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Novel peptides

A kind of peptide compound, the technology of compound, be applied in the purposes in the treatment such as inflammation, comprise the field of pharmaceutical composition of described peptide, can solve the problems such as the progress of unfavorable wound healing

Pending Publication Date: 2022-04-19
艾缇亚(上海)制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Conventional wisdom in the art is that anti-inflammatory drugs should not be applied directly to open wounds as this would impair the progress of wound healing

Method used

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  • Novel peptides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0265] Ala-Lys-Pro-Ser-Tyr-Hyp-Thr-Tyr-Hyp-Lys (SEQ ID No: 15)

[0266] Fmoc-Lys-Boc-Wang resin (9.15 g, GLS180322-41301, GL Biochem, Shanghai, China) was loaded into a glass reaction column.

[0267] Dichloromethane (DCM, 200 mL; Shandong Jinling Chemical Industry Co Ltd, Shandong, China) was added to the column and the resin was allowed to soak for about half an hour. DCM was then removed by vacuum filtration.

[0268] The resin was washed 3 times with N,N-dimethylformamide (DMF, 200 mL; Shandong Shitaifeng Fertilizer Industry Co Ltd, Shandong, China).

[0269] A 20% piperidine solution (200 mL) in DMF was added as a deprotection solution and reacted for 20 minutes. The solution was then removed by vacuum filtration and the column was washed six times with DMF. Fmoc-4-Hyp(tBu)-OH (GLS 21303; GLBiochem, Shanghai, China) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyltetrafluoroboric acid Ammonium (TBTU, 2.89 g; GLS 170805-00705, GL Biochem, Shanghai, China) was added t...

Embodiment 2

[0283] Croton oil-induced rat anal swelling model

[0284] A gel was prepared containing 0.5 g of the peptide Ala-Lys-Pro-Ser-Tyr-Hyp-Thr-Tyr-Hyp-Lys (SEQ ID No: 15; see Example 1 above), which was also prepared from Component composition: methylcellulose (2.2g; ShandongGuangda Technology Development Co., Ltd., Shandong, China), glycerin (11g) and propylene glycol 11g (both from Sinopharm Chemical Reagent Co.Ltd.) and purified water (75.3g) .

[0285] The methylcellulose and water were mixed together and stirred until a homogeneous colloidal suspension was formed. Then, the peptide powder, glycerin and propylene glycol were added to the methylcellulose / water mixture, and the resulting mixture was stirred rapidly for 5 minutes to obtain the finished product.

[0286] Six- to eight-week-old SD rats with an average weight between 180 and 220 g were provided by Changzhou Cvens Experimental Animal Co. Ltd. (Changzhou, Jiangsu Province, China), half male and half male. Rats wer...

Embodiment 3

[0301] Ala-Lys-Pro-Ser-Tyr-Hyp-Thr-DOPA-Hyp-Lys (SEQ ID No: 14)

[0302] The title compound was prepared using essentially the same method as the latter described in Example 1 above, except that Fmoc-DOPA(acetonide)-OH was used in place of Fmoc-Tyr(tBu in the relevant amino acid coupling step )-OH, yielding 3.73 g of crude title compound.

[0303] Analysis showed that the peak of interest eluted at 9.297 minutes with the expected molecular weight (MS: m / z 1199.1). The purity is 74.493%.

[0304] 3.7 g of the crude product were then purified as described above in Example 1 to give 2.01 g of pure title compound after lyophilization.

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Abstract

There is provided a peptide compound comprising the amino acid sequence: G-W-Lys-X1-Ser-U-X2-Y-Z-Q wherein: G represents an optional N-terminal 3, 4-dihydrocinnamic acid group; w represents Ala or Ser or does not exist; u represents Tyr, DOPA or a single bond; x1 and X2 independently represent Pro, Hyp or diHyp; y represents a single bond or a sequence of 1 to 5 amino acids, wherein the amino acids are selected from one or more of the group Pro, Hyp, diHyp, Thr, DOPA and Tyr; z represents Pro, Hyp, diHyp, Thr, DOPA or Tyr, and Z represents Pro, Hyp, diHyp, Thr, DOPA or Tyr; and Q represents Lys or absent, as well as regioisomers, stereoisomers, and pharmaceutically or cosmetically acceptable salts of said peptide compounds. With the proviso that when G is absent, W represents Ala or absent, and Q represents Lys, then Z represents Pro, Hyp, diHyp or Thr. The compounds are particularly useful in the treatment of conditions characterized by inflammation, including wounds, burns, and mucosal disorders such as anorectal diseases, inflammatory bowel diseases, gynecological diseases, and dental diseases.

Description

technical field [0001] The present invention relates to novel short-chain oligopeptides, the use of such peptides in human medicine, and to pharmaceutical compositions comprising said peptides. In particular, the invention relates to the use of these peptides and compositions in the treatment of eg inflammation. Background technique [0002] Inflammation is typically characterized as a local tissue reaction to the invasion of eg microorganisms, certain antigens, damaged cells or physical and / or chemical agents. The inflammatory response is generally a protective mechanism for destroying, diluting or sequestering noxious agents and damaged tissue, and for initiating tissue healing. [0003] Inflammation may result from physical trauma, infection, some chronic diseases (e.g., psoriasis and autoimmune diseases such as rheumatoid arthritis), and / or chemical and / or physiological responses to external stimuli (e.g., as allergic reactions part) caused by. A complex series of eve...

Claims

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Application Information

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IPC IPC(8): C07K2/00A61P17/10A61P29/00A61K47/64
CPCA61P29/00A61P17/10C07K7/06A61K38/00A61K8/64A61Q19/00
Inventor J-C·詹森顾铭B·I·塞缪森M·宋
Owner 艾缇亚(上海)制药有限公司
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