Method for full-liquid-phase synthesis of leuprorelin

A liquid-phase synthesis technology of leuprolide, applied in the field of medicine, can solve the problems of low purity of crude product, use of many solvents, and high cost

Pending Publication Date: 2022-03-08
HUNAN MICRO PEPTIDE BIOMEDICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, at present, leuprolide is mainly prepared by solid-phase reaction, which has high cost, many solvents are used, environmental protection pressure is high, and the purity of the crude product is low.

Method used

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  • Method for full-liquid-phase synthesis of leuprorelin
  • Method for full-liquid-phase synthesis of leuprorelin
  • Method for full-liquid-phase synthesis of leuprorelin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] 1. Synthesis of compound 1: Fmoc-Trp(Boc)-Ser(tBu)-Tyr(tBu)-OH

[0071] 1.1 Feeding:

[0072] Feed according to the materials in Table 2.

[0073] Table 2 Types and dosage of materials

[0074]

[0075]

[0076] 1.2 Operation process

[0077] After the synthesized Fmoc-Trp(Boc)-Ser(tBu)-OSu was completely dissolved in DMF, the H-Tyr(tBu)-OH was accurately weighed and added to the above reaction flask, and TEA 110mmol was added to start the reaction. After stirring and reacting for 60 min, HPLC detected that the reaction was complete.

[0078] The reaction solution was poured into the Erlenmeyer flask twice, and then 0.5M hydrochloric acid was added to rapidly stir and precipitate, and the filtered solid was then washed with purified water until neutral, and dried at 30°C. Collect the solids into containers and weigh.

[0079] The obtained compound 1 was analyzed by HPLC, and the liquid chromatogram was obtained as figure 1 shown.

[0080] The analysis metho...

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Abstract

The invention provides a method for synthesizing leuprorelin in a full liquid phase, which comprises the following steps: carrying out condensation reaction on R4-Pyr-His (R3)-Trp (Boc)-Ser (tBu)-Tyr (tBu)-D-Leuu-Leg-Pro-NHEt and H-Arg (pbf)-Pro-NHEt to obtain R4-Pyr-His (R3)-Trp (Boc)-Ser (tBu)-Tyr (tBu)-D-Leuu-Leg-Arg (pbf)-Pro-NHEt, and then carrying out reaction on the R4-Pyr-His (R3)-Trp (Boc)-Ser (tBu)-Tyr (tBu Compared with the prior art, the preparation method adopts a full liquid phase synthesis method, the production process is green and mild, any highly toxic and precursor reagent is not used, the purity of the produced product is high, the crude product can reach 90% or above, the cost is greatly reduced, and the preparation method is very suitable for large-scale production.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on November 05, 2021, the application number is 202111308458.X, and the invention title is "a method for synthesizing leuprolide in full liquid phase", the entire content of which Incorporated in this application by reference. technical field [0002] The invention belongs to the technical field of medicine, and in particular relates to a method for synthesizing leuprolide in full liquid phase. Background technique [0003] Leuprolide is a gonadotropin-releasing hormone (GnRH) with a structure of Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt. Clinically, leuprolide is often used in endometriosis, uterine fibroids accompanied by menorrhagia, lower abdominal pain, low back pain and anemia, premenopausal breast cancer, and estrogen receptor positive patients, prostate cancer, central nervous system Sexual precocious puberty. [0004] Leuprolide was first discovered ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/23C07K1/06C07K1/02
CPCC07K7/23Y02P20/55
Inventor 孙鹏程唐勇擘杜一雄
Owner HUNAN MICRO PEPTIDE BIOMEDICAL CO LTD
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