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N-substituted peptide amide, pharmaceutical composition and use thereof

A composition and drug technology, applied in the directions of drug combinations, peptides, cyclic peptide components, etc., to achieve the effects of strong biological stability and immunomodulatory activity, simple and feasible preparation method, and low cost

Inactive Publication Date: 2012-09-05
CHIA TAI TIANQING PHARMA GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, TP-5 is metabolized too quickly in the body, and the half-life is only 30 seconds.

Method used

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  • N-substituted peptide amide, pharmaceutical composition and use thereof
  • N-substituted peptide amide, pharmaceutical composition and use thereof
  • N-substituted peptide amide, pharmaceutical composition and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Synthesis of H-Arg-Lys-Asp-Val-Tyr-Gol·2HCl(I)

[0072] First, the classic solid-phase peptide synthesis strategy was adopted, using chloromethyl resin (substitution degree: 1 mmol / g, cross-linking degree: 1%, particle size: 100-200 mesh) as the solid-phase carrier, and the synthesis of the target sequence was completed step by step. Assemble. Among them, Tyr, Val and Arg all use Boc to protect the a-amino group, and the protection forms of the other two amino acids are: Fmoc-Lys(Boc)-OH and Fmoc-Asp(OtBu)-OH. The degree of condensation was monitored by ninhydrin color reaction after each condensation step. After all the condensation is completed, use aminoethanol (Gol) / H 2 O / DMF (2:1:3, v / v) solution was mixed with fully protected peptide resin and shaken for 30 h. The collected filtrate was mixed with an appropriate volume of distilled water, then passed through the C-18 filter layer under reduced pressure, and then rinsed with an appropriate volume of distilled wa...

Embodiment 2

[0078] H-Arg-Lys-Asp-Val-Tyr-NH(CH 2 ) 2 NH(CH 2 ) 2 The solid-phase synthesis of the synthetic peptide sequence of OH 2HCl(II) is the same as in Example I, except that the ammonolysis uses H 2 N(CH 2 ) 2 NH(CH 2 ) 2 OH is an amine component.

[0079] Other concrete reaction conditions are also the same with embodiment 1.

[0080] The yield of II was 87.5%,

[0081] Its ESI-MS analysis result was 766.3 (M+H).

Embodiment 3

[0083] Synthesis of H-Arg-Lys-Asp-βAla-Tyr-NHEt(III)

[0084] In the solid-phase synthesis of the peptide chain sequence, Boc-β-Ala-OH was used to replace the original Boc-Val-OH at the second position of the C-terminus, and the rest of the conditions were the same as in Example 1. In addition, another difference from Example I is that the Boc and tBu protecting groups are removed before the ammonolysis, and the free product IIIi is obtained after the ammonolysis:

[0085]

[0086] The yield of III is 93.6%, and the result of ESI-MS is: 679.4 (M+H).

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Abstract

The invention discloses a kind of novel peptidyl amine compound, the production method of the compound, the pharmaceuticals composition containing the compound, and the application of the compound in precaution and / or remedy for immune hypofunction related illnesses.

Description

technical field [0001] The invention is a new kind of N-substituted peptide amide for promoting immune function and bidirectional immune regulation, and relates to the field of peptides and small organic molecules. Background technique [0002] Literature reports and a large number of clinical practices in various countries have proved that TP-5 has two-way immune regulation function. It can induce and promote the differentiation, maturation and activation of human T lymphocytes and their subsets; regulate the proportion of T lymphocytes, so that CD 4 + / CD 8 + Tend to normal; increase the secretion of various lymphokines, such as a., r interferon, interleukin 2 and interleukin 3; enhance the viability of NK cells, etc. However, TP-5 is metabolized too quickly in the body, and the half-life is only 30 seconds. Contents of the invention [0003] Aiming at the shortcoming of TP-5 in the prior art that it metabolizes quickly in the body and its half-life is only 30 se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K7/02C07K7/64A61K38/08A61K38/10A61K38/12A61P31/12A61P1/16A61P1/02A61P35/00
Inventor 王德心张莉杜冠华龚喜杨潇骁
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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