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Tigecycline without crystal habit and method of preparing the same

A tigecycline, crystal-free technology, used in organic chemistry, separation/purification of carboxylic acid amides, etc., can solve problems such as tigecycline that has not yet seen a crystal-free form, and achieve the effect of obvious bacteriostatic activity

Inactive Publication Date: 2009-02-18
SHANGHAI LAIYI BIOMEDICAL RES & DEV CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And so far, there is no report about tigecycline without crystalline form

Method used

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  • Tigecycline without crystal habit and method of preparing the same
  • Tigecycline without crystal habit and method of preparing the same
  • Tigecycline without crystal habit and method of preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 , the preparation of tigecycline without crystalline form

[0029] Weigh 0.2 g of crude tigecycline (content about 70%), dissolve it completely with 40 ml of water, and then adjust the pH of the solution to 2.0 with 1 mol / L HCl;

[0030] Add 20ml of HP2MG macroporous adsorption resin (Mitsubishi Chemical) to the solution, stir and adsorb at 100rpm for 1 hour, filter to remove the resin, adjust the pH of the adsorption residue to 8.5 with 1mol / L NaOH; then use dichloromethane and acetonitrile 2:1 to form The mixed solvent was extracted twice, 40ml each time, and the extracts were collected and combined;

[0031] The collected extract was concentrated and dried under vacuum at 20°C to obtain 0.08 g of tigecycline powder.

[0032] Use the X-ray powder diffraction method to detect the powder obtained, and the diffraction pattern is as follows figure 2 shown. Depend on figure 2 As can be seen from the results, the diffraction pattern shows a flat curve and ...

Embodiment 2

[0037] Example 2 , the preparation of tigecycline without crystalline form

[0038] Weigh 5.4g of crude tigecycline (content about 70%), dissolve it completely with 800ml of water, and then adjust the pH of the solution to 3.0 with 1mol / L HCl;

[0039] Add 400ml of prepared Amberlite XAD-6 macroporous adsorption resin (Rohm and Haas, USA) to the solution, stir and adsorb at 100rpm for 1 hour, remove the resin by filtration, and adjust the pH of the adsorption raffinate to 8.0 with 1mol / L NaOH; Extract twice with methane, 800ml each time, collect and combine the extracts;

[0040] The collected extract was concentrated and dried under vacuum at 30° C. to obtain 2.3 g of tigecycline powder.

[0041] The obtained powder sample is detected by X-ray powder diffraction method, and the diffraction pattern is as follows image 3 shown. Depend on image 3 As can be seen from the results, the diffraction pattern shows a flat curve and does not show any peak shape, so it can be det...

Embodiment 3

[0043] Example 3 , the preparation of tigecycline without crystalline form

[0044] Weigh 40 g of crude tigecycline (content about 70%), dissolve it completely with 4000 ml of water, and then adjust the pH of the solution to 2.5 with 1 mol / L HCl;

[0045] Add 2000ml of prepared HP2MG macroporous adsorption resin (Mitsubishi Chemical) to the solution, stir and adsorb at 100rpm for 1 hour, filter to remove the resin, and adjust the pH of the adsorption raffinate to 8.3 with 1mol / L NaOH;

[0046] Then extract twice with the mixed solvent that dichloromethane and methanol 3:1 constitute, each 4000ml, collect and combine extract;

[0047] The collected extract was concentrated and dried under vacuum at 15°C to obtain 18.0 g of tigecycline powder.

[0048] Use the X-ray powder diffraction method to detect the powder obtained, and the diffraction pattern is as follows Figure 4 shown. Depend on Figure 4 As can be seen from the results, the diffraction pattern shows a flat curv...

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Abstract

The present invention provides a no-crystalline state tigecycline and a preparation method of the tigecycline. The present invention has obvious bacteriostasis activity.

Description

technical field [0001] The invention belongs to the field of chemical industry and pharmacy, and in particular relates to tigecycline without crystal form and a preparation method thereof. Background technique [0002] Tigecycline (tigecycline), chemical name: (4S, 4aS, 5aR, 12aS)-4,7-bis(dimethylamino)-9-[(tert-butylamino)acetamido]-3,10, 12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, also known as 9-tert-butylglycerol Aminoamido minocycline or Dingglyminocycline, which was approved by the FDA in June 2005, is the first glycylcycline antibiotic approved for marketing. The molecular structure is as follows: [0003] [0004] Although tigecycline and minocycline have many similarities in structure, the former is obviously superior to traditional tetracyclines in terms of antibacterial spectrum range and drug-resistant bacteria, and has broad-spectrum antimicrobial activity. Treatment of complicated intra-abdominal infections (cIAI) ...

Claims

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Application Information

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IPC IPC(8): C07C237/26C07C231/24
Inventor 邵昌王涛杨志钧袁建勇陈鹏叶伟东罗敏玉戈梅
Owner SHANGHAI LAIYI BIOMEDICAL RES & DEV CENT
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