133242-30-5

Basic information

• Product Name: Landiolol
• Synonyms: [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-2-hydroxy-3-[2-(morpholine-4-carbonylamino)ethylamino]propoxy]phenyl]propanoate;Landiolol;((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;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
• CAS NO: 133242-30-5
• Molecular Formula: C₂₅H₃₉N₃O₈
• Molecular Weight: 509.59
• EINECS: 1592732-453-0
• Mol File: 133242-30-5.mol

Chemical Properties

• Boiling Point: 727.513 °C at 760 mmHg
• Flash Point: 393.786 °C
• Appearance: /
• Density: 1.201 g/cm³
• CAS DataBase Reference: Landiolol(CAS DataBase Reference)
• NIST Chemistry Reference: Landiolol(133242-30-5)
• EPA Substance Registry System: Landiolol(133242-30-5)

Safety Data

• Hazardous Substances Data: 133242-30-5(Hazardous Substances Data)

Usage

Uses

Used in Cardiology:
Landiolol is used as an intravenous infusion for the treatment of tachyarrhythmia during surgery. It is effective against a variety of arrhythmias, including atrial fibrillation, paroxysmal supraventricular tachycardia, ventricular tachycardia, and premature complexes.
Used in Pharmaceutical Industry:
Landiolol is used as an active pharmaceutical ingredient for the development of medications targeting cardiovascular conditions, specifically tachyarrhythmias. Its ultra-short half-life and rapid onset of action make it a valuable asset in the management of heart rate and rhythm during surgical procedures.

Originator

Ono Pharmaceutical (Japan)

InChI:InChI=1/C25H39N3O8.ClH/c1-25(2)35-17-22(36-25)21(14-23(30)32-3)18-4-6-20(7-5-18)34-16-19(29)15-26-8-9-27-24(31)28-10-12-33-13-11-28;/h4-7,19,21-22,26,29H,8-17H2,1-3H3,(H,27,31);1H/t19-,21?,22+;/m0./s1

Upstream product

• 69630-16-6 N-(2-aminoethyl)-4-morpholine carboxamide 
• 144256-12-2 2,2-dimethyl-1,3-dioxolan-4S-ylmethyl 3-<4-<2(S),3-epoxypropoxy>phenyl>propionate 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 1398109-46-0 (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate 
• 154467-16-0 N-(2-aminoethyl)-4-morpholine carboxamide oxalic acid 
• 88017-03-2 2-(morpholine-4-carboxamido)ethanamino hydrochloride 
• 144256-11-1 3-(4-hydroxyphenyl)propionic acid [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester 
• 110-91-8 morpholine 
• 93605-74-4 4-[(1H-imidazol-1-yl)carbonyl]morpholine 

Downstream Products

• 144481-98-1 Landiolol hydrochloride 
• 1253907-79-7 landiolol hydrochloride 

Relevant articles and documents

Method for preparing landiolol hydrochloride

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to an improved method for preparing landiolol and a compound shown as a formula 8. The compound shown as the formula 8 is prepared by reacting a compound shown as a formula 7 with AH (organic amine). The invention also relates to compounds of general formula 7.

Process for the enantioselective synthesis of landiolol

PROBLEM TO BE SOLVED: To provide a process for the enantioselective synthesis of landiolol.SOLUTION: The process for the enantioselective synthesis of landiolol represented by formula (B) uses a compound represented by formula (A) as an intermediate.

Preparation method of landiolol hydrochloride

The invention provides a preparation method of landiolol hydrochloride. The preparation method utilizes cheap and easily available raw materials. A key reaction utilizes a phase transfer catalysis method so reaction time is shortened. The preparation meth

Process for the enantioselective synthesis of landiolol

A process for the preparation of Landiolol 1, ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((S)-2-hydroxy-3-(2-(morpholine-4-carboxamido) ethylamino)propoxy)phenyl)propanoate) starting from (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate, an alkylating agent with epoxide structure, in particular epichlorohydrin, and 2-(morpholine-4-carboxamido)ethanamine in the form of the free base or of a salt thereof. Said process is carried out without isolating most intermediates, does not require chromatographic purifications and is particularly advantageous in terms of yields and productivity. Furthermore, the resulting Landiolol is particularly pure and can be conveniently transformed into Landiolol hydrochloride with high enantiomeric purity.

THERAPY FOR COMPLICATIONS OF DIABETES

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

Method for treating resistant hypertension

A method is provided for lowering blood pressure in a patient having clinically diagnosed resistant hypertension. The method comprises administering darusentan to the patient adjunctively with a baseline antihypertensive regimen that comprises administration of at least one diuretic and at least two antihypertensive drugs selected from at least two of (a) ACE inhibitors and angiotensin II receptor blockers, (b) beta-adrenergic receptor blockers and (c) calcium channel blockers. The darusentan is orally administered at a dose and frequency effective, in combination with the baseline regimen, to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures.

Development of a highly cardioselective ultra short-acting β-blocker, ONO-1101

A novel, highly cardioselective ultra short-acting β-blocker, ONO-1101, has been developed for application in the emergency treatment of tachycardia and better control of heart rate in surgery. This agent is approximately nine times more potent in β-blocking activity in vivo and eight times more cardioselective in vitro than esmolol. This β-blocking drug has a short duration of activity, enabling rapid recovery after cessation of administration if side effects occur. It can be used safely in patients suffering from acute heart disease and represents a major therapeutic advance in the treatment of heart disease.