586-06-1

Basic information

• Product Name: Orciprenaline
• Synonyms: 5-[1-hydroxy-2-(1-methylethylamino)ethyl]benzene-1,3-diol;5-(1-hydroxy-2-propan-2-ylamino-ethyl)benzene-1,3-diol;orciprenaline;1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol;1,3-Benzenediol, 5-1-hydroxy-2-(1-methylethyl)aminoethyl-;1,3-Benzenediol, 5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]- (9CI);3,5-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol;Benzyl alcohol, 3,5-dihydroxy-a-[(isopropylamino)methyl]- (6CI, 8CI)
• CAS NO: 586-06-1
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.26
• EINECS: 209-569-1
• Product Categories: Orciprenaline
• Mol File: 586-06-1.mol

Chemical Properties

• Melting Point: 100°
• Boiling Point: 350.94°C (rough estimate)
• Flash Point: 179.7°C
• Appearance: /
• Density: 1.1240 (rough estimate)
• Vapor Pressure: 1.02E-07mmHg at 25°C
• Refractive Index: 1.5718 (estimate)
• PKA: 9.11±0.10(Predicted)
• CAS DataBase Reference: Orciprenaline(CAS DataBase Reference)
• NIST Chemistry Reference: Orciprenaline(586-06-1)
• EPA Substance Registry System: Orciprenaline(586-06-1)

Safety Data

• Hazardous Substances Data: 586-06-1(Hazardous Substances Data)

Usage

Originator

Alupent, Boehringer Ingelheim ,W. Germany ,1961

Uses

Bronchodilator.

Manufacturing Process

In an initial operation, 3,5-diacetoxyacetophenone was reacted first with bromine and then with isopropylamine to give 1-(3,5-dihydroxyphenyl)-2- isopropylaminoethanone. 59 g of 1-(3,5-dihydroxy-phenyl)-2-isopropylaminoethanone (free base) were dissolved in 590 cc of methanol, and the solution was hydrogenated in the presence of about 80 g Raney nickel at room temperature and under a pressure of 5 atm. Hydrogen absorption was terminated after a few minutes. The catalyst was separated by vacuum filtration, and the filtrate, an ethanolic solution of 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane, was admixed with the calculated amount of an alcoholic 20% sulfuric acid solution. A crystalline precipitate formed which was filtered off and washed with alcohol. For purification, the product was dissolved in water and the solution was filtered through iron-free charcoal. Thereafter, the filtrate was evaporated to dryness in vacuo and the residue was taken up in alcohol. The crystalline precipitate which separated out after some standing was separated by vacuum filtration and washed with alcohol. After recrystallization from 90% alcohol, 61 g (83.2% of theory) of 1-(3,5- dihydroxyphenyl)-1-hydroxy-2-isopropylamino-ethane sulfate, MP 202° to 203°C, was obtained.

Therapeutic Function

Bronchodilator

InChI:InChI=1/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3

Relevant articles and documents

Combined doses

The present invention discloses a method and a pharmaceutical dry powder combined dose for the prophylaxis or treatment of a respiratory disorder in a mammalian host by inhalation of a metered dry powder combined dose of finely divided dry medication powders. At least one dry powder medicament is selected from a first group of bronchodilating medicaments and at least one dry powder medicament from a second group of anti-inflammatory medicaments. A metered dry powder medicinal combined dose comprising separately metered deposits of medicinally suitable quantities of each of the selected medicaments is prepared, in which the sum of the metered deposits constitutes the metered quantities of powder of the combined dose and the medicinal combined dose is introduced into an adapted inhaler device for a generally simultaneous delivery of the medicinal combined dose during the course of a single inhalation by a user, such that the delivered medicinal combined dose is composed of a high proportion of mixed de-aggregated fine particles of the selected medicaments, whereby an desired therapeutic or treating effect to the user is achieved.

Pharmaceutical formula

The present invention concerns a pharmacological vehicle or carrier system, which makes possible administration of the active ingredient with a high absorption thereof in the blood circulation of the patient treated therewith, in particular also in the case of oral administration. The pharmacological vehicle system according to the invention comprises ultrafine particles of a reaction product of a reactive derivative of an at least dibasic inorganic acid or an alkane-carboxylic acid having 2 or 3 carboxyl groups and optionally one or two hydroxy groups, wherein one bond of the dibasic inorganic acid or one carboxy group of the alkane-carboxylic acid is bonded to a pharmacological active ingredient containing a hydroxy group, SH group and/or a primary or secondary amino group having a ractive hydrogen atom on this group, and the other bond is bonded to the free hydroxy group of a glycerolipid having at least one free hydroxy group on the glycerol. The invention further concerns these reaction products and a process for the preparation of ultrafine particles of these reaction products.