79307-93-0

Basic information

• Product Name: Azelastine hydrochloride
• Synonyms: a5610;azeptin;e-0659;w-2979m;AZELASTINE HCL;AZELASTINE HYDROCHLORIDE;4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-phthalazin-1-one hydrochloride;4-[(4-Chlorophenyl)methyl]-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)-phthalazinone Hydrochloride
• CAS NO: 79307-93-0
• Molecular Formula: C22H25Cl2N3O
• Molecular Weight: 418.36
• EINECS: 1312995-182-4
• Product Categories: Antihistaminic;Intermediates & Fine Chemicals;Pharmaceuticals;Histamine receptor;Astelin
• Mol File: 79307-93-0.mol

Chemical Properties

• Melting Point: 225--2290C
• Boiling Point: 533.9 °C at 760 mmHg
• Flash Point: 276.7 °C
• Appearance: white to off-white/
• Density: 1.25 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: >10mg/mL
• Stability: Incompatible with strong oxidizing agents.
• Merck: 14,906
• CAS DataBase Reference: Azelastine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Azelastine hydrochloride(79307-93-0)
• EPA Substance Registry System: Azelastine hydrochloride(79307-93-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RTECS: TH9203900
• Hazardous Substances Data: 79307-93-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Azelastine hydrochloride is used as a therapeutic agent for treating allergic conditions such as asthma and nasal allergies. It is effective in reducing the symptoms associated with these conditions by inhibiting histamine release and antagonizing its action, thus providing relief to patients suffering from these ailments.

Originator

Asta-Werke(Degussa) (W. Germany)

Biochem/physiol Actions

H1 histamine receptor antagonist; NF-kB activator.

Safety Profile

Poison by ingestion andintravenous routes. An experimental teratogen. Otherexperimental reproductive effects. When heated todecomposition it emits toxic fumes of NOx and HCl.

InChI:InChI=1/C22H24ClN3O.ClH/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16;/h2-3,6-11,18H,4-5,12-15H2,1H3;1H/t18-;/m1./s1

Synthetic route

2-(2-methylphenyl)pyridine (10273-89-9) + azelastine hydrochloride (79307-93-0) → C34H34N4O

Conditions	Yield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Inert atmosphere; Glovebox;	90%

azelastine hydrochloride (79307-93-0) → 7-oxo-azelastine + 2-oxo-azelastine

Conditions	Yield
With water; iodine; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h; chemoselective reaction;	A 37% B 6%

azelastine hydrochloride (79307-93-0) → azelastine (58581-89-8)

Conditions	Yield
With sodium hydroxide In water pH=10; Inert atmosphere;

azelastine hydrochloride (79307-93-0) → 2-(1-benzylazepan-4-yl)-4-(4-chlorobenzyl)phthalazin-1(2H)-one (103541-65-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / pH 10 / Inert atmosphere 2.1: tri(4-tolyl)aminium hexafluorophosphate; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / -5 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere View Scheme

Upstream product

• 606-83-7 3,3-Diphenylpropionic acid 
• 4279-81-6 3,3-diphenylpropanal 
• 530-48-3 1,1-Diphenylethylene 
• 504-24-5 4-aminopyridine 
• 37089-77-3 3,3-diphenylpropanoyl chloride 
• 613-94-5 benzoic acid hydrazide 
• 58581-89-8 azelastine 
• 110406-94-5 C₁₄H₂₁N₃O 
• 1859-33-2 1-methyl-1,2,3,5,6,7-hexahydroazepin-4-one 

Downstream Products

• 103541-65-7 2-(1-benzylazepan-4-yl)-4-(4-chlorobenzyl)phthalazin-1(2H)-one 
• 58581-89-8 azelastine 

Relevant articles and documents

Preparation method of azelastine hydrochloride

The invention relates to the technical field of synthesis of raw material medicines, and particularly discloses a preparation method of azelastine hydrochloride. The method comprises the following steps: condensing benzoyl hydrazine and 1-methylhexahydroazepine-4-one serving as raw materials, reducing with sodium borohydride, and reacting to obtain a compound 1; preparing a solid intermediate compound 2 from the compound 1 and organic binary weak acid; hydrolyzing the compound 2, and cyclizing with a compound 3 to form a compound 4; and salifying the compound 4 by hydrochloric acid, and separating water by toluene to obtain a compound 5, namely azelastine hydrochloride. The intermediate compound 2 prepared by the invention is a solid, the stability of the intermediate compound 2 is greatly improved compared with that of hydrochloride obtained in other literatures, the intermediate compound 2 is free of hygroscopicity, the purity can reach 99% or above, the quality risk of subsequent bulk drugs can be greatly reduced, and the process production operation space is larger; and the obtained azelastine hydrochloride does not contain water and meets related quality standards, the yield is increased to 80% or above compared with other literatures, and the purity can reach 99% or above.

Azelastine hydrochloride-containing percutaneous preparation having good percutaneous absorbability and reduced skin irritation

The invention relates to azelastine hydrochloride-containing percutaneous preparations which comprises, as base ingredients; hydrocarbon and/or beeswax, and a surfactant.

Use of combinations comprising non-sedating antihistamines and alpha-adrenergic drugs for the topical treatment of rhinitis/conjunctivitis and cold, cold-like and/or flu symptoms

Pharmaceutical combination, applicable topically, containing a non-sedating antihistamine in combination with an α-adrenergic agonist and optionally conventional physiologically acceptable carriers, diluting agents and auxiliaries substances for the prophylaxis and treatment of allergic and/or vasomotoric rhinitis, conjunctivitis, cold, cold-like and/ or flu symptoms are claimed.

Preparation of pharmaceuticals by hydroformylation. Part III. The synthesis of N-(4-Pyridyl)-3,3-diphenyl-1-aminopropane (Phenpyramine, Milverine)

N-(4-Pyridyl)-3,3-diphenyl-1-aminopropane (1) (Phenpyramine, Milverine), an important amino-pyridine derivative endowed with Muscarinic antagonist activity, is prepared starting from 1,1-diphenylethene using the hydroformylation as key the step in the reaction scheme: the obtained aldehyde was transformed in the desired compound 1 by a three steps reaction sequence; the overall yield was up to 42.8%.