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Novel porphin diether salt compound as well as preparation method and application thereof

A technology of salt compounds and porphine bisethers, applied in the application of photodynamic therapy drugs, new porphine bisether salt compounds and the field of preparation thereof, can solve the problem that porphine bisether derivatives cannot be directly dissolved in water and the like , to achieve the effect of maintaining photodynamic activity, a single component, and eliminating potential adverse effects

Inactive Publication Date: 2018-12-21
陈志龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the shortcoming that the porphine diether derivatives with high photodynamic activity could not be directly dissolved in water, the present invention designed and prepared porphine diether disodium salt and dipotassium salt with good water solubility after paying a lot of creative work. , dilithium salt and diammonium salt class new compound, completed the present invention

Method used

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  • Novel porphin diether salt compound as well as preparation method and application thereof
  • Novel porphin diether salt compound as well as preparation method and application thereof
  • Novel porphin diether salt compound as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0042] 3, the preparation of 8-bis (1-methoxyethyl) hypoporphyrin IX disodium salt (abbreviated as porphine dimethyl ether disodium salt):

[0043] Add 10 g (16.0 mmol) of 3,8-bis(1-methoxyethyl) hypoporphyrin IX (porphine dimethyl ether for short) into a 100 mL flask, add 60 mL of ethanol, and stir to dissolve the solid. 16.0 mL (32.0 mmol) of 2 mol / L aqueous sodium hydroxide solution was slowly added, and stirring was continued for 30 minutes. The solvent was removed under reduced pressure and dried in vacuo to obtain 10.7 g of 3,8-bis(1-methoxyethyl) hypoporphyrin IX disodium salt with a yield of about 100%. MS (ESI) m / z: 627.2 [M-2Na+1] + , 648.2 [M-Na] + , 670.3[M] + . Elemental analysis: C, 64.47; H, 5.97; N, 8.35; O, 14.31; Na, 6.86. Flame reaction is yellow.

[0044]

Embodiment 2

[0046] 3, the preparation of 8-bis (1-n-propoxyethyl) hypoporphyrin IX disodium salt (abbreviated as porphine dipropyl ether disodium salt)

[0047] Add 10.9 g (16.0 mmol) of 3,8-bis(1-n-propoxyethyl) hypoporphyrin IX (abbreviated as porphin dipropyl ether) into a 100 mL flask, add 60 mL of ethanol, and stir to dissolve the solid. 16.0 mL (32.0 mmol) of 2 mol / L aqueous sodium hydroxide solution was slowly added, and stirring was continued for 30 minutes. The solvent was removed under reduced pressure and dried in vacuo to obtain 11.6 g of 3,8-bis(1-n-propoxyethyl) hypoporphyrin IX disodium salt with a yield of about 100%. MS (ESI) m / z: 682.2 [M-2Na+1] + , 704.2 [M-Na] + , 726.3[M] + . Elemental analysis: C, 66.10; H, 6.66; N, 7.71; O, 13.21; Na, 6.33. Flame reaction is yellow.

[0048]

Embodiment 3

[0050] Preparation of 3,8-two (1-n-butoxyethyl) hypoporphyrin IX disodium salt (abbreviated as porphine dibutyl ether disodium salt)

[0051] Add 11.4 g (16.0 mmol) of 3,8-bis(1-n-butoxyethyl) hypoporphyrin IX (abbreviated as porphine bis-butyl ether) into a 100 mL flask, add 60 mL of ethanol, and stir to dissolve the solid. 16.0 mL (32.0 mmol) of 2 mol / L aqueous sodium hydroxide solution was slowly added, and stirring was continued for 30 minutes. The solvent was removed under reduced pressure and dried in vacuo to obtain 12.1 g of 3,8-bis(1-n-butoxyethyl) hypoporphyrin IX disodium salt with a yield of about 100%. MS (ESI) m / z: 710.4 [M-2Na + +1] + , 732.3[M-Na] + , 754.4[M] + . Elemental analysis: C, 66.83; H, 6.94; N, 7.42; O, 12.72; Na, 6.09. Flame reaction is yellow.

[0052]

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Abstract

The invention relates to a novel porphin diether salt compound (I) as well as a preparation method and application thereof. The compound (namely, porphin diether disodium salt, porphin diether dimethyl salt, porphin diether dilithio salt and porphin diether diammonium salt compound) has a structure shown in the description. The compound provided by the invention has the advantages of single component, stable property, controllable quality, simple and convenient preparation method and high water solubility, and can be easily prepared into an injection or a freeze-drying preparation. The compound has remarkable photodynamic activity, and can be applied to photodynamic therapy of tumors, retina macular degeneration, actinic keratosis, nevus flammeus, verruca acuminate and the like.

Description

technical field [0001] The present invention relates to the fields of photosensitive drugs and photodynamic therapy, in particular to a class of novel porphine diether salt compounds (i.e. porphine diether disodium salt, porphine diether dipotassium salt, porphine diether dilithium salt) and porphine diether diammonium salt compound) and its preparation method and its application as a photodynamic therapy drug. Background technique [0002] Photodynamic therapy (PDT) is a new method for the treatment of tumors, macular degeneration, actinic keratosis, port wine stains, genital warts and other diseases. Since entering clinical research in the 1970s, PDT has made remarkable achievements in clinical treatment because of its good selectivity, low toxicity, good reproducibility, safety, minimal invasiveness, synergy and Advantages such as relatively low cost stand out, showing huge potential and strong vitality. [0003] Photosensitizers have always been the focus of photodynam...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61K31/409A61P35/00A61P27/02A61P17/00
CPCA61K41/0071C07D487/22
Inventor 陈聃烨陈志龙严懿嘉朱维高迎华
Owner 陈志龙
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