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Ospemifene polymorphic substance

A polymorph, crystal form technology, applied in ether separation/purification, ether preparation, organic chemistry, etc., can solve problems such as unseen ospemifene

Active Publication Date: 2015-07-22
NANJING HUAWE MEDICINE TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The patents on ospemifene mainly include: WO1996007402, US4996225, WO1997032574, US6245819, WO2003103649, WO2005077350, WO2005079776, WO2008099059, WO2011089385, US2012270952, etc. protection of ospemifene, but so far there is no relevant report on the crystal form of ospemifene

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: Ospemifene polymorph I

[0046] Add ospemifene sample (1g, 2.64mmol) in the reaction flask, acetonitrile (5mL) is heated up to 60 ℃, after the sample is completely dissolved, add water (2.5mL) dropwise, after stirring for 10min, slowly cool down to 25 ℃, in the Stirring was continued at high temperature for 30 min, and then filtered under reduced pressure to obtain a white solid.

[0047] Form I is characterized by an X-ray powder diffraction pattern with peaks at the following approximate diffraction angles (2Θ): 11.2, 18.4, 21.1, 22.7, and 23.5. figure 1 An X-ray powder diffraction pattern of Form I is provided. figure 2 The Type I DSC curve shown in shows an endotherm onset at 116-118°C at a scan rate of 10°C / min. image 3 The Type I TGA curve shown indicates the onset of weight loss decomposition around 200°C at a scan rate of 20°C / min.

Embodiment 2

[0048] Embodiment 2: Ospemifene polymorphic form II

[0049] A sample of ospemifene (1 g, 2.64 mmol) was added to the reaction flask, and methanol (4 mL) was heated to 65 ° C. After the sample was completely dissolved, the temperature was slowly lowered to 30 ° C, and the organic solvent was concentrated to dryness to obtain a white solid.

[0050] Form II is characterized by an X-ray powder diffraction pattern with peaks at the following approximate diffraction angles (2Θ): 11.2, 17.3, 18.3, 22.7, and 23.5. Figure 4 An X-ray powder diffraction pattern of Form II is provided.

Embodiment 3

[0051] Embodiment 3: Ospemifene polymorphic form III

[0052] Add ospemifene sample (1g, 2.64mmol) into the reaction flask, heat up acetonitrile (2mL) to 65°C, and slowly cool down to 25°C after the sample is completely dissolved, let stand to precipitate a large amount of crystals, and filter under reduced pressure to obtain white solid.

[0053] Form III is characterized by an X-ray powder diffraction pattern with peaks at the following approximate diffraction angles (2Θ): 11.2, 18.4 and 21.1. Figure 5 An X-ray powder diffraction pattern of Form III is provided.

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Abstract

The invention provides a polymorphic substance of ospemifene, wherein ospemifene is (Z)-2-[4-(4-chloro-1,2-diphenyl-buten-1-yl)phenoxy] ethanol. Stability of the polymorphic substance is excellent; and crystal structure of the polymorphic substance is reproducible. And in addition, the invention also provides a preparation method of the ospemifene polymorphic substance.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a polymorphic form (crystalline form) of ospemifene (ospemifene) having a chemical formula such as formula I and a preparation method thereof. [0002] Background technique [0003] Ospemifene (ospemifene), the chemical name is (Z)-2-[4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy]ethanol, which is Japanese Nogi A new generation of selective estrogen receptor modulator (selective estrogen receptor modulator, SERM) developed by a pharmaceutical company (Shionogi Inc.) was approved by the US FDA on February 26, 2013, and the product is Osphena. As a new type of triphenylethylene SERM, preclinical and clinical research results show that it has good safety, efficacy and tolerability, and has fewer adverse reactions than other SERMs, without the liver toxicity caused by tamoxifen . Ospemifene is an important metabolite of toremifene, known as estrogen agonist and antag...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/40
Inventor 胡丹丹刘宝张孝清蒋玉伟
Owner NANJING HUAWE MEDICINE TECH DEV
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