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

Process for producing polymer

A technology of polymers and compounds, which is applied in the direction of pharmaceutical formulations, medical preparations of non-active ingredients, emulsion delivery, etc., and can solve problems such as difficult adjustment of molecular weight of biodegradable polymers, addition of difficult physiologically active substances, etc.

Inactive Publication Date: 2004-01-14
TAKEDA PHARMA CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Since polymers prepared by the above-mentioned known ring-opening polymerization method do not always have free carboxyl groups at the omega end of the resulting polymers, it is difficult to effectively incorporate physiologically active substances into sustained-release preparations
In addition, it is difficult to adjust the molecular weight of the target biodegradable polymer at the raw material addition stage

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0155] Example 1: Synthesis of PLA by D-tert-butyl lactate / diethylzinc / DL-lactide

[0156] A toluene solution of diethylzinc (1 / 2 molar equivalent) was added to 40.6 mg of tert-butyl D-lactate cooled to -78°C in a nitrogen atmosphere, followed by reaction at room temperature for 30 minutes. The resulting mixture was then mixed with 4.14 g of molten DL-lactide under a nitrogen atmosphere, followed by polymerization at 130°C for 2 hours.

[0157] Polymerization was terminated by dissolving the reagents in dichloromethane. After mixing with 0.1 N aqueous HCl and stirring for 20 minutes, washing with water was repeated until the mixture became neutral. Next, the dichloromethane solution was concentrated and dried by vacuum (40° C., 2 days) to obtain poly(DL-lactic acid) in which the ω residue was tert-butyl D-lactate. 1 As a result of H-NMR analysis, methine hydrogen (5.1-5.3 ppm), methyl hydrogen (1.5-1.6 ppm) and t-butyl hydrogen (1.46 ppm) in the lactic acid residue were conf...

Embodiment 2

[0159] Example 2: Synthesis of PLA by D-tert-butyl lactate / diethylzinc / DL-lactide

[0160] A toluene solution of diethylzinc (1 / 2 molar equivalent) was added to tert-butyl D-lactate cooled to -78°C in a nitrogen atmosphere, followed by reaction at room temperature for 10-30 minutes. The resulting mixture was then mixed with molten DL-lactide under a nitrogen atmosphere, followed by polymerization at 130°C for 1-5 hours.

[0161] The reaction reagents were dissolved in trifluoroacetic acid to terminate the polymerization and remove the protecting group, followed by stirring at room temperature for 1 hour. Next, the polymer was mixed with cold isopropyl ether, precipitated and collected, followed by two reprecipitation purifications with dichloromethane / cold isopropyl ether. The purified precipitate was dissolved in dichloromethane and washed repeatedly with water until it became neutral. Then, the dichloromethane solution was concentrated and dried in vacuo (40°C, 2 days) to ...

Embodiment 3

[0163] Example 3: Synthesis of PLA by L-benzyl lactate / diethylzinc / DL-lactide

[0164] A toluene solution of diethylzinc (1 / 2 molar equivalent) was added to 181.7 mg of benzyl D-lactate cooled to -78°C in a nitrogen atmosphere, followed by reaction at room temperature for 20 minutes. After adding 1 ml of distilled toluene for dilution, 15.03 g of DL-lactide was added under a nitrogen atmosphere and polymerized at 130°C for 1.5 hours.

[0165] Polymerization was terminated by dissolving the reagents in dichloromethane. After mixing with 0.1 N aqueous HCl and stirring for 20 minutes, washing with water was repeated until the mixture became neutral. Next, the dichloromethane solution was concentrated and dried in vacuo (40°C, 2 days) to obtain poly(DL-lactic acid) whose omega residue was benzyl L-lactate. 1 As a result of H-NMR analysis, methine hydrogen (5.1-5.3 ppm) and methyl hydrogen (1.5-1.6 ppm) of lactic acid residue and phenyl hydrogen (7.35 ppm) of benzyl group were co...

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

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
molecular weightaaaaaaaaaa
number average molecular weightaaaaaaaaaa
Login to View More

Abstract

A process for producing a biodegradable polymer having free carboxyl at the omega -end charcterized by polymerizing a cyclic ester compound in the presence of a hydroxymonocarboxylic acid derivative having protected carboxyl or a hydroxydicarboxylic acid derivative having protected carboxyl, and then deprotecting the thus obtained polymer having protected carboxyl at the omega -end. Use of the above process makes it easy to control the molecular weight of the target biodegradable polymer and the content of free carboxyl therein, thereby enabling the efficient production of a polymer having a high purity and being contaminated with littel catalyst remaining therein.

Description

technical field [0001] The present invention relates to a process for the preparation of new biodegradable polymers. Background technique [0002] EP-A-0839525 discloses a sustained-release preparation consisting of a physiologically active peptide or its salt and a biodegradable polymer, and a method for preparing the same. The biodegradable polymer described in this disclosure is made of Biodegradable polymers prepared by known ring-opening polymerization are prepared by a hydrolysis process which is known per se. [0003] The ring-opening polymerization method using the cyclic dimer of lactic acid by adding a catalyst while heating is described in J.H.R Woodland et al., J. Med. Chem., Vol. 16, p. 897 (1973). In addition, methods starting from cyclic diester compounds such as cyclic diesters or glycolipids with catalysts are described in Encyclopedia of Biomaterials and Bioengineering, Part A: Materials, Vol. 2, Marcel Dekker, Inc. (1995). [0004...

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 Patents(China)
IPC IPC(8): A61K9/113A61K9/16A61K47/34C08G63/08
CPCA61K9/1647A61K47/34A61K9/113C08G63/08C08G63/06
Inventor 畑善夫猪狩康孝
Owner TAKEDA PHARMA CO LTD
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