Barnidipine hydrochloride

Base Information

• Chemical Name: Barnidipine hydrochloride
• CAS No.: 104757-53-1
• Molecular Formula: C27H29N3O6^.HCl
• Molecular Weight: 528.005
• European Community (EC) Number: 682-698-2
• UNII: 7LZ6R3AEM1
• DSSTox Substance ID: DTXSID8048654
• Wikidata: Q27268545
• ChEMBL ID: CHEMBL2093893,CHEMBL2356712
• Mol file: 104757-53-1.mol

Synonyms:1-benzyl-3-pyrrolidinyl methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;barnidipine;Cyress;Libradin;mepirodipine;mepirodipine hydrobromide, (S,S)-isomer;mepirodipine hydrochloride, (R,R)-isomer;mepirodipine hydrochloride, (R,S)-isomer;mepirodipine hydrochloride, (S,R)-isomer;mepirodipine hydrochloride, (S,S)-isomer;mepirodipine malate, (S,S)-isomer;mepirodipine oxalate, (R,S)-isomer;mepirodipine oxalate, (S,S)-isomer;mepirodipine, (R,R)-isomer;mepirodipine, (R,S)-isomer;mepirodipine, (S,R)-isomer;YM 09730;YM-09730

Chemical Property of Barnidipine hydrochloride

Chemical Property:

• Vapor Pressure: 4.94E-15mmHg at 25°C
• Melting Point: 223-226°C
• Boiling Point: 614.5 °C at 760 mmHg
• Flash Point: 325.4 °C
• PSA: 113.69000
• LogP: 5.41220
• Storage Temp.: Refrigerator
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥16.3 mg/mL in DMSO with gentle warming
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 527.1823134
• Heavy Atom Count: 37
• Complexity: 917

Purity/Quality:

98%,99%, ^*data from raw suppliers

BarnidipineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC2CCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC.Cl
• Isomeric SMILES: CC1=C([C@@H](C(=C(N1)C)C(=O)O[C@H]2CCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC.Cl
• Recent EU Clinical Trials: Etude des effets d'un antagoniste calcique(la barnidipine) sur la sensibilité des chémorécepteurs et l'activité orthosympathique.
• Description: Barnidipine hydrochloride is a vasodilating dihydropyridine calcium antagonist useful in the treatment of hypertension. In experimental animals, its hypotensive effect was more potent and longer acting than nicardipine, nifedipine and nitrendipine. Barnidipine is a dihydropyridine calcium channel blocker that has an IC50 value of 0.35 nM in potassium-induced tonic contraction of pig coronary artery. It demonstrates antihypertensive activity by reducing peripheral vascular resistance. It decreases blood pressure in spontaneously hypertensive rats when administered orally at 1 and 3 mg/kg per day. Formulations containing barnidipine have been used as a treatment for hypertension.
• Uses: 1,4-Dihydropyridine calcium antagonist with antihypertensive and diuretic effects. A potential candidate in the treatment of patients with renal parenchymal hypertension.
• Therapeutic Function: Coronary vasodilator

Technology Process of Barnidipine hydrochloride

There total 13 articles about Barnidipine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

(+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid (76093-34-0) + (S)-N-benzyl-3-hydroxypyrrolidine (101385-90-4) → [14C]-Barnidipine hydrochloride (104757-53-1,101979-04-8)

Guidance literature:

(+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid; With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at -5 - 10 ℃; for 3h; Inert atmosphere;

(S)-N-benzyl-3-hydroxypyrrolidine; In dichloromethane; N,N-dimethyl-formamide; at -5 - 10 ℃; for 1h;

With hydrogenchloride; In ethanol; tert-butyl methyl ether; at -5 - 10 ℃;

Reference yield: 65.5%

barnidipine (104713-75-9) → [14C]-Barnidipine hydrochloride (104757-53-1,101979-04-8)

Guidance literature:

With hydrogenchloride; In ethanol; dichloromethane;

DOI:10.3390/molecules19011344

Reference yield:

3-(3S)-1-benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-(4S)-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate malate → [14C]-Barnidipine hydrochloride (104757-53-1,101979-04-8)

Guidance literature:

With hydrogenchloride; In ethanol; at 15 ℃; for 4h;

upstream raw materials:

methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

(S)-N-benzyl-3-hydroxypyrrolidine

(R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

1-benzyl-3-pyrrolidinol

Downstream raw materials:

(R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

2,6-Dimethyl-4-(3-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-pyrrolidin-3-yl) ester 5-methyl ester

Refernces

• 1、 -. "Process for synthesis of hydrochloric acid ramiah of lercanidipine (by machine translation)". . . Retrieved 2016/12/01.
• 2、 -. "POLYMORPH OF BARNIDIPINE HYDROCHLORIDE AND PROCESSES FOR ITS PREPARATION". Page/Page column 23. . Retrieved 2013/10/21.