75130-24-4

Basic information

• Product Name: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester
• Synonyms: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester;2-Cyanoethyl 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate;2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester
• CAS NO: 75130-24-4
• Molecular Formula: C₁₉H₁₉N₃O₆
• Molecular Weight: 385.37
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 75130-24-4.mol

Chemical Properties

• Melting Point: 128-131°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester(75130-24-4)
• EPA Substance Registry System: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester(75130-24-4)

Safety Data

• Hazardous Substances Data: 75130-24-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester is used as a therapeutic agent for the prevention and treatment of atherosclerotic degradation of arterial walls. Its application is based on its ability to target and alleviate the conditions that contribute to the hardening and narrowing of arteries, which can lead to heart disease and stroke.
Used in Cardiovascular Medicine:
In the field of cardiovascular medicine, 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester is utilized as a preventive measure against atherosclerosis. Its role is to help maintain the health and flexibility of arterial walls, reducing the risk of cardiovascular events such as heart attacks and strokes.
Chemical Properties:
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Cyanoethyl) 5-Methyl Ester is a white crystalline solid, which indicates its stable and solid-state nature at room temperature. This property is essential for its formulation and administration in the pharmaceutical industry, as it allows for easy handling, storage, and incorporation into various drug delivery systems.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 99-61-6 3-nitro-benzaldehyde 
• 65193-87-5 2-cyanoethylacetoacetate 
• 14205-39-1 methyl 3-aminocrotonate 
• 102993-38-4 2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate 
• 21731-17-9 methyl 3-aminocrotonate 
• 193539-61-6 (Z)-3-Amino-but-2-enoic acid 2-cyano-ethyl ester 

Downstream Products

• 76093-33-9 (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 
• 104713-75-9 barnidipine 
• 172331-68-9 3-(R)-1-benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate 
• 88712-56-5 methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 80873-62-7 (-)-Nitrendipine 
• 88712-56-5 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride 
• 104757-53-1 [14C]-Barnidipine hydrochloride 
• 76093-34-0 (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 114208-23-0 (+)-2-cyanoethyl methyl (S)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate 
• 143167-32-2 2-cyanoethyl (R)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylate 
• 74936-72-4 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 

Relevant articles and documents

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.

3 - (2 - Nitrile ethyl) -5 - methyl - 2, 6 - dimethyl -4 - (3 - nitrophenyl) - 1, 4 - dihydropyridine - 3, 5 - dicarboxylic ester

The invention relates to a preparation method of a barnidipine intermediate 3-(2-nitrile-ethyl)-5-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. The preparation method is characterized by enabling 3-hydroxylpropionitrile and methyl acetoacetate to be subjected to ester exchange under the catalysis of N-bromosuccinimide (NBS), then, ammoniating with a mixture of ammonium acetate and ammonia water, and then, carrying out catalytic reaction by an organic acid, thereby obtaining a final product. The preparation method provided by the invention is used for overcoming the defects of the existing preparation methods that the yield is relatively low and the like, and is applicable to industrial production.

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)

Synthesis and characterization of impurities of barnidipine hydrochloride, an antihypertensive drug substance

Barnidipine hydrochloride is a long term dihydropyridine calcium channel blocker used for the treatment of hypertension. During the process development of barnidipine hydrochloride, four barnidipine impurities were detected by high-performance liquid chromatography (HPLC) with an ordinary column (Agilent ZORBAX Eclipse XDB-C18, 150 mm × 4.6 mm, 5 m). All these impurities were identified, synthesized, and subsequently characterized by their respective spectral data (MS, 1H-NMR, and 13C-NMR). The identification of these impurities should be useful for quality control in the manufacture of barnidipine.

Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates

Several 3-(2-cyanoethyl)-1,4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1,4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.

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.

Antihypertensive dihydropyridine derivatives

Compound of formula 1 are calcium entry antagonists useful for treating hypertension, congestive heart failure, angina, and vasospastic disorders: STR1 wherein n is an integer from 1 to 4; R1 and R2 are lower alkyl; R3 is lower alkyl or alkoxyalkyl; A is alkylene of two to eight carbon atoms; X1 and X2 are each independently --NO2, --CF3, CH3 O--, --CN, --H, lower alkyl or halo; Y is --O--, --S--, --S(O)--, or --S(O)2 --; and R is H, lower alkyl, cycloalkyl, alkoxyalkyl, cycloalkyloxy-alkyl, alkoxycycloalkyl, acyl, or saturated or unsaturated 5- or 6-membered heterocyclyl optionally substituted with lower alkyl or alkoxy, wherein the heteroatom is one oxygen atom.