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New crystal forms of benzene sulfonamide thiazole and preparation method thereof

A technology of benzenesulfonamide thiazole and compound is applied in the new crystal form of benzenesulfonamide thiazole compound and the field of preparation thereof, and can solve the problems of inability to maintain crystal form, instability and the like

Inactive Publication Date: 2014-10-22
HANGZHOU PUSHAI PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] During the research process, the present inventors found that the known crystal form 1 has the following defects: anhydrous, the weight change is about 1.9% in the range of 20-80%RH humidity change; Invented hydrates, which cannot maintain the original crystal form
[0010] During the research process, the inventors found that the known crystal form 2 has the following defects: instability, it will transform into other anhydrous crystal forms at room temperature, and it will transform into the hydrate of the present invention in water or other water-containing systems, so as not to maintain its original crystalline form
[0011] During the research, the inventor found that the known crystal form 3 has the following defects: extremely unstable, it will be converted into other anhydrous crystal forms at room temperature, and it will be converted into the hydrate of the present invention in water or other water-containing systems , thus unable to maintain its original crystalline form

Method used

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  • New crystal forms of benzene sulfonamide thiazole and preparation method thereof
  • New crystal forms of benzene sulfonamide thiazole and preparation method thereof
  • New crystal forms of benzene sulfonamide thiazole and preparation method thereof

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Effect test

preparation example Construction

[0181] Preparation of known crystal form 1: preparation by referring to the method described in Example 58a of patent document WO2009 / 137391 or CN200980126781.6. Specifically:

[0182]

[0183] N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl }-2,6-Difluorobenzenesulfonamide (19.6mg, 0.364mmol) and 7M methanol solution of ammonia were added to a 25mL autoclave, heated to 90°C for 24 hours, TLC showed that the reaction of the raw materials was complete, and the above reaction system was cooled After reaching room temperature, the residue was chromatographed after the solvent was concentrated to obtain N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3 -Thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide 94 mg, yield: 47%. 1 H-NMR (400MHz, DMSO-d6) δppm10.83 (s, 1H), 7.93 (d, J=5.2Hz, 1H), 7.55-7.70 (m, 1H), 7.35-7.43 (m, 1H), 7.31 (t, J=6.3Hz, 1H), 7.14-7.27(m, 3H), 6.70(s, 2H), 5.79(d, J=5.13Hz, 1H), 1.35(s, 9H).MS(ES...

Embodiment 1

[0199] Take 7.0 mg of the known crystal form 2 and place it in a 5 mL glass vial, add 0.5 mL of water, obtain a suspension by ultrasonication, stir at room temperature for one week, centrifuge and then vacuum-dry at 40°C for 16 hours to obtain the crystal form VI of the present invention. Yield 6.8 mg; 97% yield.

[0200] X-ray powder diffraction pattern as figure 1 shown.

[0201] PLM map such as figure 2 shown. Appearance: fine crystals.

[0202] DSC spectrum such as image 3 shown. It shows that the crystal form VI has a broad endothermic peak (solvent peak) at 64-128°C, and the melting point of the sample after removing the solvent is 206°C.

[0203] TGA spectrum such as Figure 4 shown. It shows that the weight loss of Form VI is about 3.8% before 112°C, and the decomposition temperature is 271°C.

[0204] The adsorption isotherm is as Figure 5 As shown, the dynamic moisture adsorption diagram is shown in Figure 6 shown. Display: 20%RH~80%RH weight change ...

Embodiment 2

[0207] Take 6.9 mg of known crystal form 2 and place it in a 5 mL glass vial, add 0.5 mL of nitromethane, obtain a suspension by ultrasonication, stir at room temperature for one week, centrifuge, and vacuum-dry at 40°C for 16 hours to obtain the crystal form VI of the present invention. Yield 5.4 mg; 78% yield. X-ray powder diffraction pattern as Figure 7 shown, with figure 1 basically the same.

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Abstract

The invention relates to a new crystal form of dabrafenib and preparation method thereof. With respect to known crystal forms, the new crystal form has the advantage of being more stable at room temperature or in aqueous systems, and has low hygroscopicity, and thus is more suitable for a wet granulation process or being prepared into a suspension. The present invention also relates to a pharmaceutical composition and formulations comprising the new crystal form, and their use in the treatment of Raf family kinase-related diseases.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical crystals. Specifically, it relates to a new crystal form of benzenesulfonamide thiazole compound and a preparation method thereof. Background technique [0002] Polymorphism is a property of some molecules and molecular compositions. The same molecule may form different crystals with different arrangements. The polymorphs have different crystal structures and physical properties, such as solubility, stability, thermal properties, mechanical properties, purification capabilities, X-ray diffraction patterns, infrared absorption patterns, Raman spectra, and solid-state NMR. One or more analytical detection methods can be used to distinguish between different crystalline forms of the same compound. [0003] Discovery of new crystal forms (including anhydrate, hydrate, solvate) of pharmaceutical active ingredients can provide materials with advantageous processing properties, and discovery of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61K31/506A61P35/00
CPCC07B2200/13C07D417/04A61P35/00C30B7/06C30B7/14C30B29/54
Inventor 劳海萍章中华盛晓红盛晓霞
Owner HANGZHOU PUSHAI PHARMA TECH
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