N-(pyridin-2-yl)pyrimidin-4-amine derivatives containing a sulfone group

Patent metadata

Field	Value
Publication number	US-9708293-B2
Application number	US-201314436973-A
Country	US
Kind code	B2
Filing date	Oct 16, 2013
Priority date	Oct 18, 2012
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

The present invention relates to N-(pyridin-2-yl)pyrimidin-4-amine derivatives containing a sulfone group of general formula (I) as described and defined herein, and methods for their preparation, their use for the treatment and/or prophylaxis of disorders, in particular of hyper-proliferative disorders and/or virally induced infectious diseases and/or of cardiovascular diseases. The invention further relates to intermediate compounds useful in the preparation of said compounds of general formula (I).

First claim

The invention claimed is:

1. A compound of general formula (I)

wherein
R 1 represents a group selected from C 1 -C 6 -alkyl-, C 3 -C 7 -cycloalkyl-, heterocyclyl-, phenyl, heteroaryl, phenyl-C 1 -C 3 -alkyl- or heteroaryl-C 1 -C 3 -alkyl-,
wherein said group is optionally substituted with one or two or three substituents, identically or differently, selected from the group of hydroxy, cyano, halogen, halo-C 1 -C 3 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 3 -fluoroalkoxy-, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, —OP(O)(OH) 2 , —C(O)OH, —C(O)NH 2 ;

R 2 represents a group selected from

R 3 , R 4 represent, independently from each other, a group selected from a hydrogen atom, fluoro atom, chloro atom, bromo atom, cyano, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;
R 5 represents a group selected from
a) a C 1 -C 6 -alkyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-, C 2 -C 3 -alkenyl-, C 2 -C 3 -alkynyl-, C 3 -C 7 -cycloalkyl-, heterocyclyl-, phenyl, heteroaryl, wherein said C 3 -C 7 -cycloalkyl-, heterocyclyl-, phenyl or heteroaryl group is optionally substituted with one, two or three substituents, identically or differently, selected from halogen, hydroxy, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;
b) a C 3 -C 7 -cycloalkyl- group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-, C 2 -C 3 -alkenyl-, C 2 -C 3 -alkynyl-;
c) a heterocyclyl- group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-, C 2 -C 3 -alkenyl-, C 2 -C 3 -alkynyl-;
d) a phenyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-;
e) a heteroaryl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-;
f) a phenyl-C 1 -C 3 -alkyl- group, which phenyl group is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-;
g) a heteroaryl-C 1 -C 3 -alkyl- group, which heteroaryl group is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, —NH 2 , alkylamino-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-;
h) a C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl- group, which C 3 -C 6 -cycloalkyl group is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;
i) a heterocyclyl-C 1 -C 3 -alkyl- group, which heterocyclyl group is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;

R 6 , R 7 represent, independently from each other, a group selected from a hydrogen atom, fluoro atom, chloro atom, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;
or its salts, solvates or salts of solvates.

2. The compound of general formula (I) according to claim 1 , wherein
R 1 represents a group selected from C 1 -C 6 -alkyl-, C 3 - 5 -cycloalkyl-,
wherein said group is optionally substituted with one substituent selected from the group of hydroxy, C 1 -C 3 -alkoxy-, halo-C 1 -C 2 -alkyl-, C 1 -C 2 -fluoroalkoxy-, —NH 2 , —OP(O)(OH) 2 , —C(O)OH, —C(O)NH 2 ;

R 2 represents a group selected from

R 3 represents a hydrogen atom, a fluoro atom, a chloro atom, C 1 -C 3 -alkyl or halo-C 1 -C 3 -alkyl-;
R 4 represents a hydrogen atom or a fluoro atom;
R 5 represents a group selected from
a) a C 1 -C 6 -alkyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, hydroxy, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-, C 3 -C 7 -cycloalkyl-, heterocyclyl-, phenyl, heteroaryl, wherein said C 3 -C 7 -cycloalkyl-, heterocyclyl-, phenyl or heteroaryl group is optionally substituted with one, two or three substituents, identically or differently, selected from halogen, hydroxy, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;
b) a phenyl-C 1 -C 3 -alkyl- group, which phenyl group is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-;
c) a heteroaryl-C 1 -C 3 -alkyl- group, which heteroaryl group is optionally substituted with one or two or three substituents, identically or differently, selected from the group of halogen, hydroxy, dialkylamino-, acetylamino-, N-methyl-N-acetylamino-, cyclic amines, cyano, C 1 -C 3 -alkyl-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-, C 1 -C 3 -alkoxy-;
d) a C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl- group, which C 3 -C 6 -cycloalkyl group is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;
e) a heterocyclyl-C 1 -C 3 -alkyl- group, which heterocyclyl group is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-, C 1 -C 3 -fluoroalkoxy-;

R 6 , R 7 represent, independently from each other, a group selected from a hydrogen atom, fluoro atom, chloro atom, C 1 -C 3 -alkyl-, C 1 -C 3 -alkoxy-, halo-C 1 -C 3 -alkyl-,

Assignees

• Bayer Pharma AG

Inventors

• Lücking Ulrich
• Böhnke Niels
• Scholz Arne
• Lienau Philip
• Siemeister Gerhard
• Bömer Ulf
• Kosemund Dirk
• Bohlmann Rolf
• Zorn Ludwig

Classifications

• A61P9/14

  Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P9/02

  Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives · CPC title

• A61P9/04

  Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title