Tiopronin amidate and its prepn

A technology of tiopronin amino acid salt and amino acid, which can be applied in pharmaceutical formulations, medical preparations containing active ingredients, digestive system, etc. And other issues

Inactive Publication Date: 2007-01-03
GRAND PHARM (CHINA) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] But tiopronin has its major defect, that is, it is very unstable, and it is easy to oxidize and degrade in the presence of water, which affects the curative effect and safety of its clinical treatment.
Moreover, the melting point of tiopronin is relatively low at 96-99°C, so it is also unstable to heat.
The physical and chemical properties of tiopronin directly limit its use in the preparation of various pharmaceutical preparations
Therefore, in order to improve the use effect of tiopronin, many researchers prepare it and other components into a composition, and its use effect is still not good
For example, the invention patent application with publication date of February 23, 2005 and publication number CN1582911A discloses a new freeze-dried powder of tiopronin, which uses tiopronin as an active ingredient and pharmaceutical excipient amino acid to form a drug. Composition, it improves the stability of tiopronin in aqueous solution to a certain extent, and has a certain inhibitory effect on the oxidative degradation of tiopronin, but a considerable part of tiopronin will still be oxidatively degraded
In particular it shows little improvement in the thermal stability of tiopronin
So for a long time, how to solve the problem of easy oxidative degradation and poor thermal stability of tiopronin has always been the subject of research by those skilled in the art

Method used

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  • Tiopronin amidate and its prepn
  • Tiopronin amidate and its prepn
  • Tiopronin amidate and its prepn

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of tiopronin arginine salt

[0030] raw material name

Feeding amount

mole ratio

Tiopronin

L-Arginine

Methanol (95%)

100g

112g

600ml

1

1.05

[0031] operate:

[0032] Put tiopronin, L-arginine, and methanol into a 1000ml three-neck reaction flask, stir, heat to reflux, and after 3 hours of reflux reaction, filter while hot, and place the filtrate in a refrigerator at 5-10°C to cool and crystallize. After 5 hours, it was filtered to obtain white crystals, which were dried in an oven at 80°C for 6 hours to obtain 196 g of white crystalline solids, yield 94.8%, mp 197-200°C.

[0033] The infrared absorption spectrum data of the sample:

[0034] Absorption peak (cm -1 ): 2957.92, 1647.58, 1604.88, 1525.77, 1457.23, 1407.90, 1386.21, 1357.38, 1335.77, 1313.99, 1246.37, 1159.37, 1012.96, 670.43, 555.97.

Embodiment 2

[0035] Embodiment 2: the preparation of tiopronin lysine salt

[0036] raw material name

Feeding amount

mole ratio

Tiopronin

L-Lysine

Ethanol (95%)

100g

94g

600ml

1

1.0

[0037] operate:

[0038] Put tiopronin, L-lysine, and ethanol into a 1000ml three-necked reaction flask, stir, heat to reflux, and after 3 hours of reflux reaction, filter while hot, and place the filtrate in a refrigerator at 5-10°C to cool and crystallize. After 5 hours, it was filtered to obtain white crystals, which were dried in an oven at 80° C. for 6 hours to obtain 177 g of white crystalline solids, yield 93.4%, mp 172-175° C.

[0039] The infrared absorption spectrum data of the sample:

[0040] Absorption peak (cm -1 ): 3328.57, 2939.20, 1646.85, 1593.90, 1521.17, 1405.00, 1357.70, 1316.94, 1023.31, 904.87, 701.58, 550.03, 420.12.

Embodiment 3

[0041] Embodiment 3: the preparation of tiopronin ornithine salt

[0042] raw material name

Feeding amount

mole ratio

Tiopronin

Ornithine

90% aqueous methanol

100g

89g

500ml

1

1.1

[0043] operate:

[0044] Put 100g of tiopronin, 89g of ornithine, and 500ml of 90% aqueous methanol into a 1000ml three-neck reaction flask, stir, heat to reflux, and after 3 hours of reflux reaction, filter while hot, and put the filtrate in a refrigerator at 5-10°C to cool and crystallize. After 5 hours, it was filtered to obtain white crystals, which were dried in an oven at 80°C for 6 hours to obtain white crystalline solids, mp 238-240°C.

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PUM

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Abstract

The present invention relates to one kind of Tiopronin amidate for treating acute and chronic hepatosis and its preparation process. The general expression of Tiopronin amidate is shown. The present invention changes Tiopronin with easy oxidation, degradation, volatilation and decomposition into stable Tiopronin amidate with raised smelting point and raised medicinal effect. The Tiopronin amidate may be further used to prepare other medicine preparation.

Description

technical field [0001] The invention relates to an amino acid salt used for preparing medicine and a preparation method thereof, in particular to a tiopronin amino acid salt used for treating acute and chronic liver diseases and a preparation method thereof. Background technique [0002] Tiopronin (English name Tiopronin, chemical name: N-(2-mercaptopropionyl) glycine) is a metabolic improvement antidote, its molecular formula: C 5 h 9 NO 3 S, molecular weight: 163.20, structural formula as follows: [0003] [0004] It can activate metabolic enzymes, improve protein metabolism, and promote liver function repair. It is mainly used for the treatment of acute and chronic liver diseases. Since the 1990s, my country has successfully developed the API of tiopronin, and after that, various preparations of tiopronin have been listed on the market: including tablets, capsules, aqueous injections and freeze-dried powder injections, etc., which are now widel...

Claims

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Application Information

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IPC IPC(8): C07C233/05A61K31/197A61P1/16A61P31/14
Inventor 谢国范钱自强杨波周建明黄璐
Owner GRAND PHARM (CHINA) CO LTD
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