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Dimethyldiguanide of the thiazolidinedione pharmaceutical, preparation method and use thereof

A technology of thiazolidinedione and metformin, applied in the field of salt or adduct

Inactive Publication Date: 2009-09-16
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dual function of etidronate is estimated to have clinical significance only after a large amount of continuous and uninterrupted use for a long period of time, but its side effects still need further investigation

Method used

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  • Dimethyldiguanide of the thiazolidinedione pharmaceutical, preparation method and use thereof
  • Dimethyldiguanide of the thiazolidinedione pharmaceutical, preparation method and use thereof
  • Dimethyldiguanide of the thiazolidinedione pharmaceutical, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of metformin free base

[0026] In the round bottom flask, add metformin hydrochloride 4.99g (0.03mol), add dehydrated alcohol 200ml, add the sodium ethylate dehydrated alcohol solution of equimolar under the situation of stirring again, stir overnight at room temperature, filter off the precipitate that produces, Ethanol was distilled off from the filtrate under reduced pressure to obtain a solid, which was dried under reduced pressure at room temperature to obtain 3.92 g of metformin free base.

Embodiment 2

[0028] Synthesis of Rosiglitazone Metformin Salt (Adduct)

[0029] Take 2.27g (0.006mol) of rosiglitazone sodium and 1.00g (0.006mol) of metformin hydrochloride, put them in a round bottom flask; add 120ml of absolute ethanol, heat to reflux while stirring, after reflux for about 10 minutes, filter while hot , the filtrate was distilled off part of the ethanol under reduced pressure and then cooled to room temperature, a large amount of off-white solid precipitated, recrystallized with absolute ethanol to obtain 2.26 g of white solid, yield 77%, mp; 182-184 ° C.

[0030] Take 2.14g (0.006mol) of rosiglitazone free base and 0.78g (0.006mol) of metformin free base and put them in a round-bottomed flask, add 70ml of ethanol and heat to reflux for about 5 minutes, cool, and recrystallize the precipitated solid with ethanol to obtain a white Crystalline solid 2.16g, yield 74%, melting point 182-184°C

Embodiment 3

[0032] Synthesis of Pioglitazone Metformin Salt (Adduct)

[0033] Take 1.00g of metformin hydrochloride, add 50ml of ethanol, heat and reflux to dissolve, then add 2.28g of pioglitazone sodium dissolved and clarified with 50ml of absolute ethanol, and sodium chloride precipitates immediately. After evaporation under reduced pressure, a white solid was obtained, which was recrystallized from a mixed solvent of ethanol / ethyl acetate to obtain 2.28 g of a white solid, with a yield of 78% and a melting point of 172-174°C.

[0034] Get 2.14g (0.006mol) of pioglitazone free base and 0.78g (0.006mol) of metformin free base in a round-bottomed flask, add 50ml of ethanol and heat to reflux. After the solution becomes clear, ethanol is distilled off under reduced pressure to obtain a white solid. Recrystallized with ethanol / ethyl acetate to obtain 2.37g of white crystalline solid, yield 81%, melting point 172-174°C

[0035] Example 3

[0036] Growth and Single Crystal Structure of Ros...

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Abstract

A dimethyldiguanide salt of a thiazolidinedione pharmaceutical and a preparation method and use thereof are disclosed. The invention provides a salt or adduct or solvent thereof formed by the thiazolidinedione pharmaceutical and dimethyldiguanide via special chemical bonds and corresponding preparation method; further pharmaceutical composition of dimethyldiguanide of the thiazolidinedione pharmaceutical, dimethyldiguanide (adduct) of the thiazolidinedione pharmaceutical or solvent thereof and one or more consistent pharmaceutical preparation or pharmaceutical composition obtained by pharmaceutical or / and carrier or / and excipient optionally. The pharmaceutical preparation or pharmaceutical composition is applied to treating or preventing various diseases by thiazolidinedione pharmaceutical and / or dimethyldiguanide, in particular metabolic syndrome for instance diabetes.

Description

technical field [0001] The invention relates to a salt or adduct composed of thiazolidinediones and metformin, as well as their preparation and application. technical background [0002] Thiazolidinedione drugs (such as rosiglitazone, pioglitazone, etc.) appear to be alkaline to a certain extent, therefore, various acid salt compounds and their compounds have been reported in the literature. Combinations and various crystal forms, such as rosiglitazone maleate, hydrochloride, sulfate, citrate, phosphate, tartrate, hydrobromide, and even etidronate. On the other hand, the nitrogen and hydrogen on the thiazolidinedione ring show a certain degree of acidity. Therefore, there are alkali metal salts, alkaline earth metal salts, basic amino acid salts and choline salts of rosiglitazone. . Among these salt compounds, the maleate, hydrochloride, sulfate, hydrobromide, alkali metal salt, alkaline earth metal salt, amino acid salt and choline salt of thiazolidinedione drugs are outs...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07C279/26A61K31/4439A61K31/155A61P3/10A61P3/00
Inventor 胡湘南甘勇军方大树吴禄春张检胡思星
Owner CHONGQING MEDICAL UNIVERSITY
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