52560-77-7

Basic information

• Product Name: arotinolol
• Synonyms: 2-(3'-tert-Butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)thiazole hydrochloride;5-(2-((3-((1,1-Dimethylethyl)amino)-2-hydroxypropyl)thio)-4-thiazolyl)-2-thiophenecarboxamide;68377-91-3 (Hydrochloride)
• CAS NO: 52560-77-7
• Molecular Formula: C15H21N3O2S3
• Molecular Weight: 371.54114
• Mol File: 52560-77-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 599.8°Cat760mmHg
• Flash Point: 316.6°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 3.09E-15mmHg at 25°C
• CAS DataBase Reference: arotinolol(CAS DataBase Reference)
• NIST Chemistry Reference: arotinolol(52560-77-7)
• EPA Substance Registry System: arotinolol(52560-77-7)

Safety Data

• Hazardous Substances Data: 52560-77-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H21N3O2S3.ClH/c1-15(2,3)17-6-9(19)7-21-14-18-10(8-22-14)11-4-5-12(23-11)13(16)20;/h4-5,8-9,17,19H,6-7H2,1-3H3,(H2,16,20);1H

Upstream product

• 68377-92-4 arotinolol 
• 75-64-9 tert-butylamine 
• 101540-26-5 arotinolol hydrochloride 
• 52560-89-1 5-(2-mercapto-1,3-thiazol-4-yl)-2-thiophene carboxamide 

Downstream Products

• 101540-26-5 arotinolol hydrochloride 
• 52560-77-7 C₁₅H₂₁N₃O₂S₃ 
• 52560-77-7 C₁₅H₂₁N₃O₂S₃ 

Relevant articles and documents

Preparation method of arotinolol hydrochloride

The invention relates to the technical field of medicines, particularly provides a preparation method of arotinolol hydrochloride, and relates to the technical field of medicines. The preparation method of the arotinolol hydrochloride, provided by the invention, comprises the following steps: (1) enabling tetrahydrofuran, 2-formamide-5-(2-sulfydryl-1, 3-thiazole-4-yl)-thiophene, water, sodium bicarbonate and epoxy chloropropane to react to generate an intermediate product C181101170-I03; (2) carrying out a reaction on absolute ethyl alcohol, C181101170-I03 and tert-butylamine, so as to obtain an intermediate product C181101170-I02; (3) subjecting methanol, ethyl acetate, C181101170-I02 and concentrated hydrochloric acid to a reaction, and obtaining an arotinolol hydrochloride crude product; and (4) treating the arotinolol hydrochloride crude product with DMSO and acetone to obtain arotinolol hydrochloride. The product arotinolol hydrochloride obtained by the method is high in yield, high in purity and small in impurity, the purity of the product can be well controlled, and the method is suitable for industrial production.

Preparation process for arotinolol hydrochloride with high purity

The invention discloses a preparation process for arotinolol hydrochloride with high purity. The preparation process comprises the following steps: pouring an acid-binding agent into an alcohol-watercompounded solvent, adding a compound namely 5-(2-sulfhydryl-4-thiazole)-2-thiophenecarboxamide, then adding epichlorohydrin, carrying out a reaction at a room temperature, and carrying out filteringand drying so as to obtain an intermediate III; pouring tert-butylamine into anhydrous ethanol, adding the intermediate III, carrying out a micro-reflux reaction, carrying out concentration, adding purified water, carrying out dissolving under heating, carrying out cooling, adjusting the pH value of an obtained solution to be acidic, carrying out washing with an organic solvent, adding ethanol into an aqueous layer, carrying out dissolving under heating, and carrying out cooling crystallization, and carrying out filtering so as to obtain a crude product; and pouring the crude product into an alcohol-water compounded solvent, carrying out dissolving under heating, and carrying out cooling crystallization, filtering and drying so as to obtain the arotinolol hydrochloride with high purity. The preparation process provided by the invention can effectively remove impurities from arotinolol hydrochloride, can reach a purity of 99.95% or above, and has simple operation and high yield.

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.