58194-26-6

Basic information

• Product Name: Tetraethyl ranelate
• Synonyms: 2-[N,N-di(ethoxycarbonylmethyl)amino]-3-cyano-4-ethoxycarbonylmethylthiophene-5-carboxylic acid ethyl ester;TETRAETHYL RANELATE;5-[Bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid ethyl ester;INTERMEDIATE:STRONTIUMRANELATE;Diethyl 2,2'-(3-cyano-4-(2-ethoxy-2-oxoethyl)-5-(ethoxycarbonyl)thiophen-2-ylazanediyl)diacetate;Diethyl 2,2'-((3-cyano-4-(2-ethoxy-2-oxoethyl)-5-(ethoxycarbonyl)thiophen-2-yl)azanediyl)diacetat;Intermediate of Strontium ranelate;Diethyl 2,2'-((3-cyano-4-(2-ethoxy-2-oxoethyl)-5-(ethoxycarbonyl)thiophen-2-yl)azanediyl)diace
• CAS NO: 58194-26-6
• Molecular Formula: C₂₀H₂₆N₂O₈S
• Molecular Weight: 454.49
• EINECS: 1806241-263-5
• Product Categories: Strontium Ranelate
• Mol File: 58194-26-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 103-106 °C
• Boiling Point: 579.2 °C at 760 mmHg
• Flash Point: 304.1 °C
• Appearance: Powder
• Density: 1.28
• Vapor Pressure: 2.06E-13mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: 2-8°C(protect from light)
• PKA: -3.75±0.50(Predicted)
• CAS DataBase Reference: Tetraethyl ranelate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraethyl ranelate(58194-26-6)
• EPA Substance Registry System: Tetraethyl ranelate(58194-26-6)

Safety Data

• Hazardous Substances Data: 58194-26-6(Hazardous Substances Data)

Usage

General Description

Tetraethyl ranelate is a chemical compound used in the treatment of osteoporosis. It works by stimulating the formation of new bone and inhibiting the breakdown of existing bone. It is believed to have a dual action of both increasing bone formation and decreasing bone resorption. It is also thought to have anti-inflammatory effects. However, due to concerns about potential cardiovascular risks, tetraethyl ranelate has been withdrawn from the market in some countries and its use is now limited in others. Research into its safety and effectiveness continues, and it is not currently available for prescription in several countries.

InChI:InChI=1/C20H26N2O8S/c1-5-27-15(23)9-13-14(10-21)19(31-18(13)20(26)30-8-4)22(11-16(24)28-6-2)12-17(25)29-7-3/h5-9,11-12H2,1-4H3

Upstream product

• 58168-20-0 ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl) thiophene-2-carboxylate 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 105-36-2 ethyl bromoacetate 

Relevant articles and documents

In a HPLC method for controlled for preparing high-purity of strontium ranelate method

The invention discloses a method for preparing high-purity strontium ranelate through centralized control of the HPLC (High Performance Liquid Chromatography) method, and belongs to the field of pharmaceutical synthesis. The method comprises the following steps: (1) preparing a compound as shown in formula (II), namely, feeding a compound as shown in formula (I), tetrahydrofuran, anhydrous potassium carbonate and ethyl bromoacetate to a reaction kettle, and performing catalytic reaction through a catalyst, wherein the reaction endpoint is monitored through the HPLC; and (2) preparing a compound as shown in formula (III), namely, dropping a tetrahydrofuran solution in which the compound as shown in formula (II) is dissolved to inorganic aqueous alkali to saponify under the centralized control of the HPLC; performing reduced pressure distillation and filtering; regulating the pH (Power of Hydrogen) with hydrochloric acid; then adding a strontium chloride aqueous solution to obtain crude strontium ranelate which is characterized in that the purity is more than 99.7%, the single impurity is less than 0.1%, and the total impurity is less than 0.5%; and finally drying to obtain the targeted strontium ranelate. The strontium ranelate prepared by the method has the advantages that by means of the HPLC based centralized control, the optimal reaction time is determined and the refining and purifying steps are reduced; in addition, the method is simple in process, easy to control, high in product purity, less in waste liquid, low in energy consumption, relatively low in cost, and applicable to industrial production.

SUBSTANTIALLY PURE STRONTIUM RANELATE

Provided herein is an improved, commercially viable and industrially advantageous process for the preparation of strontium ranelate, and its intermediates, in high yield and purity. Provided further herein is a highly pure strontium ranelate substantially free of impurities, and pharmaceutical compositions comprising highly pure strontium ranelate substantially free of impurities.