14556-46-8

Usage

Uses

Used in Pharmaceutical Industry:
Bupranolol is used as an antihypertensive agent for treating hypertension. It helps in regulating blood pressure by blocking the effects of adrenaline on the heart and blood vessels, thus reducing the force and rate of heart contractions.
Additionally, Bupranolol is used as an anti-tachycardic agent for managing tachycardia. It slows down the heart rate by counteracting the overstimulation of the sympathetic nervous system, which can lead to a rapid or irregular heartbeat.

Originator

Betadrenol,Pharma-Schwarz,W. Germany,1969

Manufacturing Process

A mixture of 16.3 g of (2-chloro-5-methylphenyl)glycidic ether (from epichlorohydrin and 2-chloro-5-methylphenol) and 6.2 g of t-butylamine in 50 ml of ethanol is heated at reflux for 6 hours. The solvent is removed, the residue is washed with water and then extracted with benzene. The dried extract is evaporated to give 1-t-butylamino-3-(2-chloro-5-methylphenoxy)-2- propanol. Treatment of the free base in benzene solution with dry hydrogen chloride yields the hydrochloride salt.

Therapeutic Function

Antiarrhythmic

InChI:InChI=1/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3

Upstream product

• 53732-26-6 1,2-epoxy-3-[2-chloro-5-methylphenoxy]propane 
• 75-64-9 tert-butylamine 
• 615-74-7 2-chloro-5-methylphenol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 15148-80-8 rac-bupranolol hydrochloride 
• 125721-14-4 3-(2-Chloro-5-methyl-phenoxy)-2-[(Z)-hydroxyimino]-propionaldehyde oxime 
• 125721-05-3 3-(2-Chloro-5-methyl-phenoxy)-2-[(E)-hydroxyimino]-propionaldehyde oxime 
• 125720-93-6 1-tert-Butylamino-3-(2-chloro-5-methyl-phenoxy)-propan-2-one oxime 
• 125720-83-4 1-tert-Butylamino-3-(2-chloro-5-methyl-phenoxy)-propan-2-one oxime 

Relevant academic research and scientific papers

Synthesis, phase behavior and absolute configuration of β-adrenoblocker bupranolol and related compounds

β-Blocker bupranolol 1, it's hydrochloride and their precursors 1-(2-chloro-5-methylphenoxy)-2,3-epoxypropane 2 and 3-(2-chloro-5-methylphenoxy)propane-1,2-diol 3 were prepared in racemic and single-enantiomer forms. For all the studied compounds phase behavior during crystallization was established on the basis of IR, DSC and X-ray investigations. Absolute configurations were established for compounds 1 and 2. Being conglomerate, racemic oxirane 2 was resolved by direct entrainment procedure. Being anticonglomerate, in the process of recrystallization, almost enantiopure 1·HCl accumulates in the mother liquor, not in the crystalline precipitate.

Continuous and convergent access to vicinyl amino alcohols

Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.

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.

Enteric coated mixture of 4-(2-hydroxy-3-isopropylamino-propoxy) indole and sodium lauryl sulphate

The present invention provides a pharmaceutical composition for controlled release of 4-(2-hydroxy-3-isopropylamino-propoxy) indole in the intestinal tract, admixed with sodium lauryl sulphate, and enteric coated.