Unlock instant, AI-driven research and patent intelligence for your innovation.

Oseltamivir preparation method

An oseltamivir and reaction technology, applied in the field of drug synthesis, can solve problems such as uneconomical and long reaction time, and achieve the effects of cost saving, reaction time reduction and high yield

Inactive Publication Date: 2016-03-30
SHENYANG PHARMA UNIVERSITY
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction time of this method is too long and uneconomical

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
  • Oseltamivir preparation method
  • Oseltamivir preparation method
  • Oseltamivir preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add ethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate into a 100mL reaction flask 100mg, 5mg Lindlar catalyst, add hydrogen, the pressure is 0.5atm, react at room temperature for 3h. After the reaction, the reaction solution was filtered, and the solvent in the filtrate was evaporated to dryness to obtain 90.74 mg of the product with a yield of 98%.

[0033] MS(m / z):[M+H] + 313.1,[2M+H] + 625.3

[0034] 1 HNMR (400MHz, CD 3 OD)δ6.77(s,1H),4.21(q,J=7.1Hz,2H),4.09–4.04(m,1H),3.69(dd,J=10.8,8.8Hz,1H),3.42-3.34( m,1H),2.88(td,J=10.4,5.4Hz,1H),2.78(dd,J=17.7,5.2Hz,1H),2.20–2.09(m,1H),2.02(s,3H),1.57 -1.46 (m, 4H), 1.29 (t, J=7.1Hz, 3H), 0.92 (t, J=6.1Hz, 3H), 0.89 (t, J=6.2Hz, 3H). The proton nuclear magnetic resonance spectrum was determined by Bruker ARX-400 nuclear magnetic resonance instrument, and the liquid phase mass spectrometry was determined by Waters QuattromicroAPI triple quadrupole mass spectrometer (equipped with electro...

Embodiment 2

[0036] Add ethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate into a 100mL reaction flask 100mg, 5mg Lindlar catalyst, add hydrogen, the pressure is 0.5atm, react at room temperature for 3h. After the reaction was finished, the reaction solution was filtered, and the solvent in the filtrate was evaporated to dryness to obtain 90.27 mg of product with a yield of 97.8%. The verification method is the same as in Example 1.

Embodiment 3

[0038] Add ethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate into a 100mL reaction flask 150mg, 7.5mg Lindlar catalyst, add hydrogen, the pressure is 0.5atm, react at room temperature for 3h. After the reaction, the reaction solution was filtered, and the solvent in the filtrate was evaporated to dryness to obtain 136.4 mg of the product with a yield of 98.5%. The verification method is the same as in Example 1.

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 present invention relates to the field of pharmaceutical synthesis, in particular a novel oseltamivir preparation method. By using an organic solvent agent, a reaction is performed for 2-4 hours by the Lindlar catalyst, the palladium content of which is 5%, under a certain pressure to obtain oseltamivir, wherein the reaction temperature is room temperature. According to the preparation method provided by the present invention, a column chromatography method is not necessarily used for purification, the experiment operation is simplified, the reaction time is shortened, the cost is lowered, and the obtained yield is high.

Description

Technical field: [0001] The invention belongs to the field of drug synthesis, and in particular relates to a novel preparation method of oseltamivir. Background technique: [0002] Oseltamivir Phosphate is an effective neuraminidase inhibitor with the chemical name (3R, 4R, 5S)-4-acetamido-5-amino-3-(1-ethylpropoxy Base)-1-cyclohexene-1-carboxylic acid ethyl ester, the structural formula is as follows: [0003] [0004] Oseltamivir phosphate is a highly efficient and highly selective influenza virus neuraminidase inhibitor drug developed by Roche Pharmaceutical Company. It was approved by the US FDA in 1999 and listed in my country in July 2004 under the trade name of Tamiflu. Clinically, it is mainly used to prevent and treat diseases caused by neuraminidase, such as influenza A and influenza B. Oseltamivir phosphate is the drug of choice for influenza outbreaks that countries around the world are scrambling to stockpile. [0005] In the method for synthesizing oselt...

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): C07C231/12C07C233/52
CPCC07C231/12C07C233/52
Inventor 田永寿王矿磊李蕾
Owner SHENYANG PHARMA UNIVERSITY