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Sodium phenylaminopropionate derivative and preparation method and applications thereof

A technology of derivatives and reactions, applied in the field of sodium phenylalanine propionate derivatives, can solve problems such as unknown pharmacological and toxicological properties, unknown structure, safety drug risks, etc., and achieve accurate and reliable measurement results, good separation, and strong practicability Effect

Pending Publication Date: 2019-11-19
SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the existence and structure of this impurity have not been disclosed and reported in the prior art, its pharmacological and toxicological properties are also unknown, thus bringing risks to safe drug use
At the same time, since the structure of the impurity is unknown, and the prior art has not publicly reported any impurity information and separation methods of siglitastat sodium, this brings great difficulties to the separation and identification of the impurity

Method used

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  • Sodium phenylaminopropionate derivative and preparation method and applications thereof
  • Sodium phenylaminopropionate derivative and preparation method and applications thereof
  • Sodium phenylaminopropionate derivative and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: Isolation, preparation and identification of formula (I) compound

[0053]

[0054] 1. Separation

[0055] 0.5g siglitastat sodium (prepared according to the method of Chinese patent application 201410856282.5 and 201610855107.3) was separated by semi-preparative liquid chromatography column (chromatographic column: YMC-Pack ODS-AQ 5μm 250L×20; mobile phase: methanol-water- Tetrahydrofuran-glacial acetic acid 48:22:30:0.5; detection wavelength: 236nm; flow rate: 8ml / min), collect the effluent for 30-42min, and neutralize it to pH 7 with 1mol / L sodium bicarbonate aqueous solution. Repeat the above separation operation 40 times, combine the neutralized liquid each time, concentrate in vacuo to remove the organic solvent, neutralize with 1 mol / L dilute hydrochloric acid to pH 5-6, filter, wash with water, collect the solid, and dry it in vacuum at room temperature for 24 hours to obtain 5 mg of the compound (f), purity (HPLC) 97.8%, LC-MS (m / z) 933 (M+1)....

Embodiment 2

[0067] Embodiment 2: the compound of formula (I) is used as the reference substance of impurity content determination in siglitastat sodium medicine

[0068] 1. Test conditions

[0069] Instrument: UltiMate3000; Column: C 18 Column, Shim-pack VP-ODS 5μm 250L×4.6; detector: VWD-3100, mobile phase: methanol-water-tetrahydrofuran-acetic acid 40:30:30:0.5; detection wavelength: 236nm; flow rate: 1.5mL / min.

[0070] 2. Test method

[0071] (1) Take about 10 mg of siglitastat sodium sample, weigh it accurately, place it in a 100ml volumetric flask, dissolve it with the solvent methanol-water-tetrahydrofuran (40:30:30) and dilute to the mark, shake it well, and use it as the test sample Product solution A, accurately draw 20 μl, inject liquid chromatograph, record the chromatogram.

[0072](2) Take about 10mg of the compound of formula (I), weigh it accurately, place it in a 100ml volumetric flask, dissolve it with the solvent methanol-water-tetrahydrofuran (40:30:30) and dilute t...

Embodiment 3

[0079] Embodiment 3: Formula (I) compound is used as the standard substance of impurity content determination in siglitastat sodium medicine

[0080] 1. Test conditions

[0081] Instrument: UltiMate3000; Column: C 18 Column, Shim-pack VP-ODS 5μm 250L×4.6; detector: VWD-3100, mobile phase: methanol-water-tetrahydrofuran-acetic acid 40:30:30:0.5; detection wavelength: 236nm; flow rate: 1.5mL / min.

[0082] 2. Test method

[0083] Take about 10 mg of siglitastat sodium sample, accurately weigh it, place it in a 100ml volumetric flask, dissolve it with the solvent methanol-water-tetrahydrofuran (40:30:30) and dilute to the mark, shake well, and use it as the test solution. Take about 10mg of the standard compound of formula (I), accurately weigh it, put it in a 100ml volumetric flask, dissolve it with the solvent methanol-water-tetrahydrofuran (40:30:30) and dilute to the scale, shake well, and pipette 1mL precisely Place in a 1000ml volumetric flask, dissolve and dilute to the ...

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Abstract

The invention discloses a sodium phenylaminopropionate derivative and a preparation method and applications thereof. Concretely, the invention discloses a 3-(4-(2-(9H-carbazole-9-yl)ethoxy)phenyl)-2-((2-(4-(4-(2-sodium formate-2-((2-(4-fluorobenzoyl)penyl)amino)ethyl)phenoxyl)benzoyl)phenyl)amino)sodium propionate represented by a formula (I) shown in the description, a preparation method thereofand applications in quality control of bulk drug or preparations of chiglitazar or derivatives of the same. In particular, the compound of the formula (I) can be used as a reference or a standard forthe examination of impurities / related substances in the chiglitazar or sodium salt medicine of the chiglitazar.

Description

technical field [0001] The present invention belongs to the field of chemical pharmacy, and in particular relates to a sodium phenylalanine derivative, and the present invention also relates to a preparation method of the sodium phenylalanine derivative and its use as siglitastat or its derivative drug The purpose of the quality control of the raw material drug or preparation in; In particular, the phenylalanine sodium derivative can be used as impurity or related substance in the raw material drug or preparation of siglitastat or its salt (such as sodium salt) Checked reference or standard. Background technique [0002] 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propanoic acid, common name Glitastat is a phenylalanine compound with therapeutic and preventive activities for metabolic diseases, and its chemical structure is as follows: [0003] [0004] The pharmacological activity of this compound is described in Chinese patent applicatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86G01N1/28G01N30/02G01N30/06
CPCC07D209/86G01N1/28G01N30/02G01N30/06G01N2001/2893G01N2030/027G01N2030/062G01N30/34G01N2030/047G01N2030/884
Inventor 鲁先平李志斌王祥辉高伟君邓兴玉
Owner SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD