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Tetrapeptide analogs

A compound and derivative technology, applied in animal repellents, peptide/protein components, plant growth regulators, etc., can solve the problem of lack of molecular specificity

Inactive Publication Date: 2007-12-26
IDUN PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these treatments lack molecular specificity, thus requiring more specific molecular targets

Method used

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Examples

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preparation example Construction

[0745] C. Preparation of compounds

[0746] The raw materials in the synthesis examples provided by the present invention are commercially available or obtained through literature methods. Unless otherwise indicated, all commercially available compounds were used without further purification. HPLC was done on a Zorbax C8 4.6x150mm column eluting with 10%-50% acetonitrile in water containing 0.1% TFA for 20 minutes.

[0747] The following schemes describe the general preparation of the compounds claimed in the present invention, consisting of reactions generally known to those skilled in chemical synthesis. Substituents indicated in the schemes are described elsewhere herein. It is well known to those skilled in the art that many products may exist as one or more isomers, be E / Z isomers, enantiomers and / or diastereomers.

[0748] The coupling reactions performed in the schemes below were accomplished in the presence of one of the standard peptide coupling reagents: dicyclohe...

Embodiment 1

[0902]

[0903] 2-[2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3,3-dimethyl-butanoic acid

[0904] Part A: 2-[2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3,3-dimethyl-butyric acid methyl ester

[0905]

[0906] To 2-(tert-butoxycarbonyl-methyl-amino)-propionic acid (1.76 g, 8.68 mmol) and 2-amino-3,3-dimethyl-butyric acid in tetrahydrofuran (THF) (100 mL) To a solution of methyl ester; hydrochloride (1.58 g, 8.70 mmol) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) (3.2 g, 16.7 mmol) ) and 1-hydroxybenzotriazole monohydrate (HOBt) (1.5 g, 11.1 mmol), then N-methyl-2-pyrrolidone (2 mL) and 4-methylmorpholine (4 mL) were added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was treated with water (30 mL), then partitioned with ethyl acetate / water. The organic phase was washed with 1N HCl (2×50 mL), saturated sodium bicarbonate solution (100 mL) and brine solution (50 mL), washed with Na 2 S...

Embodiment 2

[0911]

[0912] 2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butanoic acid

[0913] Part A: 2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid methyl ester

[0914]

[0915] To 2-(tert-butoxycarbonyl-methyl-amino)-propionic acid (5.30 g, 26.1 mmol) and 2-amino-3-methyl-butyric acid methyl ester in tetrahydrofuran (THF) (100 mL) ; Hydrochloride (6.03g, 36.0mmol) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI) (10.2g, 53.2mmol) and 1- Hydroxybenzotriazole monohydrate (HOBt) (5.17 g, 38.2 mmol), then N-methyl-2-pyrrolidone (6 mL) and 4-methylmorpholine (12 mL) were added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was treated with water (30 mL), then partitioned with ethyl acetate / water. The organic phase was washed with 1N HCl (2×75 mL), saturated sodium bicarbonate solution (150 mL) and brine solution (50 mL), washed with Na 2 SO 4 Drying and evaporation t...

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Abstract

Compounds, compositions and methods for treatment of hyperproliferative diseases, such as cancer are provided.

Description

technical field [0001] Compounds, compositions and methods for treating cell proliferative diseases are provided. The compounds provided are peptidomimetics of the N-terminal tetrapeptide of the mitochondrial protein Smac. Smac is believed to promote apoptosis through a pathway involving inhibitors of apoptosis proteins (IAPs). These peptidomimetics bind IAPs. Background technique [0002] Apoptosis or programmed cell death plays an important role in the development and homeostasis of all multicellular organisms. Alterations in the apoptotic pathway are implicated in many types of human pathologies, including dysplasia, cancer, autoimmune diseases, and neurodegenerative diseases. [0003] The pathway of apoptosis has become an attractive target for the development of therapeutic agents. In particular, attention has been paid to anticancer treatments using pro-apoptotic agents such as conventional radiation and chemotherapy. These treatments are generally thought to trig...

Claims

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Application Information

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IPC IPC(8): C07D207/00A01N43/64A61K38/00
CPCY02A50/30
Inventor B·朝T·L·德科沃斯P·S·福斯S·D·林顿A·P·斯帕达B·R·乌尔曼M·I·韦恩豪斯
Owner IDUN PHARMA INC
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