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Pharmaceutically useful heterocycle-substituted lactams

A pharmacy and prodrug technology, which can be used in medical preparations containing active ingredients, antipyretics, drug combinations, etc., and can solve problems such as poor clinical effects.

Inactive Publication Date: 2012-08-01
CYCLENE PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, because conventional therapies for pancreatic cancer do not respond clinically well, Pim-3 may represent a new and important molecular target for the successful management of this incurable disease

Method used

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  • Pharmaceutically useful heterocycle-substituted lactams
  • Pharmaceutically useful heterocycle-substituted lactams
  • Pharmaceutically useful heterocycle-substituted lactams

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0164] In one embodiment, the present invention provides a compound having structural formula (I):

[0165]

[0166] Or a pharmaceutically acceptable salt, solvate and / or prodrug thereof,

[0167] among them:

[0168] The double ring ring system includes Z 1 -Z 4 Is aromatic

[0169] Z 1 And Z 2 One of them is C, Z 1 And Z 2 The other one is N;

[0170] Z 3 And Z 4 Independently CR 1a Or N,

[0171] R 1 And R 1a Independently H, halo, CN, optionally substituted C1-C4 alkyl, optionally substituted C2-C4 alkenyl, optionally substituted C2-C4 alkynyl, optionally substituted C1-C4 alkoxy , Or -NR 7 R 8 ;

[0172] R 2 Is H, halo, CN, or an optionally substituted group selected from C1-C4 alkyl, C2-C4 alkenyl and C2-C4 alkynyl;

[0173] R 3 And R 4 Independently selected from H and optionally substituted C1-C10 alkyl;

[0174] π is sp 2 -Hybrid C or N;

[0175] If π is C=Y, where Y is O or S, the bond shown by the dotted line is a single bond;

[0176] Or if π is N or CR 1 , The bond shown by the ...

Embodiment 1

[0361] Synthesis of 3-((5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)-5-fluoroindoline -2-one

[0362]

[0363] Add POCl to 1.5ml DMF containing 5-chloropyrazolo[1,5-a]pyrimidine (200mg, 1.31mmol) 3 (358 μL, 3.92 mmol). The reaction was stirred overnight at room temperature. The mixture was cooled to 0°C in an ice bath and then neutralized with 6M NaOH. The formed solid was separated by filtration and air dried to obtain 165 mg of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (70% yield) as a yellow solid. LCMS(M+1=182)

[0364]

[0365] To 1.5 ml of dioxane containing 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (120 mg, 0.66 mmol) was added 3-chloroaniline (35 μL, 3.31 mmol). The mixture was heated in the microwave at 120°C for 10 minutes. The formed solid was separated by filtration and air dried to obtain 5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde as an orange solid. LCMS(M+1=273)

[0366]

[0367] To 1mL EtOH containing 5-(3-...

Embodiment 2

[0369] Synthesis of 4-((5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)-3-methyl-1H- Pyrazole-5(4H)-one

[0370]

[0371] To 5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (80mg, 0.294mmol) in EtOH was added 3-methyl-1H-pyrazole-5(4H )-Ketone (29 mg, 0.294 mmol) and piperidine (30 μL, 0.294 mmol). The mixture was heated at 70°C overnight. The formed solid was separated by filtration to obtain 4-((5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)-3-methyl- 1H-pyrazole-5(4H)-one. LCMS(M+1=353)

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Abstract

The invention provides compounds that inhibit CK2 and / or Pim kinases and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, infections, and certain immunological disorders.

Description

[0001] Cross references to related applications [0002] This application requires the U.S. Provisional Application No. 61 / 241,806 filed on September 11, 2009 with the title "PHARMACEUTICALLY USEFUL HETEROCYCLE-SUBSTITUTED LACTAMS" and the file titled "PHARMACEUTICALLY USEFUL HETEROCYCLE-SUBSTITUTED LACTAMS" filed on August 5, 2010 Benefit of U.S. Provisional Application No. 61 / 371,147, the content of which is hereby incorporated by reference in its entirety for all purposes. Invention field [0003] The present invention partly relates to molecules with certain biological activities, including but not limited to inhibiting cell proliferation and regulating certain protein kinase activities. The molecules of the present invention can modulate protein kinase CK2 activity previously known as casein kinase activity and / or Pim kinase activity (for example, Pim-1 activity), and are used to treat cancer and inflammatory diseases and certain infectious conditions. The present invention a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/00
CPCC07D471/04C07D487/04A61P29/00A61P31/00A61P35/00A61P37/00A61P43/00A61P9/00A61P9/14C07D403/06A61K31/4738
Inventor M·哈达齐D·雷克曼N·拉法勒
Owner CYCLENE PHARM INC
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