| Identification | More | [Name]
Benidipine hydrochloride | [CAS]
91599-74-5 | [Synonyms]
1-(BENZYLMETHYL)-3-PIPERIDINYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3,5-PYRIDINEDICARBOLATE
(R,R)-(+/-)-2,6-DIMETHYL-4-(3-NITROPHENYL)-1,4-DIHYDRO-3,5-PYRIDINE,DICARBOXYLIC ACID METHYL-1-BENZYL-3-PIPERIDYL-ESTER,MONOHYDROCHLORIDE SALT
monohydrochloride,(r*,r*)-(+-)-hyl1-(phenylmethyl)-3-piperidinyleste
2,6-Dimethyl-4-(3-Nitrophenyl)-1,4-Dihydropyridine-3,5-DimethoxyCarboxylate
(R,R)-(+/)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylicacidmethyl-1-(phenylmethyl)-3-piperidiny
Coniel, Capadipine, KW-3049, Nacadipine
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl (3R)-1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (4R)-rel-
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (R*,R*)-(+-)-
(R,R)-(+/-)-2,6-Dimethyl-4-(3-nitrophenyl)-1,4-Dihydro-3,5-pyridine-dicarboxylic acid methyl-1-benzyl-3-piperidyl-ester hydrochloride
Benidipine hydrochloride
Conipros
rac-(4R*)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-methyl 5-[(3R*)-1-benzylpiperidine-3-yl]·hydrochloride | [EINECS(EC#)]
663-500-3 | [Molecular Formula]
C28H31N3O6 | [MDL Number]
MFCD06797587 | [Molecular Weight]
505.56 | [MOL File]
91599-74-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Crystalline Powder | [Melting point ]
199-201°C | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
DMSO: ≥20mg/mL | [form ]
powder | [pka]
7.34(at 25℃) | [color ]
yellow | [Usage]
A dihydropyridine calcium channel blocker | [InChIKey]
DGVVISBYHUXFIU-UHFFFAOYSA-N | [SMILES]
C(C1=C(NC(=C([C@H]1C1C=CC=C(C=1)N(=O)=O)C(=O)OC)C)C)(=O)O[C@@H]1CCCN(C1)CC1C=CC=CC=1.Cl | [CAS DataBase Reference]
91599-74-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGIII | [WGK Germany ]
3 | [RTECS ]
US7975657 | [HS Code ]
2933.99.5300 | [HazardClass ]
6.1 | [Toxicity]
LD50 orally in male mice: 218 mg/kg (Muto, 1988) |
| Hazard Information | Back Directory | [Description]
Benidipine hydrochloride is a new, long acting dihydropyridine calcium antagonist useful in the treatment of hypertension and angina pectoris. In experimental animals,
benidipine hydrochloride dose dependently induced hypotension with a potency of
6 and 12 times more than nifedipine and nicardipine, respectively. It also exhibited a
slow onset of action. | [Chemical Properties]
Yellow Crystalline Powder | [Originator]
Kyowa Hakko (Japan) | [Uses]
A dihydropyridine calcium channel blocker. Antihypertensive. | [Brand name]
Coniel | [Biological Activity]
Orally active antihypertensive agent which displays a wide range of activities in vitro and in vivo . Inhibits L-, N- and T-type Ca 2+ channels. Also inhibits aldosterone-induced mineralocorticoid receptor activation. Exhibits cardioprotective and antiartherosclerotic effects. | [Safety Profile]
A poison by ingestion,intraperitoneal, and intravenous routes. When heated todecomposition it emits toxic vapors of NOx and HCl. | [Synthesis]
Under sonication conditions, 10 g of monomethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate was placed in a 200 mL reaction flask, to which 14 mL of N,N-dimethylformamide (DMF) and 56 mL of dichloromethane were added. Under ice bath conditions, 2.4 mL of thionyl chloride was slowly added to the resulting homogeneous suspension, followed by stirring the reaction mixture for 1 hour until a clarified solution was formed. Next, 6.3 g of 1-benzyl-3-piperidinol was added and stirring was continued for 2.5 hours under ice bath conditions. Upon completion of the reaction, the reaction solution was washed with 40 mL of water (repeated 4 times) and 40 mL of saturated brine solution (1 time). The organic phase was dried by adding 4 g of anhydrous sodium sulfate for 2 hours. After drying, the sodium sulfate solid was removed by filtration and the dichloromethane was recovered by distillation under reduced pressure to give the crude yellow to red (R)-rel-3-((R)-1-benzylpiperidin-3-yl)5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride. The crude product was dissolved in 100 mL of acetone and sonicated at 150 W and 40 kHz for 7 min, followed by filtration under reduced pressure and drying to give 5.9 g of yellow powdery product in 36.2% yield. | [storage]
room temperature (desiccate) | [References]
[1] Patent: WO2012/142815, 2012, A1. Location in patent: Page/Page column 5; 6 |
|
|