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IAP BIR domain binding compounds

A compound, alkyl technology, applied in the field of IAP BIR domain binding compounds, can solve the problem of no RING domain and so on

Inactive Publication Date: 2013-03-20
PHARMASCIENCE INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another IAP called NAIP has 3 BIR domains (BIR1, BIR2 and BIR3) but no RING domain

Method used

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  • IAP BIR domain binding compounds
  • IAP BIR domain binding compounds
  • IAP BIR domain binding compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0036] According to one embodiment, G is:

[0037]

[0038] Or substituted or unsubstituted pyrrole, specific examples of which include but are not limited to:

[0039]

[0040] Or substituted or unsubstituted imidazole, specific examples thereof include but are not limited to:

[0041]

[0042] Or substituted or unsubstituted pyrazole, specific examples thereof include but are not limited to:

[0043]

[0044] Or substituted or unsubstituted triazoles, specific examples of which include but are not limited to:

[0045]

[0046] Or substituted or unsubstituted thiazole, specific examples of which include but are not limited to:

[0047] Where R 11 NHC(O)CH 3 Or phenyl;

[0048] Or substituted or unsubstituted tetrazole, specific examples of which include but are not limited to:

[0049]

[0050] Or substituted or unsubstituted oxazoles, specific examples of which include but are not limited to:

[0051]

[0052] Or substituted or unsubstituted isoxazole, specific examples thereof include b...

Embodiment 1

[0247] The following examples illustrate the preparation of compound 5-e, which can be used as an intermediate in the preparation of the compound of formula 1 or its salt.

[0248] Route 5: Synthesis of Intermediate 5-e

[0249]

[0250] Step 1: Add DIPEA (10.33mL, 59.3mmol), HOBt (4.81g, 35.6mmol) and HBTU (13.50) to the DMF solution of Boc-Chg-OH (9.16g, 35.6mmol) cooled to 0°C.

[0251] g, 35.6 mmol). After stirring for 10 minutes, (S)-prolinol (3.0 g, 29.7 mmol) was added and the reaction mixture was stirred overnight at room temperature. Add water and ethyl acetate, separate the organic layer, use 10% citric acid, NaHCO 3 Aqueous and brine washing, anhydrous MgSO 4 Dry, filter and concentrate in vacuo. Purification by silica gel chromatography provided intermediate 5-a as a colorless oil.

[0252] Step 2: To Intermediate 5-a (10.10 g, 29.7 mmol) was added 1,4-dioxane (30 mL) containing 4N HCl and the solution was stirred at room temperature for 1 hour. The volatiles were remov...

Embodiment 2

[0257] The following example illustrates the preparation of compound 6-h, which can be used as an intermediate in the preparation of the compound of formula 1 or its salt.

[0258] Route 6: Synthesis of Intermediate 6-h

[0259]

[0260] Step 1: To a dichloromethane solution (300 mL) of N-(tert-butoxycarbonyl)-L-prolinal 6-a (10.0 g, 50.2 mmol) was added phenethylamine (6.52 mL, 50.2 mmol). After stirring for 2 hours at room temperature, the reaction was cooled to 0°C, sodium triacetoxyborohydride (21.0 g, 100.3 mmol) was added portionwise and then the reaction mixture was stirred at room temperature overnight. Add 10% Na 2 CO 3 Aqueous solution, separate the organic layer, extract the aqueous phase with dichloromethane, wash the combined organic extracts with brine, anhydrous MgSO 4 Dry, filter and concentrate in vacuo to provide intermediate 6-b as a colorless oil. Intermediate 6-b was dissolved in diethyl ether (125 mL), the solution was cooled to 0° C. and 1N HCl in diethyl et...

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Abstract

A compound of Formula 1 : (I) or salt thereof, as well as methods of making compounds of Formula 1, methods of using compounds of Formula 1 to treat proliferative disorders such as cancer, and related compounds, composition, and methods.

Description

[0001] Cross references to related applications [0002] This application claims priority for US provisional patent application 61 / 303,809 filed on February 12, 2010 and US provisional patent application 61 / 415,638 filed on November 19, 2010. Background of the invention [0003] Apoptosis or programmed cell death usually occurs in the normal formation and maintenance of healthy tissues in multicellular organisms. It is a complex process that leads to the removal of damaged, diseased or developmental redundant cells without signs of inflammation or necrosis. [0004] The intrinsic apoptotic pathway is known to be dysregulated in a variety of diseases, including cancer and lymphoproliferative diseases, neurodegenerative diseases, autoimmune diseases, and inflammatory diseases, such as multiple sclerosis and rheumatoid arthritis. For example, cancer cells have acquired the ability to overcome or avoid apoptosis and continue to proliferate inappropriately despite the presence of strong ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/062A61K38/05C12N9/64
CPCC07K5/06026A61K38/00C07K5/06034A61P29/00A61P35/00A61P37/00A61K31/437A61K31/519C07D403/12C07D471/04C07D487/04
Inventor A·劳伦特M·普罗克斯Y·罗丝I·德尼索瓦K·达伊里S·贾维斯J·B·贾奎斯
Owner PHARMASCIENCE INC
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