Tricyclic compounds and pharmaceutical uses thereof

A compound and pharmaceutical technology, applied in the field of tricyclic compounds and their pharmaceutical uses, can solve problems such as poor clinical effects

Inactive Publication Date: 2012-08-22
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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  • Tricyclic compounds and pharmaceutical uses thereof
  • Tricyclic compounds and pharmaceutical uses thereof
  • Tricyclic compounds and pharmaceutical uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0140] The present invention provides compounds of formula (I):

[0141]

[0142] in:

[0143] Z 1 ,Z 2 ,Z 3 and Z 4 Each independently is CR 1 or N if Z 1 to Z 4 At most two of are N and contain Z 1 to Z 4 The ring of is aromatic;

[0144] Each R 1 independently H, halo, CN, optionally substituted C1-C4 alkyl, optionally substituted C2-C4 alkenyl, optionally substituted C2-C4 alkynyl, optionally substituted C1-C4 alkoxy , SR, SO 2 R, COOR, COONR 7 R 8 or -NR 7 R 8 ;

[0145] Y 1 and Y 4 Each is C or N, and Y 1 and Y 4 Not both are N at the same time; the condition is Y 1 to Y 4 At least one of is N;

[0146] Y 2 Yes N, NR 2 、CR 2 or CX 2 ,

[0147] where each R 2 are independently H, -OR, halo, CN or optionally substituted C1-C4 alkyl,

[0148] where each R 2 Yes-(CH 2 ) 0-2 COOR or polar groups;

[0149] X is -(CH 2 ) 0-2 COOR or polar group, or when Y 2 is CX 2 when X is R 2 ;

[0150] each R is independently H or an optionally sub...

Embodiment

[0299]The following examples illustrate but do not limit the invention. In particular embodiments, the invention includes any compound of formula (I) or formula (II) described in the reaction schemes and examples. A variety of compounds of formula (I) and / or II can be readily prepared by one of ordinary skill by using the following general schemes, together with knowledge and reagents available in the art. It is to be understood that said compounds are within said formula (I) or (II), even if the atomic symbols used in the schemes are different from those used in formulas (I) and (II).

[0300] Reaction scheme 1

[0301] Certain compounds of formula (I) can be prepared by the general methods illustrated in Scheme 1 . Nitrile (3) can be deprotonated by (a) using a base such as but not limited to N-butyllithium, then (b) contacting the anion obtained from step (a) with acid chloride (2) or ester (1) to Compound (4) is provided, whereby a compound of formula (8) is obtained. ...

Embodiment 7

[0326] Compounds of formula (II), such as compounds (8) in Scheme 7, can be prepared using the transformations described in Scheme 3, as described below.

[0327] Option 7

[0328]

[0329] Reaction scheme 8

[0330] Compounds of formula (II), such as compounds (8) in Scheme 8, can be prepared using the transformations described in Scheme 3, as described below.

[0331] Option 8

[0332]

[0333] Reaction scheme 9

[0334] Compounds of formula (II), such as compounds (8) in Scheme 9, can be prepared using the transformations described in Scheme 3, as described below.

[0335] Option 9

[0336]

[0337] Reaction scheme 10

[0338] Compounds of formula (I), such as compound (3) in scheme 10, can be prepared as described in Journal fuer Praktische Chemie 1981, 323, 647-653. Compound (8) can be prepared from compound (3) as described in Scheme 3.

[0339] Scheme 10

[0340]

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Abstract

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

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Application No. 61 / 243,107, filed September 16, 2009, entitled "TRICYCLIC COMPOUNDS AND PHARMACEUTICAL USES THEREOF," the contents of which are hereby incorporated by reference in their entirety for all purposes. enter. field of invention [0003] The present invention relates in part to molecules having certain biological activities including, but not limited to, inhibition of cell proliferation and modulation of certain protein kinase activities. The compounds of the present invention have a tricyclic core comprising a five-membered aromatic nitrogen heterocycle with polar groups on the five-membered ring. Molecules of the invention modulate protein kinase CK2 activity previously referred to as casein kinase activity and / or Pim kinase activity (eg, Pim-1 activity), and are useful in the treatment of cancer and inflammatory disorders, as well as certain infectious...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/42A61K31/44
CPCA61K31/5025A61K31/519C07D471/14C07D487/04C07D487/14A61P1/04A61P1/16A61P1/18A61P11/00A61P13/08A61P13/12A61P15/00A61P17/00A61P25/00A61P29/00A61P31/00A61P31/04A61P35/00A61P35/02A61P37/02A61P43/00A61P9/00C07D487/12C07D471/12A61K31/4738
Inventor M·哈达齐F·皮埃尔
Owner CYCLENE PHARM INC
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