Landiolol

Landiolol Struktur
133242-30-5
CAS-Nr.
133242-30-5
Englisch Name:
Landiolol
Synonyma:
[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-2-hydroxy-3-[2-(morpholine-4-carbonylamino)ethylamino]propoxy]phenyl]propanoate;ONO1101;ONO 1101;ONO-1101;Landiolol;Landiolol D8;Landiolol USP/EP/BP;Landiolol HCL EP USP;((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((S)-2-hydroxy-3-((2-(morpholine-4-carboxamido)ethyl)amino)propoxy)phenyl)propanoate;((–)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-3-{4-[(S)-2-hydroxy-3-(2-morpholino-carbonylamino)ethylamino] propoxy}phenylpropionate)
CBNumber:
CB01011742
Summenformel:
C25H39N3O8
Molgewicht:
509.59
MOL-Datei:
133242-30-5.mol

Landiolol Eigenschaften

Siedepunkt:
727.5±60.0 °C(Predicted)
Dichte
1.201±0.06 g/cm3(Predicted)
pka
13.73±0.20(Predicted)

Sicherheit

Landiolol Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Landiolol was launched as iv infusion for the treatment of tachyarrhythmia during surgery. This structurally related derivative of esmolol can be synthesized in 3 linear steps from 3-(4-hydroxyphenyl)propionic acid by successive esterification followed by alkylation of the phenol function with (2S)-glycidyltosylate and opening of the resulting epoxide by the appropriate amine. Landiolol is an ultra short acting PI-adrenergic blocker more cardioselective (βI/β2 = 255) than esmolol (βi/β2 = 32). It showed 6-8 times greater efficiency compared to esmolol in reducing isoproterenol-induced increase in heart rate and ventricular contraction in anesthetized dogs. In clinical trials, landiolol was effective against a variety of arrhythmias with efficacy seen in patients with atrial fibrillation, proxysmal supraventricular tachycardia, ventricular tachycardia and premature complexes. Landiolol produced a doserelated pharmacokinetic behavior, has a rapid onset of action (10 min.) and is rapidly hydrolyzed to inactive acidic metabolites by esterases after iv administration. This results in an ultra-short half-life (approx. 3 min.) and p-blocade, allowing rapid termination of the drug effect by termination of infusion if side effects occur. Hypertension was the most frequent adverse event and resolved in less than 30 min. after drug withdrawal.

Originator

Ono Pharmaceutical (Japan)

Trademarks

Onoact

Synthese

Landiolol is prepared by the reaction of 2-(morpholine-4-carboxamido)ethanamino hydrochloride and (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate. The steps are as follows:
A suspension of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate prepared according Example 3 (0.50 g, 0.00134 mol) in isopropanol (10 ml) is added with 2-(morpholine-4-carboxamido)ethanamino hydrochloride (18) (1.4 g, 0.00670 mol), heated to 30-35°C and dropwise added with 30% NaOH, keeping pH at 10-11. The mixture is left under stirring at 35-40°C, monitoring by UPLC. After completion of the reaction, ethyl acetate (20 ml) and water (20 ml) are added and the phases are separated. The organic phase is added with water (20 ml) and adjusted to pH 3-4 with hydrochloric acid. The phases are separated and the resulting aqueous phase is then adjusted to pH 10-11 with sodium hydroxide and re-extracted with ethyl acetate (20 ml). The solvent is then evaporated off under reduced pressure to obtain 0.38 g (55.6%) of a pale yellow oil which solidifies in time to a pale yellow solid.
Landiolol synthesis

Landiolol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Landiolol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 60)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Chengdu Aupone Pharmaceutical Co.Ltd.
+86-28-+86-28-87843998-6060-6060 +8618631098571
lijiaqi@aupone.com China 43 58
airuikechemical co., ltd.
+undefined86-15315557071
sales02@airuikechemical.com China 994 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21691 55
CONIER CHEM AND PHARMA LIMITED
+8618523575427
sales@conier.com China 49390 58
career henan chemical co
+86-0371-86658258 15093356674;
factory@coreychem.com China 29826 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-81138252 +86-18789408387
1057@dideu.com China 3487 58
WinWin Chemical CO., Limited
+86-0577-64498589 +8615325081899
sales@win-winchemical.com China 13854 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250
1026@dideu.com China 29016 58
AFINE CHEMICALS LIMITED
0571-85134551
info@afinechem.com CHINA 15377 58
Sinoway Industrial co., ltd.
0592-5800732; +8613806035118
xie@china-sinoway.com China 992 58

133242-30-5()Verwandte Suche:


  • Landiolol
  • ONO-1101
  • ONO1101
  • ONO 1101
  • Landiolol D8
  • Landiolol HCL EP USP
  • Landiolol USP/EP/BP
  • ((–)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-3-{4-[(S)-2-hydroxy-3-(2-morpholino-carbonylamino)ethylamino] propoxy}phenylpropionate)
  • (-)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-hydroxy-3-(2-morpholino-carbonylamino)ethylamino]propoxy]phenylpropionate monohydrochloride
  • Benzenepropanoic acid, 4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-, [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester
  • ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((S)-2-hydroxy-3-((2-(morpholine-4-carboxamido)ethyl)amino)propoxy)phenyl)propanoate
  • [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-2-hydroxy-3-[2-(morpholine-4-carbonylamino)ethylamino]propoxy]phenyl]propanoate
  • 133242-30-5
  • C25H39N3O8
  • C25H39N3O8ClH
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