Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

New tigecycline crystal form and preparation method thereof

A technology of tigecycline and crystal form, applied in the field of new crystal form of tigecycline and its preparation, can solve the problems of inconvenient transportation or storage, limited medical use, unstable tigecycline powder, etc. Transportation and long-term storage, the effect of good stability

Active Publication Date: 2012-04-18
宫宁瑞
View PDF7 Cites 17 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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 crystal for 20-24 hours at 25°C to 30°C to obtain the new crystal form described in this patent, and obtain 9.1g of 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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/26C07C231/24A61K9/19A61K31/65A61P31/04
Inventor 宫宁瑞
Owner 宫宁瑞
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com