2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridin-3,5-dicarboxylat

Bezeichnung:2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridin-3,5-dicarboxylat

CAS-Nr55985-32-5

Englisch Name:Nicardipine

CBNumberCB2487861

SummenformelC26H29N3O6

Molgewicht479.53

MOL-Datei55985-32-5.mol

Synonyma

2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridin-3,5-dicarboxylat

2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridin-3,5-dicarboxylat physikalisch-chemischer Eigenschaften

Schmelzpunkt	136-138 °C
Siedepunkt	603.4±55.0 °C(Predicted)
Dichte	1.230±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
Löslichkeit	Dichloromethane; Methanol
Aggregatzustand	Solid
pka	7.30±0.50(Predicted)
Farbe	Yellow
CAS Datenbank	55985-32-5(CAS DataBase Reference)

Gefahreninformationscode (GHS)

Nicardipine Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Nicodel,Mitsui,Japan,1981
Verwenden
It is used for arterial hypertension, chronic, stable angina pectoris, preventing angina pectoris, and for ischemic-type abnormalities of brain blood flow.
Verwenden
Vasodilator.
Verwenden
Nicardipine is a dihydropyridine calcium channel blocker. Antianginal; antihypertensive. Neuroprotective & Neuroresearch products.
Definition
ChEBI: Nicardipine is a racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. It has a role as an antihypertensive agent, a calcium channel blocker, a vasodilator agent and an autophagy inhibitor. It contains a (S)-nicardipine and a (R)-nicardipine.
Manufacturing Process
A mixture of 4.98 g of acetoacetic acid N-benzyl-N-methylaminoethyl ester, 2.3 g of β-aminocrotonic acid methyl ester, and 3 g of m-nitrobenzaldehyde was stirred for 6 hours at 100°C in an oil bath. The reaction mixture was subjected to a silica gel column chromatography (diameter 4 cm and height 25 cm) and then eluted with a 20:1 mixture of chloroform and acetone. The effluent containing the subject product was concentrated and checked by thin layer chromatography. The powdery product thus obtained was dissolved in acetone and after adjusting the solution with an ethanol solution saturated with hydrogen chloride to pH 1-2, the solution was concentrated to provide 2 g of 2,6-dimethyl-4-(3'-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-methylester-5-β-(N-benzyl-N-methylamino)ethyl ester hydrochloride. The product thus obtained was then crystallized from an acetone mixture, melting point 136°C to 140°C (decomposed).
Trademarks
Cardene(PDL Biopharma); Cardene (Roche).
Therapeutic Function
Vasodilator
Mechanism of action
Nicardipin relaxes smooth musculature of vessels, lowers resistance of coronary and peripheral vessels, increases blood flow in vessels of the brain, causes a moderate and stable hypotensive effect, and reduces the myocardial need for oxygen.
Synthese
Nicardipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-methyl-2-[(methylphenylmethyl)- amino]ethyl ester 3,5-pirididincarboxylic acid (19.3.7), is synthesized in a manner analogous to the synthesis of nifedipine, the only difference being that in the Hantsch synthesis, two different |?-dicarbonyl compounds are used simultaneously with o-nitrobenzaldehyde. During this, one of these in the enamine form of acetoacetic ester is simultaneously used as an amine component. A heterocyclization reaction is accomplished by reacting, the methyl ester of |?-aminocrotonic acid with the 2-methyl-2-benzylaminoethyl ester of acetoacetic acid.

Nicardipine Upstream-Materialien And Downstream Produkte

2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridin-3,5-dicarboxylat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

55985-32-5, Nicardipine Verwandte Suche:

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