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Chlorin compound, its preparation method, pharmaceutical composition and application
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A chlorin and compound technology, applied in the field of chlorin compounds, can solve the problems of insufficient stability, high phototoxicity or dark toxicity, limited development and the like
Active Publication Date: 2016-08-24
海宁市绿升医药科技有限公司
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Temporfin has high phototoxicity or dark toxicity to normal tissues, and due to the presence of phenolic hydroxyl groups in the molecular structure, it is easily oxidized and not stable enough
The above-mentioned shortcomings limit their development as new drugs from three aspects of safety, effectiveness and quality control
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Embodiment 1
[0089] Example 1: 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-acetoxyethyl-17-propionic acid-17,18-chlorin :
[0090] .
[0091] Step 1 Preparation of 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-acetoxyethyl-17-acetoxypropyl-17,18-chlorine Phenomenal:
[0092] Chlorin e 6 (6g, 10mmol) was added to ethanol (120ml), stirred at room temperature and added dropwise with 98% concentrated sulfuric acid (3.6ml), and reacted overnight at 60°C under nitrogen protection. The reaction solution was cooled, most of the solvent was distilled off, and the residue was poured into ice water (600ml). Dichloromethane (300ml) was extracted, and the organic phases were combined and washed successively with saturated brine (200ml) and water (100ml). After drying, silica gelcolumn chromatography gave 3.6 g of brown product, yield: 60%. LC-MS (ESI): [M+H] + = 653.
[0093] Step 2 Preparation of 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-acetoxyethyl-17-propionic aci...
Embodiment 2
[0095] Example 2: 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-propionyloxyethyl-17-propionic acid-17,18-chlorine Phenomenal:
[0096] Prepared according to the same method as in Example 1, substituting propanol for ethanol. LC-MS (ESI): [M+H] + =639; 1 H-NMR (δ ppm, DMSO-d 6 , 500 MHz): 14.01(brs, 1H), 12.27(brs, 1H), 9.80(s, 1H), 9.67(s, 1H), 9.10(s, 1H), 8.25(dd, 1H), 6.38(d , 1H), 6.20(d, 1H), 5.42(s, 2H), 4.58~4.65(m, 1H), 4.40(t, 1H), 4.10~4.18(m, 2H), 3.75(q, 2H), 3.57(s, 3H), 3.50(s, 3H), 3.25(s, 3H), 2.60-2.70 and 2.10-2.20(2m, 2H), 1.40-1.50 and 2.00-2.10(2m, 4H), 1.65(d ,3H), 1.60(t, 3H), 0.9~0.7(m, 3H), -1.63(s, 1H), -1.88(s, 1H).
Embodiment 3
[0097] Example 3: 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-butyryloxyethyl-17-propionic acid-17,18-chlorine Phenomenal:
[0098] It is prepared according to the same method as in Example 1, butanol is used instead of ethanol. LC-MS (ESI): [M+H] + =653; 1 H-NMR (δ ppm, DMSO-d 6 , 500MHz): 14.03(brs, 1H), 12.28(brs, 1H), 9.80(s, 1H), 9.65(s,1H), 9.10(s, 1H), 8.25(dd, 1H), 6.41(d, 1H), 6.14(d, 1H), 5.42(s, 2H), 4.56~4.66(m,1H), 4.40(t, 1H), 4.11~4.19(m, 2H), 3.75(q, 2H), 3.57 (s, 3H), 3.49(s, 3H), 3.25(s, 3H), 2.27~2.70(m, 2H), 1.6~2.10(m, 9H), 1.60(d, 3H), 0.9~0.7(m , 3H), -1.63(s, 1H), -1.88(s, 1H).
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Abstract
The invention provides a compound shown in a formula (I), of which the chemical name is 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxyl-15-acetoxyl-17-propionyloxy-17,18-dihydroporphin (a popular name is dihydroporphin e6-15-ethyl ester or dihydroporphin e6-15-acetoxyl, and the international general new drugdeclaration name is Hanbenbofen). The invention also provides a preparation method and a purification method of the compound and a tumour photodynamic therapy agent containing the compound. The compound is a monomer with a clear chemical structure and high purity (more than or equal to 98%), a photodynamic sensitizationaction spectrum is located in the best band of red light (660nm), absorption coefficient is about one order of magnitude higher than those of the existing clinical photodynamic therapymedicinesodium profimer (produced in Canada) and HiPorfin (produced in China), epsilon is more than or equal to 10<4>M<-1>cm<-1>, and killing effect on tumour tissues is strong (an animal transplantation tumour can be healed at one time in dosage of iv1mg.kg<-1> and light dosage of 90J.cm<2>).
Description
technical field [0001] The invention belongs to the field of chlorin compounds, in particular to a class of chlorin e 6 Compounds, their preparation methods, pharmaceutical compositions and applications. Background technique [0002] Photodynamic therapy (PDT) is a very promising new technology developed in the past 20 years. Since entering clinical research in the 1970s, breakthroughs have been made in the treatment of tumors. At present, photodynamic therapy is not only limited to the treatment of malignant tumors, but also shows good prospects in the treatment of many other diseases, such as Verteporfin (Verteporfin), which is applied to photodynamic therapy secondary to age-related macular degeneration. Compared with traditional tumor therapy, its outstanding advantages are: (1) selectively damage tumor tissue without endangering the normal tissue of the body; (2) have a certain degree of synergy with chemotherapy and radiotherapy; The extent or depth of invasion help...
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