IP Library › Granted Patent US 9,676,766

Granted Patent B2

US 9,676,766 · App. 13/512,701 · Granted Jun 13, 2017

Triazolopyridines

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Quick Facts

Patent No.: US 9,676,766
App. No.: 13/512,701
Granted: Jun 13, 2017
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 (165)

1. A compound of formula (I):

wherein:

R 1 is an aryl group,

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 , and —N═S(═O)(R 6 )R 7 ;

and

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 , and —N═S(═O)(R 8 )R 7 ;

R 2 is an aryl group or heteroaryl group,

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 , and —N═S(═O)(R 8 )R 7 ;

R 3 is 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 is 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 is a hydrogen atom;

wherein said group 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—, 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 , and —N═S (═O)(R 8 )R 7 ;

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

NR 6 R 7 together form a 3- to 10-membered heterocyclyl group, 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 is a hydrogen atom, a C 1 -C 6 -alkyl-, or a C 3 -C 6 -cycloalkyl- group;

n, m, and p

are each independently an integer of 0, 1, 2, 3, 4, or 5; and

q is 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 any of the foregoing.

2. The compound according to claim 1 , wherein:

R 1 is an aryl group,

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 , and —N═S(═O)(R 6 )R 7 ;

and

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 , and —N═S(═O)(R 8 )R 7 ;

R 2 is an aryl group or heteroaryl group,

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 , and —N═S(═O)(R 8 )R 7 ;

R 3 is 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 is 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;

R 5 is a hydrogen atom;

R 6 is 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, and —(CH 2 ) q -heteroaryl, wherein said group 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—, 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 , and —N═S(═O)(R 8 )R 7 ;

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

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

n, m, and p

are each independently an integer of 0, 1, 2, or 3; and

q is 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 any of the foregoing.

3. The compound according to claim 1 , wherein:

R 1 is an aryl group,

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

and

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

R 2 is an aryl group or heteroaryl group,

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 , and —N═S(═O)(R 8 )R 7 ;

R 3 and R 4 are each a hydrogen atom;

R 5 is a hydrogen atom;

wherein said group 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—, 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 , and —N═S(═O)(R 8 )R 7 ;

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

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

n is an integer of 0 or 1;

m is an integer of 0, 1 or 2;

p is an integer of 1 or 2; and

q is 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 any of the foregoing.

4. The compound according to claim 1 , wherein:

R 1 is a phenyl group,

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 , and —S(═O) 2 N(H)R 6 , and

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 , and —N(H)S(═O) 2 R 8 ;

R 2 is a phenyl group or pyridinyl group,

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 , and —S(═O) 2 NR 8 R 7 ;

R 3 and R 4 are each a hydrogen atom;

R 5 is a hydrogen atom;

wherein said group 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-, —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)—, and R 8 —S(═O) 2 —;

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

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

n is an integer of 0 or 1; and

q is 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 any of the foregoing.

5. The compound according to claim 1 , which is selected from the group consisting of:

N-Cyclopropyl-4-[2-(2-methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-benzamide;

3-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-phenylbenzamide;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-[4-(trifluoromethyl)phenyl]acetamide;

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

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-[3-(trifluoromethyl)phenyl]acetamide;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(2-fluorophenyl)acetamide;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(3-fluorophenyl)acetamide;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(4-fluorophenyl)acetamide;

1-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-3-phenylurea;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(pyridin-3-yl)acetamide;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(3-methoxyphenyl)acetamide;

N-(4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(3,4-difluorophenyl)acetamide;

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

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

2-cyclopropyl-N-(4-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)acetamide;

N-(4-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)cyclopropanecarboxamide;

2-phenyl-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]cyclopropanecarboxamide;

2-cyclopropyl-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

2-(4-methylpiperazin-1-yl)-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

2-(morpholin-4-yl)-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

2-(piperidin-1-yl)-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

2-amino-2-phenyl-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

2-(pyridin-3-yl)-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

2-methoxy-2-phenyl-N-[4-(2-{[2-(trifluoromethyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide;

N-(4-{2-[(2-cyano-5-methylphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-phenylacetamide;

N-(4-{2-[(2-cyano-3-fluorophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-phenylacetamide;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-phenylacetamide;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)cyclopropanecarboxamide;

1-Cyclopropyl-N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)methanesulfonamide;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)cyclopropanesulfonamide;

1-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-3-phenylurea;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)benzenesulfonamide;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)benzamide;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-4-methylpiperazine-1-carboxamide;

1-cyclopropyl-3-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)urea;

N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)morpholine-4-carboxamide;

4-(dimethylamino)-N-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)piperidine-1-carboxamide;

1-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-3-pyridin-3-ylurea;

1-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-3-[2-(morpholin-4-yl)ethyl]urea;

1-(3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-3-pyridin-4-ylurea;

2-[(6-{3-[(4-methylpiperazin-1-yl)carbonyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)amino]benzonitrile;

3-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-cyclopentylbenzamide;

3-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-(1-methylpiperidin-4-yl)benzamide;

N-benzyl-3-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}benzamide;

3-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-cyclopropylbenzamide;

N-cyclopropyl-3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}benzamide; and

N-benzyl-3-{2-[(2-methoxyphenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}benzamide,

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

6. A method of preparing the compound of formula (I) according to claim 1 , comprising reacting an intermediate compound of formula (5):

wherein R 1 , R 3 , R 4 , and R 5 are as defined in claim 1 ,

with an aryl halide of formula (5a):

R 2 —Y (5a)

wherein R 2 is as defined in claim 1 , and Y represents a leaving group,

to form the compound of formula (I):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in claim 1 .

7. A method of preparing the compound of formula (I) according to claim 1 , comprising reacting an intermediate compound of formula (7):

wherein R 2 , R 3 , R 4 , and R 5 are as defined in claim 1 , and R 1a is an aryl group to which an —NH 2 substituent is bound,

with a compound of formula:

R 1b —X (7a)

wherein R 1b is —C(═O)R 6 , —C(═O)NR 6 R 7 , —S(═O)R 6 , or —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, onto the —NH 2 substituent bound to the aryl group R 1a of compound (7), thereby replacing said X with said R 1a ,

to form the compound of formula (I):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in claim 1 .

8. A pharmaceutical composition comprising the compound according to claim 1 , and a pharmaceutically acceptable diluent or carrier.

9. A pharmaceutical combination comprising:

the compound according to claim 1 ; and

one or more agents selected from: a taxane, Docetaxel, Paclitaxel, or Taxol; an epothilone, 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, Flutamide, Cyproterone acetate, or Bicalutamide; Bortezomib; a platinum derivative, Cisplatin, or Carboplatin; Chlorambucil; Methotrexate; and Rituximab.

10. A method of inhibiting Mps-1 kinase activity comprising contacting Mps-1 kinase with an effective amount of the compound according to claim 1 .

11. A method of inhibiting Mps-1 kinase activity comprising contacting Mps-1 kinase with an effective amount of the compound according to claim 2 .

12. A method of inhibiting Mps-1 kinase activity comprising contacting Mps-1 kinase with an effective amount of the compound according to claim 3 .

13. A method of inhibiting Mps-1 kinase activity comprising contacting Mps-1 kinase with an effective amount of the compound according to claim 4 .

14. A method of inhibiting Mps-1 kinase activity comprising contacting Mps-1 kinase with an effective amount of the compound according to claim 5 .

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2013

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

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 030032/0959 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2013

From: BAYER PHARMA AKTIENGESELLSCHAFT

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 029906/0035 →