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Preparation method of beta type silodosin crystal

A technology of silodosin and beta crystal form, which is applied in the field of medicinal chemistry, can solve the problems of many process steps, low yield and purity of beta crystal form silodosin, and is suitable for large-scale industrial production. High purity, high yield, simple and convenient process

Inactive Publication Date: 2013-10-23
KUNMING JIDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the disadvantages of preparing β crystal form silodosin in the prior art that there are many processing steps and the yield and purity are low, the present invention is proposed

Method used

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  • Preparation method of beta type silodosin crystal
  • Preparation method of beta type silodosin crystal
  • Preparation method of beta type silodosin crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: Preparation of silodosin in β crystal form

[0028] 1) Weigh 1.0g of crude silodosin into a round bottom flask, add 5ml of chloroform and stir to dissolve, then add 10ml of cyclohexane and stir evenly, filter, crystallize the filtrate at 0-5°C for 0-2 hours, filter The crystals were collected and dried to obtain 0.8 g of silodosin in the β crystal form, with a purity of 99.43%, a melting point of 104.3-106.1°C, and a yield of 80.0%.

[0029] 2) Weigh 1.0g of crude silodosin into a round bottom flask, add 5ml of chloroform and stir to dissolve, then add 20ml of ether and stir evenly, filter, crystallize the filtrate at 0-5°C for 0-2 hours, and collect the crystals by filtration , and dried to obtain 0.8 g of silodosin in the β crystal form, with a purity of 99.50%, a melting point of 104.5-105.7°C, and a yield of 80.0%.

[0030] 3) Weigh 1.0g of crude silodosin into a round bottom flask, add 5ml of chloroform and stir to dissolve, then add 15ml of isopropy...

Embodiment 2

[0039] Embodiment 2: Determination of silodosin in β crystal form

[0040] Operation steps: Carry out the X-ray diffraction (XRD) pattern determination of the β crystal form silodosin prepared by 1)-11) in Example 1, wherein the Cu-Ka radiation condition The Bragg 2θ angle is 3-40°.

[0041] The β crystal form silodosin XRD figure prepared by 1) and 5) method in embodiment 1 is respectively as follows figure 1 , figure 2 shown.

[0042] Table 1 shows the X-ray diffraction data of the β-crystal form silodosin obtained from 8) and 10) in Example 1.

[0043] Table 1 Example 1 8) and 10) obtained β crystal form silodosin X-ray diffraction data

[0044]

Embodiment 3

[0045] Embodiment 3: Oral formulation of silodosin in β crystal form

[0046] The β-crystal form silodosin prepared from 1)-11) in Example 1 was prepared into an oral dosage form.

[0047] Capsule 1

[0048] formula:

[0049]

[0050] According to the above formula, 1000 capsules containing 2.0 mg of silodosin in β crystal form were prepared by conventional methods.

[0051] Capsule 1

[0052] formula:

[0053]

[0054] According to the above formula, 1000 capsules containing 2.0 mg of silodosin in β crystal form were prepared by conventional methods.

[0055] piece 1

[0056]

[0057] According to the above formula, 1000 tablets of β-crystal form silodosin tablets containing 4.0 mg were prepared by conventional methods.

[0058] piece 2

[0059]

[0060] According to the above formula, 1000 tablets of β-crystal form silodosin tablets containing 4.0 mg were prepared by conventional methods.

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Abstract

The invention discloses a preparation method of a beta type silodosin crystal. Silodosin is a medicament which is clinically used for treating benign prostatic hyperplasia, and three crystal forms, namely alpha, beta and gamma exist. Although the beta crystal form silodosin can be used as an active ingredient of an oral medicament, the preparation method in the prior art has the shortcomings of more process steps, low yield, low purity and the like. According to the preparation method disclosed by the invention, the beta crystal form silodosin is obtained by selecting an appropriate halogenated alkane type solvent and adopting a mild crystallization way. The method has the advantages of stable process, simplicity in operation, convenience, quickness, higher yield and higher purity, the used solvent is very easy to remove, and the method can be used for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a β-crystal form of a medicinal compound silodosin and a preparation method thereof. Background technique [0002] Silodosin is an α1A-adrenergic receptor antagonist with the chemical name 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2- (2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carboxamide, its structural formula is as follows: [0003] [0004] Silodosin has a selective inhibitory effect on the contraction of urethral smooth muscle, and reduces the internal pressure of the urethra, but has no great effect on blood pressure. It has curative effect on voiding disorders related to benign prostatic hyperplasia, and is clinically used for the treatment of benign prostatic hyperplasia. [0005] WO2004022538 discloses that silodosin has three crystal forms (α, β and γ) and an amorphous form and its preparation method. The hygroscopicity of the three crystal fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08A61K31/4045A61P13/08
Inventor 刘小龙刘荣昌冯朴纯
Owner KUNMING JIDA PHARMA
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