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Long lasting growth hormone releasing factor derivatives

A growth hormone and release factor technology, which is used in drug combinations, medical preparations with non-active ingredients, and medical preparations containing active ingredients, etc.

Inactive Publication Date: 2010-04-21
常山凯捷健生物药物研发(河北)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A series of GRF peptides are listed as possible candidates for stabilization by the methods disclosed in this application, but none are specifically exemplified in the specification

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp- Ile-Met-Ser-Arg-CONH 2

[0136]Step 1: The synthesis of solid-phase peptides was carried out in the order of 100 μmol. The following protected amino acids were added to the resin: Fmoc-Arg(Pbf)-OH, Fmoc-Ser(tBu)-OH, Fmoc-Met-OH, Fmoc-Ile-OH, Fmoc-Asp(tBu)-OH, Fmoc -Gln(Trt)-OH, Fmoc-Leu-OH, Fmoc-Leu-OH, Fmoc-Lys(Boc)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Ala-OH, Fmoc-Ser(tBu) -OH, Fmoc-Leu-OH, Fmoc-Gln(Trt)-OH, Fmoc-Gly-OH, Fmoc-Leu-OH, Fmoc-Val-OH, Fmoc-Lys(Boc)-OH, Fmoc-Arg(Pbf )-OH, Fmoc-Tyr(tBu)-OH, Fmoc-Ser(tBu)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Thr(tBu)-OH, Fmoc-Phe-OH, Fmoc-IIe- OH, Fmoc-Ala-OH, Fmoc-Asp(tBu)-OH, Fmoc-Ala-OH, Boc-Tyr(tBu)-OH. They were dissolved into N,N-dimethylformamide (DMF) and, in sequence, using O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate Salt (HBTU) and diisopropylethylamine (DIEA) activation. Removal of the Fmoc protecting gr...

Embodiment 2

[0139] Long-acting derivatives of the GRF peptide of Example 1

[0140] Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp- Ile-Met-Ser-Arg-Lys(MPA)-CONH 2

[0141] Step 1: This step was performed as in Example 1 above, except that the first amino acid added to the resin was Fmoc-Lys(Aloc)-OH.

[0142] Step 2: Selective deprotection of the Lys(Aloc) group was carried out manually and by dissolving in 5 mL C 6 h 6 : CHCl 3 (1:1): 2.5% NMM (v:v): 3 equivalents of Pd(PPh) in 5% AcOH (v:v) 3 ) 4 The solution treated resin was complete in 2 hours. Then the resin was washed with CHCl 3 (6x5 mL), 20% AcOH in DCM (6x5 mL), DCM (6x5 mL) and DMF (6x5 mL) washes.

[0143] Step 3: The synthesis is automated again with the addition of 3-maleimidepropionic acid (MPA). Between each coupling, the resin was washed three times with N,N-dimethylformamide (DMF) and isopropanol, respectively.

[0144] Step 4: Derivatives were cleaved from...

Embodiment 3

[0146] Tyr-(D)ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln -Asp-Ile-Met-Ser-Arg-CONH 2

[0147] Step 1: The synthesis of solid-phase peptides was performed on the order of 100 μmole. The following protected amino acids were added to the resin in sequence with the procedure described in Step 1 of Example 1: Fmoc-Arg(Pbf)-OH, Fmoc-Ser(tBu)-OH, Fmoc-MetOH, Fmoc-Ile- OH, Fmoc-Asp(tBu)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Leu-OH, Fmoc-Leu-OH, Fmoc-Lys(Boc)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Ala-OH, Fmoc-Ser(tBu)-OH, Fmoc-Leu-OH, Fmoc-Gln(Trt)-OH, Fmoc-Gly-OH, Fmoc-Leu-OH, Fmoc-Val-OH, Fmoc- Lys(Boc)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Tyr(tBu)-OH, Fmoc-Ser(tBu)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Thr(tBu)- OH, Fmoc-Phe-OH, Fmoc-Ile-OH, Fmoc-Ala-OH, Fmoc-Asp(tBu)-OH, Fmoc-(D)ala-OH, Boc-Tyr(tBu)-OH.

[0148] Step 2: The implementation of this step is the same as Step 2 of Example 1.

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Abstract

This invention relates to growth hormone releasing factor (GRF) derivatives. In particular, this invention relates to GRF peptide derivatives having an extended in vivo half-life, for promoting the endogenous production or release of growth hormone in humans and animals.

Description

[0001] This application is a divisional application of Chinese patent application 02804497.5 (corresponding to international application PCT / CA02 / 00123) filed on February 1, 2002, entitled "Long-acting growth hormone releasing factor derivatives". field of invention [0002] The present invention relates to growth hormone releasing factor (GRF) derivatives. In particular, the present invention relates to GRF peptide derivatives having an extended half-life in vivo for promoting the endogenous production or release of growth hormone in humans and animals. Background of the invention [0003] Growth hormone (GH), also called somatotropin, is a protein hormone of about 190 amino acids synthesized and secreted by somatotroph cells of the pituitary gland. It is a major player in the control of growth and metabolism. It is also an important medicinal product for humans and animals. GH production is regulated by a variety of factors, including stress, nutrition, sleep, and GH its...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/60C07K19/00A61K38/25A61K47/48A61P5/06A61K38/22A61K38/00A61P5/10
CPCA61K38/00C07K14/60A61P3/00A61P3/04A61P3/12A61P5/06A61P5/10A61P9/04A61P17/02A61P19/00A61P19/10A61P21/00A61P43/00
Inventor 多米尼克·P·布赖顿尼赛布·布杰拉布罗杰·莱杰马丁·罗比塔耶露西·热泰科琳·邦盖
Owner 常山凯捷健生物药物研发(河北)有限公司
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