54527-89-8

Usage

InChI:InChI=1/C18H19ClN2O6/c1-10-14(17(22)26-3)16(12-5-4-6-13(9-12)21(24)25)15(11(2)20-10)18(23)27-8-7-19/h4-6,9,16,20H,7-8H2,1-3H3

Upstream product

• 54527-68-3 2-chloroethyl acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 
• 21731-17-9 methyl 3-aminocrotonate 
• 118431-03-1 methyl 2-E,Z-(3-nitro-phenylmethylen)-3-oxobutanoate 
• 62760-10-5 2-chloroethyl 2-(3-nitrobenzyliden)acetoacetate 

Downstream Products

• 85677-96-9 2-hydroxyethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 85677-95-8 2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 102336-09-4 Methyl 2-[4-cyano-4-(3,4-dimethoxyphenyl)-5,N-dimethyl-hexylamino]-ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate 
• 90096-07-4 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic acid methyl ester 2-(N-4-(2,3-dichlorophenyl)piperazinyl)ethyl ester 
• 99522-55-1 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic acid methyl ester 2-(N-1-piperazinyl)ethyl ester 
• 75130-55-1 2-acetoxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 

Relevant academic research and scientific papers

Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6- dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenylpropylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4- dihydropyridines binding site labelled by 3H-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375- lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries.

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.

Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities

A series of 1,4-dihydropyridin-3,5-yl dicarboxylic acid amides and esters incorporating an arylpiperazinylalkyl moiety have been prepared possessing the general formula STR1 wherein R4 is cycloalkyl, aryl or hetaryl, generally with electronwithdrawing substituents; R2 and R6 are lower alkyl, alkanol, alkoxyalkyl, or alkylaminoalkyl; R5 is R2 or arylpiperazinylalkyl; X is 0 or NH; Y is lower alkylene, alkoxyalkylene, alkylaminoalkylene; and Z is phenyl, substituted phenyl, pyridinyl, substituted pyridinyl, or pyrimidinyl. Compounds of this series demonstrate activity as calcium and alphaadrenergic blockers in in vitro testing and antihypertensive, antiischemic, and platelet function inhibiting actions in in vivo screens.

Carbostyril Derivative

Carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof, having excellent platelate aggregation inhibitory effect, calcium antagonism, hypotensive effect and phosphodiesterase inhibitory effect are useful as prophylactic or treating agents for thrombosis, circulation improving agents for coronary blood flow such as coronary vasodilators, hypotensive agents and phosphodiesterase inhibitors. Furthermore, the carbostyril derivatives are weak in heart rate increasing activity and also in cardiac muscle contraction increasing activity, and the carbostyril derivatives are useful agents for curing and treating heart diseases such as cardiac angina and myocardial infarction caused by hypercoagulability of the platelets. Processes are disclosed for preparation of the carbostyril derivatives.

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.

1,4-Dihydropyridine derivatives

There are provided novel 1,4-dihydropyridine derivatives, particularly 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester and 5-methyl ester. The 1,4-dihydropyridine derivatives are characterized by cerebral vascular dilator activity.