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Oxdiazole compound solvate and preparation method thereof

A solvate and oxadiazole technology, applied in the field of drug crystals, can solve the problems of unfavorable crystal form stability, storage stability of preparations, affecting the operability of preparations, difficulty in filtration and drying, etc., to reduce the risk of curative effect decline and safety risks , Improve bioavailability, fast dissolution effect

Active Publication Date: 2016-04-06
SOLIPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Needle crystals generally have poor fluidity, low bulk density, and are difficult to filter and dry, which affects the operability of preparation processing; in addition, needle crystals need to be pulverized before they can be used in solid dosage forms of pharmaceutical preparations, and pulverization will affect the crystal form. Destruction, which is not conducive to the stability of the crystal form and the storage stability of the preparation

Method used

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  • Oxdiazole compound solvate and preparation method thereof
  • Oxdiazole compound solvate and preparation method thereof
  • Oxdiazole compound solvate and preparation method thereof

Examples

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preparation example 1

[0075] Preparation Example 1 (preparation of known ataluren)

[0076] Ataluren can be prepared according to the method described in Example 2 of patent document WO2004091502A2.

[0077] The specific preparation method is:

[0078] Add 62.19 g of potassium carbonate to 44.14 g of 3-cyanobenzoic acid dissolved in 0.6 liter of DMF, and stir at room temperature for 30 minutes. To the suspension was added 28 ml (450 mmol) of iodomethane over 20 minutes, and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into 1.2 liters of ice water, stirred for 30 minutes, and the precipitate was filtered off. The white filter cake was dissolved in 70 mL of methanol and reprecipitated in cold water. Methyl 3-cyanobenzoate was obtained in a yield of 79%.

[0079] 50 g of methyl 3-cyanobenzoate was dissolved in 500 ml of ethanol, and 41 ml of 50% aqueous hydroxylamine (620 mmol) was added thereto. The reaction mixture was stirred at 100°C for ...

preparation example 2

[0083] Preparation example 2 (preparation of known A crystal form)

[0084] The known crystal form A can be prepared according to the method described in Example 5.1.1.1 of patent document WO2008039431A2. Specifically: add 100 mg of ataluren prepared in Preparation Example 1, add 16.2 ml of isopropanol to sonicate at 60 ° C, filter the solution through a 0.2 micron filter, place the filtrate in a vial covered with aluminum foil with small holes, and 60 °C evaporated. The solid formed was isolated to give crystalline form A of ataluren.

[0085] It is acicular crystals.

[0086] Its XRPD pattern is shown in figure 1 , showing that it is consistent with the A crystal form of ataluren disclosed in the patent document WO2008039431A2.

preparation example 3

[0087] Preparation example 3 (preparation of known crystal form B)

[0088] The known crystal form B can be prepared according to the method described in Example 5.1.2.1 of patent document WO2008039431A2. Specifically: add 50 mg of ataluren prepared in Preparation Example 1, add 20 ml of acetone at 25 ° C to dissolve it ultrasonically, filter the solution through a 0.2 micron filter, place the filtrate in a vial covered with aluminum foil with small holes, and evaporate at 50 ° C . The solid formed was isolated to give crystalline form B of ataluren.

[0089] It is acicular crystals.

[0090] Its XRPD pattern is shown in figure 2 , showing that it is consistent with the B crystal form of ataluren disclosed in the patent document WO2008039431A2.

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Abstract

The present invention relates to the dimethyl sulfoxide solvate of 3-[5-(2-fluorophenyl)-[1,2,4]oxdiazole-3-yl]benzoic acid, wherein the dimethyl sulfoxide solvate has characteristics of good stability, high purity, excellent particle and excellent shape, and is suitable for pharmaceutical preparation applications. The present invention further relates to a preparation method of the dimethyl sulfoxide solvate, a pharmaceutical composition of the dimethyl sulfoxide solvate, and uses of the dimethyl sulfoxide solvate in preparation of drugs for treatment of genetic diseases.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical crystals. In particular, it relates to a [1,2,4]oxadiazole compound, especially 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzene The dimethyl sulfoxide solvate of formic acid, the present invention also relates to the preparation method of the dimethyl sulfoxide solvate, its pharmaceutical composition and application. Background technique [0002] 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid (English name ataluren, also known as PCT124) is an oral Experimental drug, aimed at correcting rare diseases caused by nonsense mutations by creating functional proteins, for the treatment of Duchenne / Becker muscular dystrophy (DMD / BMD) and cystic fibrosis caused by nonsense mutations ( Cysticfibrosis, CF) and other genetic diseases are currently in clinical phase III. Nonsense mutations (nonsense mutations) are also called premature stop code mutations (premature stop codon mutations...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/06A61K31/4245A61P19/02A61P37/06A61P29/00A61P25/00A61P25/28A61P25/16A61P1/16A61P37/02A61P13/12A61P27/02A61P9/10A61P5/16A61P3/04
Inventor 宋小叶盛晓红盛晓霞
Owner SOLIPHARMA
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