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New-crystal-form pteroic acid and preparation method thereof

A crystal form, pteroic acid technology, applied in the field of new pteroic acid crystal form and its preparation, can solve the problems of long purification steps, high energy consumption of concentrated water, low solubility of pteroic acid, etc., achieves less environmental pollution, improved solubility, good reproducibility

Active Publication Date: 2019-05-10
苏州华健瑞达医药技术有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of the preparation method of pteroic acid described in the above patent is that the solubility of the obtained pteroic acid is small, and the use of chromatographic purification is limited to laboratory preparation, and application to industrial production will lead to high production costs
The above-mentioned patent describes the purification method of pteroic acid to obtain pteroic acid with low solubility, and the purification steps are long, and the concentrated water consumes a lot of energy

Method used

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  • New-crystal-form pteroic acid and preparation method thereof
  • New-crystal-form pteroic acid and preparation method thereof
  • New-crystal-form pteroic acid and preparation method thereof

Examples

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preparation example Construction

[0049] On the other hand, the embodiment of the present invention discloses a method for preparing the above-mentioned new crystal form of pteroic acid. The preparation method uses a cheap and easy-to-obtain solvent to dissolve pteroic acid, and then passes carbon dioxide into the reaction until the new crystal form of pteroic acid is precipitated. ; Concretely include the following steps:

[0050]

[0051] S1. Dissolving the chemical compound of formula I in an alkaline solution; in the embodiment of the present invention, it is preferably a solution of sodium hydroxide, and the alkali can also be selected from at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate kind;

[0052] S2. Introduce carbon dioxide gas into the alkaline solution of formula I, and filter to obtain a new crystal form of pteroic acid.

[0053] Further, the solvent in the alkaline solution is a mixed solvent of water and ethanol; it can also be selected from...

specific example 1

[0057] In a 500ml three-neck flask, under nitrogen protection, add 20.0g (HPLC purity: 65%) pteroic acid crude product and 200mL sodium hydroxide aqueous solution (1N / L), stir to dissolve, and add 1g of activated carbon for decolorization, filter the mixed solution to remove the activated carbon filter residue Afterwards, an orange-red clear liquid was obtained;

[0058] Carbon dioxide gas was slowly introduced into the obtained orange-red clear liquid, and light yellow solids were precipitated successively; the precipitated light yellow solids were filtered and washed, and the obtained filter cake was vacuum-dried at 60°C to obtain 10.5 g of light yellow new Crystal pteroic acid solid, with a purity of 97%, a yield of 80.7%, and a water content of 12.1%.

[0059] Detected by X-RPD, such as figure 1 As shown, the 2θ angle (degrees) is obtained, and the specific peak list is shown in image 3 Peak tables, apparently, are distinctly different as in figure 2 The X-RPD pattern...

specific example 2

[0062] In a 250ml single-mouth bottle, add 5g of anhydrous pteroic acid, the solubility of anhydrous pteroic acid in DMSO is 0.2mg / mL, 200mL of sodium hydroxide aqueous solution (0.5N / L), stir and dissolve to obtain an orange-red clear liquid; Introduce carbon dioxide gas, and a light yellow solid precipitates out; stop feeding carbon dioxide until no solid precipitates out; filter, select vacuum filtration as the filtering method, and vacuum-dry the filter cake on the filter paper at 60°C to obtain 4.1 g of a light yellow solid. Yield 82%; Figure 5 It is the DSC-TGA curve of the new crystal form of pteroic acid involved in Example 1 of the present invention, the water content is 11.6%; the DMSO solubility of the new crystal form of pteroic acid obtained in the example of the present invention is 2.4 mg / mL.

[0063] In the embodiments of the present invention, the reagents used in the present invention can be purchased from the market or can be prepared by the methods describ...

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Abstract

The invention discloses a new-crystal-form pteroic acid. The powder X-ray diffraction pattern of the new-crystal-form pteroic acid has diffraction peaks at one or more of the positions with the Braggangles 2theta of 4.02, 8.10, 14.90, 15.16, 20.11 and 23.11 respectively. The invention further discloses a preparation method of the new-crystal-form pteroic acid. The preparation method of the new-crystal-form pteroic acid comprises dissolving pteroic acid with raw materials low in price and easy to obtain and then performing precipitation with carbon dioxide to obtain the new-crystal-form pteroic acid. The preparation method of the new-crystal-form pteroic acid is mild in reaction conditions, simple in equipment and low in environmental pollution; the prepared new-crystal-form pteroic acid can achieve significantly-increased solubility in organic solvent and accordingly facilitate subsequent application.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a new crystal form of pteroic acid and a preparation method thereof. Background technique [0002] The chemical name of pteroic acid is 4-(((2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl)amino)benzoic acid, which is used for the preparation of folate derivatives A conventional material that can be combined with drugs for use as therapeutic conjugates, including vitamin receptor-based targeting conjugates. Vitamin-drug conjugates can be targeted, for example, to cancer cells that uniquely express, overexpress, or preferentially express vitamin receptors. Pteroic acid with high quality and high solubility is an important guarantee for the preparation of this new drug. [0003] The structure of pteroic acid is the following formula I: [0004] [0005] Pteroic acid can be prepared by various conventional methods including synthesis, microbial degradation of folic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D475/04
Inventor 许磊沈赛龙肖鹏
Owner 苏州华健瑞达医药技术有限公司
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