IP Library › Granted Patent US 8,551,980

Granted Patent B2

US 8,551,980 · App. 13/512,737 · Granted Oct 8, 2013

Substituted triazolopyridines

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Quick Facts

Patent No.: US 8,551,980
App. No.: 13/512,737
Granted: Oct 8, 2013
Kind: B2

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Abstract

The present invention relates to triazolopyridine compounds of general formula (I) which are Monopolar Spindle 1 kinase (Mps-1 or TTK) inhibitors: Formula (I), in which R 1 , R 2 , R 3 , R 4 , and R 5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis proliferative of diseases, as well as to intermediate compounds useful in the preparation of said compounds.

Claims (148)

1. A compound of general formula (I):

in which:

R 1 represents an aryl group

which is substituted, one or more times, identically or differently, with a substituent selected from:

R 6 —(C 1 -C 6 -alkyl)-, R 6 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 6 —(C 1 -C 6 -alkoxy)-, R 6 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 6 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 6 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, R 6 —O—, —C(═O)R 6 , —C(═O)O—R 6 , —OC(═O)—R 6 , —N(H)C(═O)R 6 , —N(R 7 )C(═O)R 6 , —N(H)C(═O)NR 6 R 7 , —N(R 7 )C(═O)NR 6 R 7 , —NR 6 R 7 , C(═O)N(H)R 6 , —C(═O)NR 6 R 7 , R 6 —S—, R 6 —S(═O)—, R 6 —S(═O) 2 —, —N(H)S(═O)R 6 , —N(R 7 )S(═O)R 6 , —S(═O)N(H)R 6 , —S(═O)NR 6 R 7 , —N(H)S(═O) 2 R 6 , N(R 7 )S(═O) 2 R 6 , —S(═O) 2 N(H)R 6 , —S(═O) 2 NR 6 R 7 , —S(═O)(═NR 6 )R 7 , —S(═O)(═NR 7 )R 6 , —N═S(═O)(R 6 )R 7 ;

and

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R 8 )R 7 ;

R 2 represents an aryl group or heteroaryl group

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl)-O—, —O—(CH 2 ) n —C(═O)NR 8 R 7 , R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R 8 )R 7 ;

R 3 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, nitro-, C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, halo-C 1 -C 4 -alkoxy-, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl-, halo-C 2 -C 6 -alkenyl-, halo-C 2 -C 6 -alkynyl-, C 3 -C 6 -cycloalkyl-, or halo-C 3 -C 6 -cycloalkyl- group;

R 4 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, nitro-, C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, halo-C 1 -C 4 -alkoxy-, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl-, halo-C 2 -C 6 -alkenyl-, halo-C 2 -C 6 -alkynyl-, C 3 -C 6 -cycloalkyl-, or halo-C 3 -C 6 -cycloalkyl- group;

R 5 represents a C 1 -C 6 -alkyl group, which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-, —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —O—;

R 6 represents a group selected from C 3 -C 6 -cycloalkyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, —(CH 2 ) q —(C 3 -C 6 -cycloalkyl), —(CH 2 ) q -(3- to 10-membered heterocyclyl), —(CH 2 ) q -aryl, or —(CH 2 ) q -heteroaryl, said group being optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, aryl-, R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R 8 )R 7 ;

R 7 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

NR 6 R 7 together

represent a 3- to 10-membered heterocyclyl group,

which is optionally substituted, one or more times, identically or differently, with halogen, hydroxy, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl- or C 3 -C 6 -cycloalkyl-;

R 8 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

n, m, p

represent, independently from each other, an integer of 0, 1, 2, 3, 4, or 5;

q represents an integer of 0, 1, 2 or 3;

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

2. The compound according to claim 1 , wherein:

R 1 represents an aryl group

which is substituted, one or more times, identically or differently, with a substituent selected from:

