123524-52-7 Usage
Description
Azelnidipine, a member of the 1,4-dihydropyridine class of L-type calcium channel blockers with a slow onset profile, is a novel dihydropyridine derivative used for the treatment of hypertension. It is synthesized via the condensation of iso-propyl 2-(3-nitrobenzylidene)acetoacetate with (1-diphenylmethylazetidin-3-yl)-3,3-diamino acrylate. Azelnidipine exhibits high lipophilicity, a slow onset of activity, and a prolonged pharmacodynamic effect, which contribute to its effectiveness in treating hypertension and related conditions.
Uses
Used in Cardiovascular Applications:
Azelnidipine is used as an antihypertensive agent for treating hypertension. It helps in reducing systolic and diastolic blood pressure in patients with mild-to-moderate hypertension, providing a sustained decrease in blood pressure without causing reflex tachycardia, a common side effect of this class of drugs.
Used in Ischemic Heart Disease Treatment:
Azelnidipine is used as a treatment for ischemic heart disease and cardiac remodeling after myocardial infarction. Its slow onset and long-lasting effect make it an effective option for managing these conditions.
Used in Metabolic Disorders Prevention:
Azelnidipine is used to reduce the risk of hyperglycemia-induced metabolic disorders. Studies show that treatment with Azelnidipine can help in preventing such complications.
Used in Atherosclerosis Inflammation Protection:
Azelnidipine may have a protective role in inflammation associated with atherosclerosis, making it a potential treatment option for patients with this condition.
Used in Cardiac Function Maintenance:
Azelnidipine is used to prevent a sudden drop in cardiac function after acute stress, providing support for maintaining cardiac function during critical situations.
Application Industry:
Pharmaceutical Industry: Azelnidipine is used in the development and production of antihypertensive medications, as well as treatments for ischemic heart disease, metabolic disorders, and atherosclerosis inflammation.
Brand Name:
Calblock
Originator
Sankyo (Japan)
Biological Activity
Azelnidipine, a novel dihydropyridine derivative, is a L-type calcium channel blocker and antihypertensive. Unlike other L-type calcium channel blockers, azelnidipine causes minimal stimulation of the sympathetic nervous system despite its significant depressor effect. Azelnidipine may have a protective role in inflammation in atherosclerosis.
Synthesis
A solution of benzhydrylamine
(46) and epichlorohydrin (47) was mixed without adding
solvent to give azetidinol 48 in 57% yield. DCC
coupling between cyanoacetic acid (49) and azetidinol 48 in
hot THF gave ester 50 in 93% yield. Cyanoester 50 was
treated with ethanol and HCl gas in chloroform to give
imidate HCl salt 51, which was treated with ammonia gas in
chloroform and ammonium acetate in acetonitrile to give the
corresponding amidinoacetate 52. A modified Hantzsch
reaction was employed to construct the 2-amino-1,4-
dihydropyridine core structure. Compound 52 was
condensed with 2-(3-nitrobenzylidene)acetic acid isopropyl
ester (55) in the presence of NaOMe in refluxing isopropanol
to give the cyclized product, azelnidipine (V) in 74% yield.
Benzylideneacetoacetate 55 was obtained through the
Knoevenagel reaction employing 3-nitrobenzaldehyde (53)
and isopropyl acetoacetate (54) in isopropanol containing a
catalytic amount of piperidinium acetate at 45-55oC in 65%
yield.
Check Digit Verification of cas no
The CAS Registry Mumber 123524-52-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,3,5,2 and 4 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 123524-52:
(8*1)+(7*2)+(6*3)+(5*5)+(4*2)+(3*4)+(2*5)+(1*2)=97
97 % 10 = 7
So 123524-52-7 is a valid CAS Registry Number.
InChI:InChI=1/C33H34N4O6/c1-20(2)42-32(38)27-21(3)35-31(34)29(28(27)24-15-10-16-25(17-24)37(40)41)33(39)43-26-18-36(19-26)30(22-11-6-4-7-12-22)23-13-8-5-9-14-23/h4-17,20,26,28,30,35H,18-19,34H2,1-3H3
123524-52-7Relevant articles and documents
Azelnidipine preparation method (by machine translation)
-
Paragraph 0032; 0034, (2017/06/06)
The invention relates to a blood pressure lowering medicine azhediping preparation method, which belongs to the field of medicine. The method of the traditional synthetic route trunk compound 4 of the improved synthetic conditions, of the original anhydrous reaction conditions is changed into the water under the conditions of the reaction, not only is easy to operate, but also to reduce the requirement of anhydrous reaction solvent, thus very suitable for industrial production. (by machine translation)
OPTICALLY ACTIVE DIHYDROPYRIDINE DERIVATIVE
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Page/Page column 4, (2008/06/13)
The optically active dihydropyridine derivative is (R)-2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-(1-diphenylmethylazetidin-3-yl) ester 5-isopropyl ester or a pharmacologically acceptable salt thereof.
Dihydropyridine derivatives, their preparation and their use
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, (2008/06/13)
2-(Amino or methyl)-6-(methyl or amino)-4-(substituted phenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid esters have a specific class of heterocyclic groups as thealcohol moiety. These compounds have a variety of valuable activities, including antihypertensive and Ca++ -blocking activities, leading to their use for the treatment of circulatory and coronary disorders. They may be prepared by condensation of appropriate substituted benzylideneacetoacetic acid esters with appropriate amidinoacetic acid esters.