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A kind of androstanedione derivative crystal form and preparation method thereof

A technology of androstane and crystal form, which is applied in the field of androstanedione derivative crystal form and its preparation, can solve problems affecting drug stability, solubility and bioavailability, affecting drug quality, safety and effectiveness and Application, affecting the preparation processing performance of drugs, etc.

Active Publication Date: 2015-10-07
CVIE THERAPEUTICS COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The crystal form of the drug will directly affect the processing performance of the drug preparation, and will affect the stability, solubility and bioavailability of the drug, which in turn will affect the quality, safety, effectiveness and application of the drug
At present, there is no report of Istaroxime crystal form

Method used

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  • A kind of androstanedione derivative crystal form and preparation method thereof
  • A kind of androstanedione derivative crystal form and preparation method thereof
  • A kind of androstanedione derivative crystal form and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Embodiment 1 Preparation of compound shown in formula I

[0091] Add 20g of 3-β-hydroxy-5-androstan-17-one acetate, 300mL of methanol and 2mL of 30% sodium hydroxide to the reaction kettle, add 400mL of purified water after the reaction is complete, stir for 60min, filter the suspension, and use Wash the filter cake with purified water, and dry it under vacuum at 40°C to obtain 3-β-hydroxy-5-androstane-17-one. Based on the starting material 3-β-hydroxy-5-androstan-17-one acetate, the yield was 80.0% (±2.0%).

[0092] Dissolve the above 3-β-hydroxy-5-androstane-17-one in 250 mL THF, add 100 mL of 1 mol / L borane solution in THF, stir for 2 hours to obtain 5α-androstane-3β,17β-dihydroxy-6α -BH 2 . 250 mL of purified water and 18.5 g of sodium perborate tetrahydrate were added to the above solution and stirred overnight to obtain 5α-androstane-3β,6α,17β-trihydroxyl, which was filtered and the filter cake was washed with water.

[0093] Mix 2g sodium hypochlorite, 3.5g r...

Embodiment 2

[0095] Embodiment 2 Preparation of compound crystal form as shown in formula I

[0096] Under the condition of 25° C., 5 g of the compound represented by formula I provided in Example 1 was dissolved in 100 mL of dichloromethane, filtered, and the filtrate was concentrated to an oily state. Add 50mL90% ethanol aqueous solution to dilute. Add 45 mL of ethyl acetate and stir at 20°C to form a precipitate. After filtering, washing with ethyl acetate, and vacuum drying at 40°C for 48 hours, 4.55 g of off-white rod-shaped crystals of the compound shown in formula I were obtained, which is the crystal form of the compound shown in formula I, with a yield of 91% and a content of 99%.

[0097] use 1 H-NMR, mass spectrometry, XRD, IR and DSC detect the compound crystal form as shown in formula I, its 1 H-NMR spectrum, mass spectrum, XRD spectrum, DSC spectrum, IR spectrum, respectively see figure 1 , figure 2 , image 3 , Figure 4 , Figure 5 , 1 The characteristic data of H...

Embodiment 3

[0109] Embodiment 3 Preparation of compound crystal form as shown in formula I

[0110] Under the condition of 25° C., 5 g of the compound represented by formula I provided in Example 1 was dissolved in 100 mL of dichloromethane, filtered, and the filtrate was concentrated to an oily state. Add 75mL70% ethanol aqueous solution to dilute. 50 mL of butanone was added and stirred at 25° C. to form a precipitate. Filtration, washing with ethyl acetate, and vacuum drying at 35°C for 60 hours gave 4.48 g of off-white rod-shaped crystals of the compound shown in Formula I, which was the crystal form of the compound shown in Formula I, with a yield of 89.6% and a content of 99%.

[0111] Using XRD, IR, DSC, 1 H-NMR and mass spectrometry are used to detect the crystal form of the compound shown in formula I, and the detection results are similar to those in Example 2.

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Abstract

The invention relates to the pharmaceutical chemistry field, and especially relates to an androstanedione derivative crystal form and a preparation method therefor. The XRD pattern of the crystal form has peaks in positions of 2theta + / - 0.2, wherein 2theta is for 2.3, 3.6, 6.7, 7.7, 12.2, 13.3, 13.7, 15.3, 16.2, 16.6, 17.9, 19.0, 19.1, 19.9, 20.2, 20.7, 21.1, 22.9, 23.2, 24.0, 24.2, 24.8, 25.4, 26.5, 27.1, 28.3, 29.6, 30.0, 30.3, 30.7, 31.9, 32.6, 33.3, 34.1, 34.5, 35.7, 36.0, 36.5, 37.6, 38.4 and 39.0. The compound crystal form shown in the formula I is stable to light, heat and humidity, is suitable for long storage, and has simple preparation technology and good reproducibility.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a crystal form of an androstanedione derivative and a preparation method thereof. Background technique [0002] After entering the 21st century, with the change of lifestyle of Chinese residents, chronic diseases headed by cardiovascular disease have become the main diseases that seriously threaten the health of Chinese residents. Heart failure (HF) is the final stage of various cardiovascular diseases. It is caused by various primary cardiovascular diseases such as coronary heart disease under the condition of normal venous return. A syndrome that requires tissue metabolism. The clinical manifestations are pulmonary congestion, cough, sputum, hemoptysis, fatigue, fatigue, mental abnormalities, oliguria, and renal impairment. The causes of heart failure mainly include primary myocardial damage, hypertension, valvular stenosis, valvular regurgitation, blood regurgitation, left ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J41/00A61K31/5685A61P9/04
Inventor G·毕安祺P·费拉里戴向荣李小羿
Owner CVIE THERAPEUTICS COMPANY
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