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Method for preparing carbetocin

A carbetocin and resin technology, which is applied in the field of polypeptide drug preparation and achieves the effects of low price, mild reaction conditions and high yield

Active Publication Date: 2014-06-04
HAINAN SHUANGCHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are only imported drugs from the original research manufacturer Ferring Company and Ferring China’s product Qiaotexin in China, and the market is still in the protection period

Method used

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  • Method for preparing carbetocin
  • Method for preparing carbetocin
  • Method for preparing carbetocin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) Preparation of Fmoc-Cys(Mmt)-resin

[0043] Weigh 30g Wang resin (0.50 mmol / g) and place it in a solid-phase reactor, add 300 ml of DMF to swell for about 10 minutes, and drain it; add 18.5 g (30 mmol) of Fmoc-Cys(Mmt)-OH, 4.05 g (30 mmol) of HOBt, 7.0 mL of DIC (45.0 mmol), 183.2 mg of DMAP (1.5 mmol), the mixture was shaken at room temperature for 2.5-3 hours, the reaction solution was drained, washed 3 times with 200 ml of DMF, and then washed with 200 mL pyridine / Ac 2 O / DMF=6:5:50 (v / v / v) solution was reacted for 2 hours. After the reaction was completed, the DMF was filtered off with suction, washed with DMF (250 ml) 3 times, and sucked dry.

[0044] (2) Preparation of Fmoc-Asn(Trt)-Cys(Mmt)-resin

[0045] Add about 200 mL of 20% PIP / DMF solution, shake at room temperature for about 5 minutes; then add about 200 mL of 20% PIP / DMF solution, shake for about 5 minutes at room temperature; drain, wash with DMF 3 times, and drain , the Kaiser test (Kaiser test) ...

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Abstract

The invention discloses a method for preparing carbetocin. The method comprises the following steps: coupling Fmoc-Cys(Mmt)-OH with hydroxyl function group resin to obtain Fmoc-Cys(Mmt)-resin; removing Fmoc from the Fmoc-Cys(Mmt)-resin to obtain H-Cys(Mmt)-resin; coupling the Fmoc-Asn(Trt)-OH with the H-Cys(Mmt)-resin to obtain Fmoc-Asn(Trt)-Cys(Mmt)-resin; repeating the steps of removing Fmoc and condensation reaction according to a solid-phase synthesis method, so as to obtain peptide resin with a structure shown in A; removing the Fmoc from the A, and then reacting with bromine succinimide butyrate to obtain B; obtaining C from the B in a manner of weak acid cracking; obtaining a segment as shown in a formula D in manners of cyclizing and cracking, and obtaining E from the D by cracking in a strong acid system; mixing the Fmoc-Gly-OH with amino resin and then removing the Fmoc to obtain H-Gly-resin by coupling reaction; repeating the steps according to the solid-phase synthesis method, so as to obtain F; coupling the segment E with the F, so as to obtain the peptide resin in the formula G; and obtaining the carbetocin H after cracking the G. The method disclosed by the invention is high in total yield, less in impurity content, and high in product purity, and has a great industrial prospect.

Description

technical field [0001] The invention belongs to the field of preparation methods of polypeptide drugs, and in particular relates to a preparation method of carbetocin. Background technique [0002] Carbetocin is a chemically synthesized long-acting nonapeptide analogue of oxytocin with agonist properties. Its clinical and pharmacological properties are very similar to those of naturally occurring oxytocin. The combination of oxytocin receptors causes the rhythmic contraction of the uterus, increasing its frequency and increasing the tension of the uterus on the basis of the original contraction. Oxytocin receptor levels in the uterus are low in the non-pregnant state, increase during pregnancy, and peak at parturition. Carbetocin therefore has no effect on the non-pregnant uterus, but has potent uterotonic effects on the pregnant and newborn uterus. At present, there are only imported drugs from the original research manufacturer Ferring Company and Ferring China's product...

Claims

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Application Information

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IPC IPC(8): C07K7/16C07K1/06C07K1/04
Inventor 袁剑琳陈超张皓张巍张成广
Owner HAINAN SHUANGCHENG PHARMA
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