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| | Lercanidipine hydrochloride Basic information |
| Product Name: | Lercanidipine hydrochloride | | Synonyms: | 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-[(3,3-diphenylpropyl)methylamino]-1,1-dimethylethyl methyl ester hydrochloride;LERCANIDIPINE HCL;LERCANIDIPINE HYDROCHLORIDE;1,4-Dihydro-2,6-dimethyl-4-(3-nittrophenyl)-3,5-pyridinedicarboxylicAcid2-[(3,3-Diphenylpropyl)methylamino]-1,1-dimeth;1,4-Dihydro-2,6-dimethyl-4-(3-nittrophenyl)-3,5-pyridinedicarboxylic Acid 2-[(3,3-Diphenylpropyl)methylamino]-1,1-dimethylethyl Methyl Ester Hydrochloride;3-(1-((3,3-Diphenylpropyl)(methyl)amino)-2-methylpropan-2-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride;3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-diMethyl-4-(3-nitrophenyl)-,3-[2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl] 5-Methyl ester,hydrochloride (1:1);Lercanidipine Impurity 1 | | CAS: | 132866-11-6 | | MF: | C36H42ClN3O6 | | MW: | 648.19 | | EINECS: | 603-682-3 | | Product Categories: | API;Cardiovascular APIs;Aromatics;Dihydropyridine;Heterocycles;Miscellaneous Natural Products;Dihydropyridine Class Chemicals;Intermediates & Fine Chemicals;Pharmaceuticals;Calcium Channel Modulators;Inhibitors and Activators;Voltage-gated Ion Channels | | Mol File: | 132866-11-6.mol |  |
| | Lercanidipine hydrochloride Chemical Properties |
| Melting point | 175-177°C | | storage temp. | 2-8°C | | solubility | soluble in Methanol | | form | powder | | color | yellow | | Merck | 14,5446 | | InChIKey | WMFYOYKPJLRMJI-UHFFFAOYSA-N | | SMILES | C1(C)NC(C)=C(C(OC(C)(C)CN(CCC(C2=CC=CC=C2)C2=CC=CC=C2)C)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OC)=O.[H]Cl | | CAS DataBase Reference | 132866-11-6(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 36/37-45 | | RIDADR | UN 2811 | | WGK Germany | 3 | | HS Code | 2933.39.4100 | | Toxicity | LD50 in mice (mg/kg): 83 i.p.; 657 orally (Nardi) |
| | Lercanidipine hydrochloride Usage And Synthesis |
| Chemical Properties | Pale-Yellow Powder | | Uses | A dihydropyridine calcium channel blocker. Antihypertensive. | | Uses | long-acting dihydropyridine calcium channel blocker, antihypertensive | | Definition | ChEBI: Lercanidipine hydrochloride is a diarylmethane. | | Brand name | Cardiovasc (Recor dati, Italy); Carmen (Recordati, Italy); Corifeo (Recordati,
Italy); Lercadip (Recordati, Italy); Lercan (Recordati,
Italy); Lercapin (Recordati, Italy); Lercaton (Recordati,
Italy); Lerkamen (Recordati, Italy); Lerzam (Recordati,
Italy); Renovia (Recordati, Italy); Vasodip (Recordati,
Italy); Zandip (Recordati, Italy); Zanicor (Recordati, Italy). | | Biological Activity | L-type Ca 2+ channel blocker that displays higher vascular selectivity than Felodipine (4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester ). Causes peripheral vasodilation with only weak negative inotropic activity. Antihypertensive. | | Biochem/physiol Actions | Lercanidipine hydrochloride is a L-type (Cav1.2b) vascular channel antagonist; L-type (Cav1.2a) cardiac channel agonist voltage-dependent and highly lipophylic compound, which exhibits a slower onset and longer duration of action than other calcium channel antagonists; an antihypertensive agent in patients with mild-to-moderate hypertension; more vasoselective than lacidipine and amlodipine. | | Synthesis | The general procedure for the synthesis of 3-(1-((3,3-diphenylpropyl)(methyl)amino)-2-methylpropan-2-yl)5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride from the compound (CAS:957215-03-1) is as follows: 10 mmol of oxalate salt (Example 4) was dissolved in 100 mL of dichloromethane and 20 mL of aqueous solution containing 20 mmol of potassium carbonate was added. The organic phase was separated and the aqueous phase was extracted with 2 x 10 mL of dichloromethane. The organic phase was combined and treated with 20 mL of 1N hydrochloric acid solution. The organic phase was separated and concentrated. The residue was dissolved in 2,000 mL of water and 2 mL of 1N hydrochloric acid and 5 mL of saturated aqueous sodium chloride were added to form I hydrochloride hemihydrate and the product was collected by filtration. Yield: 6.2 g (95%); Purity: 99.8% (HPLC); Melting point: 118-122 ° C. HPLC conditions: RP 16 column, 125×3 mm ID, 5 μm, Detection wavelength: 233 nm; Eluent composition: 0.01 mol Na2HPO4/MeOH/acetonitrile=25/65/10; Retention time: about 15 min. | | References | [1] Patent: EP1860102, 2007, A1. Location in patent: Page/Page column 1; 8; 15 |
| | Lercanidipine hydrochloride Preparation Products And Raw materials |
| Raw materials | Lercanidipine Impurity 26-->2-[(3-Nitrophenyl)methylene]-3-oxo-butanoic Acid 2-[(3,3-Diphenylpropyl)methylamino]-1,1-dimethylethyl Ester Hydrochloride-->Butanoic acid, 3-oxo-,2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl ester-->N-Methyl-3,3-diphenylpropylamine-->Lercanidipine-->2,N-Dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol-->methyl 3-aminocrotonate-->3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-[2-[(3,3-diphenylpropyl)methylamino]-1,1-dimethylethyl] 5-methyl ester, ethanedioate (1:1)-->Methyl 3-aminocrotonate-->3-Nitrobenzaldehyde |
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