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Peptide antiangiogenic drugs

A technology of drugs and medicinal salts, which is applied in the field of peptide anti-angiogenic drugs, and can solve problems such as weak anti-angiogenic effects and systemic toxicity

Inactive Publication Date: 2007-02-21
ABBOTT LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, suramin is a potent angiogenesis inhibitor, but it (at doses required to achieve antitumor activity) can cause severe systemic toxicity in humans
Other compounds, such as resinous compounds, interferons, and antiestrogens, are safe for human use but have only weak antiangiogenic effects

Method used

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  • Peptide antiangiogenic drugs
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  • Peptide antiangiogenic drugs

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Experimental program
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Effect test

preparation example Construction

[0929] A particularly preferred method of preparing compounds of the invention involves solid phase peptide synthesis.

[0930] In this particularly preferred method, the α-amino function is protected with an acid- or base-sensitive group. Such protecting groups should be stable to the conditions of peptide bond formation, yet readily removable under conditions that do not disrupt the growing peptide chain or racemize any chiral centers contained therein. Suitable protecting groups are 9-fluorenylmethoxycarbonyl (Fmoc), tert-butoxycarbonyl (Boc), benzyloxycarbonyl (Cbz), biphenylisopropoxycarbonyl, tert-amyloxycarbonyl, isobornyloxycarbonyl, ( α,α)-Dimethyl-3,5-dimethoxybenzyloxycarbonyl, o-nitrobenzenesulfinyl, 2-cyano-tert-butoxycarbonyl, and the like. The 9-fluorenylmethoxycarbonyl (Fmoc) protecting group is preferred.

[0931] A particularly preferred side chain protecting group for the side chain protecting groups in lysine and arginine is: 2,2,5,7,8-pentamethylchroman-...

Embodiment 1

[0946] N-Ac-Sar-Gly-Val-D-Ile-Thr-Nva-Ile-Arg-ProNHCH 2 CH 3

[0947] A Pro(2-ClTrt) peptide synthesis column (25 μM amino acid; purchased from Nova Biochem Company) was placed at the position of the peptide synthesis column of the Perkin Elmer / Applied Biosynthesis SYNERGY_peptide synthesizer. Add the various amino acids in the following synthesis cycle order:

[0948] (1) The resin is solvated with DMF for about 5 minutes;

[0949] (2) Wash with DMF for about 5 minutes;

[0950] (3) Use HBTU (75 μM) and HOBT (75 μM) in 0.2M DMSO-NMP (N-methylpyrrolidone) solution to activate the newly added Fmoc protected amino acid (75 μM);

[0951] (4) use the DMF solution coupling of the activated Fmoc protected amino acid prepared in step (3) for about 30 minutes;

[0952] (5) washing with DMF for 5 minutes; and

[0953] (6) For the N-terminal capped peptide with acetyl, the Fmoc protected amino acid was replaced with acetic acid (87 M), and 87 M HBTU and 87 M HOBT were used.

[09...

Embodiment 2

[0959] pyroGlu-Gly-Val-D-Ile-Thr-Nva-Ile-Arg-ProNHCH 2 CH 3

[0960] Amino acid number

[0961] Lyophilization of the pure fractions yields pyroGlu-Gly-Val-D-Ile-Thr-Nva-Ile-Arg-ProNHCH 2 CH 3 , for trifluoroacetate: R t = 23.5 minutes (10%-40% gradient of acetonitrile in water containing 0.01% TFA over 30 minutes); MS (ESI) m / e 994 (M+H) + .

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Abstract

Peptides having the formula: A0-A1-A2-A3-A4-A5-A6-A7-A8-A9-A10 wherein A0 is selected from hydrogen or an acyl group; A10 is a hydroxyl group or an amino acid amide; and A1, A2, A3, A4, A5, A6, A7, A8 and A9 are amino acyl residues as defined herein.

Description

[0001] This application is a divisional application of an invention patent application with an application date of May 21, 1999, an application number of 99809104.9, and an invention title of "peptide anti-angiogenesis drug". technical field [0002] The present invention relates to novel compounds having activity useful in the treatment of diseases caused by or exacerbated by angiogenesis, pharmaceutical compositions comprising these compounds, methods of treatment using said compounds, and methods of inhibiting angiogenesis. Background of the invention [0003] Angiogenesis is the fundamental process of forming new blood vessels, which is required for a variety of normal bodily activities such as reproduction, development and wound repair. Although we do not fully understand this process, it is believed to involve a complex interplay of molecules that stimulate and inhibit the growth of endothelial cells, the primary cells of capillaries. Under normal conditions, these mol...

Claims

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Application Information

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IPC IPC(8): C07K7/06A61K38/08A61P7/00A61P43/00
Inventor J·亨金F·哈维夫M·F·布拉德利D·M·卡尔文A·J·施奈德尔
Owner ABBOTT LAB INC