6-alkynyl-pyridine derivatives

Patent metadata

Field	Value
Publication number	US-9481673-B2
Application number	US-201514821870-A
Country	US
Kind code	B2
Filing date	Aug 10, 2015
Priority date	Aug 11, 2014
Publication date	Nov 1, 2016
Grant date	Nov 1, 2016

Abstract

6-Alkynyl-pyridine of general formula (I)

their use as SMAC mimetics, pharmaceutical compositions containing them, and their use as a medicaments for the treatment and/or prevention of diseases characterized by excessive or abnormal cell proliferation and associated conditions such as cancer. An exemplary compound is

First claim

The invention claimed is:

1. A compound of formula I

wherein
R 1 is selected from the group consisting of hydrogen, —C 1-3 alkyl and halogen;
R 2 is selected from the group consisting of hydrogen, —C 1-3 alkyl and halogen;
R 3 is selected from the group consisting of phenyl,

R 4 is a 5- or 6-membered heteroaryl substituted with —C 1-3 alkyl or —O—C 1-3 alkyl;
or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 , wherein R is selected from the group consisting of hydrogen, —CH 3 and Cl.

3. A compound according to claim 1 , wherein R 2 is selected from the group consisting of hydrogen, —CH 3 and Cl.

4. A compound according to claim 1 , wherein R 1 is hydrogen and R 2 is selected from the group consisting of hydrogen, —CH 3 and Cl.

5. A compound according to claim 1 , wherein R 4 is a 6-membered heteroaryl substituted with —C 1-3 alkyl or —O—C 1-3 alkyl.

6. A compound according to claim 1 , wherein R 4 is selected from the group consisting of pyridyl, pyrimidinyl, pyrazolyl, imidazolyl, each of which is independently substituted with —C 1-3 alkyl or —O—C 1-3 alkyl.

7. A compound according to claim 1 , wherein R 4 is selected from the group consisting of pyridyl, pyrimidinyl, pyrazolyl, imidazolyl, each of which is independently substituted with —CH 3 or —O—CH 3 .

8. A compound according to claim 1 , selected from the group consisting of

#
Structure

 1

 2

 3

 4

 5

 6

 7

 8

 9

10

11

12

13

14

15

and,

16

or a pharmaceutically acceptable salt thereof.

9. A compound 1 of the formula:

or a pharmaceutically acceptable salt thereof.

10. A compound 3 of the formula:

Assignees

• Boehringer Ingelheim Int

Inventors

• Reiser Ulrich

Classifications

• A61P35/02

  specific for leukemia · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61K31/4709 Primary

  Non-condensed quinolines and containing further heterocyclic rings · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• A61K31/506

  not condensed and containing further heterocyclic rings · CPC title