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Cyclo-trans-4-l-hydroxyprolyl-l-serine-o-amino acid ester and its salts

A technology of hydroxyprolyl and amino acid esters, applied in the field of medicine

Active Publication Date: 2021-02-23
スゾウユタイファーマシューティカルテクノロジーカンパニーリミテッド +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there is no relevant report of preparing ring-trans-4-L-hydroxyprolyl-L-serine into a prodrug

Method used

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  • Cyclo-trans-4-l-hydroxyprolyl-l-serine-o-amino acid ester and its salts
  • Cyclo-trans-4-l-hydroxyprolyl-l-serine-o-amino acid ester and its salts
  • Cyclo-trans-4-l-hydroxyprolyl-l-serine-o-amino acid ester and its salts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Step 1: Dissolve compound I, compound II, and sodium carbonate in dichloromethane, fill with nitrogen, react at room temperature for 2 hours, and spin evaporate to obtain compound III.

[0053] Step 2: Dissolve compound III in tetrahydrofuran solution containing diethylamine, react at room temperature for 2 h, evaporate the solvent under reduced pressure, dilute the residue with dichloromethane, wash with 5% phosphoric acid aqueous solution, aqueous solution, and saturated saline successively, and extract Filter, and the filtrate was mixed with silica gel, subjected to silica gel column chromatography, dichloromethane and methanol (100:1-1:100) gradient elution, the column chromatography was collected and concentrated to obtain compound IV.

[0054] The third step: compound IV, compound V, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 1-hydroxybenzotriazole (HOBT) were dissolved in In dichloromethane, fill with nitrogen, react at room temperature fo...

Embodiment 2

[0059] Step 1: Dissolve compound I, compound II, and sodium carbonate in dichloromethane, fill with nitrogen, react at room temperature for 2 hours, and spin evaporate to obtain compound III.

[0060] Step 2: Dissolve compound III in tetrahydrofuran solution containing diethylamine, react at room temperature for 2 hours, evaporate the solvent under reduced pressure, dilute the residue with dichloromethane, wash with 5% phosphoric acid aqueous solution, aqueous solution, and saturated saline successively, and extract Filter, and the filtrate was mixed with silica gel, subjected to silica gel column chromatography, dichloromethane and methanol (100:1-1:100) gradient elution, the column chromatography was collected and concentrated to obtain compound IV.

[0061] The third step: compound IV, compound V, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 1-hydroxybenzotriazole (HOBT) were dissolved in Dichloromethane was reacted at room temperature for 2 h, and the...

Embodiment 3

[0066] Step 1: Dissolve compound I, compound II, and sodium carbonate in dichloromethane, fill with nitrogen, react at room temperature for 2 hours, and spin evaporate to obtain compound III.

[0067] Step 2: Dissolve compound III in tetrahydrofuran solution containing diethylamine, react at room temperature for 2 hours, evaporate the solvent under reduced pressure, dilute the residue with dichloromethane, wash with 5% phosphoric acid aqueous solution, aqueous solution, and saturated saline successively, and extract Filter, and the filtrate was mixed with silica gel, subjected to silica gel column chromatography, dichloromethane and methanol (100:1-1:100) gradient elution, the column chromatography was collected and concentrated to obtain compound IV.

[0068] The third step: compound IV, compound V, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 1-hydroxybenzotriazole (HOBT) were dissolved in In dichloromethane, fill with nitrogen, react at room temperatur...

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Abstract

The invention belongs to the technical field of medicine, and relates to cyclo-trans-4-L-hydroxyprolyl-L-serine-O-amino acid ester, pharmaceutically acceptable salts thereof and a preparation method thereof. The cyclo-trans-4-L-hydroxyprolyl-L-serine-O-amino acid ester prodrug of the present invention and its pharmaceutically acceptable salt have the structure shown in formula (I) or (II), where R 1 and R 2 is an amino acid residue. The compound can significantly improve the permeability of cyclo-trans-4-L-hydroxyprolyl-L-serine small intestinal membrane, and improve the bioavailability of the drug.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to cyclo-trans-4-L-hydroxyprolyl-L-serine-O-amino acid ester, its pharmaceutically acceptable salts and its preparation method. Background technique [0002] Cyclo-trans-4-L-hydroxyprolyl-L-serine has hepatoprotective effect on concanavalin A (Con A)-induced autoimmune liver injury, and its mechanism of action is as follows: [0003] 1. Enhance liver tissue free radical scavenging ability, inhibit liver cell lipid peroxidation damage; [0004] 2. Weaken the cytotoxic effect caused by the overexpression of NO; [0005] 3. Reduce the accumulation of inflammatory cells in areas of inflammation and tissue damage; [0006] 4. Inhibit the release of inflammatory cytokines; [0007] 5. Inhibit the apoptosis of liver cells. [0008] Due to the large polarity of the cyclo-trans-4-L-hydroxyprolyl-L-serine molecule and the poor permeability of the small intestine membrane, resulting in low ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61P1/16
CPCA61P1/16C07B2200/07C07D487/04
Inventor 何仲贵姜琪坤张天虹孙进王永军
Owner スゾウユタイファーマシューティカルテクノロジーカンパニーリミテッド
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