium antagonism, and PAF antaognism, and methods of producing the same are disclosed: STR1 wherein (*) indicates a chiral center in the case of the optically active 1,4-dihydropyridine derivatives.

Derivatives of 1,4-dihydropyridine, their preparation procedure and therapeutic compositions containing them

The invention relates to compounds having the formula: STR1 in which Ar represents a group selected from 2-nitrophenyl, 3-nitrophenyl, 2-chlorophenyl, 2,6-dichlorophenyl, 2-trifluoromethylphenyl and 3-trifluoromethylphenyl; R1 represents a C1 -C4 alkyl group or a group having the formula: STR2 A represents a group selected from groups having the formulae: STR3 and R2 represents a group selected from 2,4,6-trimethoxyphenyl, 2-thienyl and phenyl, and their addition salts with pharmaceutically acceptable acids. These compounds are calcium inhibitors with therapeutic applications.