R 6 —(C 1 -C 6 -alkyl)-, R 6 — (CH 2 ) n (CHOH)(CH 2 ) m —, R 6 —(C 1 -C 6 -alkoxy)-, R 6 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 6 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 6 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, R 6 —O—, —C(═O)R 6 , —C(═O)O—R 6 , —OC(═O)—R 6 , —N(H)C(═O)R 6 , —N(R 7 )C(═O)R 6 , —N(H)C(═O)NR 6 R 7 , —N(R 7 )C(═O)NR 6 R 7 , —NR 6 R 7 , C(═O)N(H)R 6 , —C(═O)NR 6 R 7 , R 6 —S—, R 6 —S(═O)—, R 6 —S(═O) 2 —, —N(H)S(═O)R 6 , —N(R 7 )S(═O)R 6 , —S(═O)N(H)R 6 , —S(═O)NR 6 R 7 , —N(H)S(═O) 2 R 6 , —N(R 7 )S(═O) 2 R 6 , —S(═O) 2 N(H)R 6 , —S(═O) 2 NR 6 R 7 , —S(═O)(═NR 6 )R 7 , —S(═O)(═NR 7 )R 6 , —N═S(═O)(R 6 )R 7 ;

and

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

R 2 represents an aryl group or heteroaryl group

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, —O—(CH 2 ) n —C(═O)NR 8 R 7 , R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R 8 )R 7 ;

R 3 represents a hydrogen atom, a halogen atom, a hydroxy-, C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkyl-, or C 1 -C 4 -alkoxy- group;

R 4 represents a hydrogen atom, a halogen atom, a C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, or C 1 -C 6 -alkoxy- group;

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, aryl-, R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R)R 7 ;

R 7 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

NR 6 R 7 together

represent a 3- to 10-membered heterocyclyl group,

R 8 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

n, m, p

represent, independently from each other, an integer of 0, 1, 2, or 3;

q represents an integer of 0, 1, 2 or 3;

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

3. The compound according to claim 1 or 2 , wherein:

R 1 represents an aryl group

which is substituted, one or more times, identically or differently, with a substituent selected from:

R 6 —(C 1 -C 6 -alkyl)-, R 6 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 6 —(C 1 -C 6 -alkoxy)-, R 6 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 6 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 6 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, R 6 —O—, —C(═O)R 6 , —C(═O)O—R 6 , —OC(═O)—R 6 , —N(H)C(═O)R 6 , —N(R 7 )C(═O)R 6 , —N(H)C(═O)NR 6 R 7 , —N(R 7 )C(═O)NR 6 R 7 , —NR 6 R 7 , —C(═O)N(H)R 6 , —C(═O)NR 6 R 7 , R 6 —S—, R 6 —S(═O)—, R 6 —S(═O) 2 —, —N(H)S(═O)R 6 , —N(R 7 )S(═O)R 6 , —S(═O)N(H)R 6 , —S(═O)NR 6 R 7 , —N(H)S(═O) 2 R 6 , —N(R 7 )S(═O) 2 R 6 , —S(═O) 2 N(H)R 6 , —S(═O) 2 NR 6 R 7 , —S(═O)(═NR 6 )R 7 , —S(═O)(═NR 7 )R 6 , —N═S(═O)(R 6 )R 7 ;

and

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

R 2 represents an aryl group or heteroaryl group

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, —O—(CH 2 ) n —C(═O)NR 8 R 7 , R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R 8 )R 7 ;

R 3 , R 4 , represent a hydrogen atom;

R 5 represents a C 1 -C 6 -alkyl group, which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-;

halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, R 8 —(C 1 -C 6 -alkyl)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) m —, R 8 —(C 1 -C 6 -alkoxy)-, R 8 —(CH 2 ) n (CHOH)(CH 2 ) p —O—, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-, R 8 —(C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl)-O—, aryl-, R 8 —O—, —C(═O)R 8 , —C(═O)O—R 8 , —OC(═O)—R 8 , —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , —R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —N(H)S(═O) 2 R 8 , —N(R 7 )S(═O) 2 R 8 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 , —S(═O)(═NR 8 )R 7 , —S(═O)(═NR 7 )R 8 , —N═S(═O)(R 8 )R 7 ;

R 7 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

NR 6 R 7 together

represent a 3- to 10-membered heterocyclyl group,

R 8 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

n represents an integer of 0 or 1;

m represents an integer of 0, 1 or 2;

p represents an integer of 1 or 2;

q represents an integer of 0, 1 or 2;

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

4. The compound according to claim 1 , wherein:

R 1 represents a phenyl group

which is substituted, one or more times, identically or differently, with a substituent selected from:

