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Method for full-liquid-phase synthesis of deslorelin

A liquid-phase synthesis and deslorelin technology, applied in the field of medicine, can solve the problems of low crude product purity, high environmental protection pressure, pressure on large-scale production costs and the like

Inactive Publication Date: 2021-12-24
HUNAN SANTAI PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Solid-phase synthesis requires the use of a large amount of expensive peptide resins, which not only brings cost pressures to the large-scale production of enterprises, but also uses a lot of solvents and precursor reagents, which puts a lot of pressure on environmental protection, and in the final peptide cutting process , the tert-butyl group is easily removed under acidic conditions to generate other impurity products, resulting in low purity of the crude product

Method used

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

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Experimental program
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Embodiment 1

[0062] 1. Synthesis of compound 1: Fmoc-Trp(Boc)-Ser(tBu)-Tyr(tBu)-OH

[0063] 1.1 Feeding:

[0064] Feed according to the materials in Table 2.

[0065] Table 2 Types and dosage of materials

[0066] abbreviation Dosage Fmoc-Trp(Boc)-Ser(tBu)-OSU 100mmol H-Tyr(tBu)-OH 110mmol TEA 110mmol DMF 400ml 0.5M hydrochloric acid solution 1L

[0067] 1.2 Operation process

[0068] 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.

[0069] 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 int...

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Abstract

The invention provides a method for full-liquid-phase synthesis of deslorelin. The method comprises the following steps: carrying out condensation reaction on R4-Pyr-His(R3)-Trp(Boc)-Ser(tBu)-Tyr(tBu)-D-Trp-Leu-OH and H-Arg(pbf)-Pro-NHEt to obtain R4-Pyr-His(R3)-Trp(Boc)-Ser(tBu)-Tyr(tBu)-D-Trp-Leu-Arg(pbf)-Pro-NHEt, and then carrying out reaction in a cutting fluid to obtain the deslorelin. Compared with the prior art, the 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 product is high, the crude product can reach 90% or above, the cost is greatly reduced, and the method is very suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for synthesizing deslorelin in full liquid phase. Background technique [0002] Deslorelin, whose structure is Pyr-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-NHEt, is a luteinizing hormone-releasing hormone (LHRH), which can be used to treat central Precocious puberty. In addition, American scholar Shore et al. reported that for patients with advanced prostate cancer, subcutaneous implantation of deslorelin long-acting implants once a year can stably suppress testosterone for a long time and maintain castration levels. [0003] The current synthetic method of deslorelin is mainly solid-phase synthesis. Solid-phase synthesis requires the use of a large amount of expensive peptide resins, which not only brings cost pressures to the large-scale production of enterprises, but also uses a lot of solvents and precursor reagents, which puts a lot of pressure on environment...

Claims

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Application Information

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IPC IPC(8): C07K7/23C07K1/06C07K1/02
CPCC07K7/23Y02P20/55
Inventor 孙鹏程王志锋唐勇擘杜一雄余辅松郭林
Owner HUNAN SANTAI PHARM CO LTD
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