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Ozagrel tromethamine, compound, preparation method and application thereof

A technology of tromethamine and tromethamine salt, which is applied in the field of ozagrel tromethamine and compositions thereof, can solve the problems of water-soluble ozagrel salt purity defects, decreased stability and the like, and achieves The synthesis process is simple and feasible, with high stability and high anti-platelet aggregation effect.

Active Publication Date: 2010-03-03
徐华
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the above-mentioned ozagrel salt has improved the stability of the ozagrel salt, the long-term storage stability has decreased, and there are still defects in water solubility and the purity of the ozagrel salt. For the above-mentioned defects of the prior art, this A new ozagrel salt with anti-platelet aggregation and relieving vasospasm effect proposed by the invention, i.e. ozagrel tromethamine

Method used

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  • Ozagrel tromethamine, compound, preparation method and application thereof
  • Ozagrel tromethamine, compound, preparation method and application thereof
  • Ozagrel tromethamine, compound, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Preparation of ozagrel tromethamine

[0042]Dissolve 250.7 g (2.072 mol) of tromethamine in 1125 ml of distilled water, add 450 g (1.974 mol) of ozagrel under stirring at a temperature of 45° C., and keep the reaction for 2 hours after the addition is complete. After cooling to room temperature, a large number of crystals were precipitated, and the crude product was obtained by filtration. Add the crude product to 1125ml of absolute ethanol, heat to reflux for 3 hours, stop the reaction, stir at a temperature of 5°C for 6 hours, filter with suction, rinse with absolute ethanol, and dry to obtain 598g of white powder with a yield of 86.8%. 99.8%, mp: 175-176°C (decomposes on melting). Elemental analysis measured value % (theoretical value %): C58.41 (58.44), H 6.65 (6.64), N12.02 (12.03%). 1 H-NMR (600MHz, DMSO-d 6 )δ: 3.41 (6H, s, 3×CH 2 ), 5.17 (2H, s, CH 2 ), 6.39~6.42 (1H, d, -CH=CHCOOH), 6.89 (1H, s, -N=CH-N), 7.18 (1H, s, N-CH=CH-N-CH 2 ), 7.22~7.23 (2H, d, p...

Embodiment 2

[0044] Preparation of ozagrel tromethamine

[0045] Dissolve 145.2 g (1.2 mol) of tromethamine in 570 ml of distilled water, add 228 g (1 mol) of ozagrel under stirring at a temperature of 35° C., complete the addition, and keep the reaction for 2 hours. Cooling and crystallization, suction filtration to obtain the crude product. Add the crude product to 600ml of absolute ethanol, heat to reflux for 3 hours, stir for 6 hours at a temperature of 10°C, filter with suction, wash with a small amount of absolute ethanol, and dry to obtain 305.3g of white powder with a yield of 87.5% and a content of 99.6% .

Embodiment 3

[0047] Preparation of ozagrel tromethamine

[0048] Dissolve 12.7 g (0.105 mol) of tromethamine in 32 ml of distilled water, add 22.8 g (0.1 mol) of ozagrel under stirring at a temperature of 40° C., complete the addition, and keep the reaction for 2 hours. Cooling and crystallization, suction filtration to obtain the crude product. Add the crude product to 80ml of acetone, stir at 50-60°C for 5 hours, cool, continue to crystallize below 10°C, filter with suction, wash the filter cake with a small amount of acetone, and dry to obtain 30.3g of white powder with a yield of 86.9% and a content of 99.7%.

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Abstract

The invention provides an ozagrel salt which is stable, has functions of inhibiting platelet aggregation and removing blood-vessel convulsion, has good water solubility, and is prepared into a compound suitable for clinical application. The new compound is ozagrel tromethamine; and the ozagrel and the tromethamine are prepared by reaction in a solvent. The compound has good water solubility, strong and long-term stability, and the functions of inhibiting platelet aggregation and removing blood-vessel convulsion.

Description

technical field [0001] The invention relates to a medicine with anti-platelet aggregation effect, in particular to an ozagrel salt, more specifically to ozagrel tromethamine and its composition, and a preparation method of the salt. It belongs to the field of medicinal chemistry and pharmaceutical preparation. Background technique [0002] Ozagrel is a thromboxane synthase inhibitor, which can specifically inhibit thromboxane synthase, has anti-platelet aggregation and relieves vasospasm, can inhibit cerebral thrombosis and cerebral vasospasm, and can be used in subarachnoid space Improvement of cerebral ischemic symptoms after hemorrhagic surgery. [0003] Due to the poor water solubility of ozagrel, the injection of ozagrel sodium salt is currently used more clinically, but ozagrel is unstable in aqueous solution and can be isomerized to generate cis-imidazole methyl cinnamon acid, and the long-term placement of the aqueous solution of sodium ozagrel in a glass container...

Claims

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Application Information

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IPC IPC(8): C07D233/56C07C215/10A61K31/4174A61P7/02A61P9/00
Inventor 徐华
Owner 徐华
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