R 6 —(C 1 -C 6 -alkoxy)-, R 6 —O—, —C(═O)R 6 , —C(═O)O—R 6 , —N(H)C(═O)R 6 , —N(H)C(═O)NR 6 R 7 , —NR 6 R 7 , —C(═O)N(H)R 6 , —C(═O)NR 6 R 7 , R 6 —S—, R 6 —S(═O) 2 —, —N(H)S(═O) 2 R 6 , —S(═O) 2 N(H)R 6 , and

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, hydroxyl-, nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, —N(H)C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —C(═O)N(H)R 8 , —N(H)S(═O) 2 R 8 ;

R 2 represents an aryl group

which is optionally substituted, one or more times, identically or differently, with a substituent selected from:

halo-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, —O—(CH 2 ) n —C(═O)NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 ;

R 3 , R 4 , represent a hydrogen atom;

R 5 represents a C 1 -C 6 -alkyl group;

differently, with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , —NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —;

R 7 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

NR 6 R 7 together

represent a 3- to 10-membered heterocyclyl group,

R 8 represents a hydrogen atom, a C 1 -C 6 -alkyl-, or C 3 -C 6 -cycloalkyl- group;

n represents an integer of 0 or 1

q represents an integer of 0, 1 or 2;

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

5. The compound according to claim 1 which is:

N-(4-{2-[(2-cyanophenyl)amino]-5-methyl[1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-phenylacetamide.

6. A method of preparing a compound of general formula (I) according to claim 1 , in which method an intermediate compound of general formula (5):

in which R 1 , R 3 , R 4 , and R 5 are as defined for the compound of general formula (I) in claim 1 ,

is allowed to react with an aryl halide of general formula (5a):

R 2 —Y (5a)

in which R 2 is as defined for the compound of general formula (I) in claim 1 and Y represents a leaving group,

thus providing a compound of general formula (I):

in which R 1 , R 2 , R 3 , R 4 , and R 5 are as defined for the compound of general formula (I) in claim 1 .

7. A method of preparing a compound of general formula (I) according to claim 1 , in which method an intermediate compound of general formula (7):

in which R 2 , R 3 , R 4 , and R 5 are as defined for the compound of general formula (I) in claim 1 , and R 1a is an aryl group to which an —NH 2 substituent is bound,

is allowed to react with a compound of general formula:

R 1b —X (7a)

in which R 1b is —C(═O)R 6 , —C(═O)NR 6 R 7 , —S(═O)R 6 , —S(═O) 2 R 6 , and X is a suitable functional group via which the R 1b of the R 1b —X compound (7a) can be coupled, via a coupling reaction,

thus providing a compound of general formula (I):

in which R 1 , R 2 , R 3 , R 4 , and R 5 are as defined for the compound of general formula (I) in claim 1 .

8. A pharmaceutical composition comprising a compound of general formula (I), or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, particularly a pharmaceutically acceptable salt thereof, or a mixture of same, according to claim 1 , and a pharmaceutically acceptable diluent or carrier.

9. A pharmaceutical combination comprising:

one or more compounds of general formula (I), or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, particularly a pharmaceutically acceptable salt thereof, or a mixture of same, according to claim 1 ;

and

one or more agents selected from: a taxane, such as Docetaxel, Paclitaxel, or Taxol; an epothilone, such as Ixabepilone, Patupilone, or Sagopilone; Mitoxantrone; Predinisolone; Dexamethasone; Estramustin; Vinblastin; Vincristin; Doxorubicin; Adriamycin; Idarubicin; Daunorubicin; Bleomycin; Etoposide; Cyclophosphamide; Ifosfamide; Procarbazine; Melphalan; 5-Fluorouracil; Capecitabine; Fludarabine; Cytarabine; Ara-C; 2-Chloro-2′-deoxyadenosine; Thioguanine; an anti-androgen, such as Flutamide, Cyproterone acetate, or Bicalutamide; Bortezomib; a platinum derivative, such as Cisplatin, or Carboplatin; Chlorambucil; Methotrexate; and Rituximab.

10. A compound of general formula (5):

in which R 1 , R 3 , R 4 , and R 5 are as defined for the compound of general formula (I) in claim 1 ,

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

11. A compound of general formula (7):

in which R 2 , R 3 , R 4 , and R 5 are as defined for the compound of general formula (I) in claim 1 , and R 1a is an aryl group to which an —NH 2 substituent is bound.

