Tizanidine p-toluenesulfonate crystal form A and preparation method and applications thereof

A technology of p-toluenesulfonic acid and tizanidine, which is applied in organic chemical methods, pharmaceutical formulations, medical preparations containing active ingredients, etc., can solve the differences in drug quality and clinical efficacy, and affect the stability and solubility of pharmaceutical preparations Hygroscopicity, bioavailability and other problems, to achieve the effect of short reaction time, good reproducibility and high yield

Active Publication Date: 2019-03-29
SICHUAN CREDIT PHARMA
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Problems solved by technology

And different crystal forms may have different colors, melting points, stability, apparent solubility, dissolution rate, etc. These properties will directly affect the stability, solubility, hygroscopicity, bioavailability, etc. of pharmaceutical preparations, and resulting in differences in drug quality and clinical efficacy

Method used

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  • Tizanidine p-toluenesulfonate crystal form A and preparation method and applications thereof
  • Tizanidine p-toluenesulfonate crystal form A and preparation method and applications thereof
  • Tizanidine p-toluenesulfonate crystal form A and preparation method and applications thereof

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Experimental program
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Embodiment 1

[0035] The preparation of embodiment 1 p-toluenesulfonate tizanidine crystal form A

[0036] Weigh 10g of tizanidine, add 150mL of methanol and 150mL of ethanol, add 8.82g of p-toluenesulfonic acid under stirring, heat up to 45-50°C and stir to react. Set crystallization for 4 hours. Filtration, washing, and vacuum drying at 35° C. yielded 16.02 g of white powdery tizanidine p-toluenesulfonate crystals, with a yield of 95.4% and an HPLC purity of 99.91%. Mass spectrum shows its MS (m / z): 253 (M + ).

[0037]Using DX-2700 X-ray powder diffractometer to analyze the crystal phase of the sample, Cu-Kα radiation, tube voltage 35KV, tube current 30mA, the X-ray powder diffraction pattern of tizanidine p-toluenesulfonate crystal form A was measured See figure 1 , and the diffraction related data are shown in Table 1. Among them, the 2θ measurement error is ±0.2°, and the relative intensity measurement error is ±5%, sometimes even up to ±20%.

[0038] Table 1 X-ray powder diffra...

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Abstract

The invention provides a tizanidine p-toluenesulfonate crystal form A and a preparation method thereof, and applications. The provided tizanidine p-toluenesulfonate crystal form A uses a Cu-K[alpha] radiation source to perform X-ray powder diffraction, and a 2[theta] diffraction angle has characteristic absorption peaks at 6.7 + / - 0.2, 13.5 + / - 0.2, 20.4 + / - 0.2, 21.4 + / - 0.2 and 24.3 + / - 0.2 degrees. The crystal form A has high product chemical purity, stable properties and low hygroscopicity, and effective solutions can be provided for the improvement of the security and validity of drugs; and in addition, the crystal form A is simple in preparation technology, short in reaction time, high in yield, good in reproducibility and suitable for industrial production.

Description

technical field [0001] The invention relates to a crystal form A of tizanidine p-toluenesulfonate and a preparation method and application of the crystal form, belonging to the technical field of medicinal chemistry. Background technique [0002] Tizanidine is a central skeletal muscle relaxant with an imidazoline structure, and its chemical name is 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2, 1,3-Benzothidiazol-4-amine, molecular formula: C 9 h 8 ClN 5 S, molecular weight: 253.71, its chemical structure is as follows: [0003] [0004] Tizanidine is the only new type of central skeletal muscle relaxant and central α2 adrenergic receptor agonist with gastrointestinal protective effect on the market. It was first developed by Swiss Novartis and first launched in Denmark in 1988. and Switzerland, and then successively obtained sales licenses in more than 20 countries including Europe, the United States, and Japan. It is clinically used to treat diseases such as increas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A61K31/433A61P21/00
CPCC07D417/12C07B2200/13
Inventor 刘强维李晓莉傅霖陈刚
Owner SICHUAN CREDIT PHARMA
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