69975-86-6

Basic information

• Product Name: Doxofylline
• Synonyms: DOXOFYLLINE;DOXOPHYLLINE;7-(1,3-dioxolan-2-ylmethyl)-3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione;2-(7’-teofillinmetil)-1,3-diossolano;2-(7’-theophyllinemethyl)-1,3-dioxolane;3,7-dihydro-7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-1h-purine-6-dione;7-(1,3-dioxolan-2-ylmethyl)-theophyllin;7-(1,3-dioxolan-2-ylmethyl)theophylline
• CAS NO: 69975-86-6
• Molecular Formula: C11H14N4O4
• Molecular Weight: 266.25
• EINECS: 274-239-6
• Product Categories: ZYRTEC;Respiratory system
• Mol File: 69975-86-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 144-146°C
• Boiling Point: 409.46°C (rough estimate)
• Flash Point: 259.3 °C
• Appearance: /
• Density: 1.2896 (rough estimate)
• Vapor Pressure: 2.49E-10mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 0.42±0.70(Predicted)
• Water Solubility: Soluble
• Merck: 14,3438
• CAS DataBase Reference: Doxofylline(CAS DataBase Reference)
• NIST Chemistry Reference: Doxofylline(69975-86-6)
• EPA Substance Registry System: Doxofylline(69975-86-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• RTECS: XH5135000
• Hazardous Substances Data: 69975-86-6(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 69975-86-6 differently. You can refer to the following data:
1. Doxofylline, a xanthine bronchodilator related to theophylline, is useful in the treatment of asthma and similar bronchospastic disorders. It has minimal activity on intestinal smooth muscle and the cardiovascular system, and is reportedly devoid of the behavioral effects of theophylline.
2. Doxofylline is a methylxanthine bronchodilator that has been examined in clinical trials involving patients with either bronchial asthma or chronic obstructive pulmonary disease. Its mechanism of action is related to its ability to inhibit phosphodiesterase activity and, thus, increase cAMP. Compared to other xanthine derivatives, which have direct arrhythmogenic effects, doxofylline demonstrates decreased affinity towards adenosine A1 and A2 receptors, does not interfere with calcium influx into cells, and does not antagonize the action of calcium-channel blockers.

Originator

ABC S.p.A. (Italy)

Uses

Different sources of media describe the Uses of 69975-86-6 differently. You can refer to the following data:
1. Doxofylline is a xanthine molecule that appears to be both bronchodilator and anti-inflammatory with an improved therapeutic window over conventional xanthines such as Theophylline and the evidence supporting the effects of Doxofylline in the treatment of lung diseases.
2. H1 antihistamine
3. Doxofylline is a xanthine molecule that appears to be both bronchodilator and anti-inflammatory with an improved therapeutic window over conventional xanthines such as Theophylline and the evidence su pporting the effects of Doxofylline in the treatment of lung diseases.

Brand name

Maxivent (Roberts Pharmaceutical);ANSIMAR.

InChI:InChI=1/C11H14N4O4/c1-13-9-8(10(16)14(2)11(13)17)15(6-12-9)5-7-18-3-4-19-7/h6-7H,3-5H2,1-2H3

Upstream product

• 1129-52-8 2,4,6-tris(chloromethyl)-1,3,5-trioxane 
• 58-55-9 theophylline 
• 107-21-1 ethylene glycol 
• 2568-30-1 2-chloromethyl-1,3-dioxolane 
• 4360-63-8 2-bromomethyl-1,3-dioxolane 

Relevant articles and documents

Preparation method of doxofylline

The invention relates to a preparation method of doxofylline. The preparation method comprises the following steps: reacting theophylline with chloroacetaldehyde glycol under the action of a first solvent and a first catalyst to generate an intermediate 7-(2, 2-dimethoxyethyl)theophylline, and reacting the intermediate 7-(2, 2-dimethoxyethyl)theophylline with ethylene glycol to generate doxofylline. The first solvent is N, N-dimethylformamide is adopted as a first catalyst, a mixture of tetrabutylammonium chloride hydrate and potassium bromide or a mixture of tetrabutylammonium chloride hydrate and potassium iodide is adopted as a first catalyst, and the reaction time can be obviously shortened and the reaction efficiency can be improved when the reaction system is used; and sulfuric acid is adopted as a second catalyst to replace p-toluenesulfonic acid (a genotoxicity suspected substance) or hydrosulfate in the prior art, so that the toxicity of a reaction solution is effectively reduced, and the obtained doxofylline is high in purity, high in yield and controllable in impurity. The preparation method of doxofylline is low in cost, high in yield, simple to operate, environment-friendly and beneficial to large-scale production of drugs.

Preparation method of doxofylline

The invention discloses a preparation method of doxofylline. The method comprises: S1, in a first solvent, in the presence of an alkali, heating theophylline and halogenated acetal to carry out an alkylation reaction to obtain an intermediate; and S2, in a second solvent, in the presence of a catalyst, heating the intermediate and ethylene glycol to carry out an acetal exchange reaction so as to obtain the doxofylline. According to the route designed by the invention, quality control points can be increased in the doxofylline preparation process, the impurity content is favorably controlled, the risk of drug registration declaration is reduced, the total yield reaches 85 percent or above, the operation is simple, and high-risk reaction is avoided.

Synthetic method of doxofylline

The invention discloses a synthetic method of doxofylline and belongs to the technical field of organic synthesis. The method comprises the following step: theophylline and 2-chloromethyl-1,3-dioxolane are subjected to a reaction at 60-110 DEG C in an aprotic solvent under the action of alkali and a phase transfer catalyst, and doxofylline is synthesized, wherein the mole ratio of theophylline, 2-chloromethyl-1,3-dioxolane and the alkali is 1:1-2:1-3, the phase transfer catalyst accounts for 3%-5% of the molar weight of theophylline, and the phase transfer catalyst is selected from one or moreof tetrabutylammonium chloride, tetrabutylammonium bromide and tetrabutylammonium fluoride. The provided new synthetic method of doxofylline is short in reaction time and only needs 3-6 h, is low inreaction temperature which is lower by 20-30 DG C than that of the conventional method, is high in yield which is 10% or higher than that of the conventional method, and is beneficial to industrial production of the drug.