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Triazine, pyrimidine and pyridine analogs and their use as therapeutic agents and diagnostic probes

A pyridine, triazine technology, applied in the field of detection and/or modulation of kinase activity compounds, regulation, inhibition, can solve the problems of enhanced migration, harmful cells, uncontrolled proliferation, etc.

Active Publication Date: 2011-10-05
UNIVERSITY OF BASEL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Constitutive upregulation of PI3K signaling can have deleterious effects on cells, leading to uncontrolled proliferation, enhanced migration, and attachment-independent growth

Method used

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  • Triazine, pyrimidine and pyridine analogs and their use as therapeutic agents and diagnostic probes
  • Triazine, pyrimidine and pyridine analogs and their use as therapeutic agents and diagnostic probes
  • Triazine, pyrimidine and pyridine analogs and their use as therapeutic agents and diagnostic probes

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0276] Preparation of compounds of the present invention

[0277] The compounds of the present invention may be synthesized by synthetic routes including methods analogous to those well known in the chemical arts, in particular according to the description contained herein. Starting materials are generally obtained from commercial sources, such as Aldrich Chemicals, or are readily prepared using methods well known to those skilled in the art (e.g., by methods generally described in: Louis F. Fieser and Mary Fieser, Reagents for Organic Synthesis , v.1-19, Wiley, N.Y. (1967-1999 editions), or Beilsteins Handbuch der organischen Chemie, 4, Aufl.ed. Springer-Verlag, Berlin, including its supplements (also available via the Beilstein online database)).

[0278] In certain embodiments, the compounds of the present invention can be readily prepared using well-known methods for the preparation of triazines and other heterocyclic rings, which are described in: Comprehensive Heterocycl...

specific Embodiment approach

[0624] The present invention will now be described in more detail with reference to specific embodiments and examples of the invention, which are intended to be illustrative rather than restrictive.

[0625] Table 1 gives the structures and corresponding IUPAC names of exemplary compound numbers 1-259 of formula (Ia), (Ib) or (Id) (using ChemDraw Ultra version 11.0.1 and its lower and higher software versions , CambridgeSoft Corp., Cambridge MA).

[0626] Table 1

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Embodiment P1

[0739]

[0740] 4,4'-(6-Chloro-1,3,5-triazine-2,4-diyl)dimorpholine:

[0741] Cyanuric chloride (1.00g, 5.42mmol, 1.0eq) was dissolved in DMF (5ml), and morpholine (2.11ml, 24.4mmol, 4.5eq) was slowly added to the reaction mixture at 0°C, and stirred at this temperature for 20 minutes, poured into water, filtered the colorless precipitate, washed with hexane and diethyl ether, and dried to afford the title compound as a colorless solid (860 mg, 56%).

[0742] analyze data:

[0743] 1 H-NMR (400MHz, CDCl 3 ): δ3.78-3.69 (16H, m).

[0744] 13 C-NMR (100MHz, CDCl 3 ): δ170.10, 164.88, 67.28, 66.98, 44.23.

[0745] ESI-MS (70eV, m / z): C 11 h 16 ClN 5 o 2 [M+H] + Calculated value: 286, measured 360.

[0746] X-ray analysis: The structure of 4,4'-(6-chloro-1,3,5-triazine-2,4-diyl)dimorpholine was confirmed by x-ray analysis.

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PUM

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Abstract

The invention relates to novel therapeutic agents and diagnostic probes. The invention also relates to phosphoinositide 3-kinase (PI3K) and mammalian target of rapamycin (mTOR) inhibitor triazine-, pyrimidine- and pyridine-based compounds^ Formula (I), their stereoisomers, geometric isomers, tautomers, solvates, metabolites, N-oxide derivatives, pharmaceutically acceptable salts, and prodrugs thereof compositions of the new compounds; either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier; and uses of the new compounds, either alone or in combination with at least one additional therapeutic agent, for treating disorders mediated by lipid kinases.; DEG Methods of using compounds of Formula (I) for in vitro, in situ, and in vivo diagnosis,.prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

Description

technical field [0001] The present invention relates to novel therapeutic agents and diagnostic probes, including pharmaceutically acceptable salts, prodrugs and metabolites thereof, which are useful for modulating protein or enzymatic activity that regulates processes such as signal transduction, proliferation, Cellular events such as differentiation, programmed cell death, migration, and cytokine secretion. More specifically, the present invention provides compounds that inhibit, modulate, detect and / or modulate the activity of kinases, especially phosphoinositide 3-kinase (PI3K), mammalian target of rapamycin (mTOR), DNA-PK and ATM kinase inhibitor compounds, their pharmaceutically acceptable salts and prodrugs thereof; novel compound compositions containing said compounds alone or in combination with at least one other therapeutic agent, and pharmaceutically acceptable Accepted vectors; and use of the novel compounds alone or in combination with at least one other therape...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D251/18C07D403/12C07D417/04C07D409/04C07D403/04C07D401/12C07D417/14C07D413/14C07D491/048C07D405/04C07D413/04C07D403/14C07D495/04C07D401/04
CPCC07D513/04C07D413/04C07D491/048C07D403/12C07D417/14C07D491/147C07D403/14C07D519/00C07D403/04C07D401/12C07D405/14C07D495/04C07D498/04C07D417/04C07D413/14C07D251/18C07D401/04C07D409/04C07D495/14C07D405/04A61P1/16A61P11/00A61P17/06A61P19/08A61P25/00A61P25/04A61P25/06A61P25/08A61P25/28A61P29/00A61P31/00A61P35/00A61P35/02A61P37/00A61P37/02A61P37/04A61P37/08A61P43/00A61P5/00A61P7/02A61P9/00A61P9/04A61P9/10A61P3/10A61K31/444A61K31/519A61K31/53A61K31/5377C07D213/74C07D239/70C07D251/16
Inventor V·茨米利亚诺维奇N·茨米利亚诺维奇B·吉斯M·怀曼
Owner UNIVERSITY OF BASEL
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