12. The compound according to claim 2 wherein,

R 1 represents a phenyl group, which is substitute, one or more times, identically of differently, with a substituent selected from: R 6 —(C 1 -C 6 -alkoxy)-, R 6 —O—, —C(═O)R 6 , —C(O)O—R 6 , —N(H)C(═O)R 6 , —N(H)C(═O)NR 6 R 7 , —NR 6 R 7 , —C(═O)N(H)R 6 , —C(═O)NR 6 R 7 , R 6 —S—, R 6 —S(═O) 2 —, N(H)S(═O) 2 R 6 , —S(═O) 2 N(H)R 6 , and, which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, nitro-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, hydroxyl-C 1 -C 6 -alkyl, —N(H)C(═O)R 8 , —N(H)C(═O)NR 8 R 7 , —C(═O)N(H)R 8 , —N(H)S(═O) 2 R 8 ;

R 2 represents an aryl group which is optionally substituted, one or more times, identically or differentially, with a substituent selected from: halo-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, —O—(CH 2 ) n —C(═O)NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 ;

R 3 , R 4 represent a hydrogen atom;

R 5 represents a C 1 -C 6 alkyl group;

R 6 represents a group selected from: C 3 -C 6 cycloalkyl, 3 to 10-membered heterocyclyl, aryl, heteroaryl, —(CH 2 ) q —(C 3 -C 6 -cycloalkyl), —(CH 2 ) q -(3-to-10-membered heterocycloalkyl), —(CH 2 ) q -aryl, or —(CH 2 ) q -heteroaryl, said group being optionally substituted, one or more times, identically or differently with a substituent selected from the group consisting of: halo-, hydroxyl-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, —N(H)C(═O)R 8 , —N(R 7 )C(═O)R 8 , N(H)C(═O)NR 8 R 7 , —N(R 7 )C(═O)NR 8 R 7 , NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —;

R 7 represents a hydrogen atom, a C 1 -C 6 alkyl or a C 3 -C 6 cycloalkyl group;

NR 6 R 7 together represents a 3 to 10 membered heterocyclyl group, which is optionally substituted one or more times, identically or differently with halogen, hydroxyl, cyano, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, hydroxyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 2 -C 6 alkenyl-, C 2 -C 6 -alkynyl-, or C 3 -C 6 -cycloalkyl-;

R 8 represents a hydrogen atom, a C 1 -C 6 alkyl, or a C 3 -C 6 -cycloalklyl group;

n represents an integer of 0 or 1;

q represents an integer of 0, 1, or 2;

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

13. The compound according to claim 3 , wherein

R 2 represents an aryl group which is optionally substituted, one or more times, identically or differentially, with a substituent selected from: halo-, cyano-, nitro-, C 1 -C 6 -alkyl-, halo-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, halo-C 1 -C 6 -alkoxy-, —O—(CH 2 ) n , —C(═O)NR 8 R 7 , —C(═O)N(H)R 8 , —C(═O)NR 8 R 7 , R 8 —S—, R 8 —S(═O)—, R 8 —S(═O) 2 —, —N(H)S(═O)R 8 , —N(R 7 )S(═O)R 8 , —S(═O)N(H)R 8 , —S(═O)NR 8 R 7 , —S(═O) 2 N(H)R 8 , —S(═O) 2 NR 8 R 7 ;

R 3 , R 4 represent a hydrogen atom;

R 5 represents a C 1 -C 6 alkyl group;

R 7 represents a hydrogen atom, a C 1 -C 6 alkyl or a C 3 -C 6 cycloalkyl group;

R 8 represents a hydrogen atom, a C 1 -C 6 alkyl, or a C 3 -C 6 -cycloalklyl group;

n represents an integer of 0 or 1;

q represents an integer of 0, 1, or 2;

or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2013

From: SCHULZE, VOLKER, DR.; KOPPITZ, MARCUS, DR.; KOSEMUND, DIRK, DR.; BADER, BENJAMIN, DR.; LIENAU, PHILIP, DR.; BRIEM, HANS, DR.; HOLTON, SIMON, DR.; SIEMEISTER, GERHARD, DR.; PRECHTL, STEFAN, DR.; WENGNER, ANTJE MARGRET, DR.

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 030077/0689 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2013

From: BAYER PHARMA AKTIENGESELLSCHAFT

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 029906/0035 →