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Method for separating hemporfin isomer and separated isomer

A technology of isomer and volume ratio, applied in the field of photosensitizers for photodynamic therapy, can solve problems such as single molecular structure

Active Publication Date: 2008-02-20
上海复旦张江生物医药股份有限公司 +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 isolated drug with a single molecular structure and more stable properties.

Method used

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  • Method for separating hemporfin isomer and separated isomer
  • Method for separating hemporfin isomer and separated isomer
  • Method for separating hemporfin isomer and separated isomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Embodiment 1: the preparation of hemporfin

[0076] 1.3 (8)-(1-methoxyethyl)-8(3)-(1-hydroxyethyl) hypoporphyrin IX crude product preparation

[0077] In a 50L acid-resistant glass-lined reaction pot, add 30L of methanol / water mixture with a volume ratio of 3:1, slowly drop it in from a liquid dropper under stirring, and prepare 3 according to the method described in Example 1 of the Chinese patent 01105208.2 specification , 8-bis-(1-bromoethyl)-hypoporphyrin IX hydrobromide glacial acetic acid saturated solution 10L, control the rate of addition to keep the temperature of the reaction mixture at 10-20°C. After the dropwise addition, the reaction solution continued to stir for 2h and left for 4h. Then add 10N NaOH aqueous solution dropwise under stirring until the reaction liquid is strongly alkaline (pH13 or so), let stand for more than 10h, add acetic acid to neutralize to pH4~5, add 5 times the volume of water to dilute, stand overnight, the precipitate will natural...

Embodiment 2

[0079] Example 2: HPLC Separation of Hemporfin Positional Isomers

[0080] Instrument: Agilent 1100 high performance liquid chromatography; DAD detector, detection wavelength: 395nm

[0081] Mobile phase: methanol-1.5M acetic acid-ammonium acetate buffer (pH4.76) (65:35V / V)

[0082] Column: MOS-Hypersil (C 8 ), 10×250mm

[0083] Flow rate: 2mL / min

[0084] Column pressure: 125 Bar

[0085] Take 100 mg of the hemporfin sample prepared in Example 1 above, dissolve it in HPLC mobile phase, prepare a sample solution with a concentration of 5 mg / mL, and filter it before injection. 400 microliters of the above-mentioned solutions were injected each time. After the injection, Fraction A was collected respectively according to the HPLC chromatogram (see Figure 1), the retention time was 11.94 minutes and the retention time of Fraction B was 14.35 minutes. Accumulated 40 times, a total of 136ml of fraction A and 133ml of fraction B were collected. Pour the collected solution into...

Embodiment 3

[0089] Example 3: Preparative Separation of Hemporfin Positional Isomers

[0090] The separation system adopts Flash150M with built-in prepacked C8 chromatographic column (150mm ID×30cm), produced by Biotage Company (USA), the silica gel particle size is 35-70 μm, and the pore size is 60A.

[0091] Sample preparation: get 3 (or 8)-(1-methoxyethyl)-8 (or 3)-(1-hydroxyethyl) hypoporphyrin IX pure product (content>95%) prepared in Example 1 30 g was dissolved in tetrahydrofuran and filtered, and 100 g of C8 reversed-phase silica gel was added, concentrated under reduced pressure, evaporated to dryness, and added to the loading column SIM for sample loading.

[0092] Sample loading and collection: Use methanol-1.5M acetic acid-ammonium acetate buffer (pH4.76) (65:35V / V) as the mobile phase, pass the above sample through the loading column SIM, and bring it into the chromatographic column for separation , the flow rate is controlled at 200ml / min, the detector wavelength is 395nm, ...

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Abstract

The invention pertains to photodynamic treatment field, in particular to photosencitizer of photodynamic treatment. The invention provides a reversed-phase purification method for separating a 3 (or 8)-(1-methoxyethyl)-8 (or 3)-(1-ethoxyl) deuteroporphyrin IX positional isomer. The method can be used for preparing an 8-(1- methoxyethyl)-3-(1-ethoxyl) deuteroporphyrin IX or 3-(1-methoxyethyl)-8-(1-ethoxyl) deuteroporphyrin IX single isomer. The two isomers, through an animal experiment, are proved to be applicable to blocking new-born veins effectively as the photosencitizer. The single isomer of the invention can be used for preparing medicine with single molecule structure and steadier properties.

Description

technical field [0001] The present invention relates to the field of photodynamic therapy, and more specifically, the present invention relates to a photosensitizer for photodynamic therapy. Background technique [0002] Photodynamic therapy (PDT) is to administer photoactive compounds to the patient. The photosensitizer is enriched in the neovascularization site, and then irradiated with low-intensity laser light to excite the photosensitizer to cause a photochemical reaction, and to generate free radicals at the site where the photochemical reaction occurs, which can kill wounds. The tissue cells at this site produce therapeutic effects mainly through direct cytotoxicity and sealing of blood vessels at the lesion site. [0003] Photosensitizers used in photodynamic therapy include hematoporphyrin derivatives (HPD), benzoporphyrin derivatives (BPD), chlorin e6 monoaspartic acid amide (Npe6), aluminum sulfonate phthalocyanine (CASPc ), intermediary tetrakis (m-hydroxyphenyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K31/409A61P1/16A61P35/00
Inventor 陈文辉陶纪宁李军
Owner 上海复旦张江生物医药股份有限公司
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