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New tigecycline crystal form and preparation method thereof

A technology of tigecycline and its crystal form, which is applied in the field of new tigecycline crystal form and its preparation, can solve the problems of limited medical use, inconvenient transportation or storage, unstable tigecycline powder, etc., and achieves good results. Stability, good for transportation and long-term storage

Active Publication Date: 2014-03-12
宫宁瑞
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amorphous tigecycline powder is unstable at room temperature or under cool conditions, so it is not convenient for transportation or storage, and its medical use is greatly limited

Method used

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  • New tigecycline crystal form and preparation method thereof
  • New tigecycline crystal form and preparation method thereof
  • New tigecycline crystal form and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: Preparation of tigecycline crystal form

[0056] Cool 300ml of ethanol with ice water to 15°C-20°C, add 10g of tigecycline amorphous under stirring, and stir to dissolve. Concentrate with a rotary evaporator under vacuum, and control the temperature of the water bath below 25°C. When concentrated to 100-110ml, stop concentrating. Put the concentrated solution in an ice-water bath, add 100-110ml of ethyl acetate while stirring, and when the ice-water bath is stirred to about 5°C, put it in a freezer (-20°C-0) to crystallize for 10-15 hours. After filtration, the crystal was vacuum pumped for 20-24 hours at 25°C-30°C to obtain 8.20 g of the new crystal form described in this patent (purity: 99.7%, residual solvent: ethanol 7.24%, ethyl acetate 2.9%).

[0057] This crystal is used as a sample, and powder X-ray diffraction (hereinafter referred to as XRD) is measured to obtain figure 1 The X-ray diffraction pattern shown.

[0058] This crystallization is u...

Embodiment 2

[0060] Embodiment 2: Preparation of tigecycline crystal form

[0061] Cool 400ml of methanol with ice water to 15°C-20°C, add 10g of tigecycline amorphous under stirring, and stir to dissolve. Concentrate with a rotary evaporator under vacuum, and control the temperature of the water bath below 25°C. When concentrated to 100-110ml, stop concentrating. Put the concentrated solution in an ice-water bath, add 100-110ml of ethyl acetate while stirring, and when the ice-water bath is stirred to about 5°C, put it in a freezer (-20°C-0) to crystallize for 10-15 hours. Filtrate, vacuumize the crystals at 25°C-30°C for 20-24 hours to obtain the new crystal form described in this patent, and obtain 9.1g tigecycline crystal form (purity: 99.6%, residual solvent: methanol 0.24% , ethyl acetate 3.7%). The X-ray diffraction figure of described crystal form tigecycline is as attached figure 1 shown.

Embodiment 3

[0062] Embodiment 3: Preparation of tigecycline crystal form

[0063] Cool 300ml of isopropanol with ice water to 15°C to 20°C, add 10g of tigecycline amorphous under stirring, and stir to dissolve. Concentrate with a rotary evaporator under vacuum, and control the temperature of the water bath below 25°C. When concentrated to 100-110ml, stop concentrating. Put the concentrated solution in an ice-water bath, add 100-110ml of ethyl acetate while stirring, and when the ice-water bath is stirred to about 5°C, put it in a freezer (-20°C-0) to crystallize for 10-15 hours. After filtration, the crystals are vacuumed for 20 to 24 hours in an environment of 25°C to 30°C to obtain the new crystal form described in this patent. 8.7 g of tigecycline were obtained (purity: 99.5%, residual solvent: isopropanol 7.32%, ethyl acetate 1.7%). The X-ray diffraction figure of described crystal form tigecycline is as attached figure 1 shown.

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Abstract

The invention relates to a new tigecycline crystal form and a preparation method thereof. The new tigecycline crystal form is represented by a formula (I) and is a new crystal form of (4S, 4aS, 5aR, 12aS)-9-(2-(tertiary butyl amino) acetamido)-4,7-bis(dimethyl amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacene formamide (tigecycline). The new tigecycline crystal form represented by the formula (I) is suitable for the preparation of freeze-dried powder.

Description

technical field [0001] The invention relates to a new crystal form of tigecycline and a preparation method thereof, and belongs to the field of pharmaceutical applications. Background technique [0002] Tigecycline was developed by Wyeth of the United States for the treatment of patients aged 18 and over with complicated skin and skin structure infections or complicated intra-abdominal infections. Its chemical name is (4S, 4aS, 5aR, 12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a , 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthonaphthalenecarboxamide, is the first of a new generation called glycylcycline (glycylclines) tetracycline (tetracycline) antibiotic drugs. Its structure is similar to that of tetracyclines. In June 2005, it was approved by the US FDA for complex skin and soft tissue infections (cSSSLs) in adults and complex intra-abdominal infections in adults, including complicated appendicitis, burn infection, intra-abdom...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/26C07C231/24A61K9/19A61K31/65A61P31/04
Inventor 宫宁瑞
Owner 宫宁瑞
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