85677-95-8

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 54527-89-8 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester 
• 21731-17-9 methyl 3-aminocrotonate 
• 74936-72-4 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 
• 540-51-2 2-bromoethanol 
• 33736-01-5 mono(acetoacetate)ethylene glycol 
• 14205-39-1 methyl 3-aminocrotonate 

Downstream Products

• 103785-47-3 methanesulfonyloxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 55985-32-5 Nicardipine 
• 54527-84-3 nicardipine hydrochloride 
• 103785-48-4 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-[2-(toluene-4-sulfonyloxy)-ethyl] ester 
• 85677-96-9 2-hydroxyethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 

Relevant academic research and scientific papers

Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing a nitrooxy moiety at the 3-ester position

The synthesis of a new series of dihydropyridines containing a nitrooxy moiety at the 3-ester position is described. The antihypertensive activity of the compounds was examined and compared with that of nifedipine; some of them were relatively potent. The structure-activity relationship is also discussed.

Process for the preparation of 1,4-dihydropyridine derivatives

In the preparation of 1,4-dihydropyridine derivatives of formula (I), the improvement which comprises reacting a 2-haloethyl 2-benzylidene-3-oxobutanoate of formula (IV) with a 3-aminocrotonic acid ester of formula (V) in a reaction medium in the presence of a dehydrating agent. In the formulae R1, R2, R3 and X have the same meanings as defined in the claims.

Nimodipine: Synthesis and metabolic pathway

Key step of the synthesis of the calcium antagonistic cerebral vasodilator (±) isopropyl-2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (Bay e 9736, nimodipine) is the cyclising Michael addition. A pharmacokinetic study with 14C-nimodipine in the rat revealed as major metabolites the dihydropyridines as well as the pyridines. A potential metabolic pathway is discussed involving ether cleavage and oxidation to the pyridine form as primary biotransformation steps. Reference metabolites were synthesized using 1,4-dihydropyridines with appropriate functionalities as precursors.