39562-70-4 Usage
Description
Nitrendipine, also known as Baypress, is a second-generation dihydropyridine calcium channel blocker. It is a vasodilating, dihydropyridine calcium antagonist that is more selective for vascular smooth muscle than for myocardial tissue, making it an effective vasodilator. Nitrendipine is used in the treatment of mild-to-moderate essential hypertension and has a prolonged therapeutic effect compared to other calcium channel blockers like nifedipine.
Uses
Used in Cardiovascular Applications:
Nitrendipine is used as an antihypertensive agent for the treatment of primary (essential) hypertension to decrease blood pressure. It functions as a calcium channel blocker, which helps in managing blood pressure and reducing the workload on the heart.
Used in Neurological Applications:
Nitrendipine modulates NMDA receptor channel function in mammalian neurons, which can be beneficial in treating certain neurological conditions.
Used in Vascular Applications:
Nitrendipine has been shown to inhibit neutrophil adhesion to vascular endothelium, which can help in preventing inflammation and other vascular issues.
Used in Combination Therapy:
Nitrendipine is used alone or with an angiotensin-converting enzyme inhibitor to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina, providing a comprehensive approach to managing these conditions.
Chemical Properties:
Nitrendipine is a crystalline solid with the chemical formula 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic acid methyl ethylester.
Brand Names:
Baypress (Bayer) and BAYOTENSIN are the brand names under which Nitrendipine is marketed.
Originator
Bayer (W. Germany)
Biochem/physiol Actions
Ca2+ channel blocker; anti-hypertensive.
References
1) Meyer et al., (1981), (Synthesis and comparative pharmacological studies of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylates with non-identical ester functions); Arzneimittelforschung 31 407
2) Stoepel et al., (1981), Pharmacological studies of the antihypertensive effect of nitrendipine; Arzneimittelforschung 31 2056
Check Digit Verification of cas no
The CAS Registry Mumber 39562-70-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,5,6 and 2 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 39562-70:
(7*3)+(6*9)+(5*5)+(4*6)+(3*2)+(2*7)+(1*0)=144
144 % 10 = 4
So 39562-70-4 is a valid CAS Registry Number.
InChI:InChI=1/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,15-16H,5H2,1-4H3/t15?,16-/m1/s1
39562-70-4Relevant articles and documents
Facile synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetric dicarboxylates via quaternary ammonium salts of 2-aminoethyl 1,4-dihydropyridine-3,5-dicarboxylates
Kinugawa, Masahiko,Ogasa, Takehiro
, p. 3321 - 3331 (1997)
Useful 1,4-dihydropyridine unsymmetric dicarboxylates [nitrendipine (1), nicardipine (2)] and monocarboxylic acid 4 were prepared from unsymmetric 2-aminoethyl methyl 1,4-dihydropyridine-3,5-dicarboxylates 2 and 3 via their corresponding quaternary ammonium salts 5-9.
Preparation method of nitrendipine
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Paragraph 0051-0071, (2020/05/14)
The invention belongs to the technical field of medicines, and particularly relates to a preparation method of nitrendipine, which comprises the following steps: adding (E)-2-(3-nitrobenzylidene)-3-oxobutyrate and methyl 3-aminocrotonate into a first solvent, and carrying out a reflux reaction at a first temperature to obtain a first reaction solution; adding acetic anhydride into the first reaction solution at a second temperature to react to obtain a second reaction solution; carrying out a stirring reaction on the second reaction solution at a third temperature, and filtering to obtain a crude product of nitrendipine; and recrystallizing the crude product of nitrendipine to obtain nitrendipine. The invention provides a preparation method of nitrendipine, and aims to effectively controldimethyl ester impurities and diethyl ester impurities, improve the yield and shorten the reaction time so as to improve the productivity.
Preparation method of nitrendipine
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Paragraph 0042-0058, (2019/05/22)
The invention belongs to the field of drug synthesis, and particularly relates to a preparation method of nitrendipine. The preparation method is characterized by including following steps: (1), allowing 3-nitrobenzylidene ethyl acetoacetate intermediate and 3-aminomethyl crotonate according to a molar ratio of 1:1-1.1 to react at 70-75 DEG C in advance; (2), adding concentrated hydrochloric acidinto a reaction system of the step (1), and allowing reaction at 70-75 DEG C after adding is completed, wherein adding amount of the concentrated hydrochloric acid is 10-15% of molar weight of the 3-nitrobenzylidene ethyl acetoacetate intermediate; (3), cooling to 15-20 DEG C after reaction in the step (2) is completed, continuing reaction, and performing solid-liquid separation and recrystallization to obtain nitrendipine. Through process control, content of ester exchange impurities can be lowered effectively, and product yield can be increased.