91189-59-2

Usage

Uses

Used in Pharmaceutical Industry:
Felodipine 3,5-DiMethyl Ester is used as a calcium channel blocker for the treatment of cardiovascular diseases such as hypertension, angina pectoris, and certain heart arrhythmias. It works by inhibiting the movement of calcium ions into cardiac and smooth muscle cells, leading to the relaxation of blood vessel walls and improved blood flow.
Used in Research and Development:
Felodipine 3,5-DiMethyl Ester is also used in research and development for the study of calcium channel blockers and their potential applications in various medical conditions. It serves as a valuable tool for understanding the mechanisms of action and the development of new drugs with improved efficacy and safety profiles.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 14205-39-1 methyl 3-aminocrotonate 
• 1215080-66-2 (R)-3-ethyl 5-((R)-1-hydroxy-3-(phenylthio)propan-2-yl) 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 124-41-4 sodium methylate 

Downstream Products

• 123853-39-4 (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid 

Relevant academic research and scientific papers

Compound and its as L-type calcium channel blocker or/and application of acetylcholine esterase inhibitors

Disclosed in this invention are compounds and the uses as L-type calcium channel blocker and/or acetylcholinesterase inhibitor thereof. The uses of said compounds in the manufactures of a medicament for the treatment of cardiovascular diseases, apoplexy or senile dementia are also disclosed in the present invention.

Triton-X-100 catalyzed synthesis of 1,4-dihydropyridines and their aromatization to pyridines and a new one pot synthesis of pyridines using visible light in aqueous media

A realistic and convenient synthetic method has been developed for the facile synthesis of 1,4-dihydropyridine derivatives in the presence of the non-ionic surfactant Triton X-100, in an aqueous medium at room temperature. A greener method to synthesize pyridine derivatives has also been developed by the oxidation of 1,4-dihydropyridine derivatives with almost 100% yields and also in a one pot synthesis, employing an aldehyde, ethyl acetoacetate and ammonium acetate in an aqueous micellar medium by irradiation with potassium persulphate in the presence of visible light. The one pot protocol offered excellent yields of the targeted product in a very short period of time at room temperature and the non-ionic surfactant catalyst can be recovered very easily. We also observed that during the reaction there was the formation of micelles, or micelle-like colloidal aggregates, from the non-ionic surfactant and the reaction mixture in water, measured by dynamic light scattering and visualized through an optical microscope. The process is advantageous as ammonia is generated from an ammonium salt under absolutely neutral conditions and the product purification follows a group assistant purification chemistry process (GAP).

Facile and green synthesis of 1,4-dihydropyridine derivatives in n-butyl pyridinium tetrafluoroborate

l,4-Dihydropyridine derivatives were synthesized from the one-pot condensation of aldehydes, acetoacetates, and ammonium acetate in room-temperature ionic liquid n-butyl pyridinium tetrafluoroborate ([BPy][BF4]). Compared with classical Hantzsch reaction conditions, this new method has the advantage of excellent yields, short reaction time, and easy workup. The recovered ionic liquid could be recycled for at least five runs without losing its activity. Taylor & Francis Group, LLC.

A new In-SiO2 composite catalyst in the solvent-free multicomponent synthesis of Ca2+ channel blockers nifedipine and nemadipine B

An In-SiO2 composite was prepared by the sol-gel method and was applied as a heterogeneous Lewis acid catalyst in the multicomponent Hantzsch synthesis of symmetrical and non-symmetrical 1,4-DHPs. The Ca2+ channel blockers nifedipine and nemadipine B were synthesized in a single step through a solvent-free protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.

A facile synthesis of (S)-felodipine

A short and facile synthesis of (S)-felodipine was developed starting from (R)-glycidol as the source of the chiral auxiliary. 2-Hydroxyethyl esters were found to undergo selective transesterification reactions in the presence of other esters. This selective transesterification reaction was applied to the synthesis of (S)-felodipine through selective substitution of the 2-hydroxyethyl group possessing chiral ester with sodium methoxide.

MINERALOCORTICOID RECEPTOR MODULATORS

The present invention relates to dihydropyridine mineralcorticoid receptor modulating compounds having the structure: and their use in treating cardiovascular events.

Process to prepare 1,4-dihydropyridine intermediates and derivatives thereof

An improved catalyst is disclosed for a process involving the preparation of benzylidene intermediates useful in the preparation of 1,4-dihydropyridine compounds and derivatives thereof useful as medicines such as for example felodipine. This is accomplished by the condensation of an aldehyde and an acetoacetate in the presence of a novel catalyst system that includes a pyridyl carboxylic acid and a secondary amine. It has been found that through the use of the present invention the purity and yield of the desired isomer of the benzylidene intermediate can be maximized, thus avoiding the requirement of additional purification steps. The use of these intermediates can then be further reacted to form the required dihydropyridines, again having a very high purity and yield compared with the prior art.

PROCESS FOR THE PREPARATION OF 1,4-DIHYDROPYRIDINES AND NOVEL 1,4-DIHYDROPYRIDINES USEFUL AS THERAPEUTIC AGENTS

The present invention provides a process for the preparation of 1,4-dihydropyridines of the formula (1), wherein R1 is H, NO2, Cl, OAc, OH, R2 is H, NO2, Cl, -O-CH2-O-, OMe, OAc, OEt, OH, R3 is H, NO2, Cl, N(Me)2, -O- CH2 -O-, OMe, OAc, OH, R4 is H, OMe, OAc, OH, R5 is H, Cl, I, and R6 and R7 are either methyl, ethyl or both by preparing a mixture of an aromatic aldehyde, alkyl acetoacetate and a source of ammonia, adsorbing the prepared mixture and adsorbent till adsorbent becomes free flowing, heating the material so obtained under microwave irradiation, cooling the reaction mixture and recovering the compound of formula (1). The present invention also relates to novel 1,4-dihydropyridines with cardiovascular activity.

4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl) , 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl) , and 4-(2,3,5-trichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbon yl):

Hydrogen bonding interactions displayed by three crystalline chloro-substituted 4-phenyl-1,4-dihydropyridine molecules 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl) , 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridi