IP Library Granted Patent US 9,951,086
Granted Patent B2
US 9,951,086 · App. 15/106,073 · Granted Apr 24, 2018

Indazolecarboxamides, processes for their preparation, pharmaceutical preparations comprising them and their use for producing medicaments

Inventors: Ulrich Bothe (Berlin, DE); Holger Siebeneicher (Berlin, DE); Nicole Schmidt (San Francisco, CA); Andrea Rotgeri (Berlin, DE); Ulf Bömer (Glienicke, DE); Sven Ring (Jena, DE); Horst Irlbacher (Berlin, DE); Judith Günther (Berlin, DE); Holger Steuber (Berlin, DE); Martin Lange (Berlin, DE); Martina Schäfer (Berlin, DE)
Assignee: BAYER PHARMA AKTIENGESELLSCHAFT
C07D495/10C07D401/12C07D401/14C07D403/12C07D405/14C07D409/12C07D409/14C07D413/12C07D413/14C07D417/12C07D417/14C07D471/10C07D487/10C07D491/107
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Quick Facts
Patent No.
US 9,951,086
App. No.
15/106,073
Granted
Apr 24, 2018
Kind
B2
Abstract

The present application relates to novel 6-substituted indazoles having a carboxamide side chain, to processes for their preparation, to their use alone or in combinations for the treatment and/or prophylaxis of diseases, and to their use for producing medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of endometriosis, lymphomas, macular degeneration, COPD and psoriasis.

Claims (446)

1. A compound of the formula (I)

in which:

R 0 represents hydrogen or C 1 -C 4 -alkyl, where the C 1 -C 4 -alkyl radical may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy and halogen;

R 1 represents hydrogen, halogen, cyano, C(═O)OH, C(═O)OR a , C(═O)NH 2 , C(═O)N(H)R a , C(═O)N(R a )R b , C(═O)R d , hydroxy or C 1 -C 6 -alkyl, where the C 1 -C 6 -alkyl radical is optionally mono- or polysubstituted by identical or different radicals from the group consisting of

hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, NH 2 , NHR a , N(R a )R b , C 1 -C 6 -alkoxy which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, C 3 -C 8 -cycloalkoxy which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, heterocycloalkyl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c ,

or represents C 1 -C 6 -alkoxy, where the C 1 -C 6 -alkoxy radical may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of

hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, NH 2 , NHR a , N(R a )R b , C 3 -C 8 -cycloalkyl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, C 1 -C 6 -alkoxy which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, C 3 -C 8 -cycloalkoxy which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, heterocycloalkyl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c , aryl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c , or 5- or 6-membered heteroaryl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c ,

or represents C 3 -C 8 -cycloalkoxy or heterocycloalkoxy which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl,

or represents aryloxy or 5- or 6-membered heteroaryloxy in which aryloxy and 5- or 6-membered heteroaryloxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy,

or represents C 3 -C 8 -cycloalkyl or heterocycloalkyl which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl,

or represents C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl,

or represents aryl, 5- to 10-membered heteroaryl, aryl-C 1 -C 4 -alkyl or 5- or 6-membered heteroaryl-C 1 -C 4 -alkyl, where aryl and heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, hydroxy, cyano, C(═O)OH, C(═O)OR a , C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl and C 1 -C 6 -alkoxy;

R a represents C 1 -C 6 -alkyl, C 3 -C 10 -cycloalkyl, heterocycloalkyl, aryl or heteroaryl, where alkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, hydroxy, cyano, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, heterocycloalkyl, —C(═O)O—C 1 -C 6 -alkyl and S(═O) 2 —C 1 -C 6 -alkyl;

R b represents C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl;

or R a and R b together with the nitrogen atom form a 5- or 6-membered heterocycle which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, and C 1 -C 6 -alkyl;

R c represents hydroxy, halogen, cyano, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy;

R d represents hydrogen, C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl;

R 2 represents hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl;

R 13 represents hydrogen or C 1 -C 6 -alkyl;

W represents 5-membered heteroaryl which contains one to three heteroatoms selected from the group consisting of N, O and S and may optionally be monosubstituted by R 3 and optionally be mono- or polysubstituted by identical or different radicals R 4 or

W represents pyridyl, pyrazinyl, pyridazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl which may optionally be monosubstituted by R 3 and optionally be mono- or polysubstituted by identical or different radicals R 4 ;

R 3 represents hydrogen, halogen, cyano, C(═O)R a , NH 2 , NHR a , N(R a )R b , N(H)C(═O)R a or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)R a , C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, NH 2 , NHR a , N(R a )R b , C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy,

where C 1 -C 6 -alkoxy and C 3 -C 8 -cycloalkoxy may optionally be mono- or polysubstituted by identical or different halogen radicals;

or C 1 -C 6 -alkyl is optionally mono- or polysubstituted by identical or radicals from the group consisting of C 3 -C 6 -cycloalkyl and heterocycloalkyl,

where C 3 -C 6 -cycloalkyl and heterocycloalkyl may optionally be mono-, di- or trisubstituted by identical or different radicals from the group consisting of halogen, cyano, C 1 -C 3 -alkyl and C 1 -C 3 -alkoxy,

or C 1 -C 6 -alkyl is optionally mono- or polysubstituted by identical or different radicals from the group consisting of aryl and 5- or 6-membered heteroaryl,

where aryl and 5- or 6-membered heteroaryl may optionally be mono-, di- or trisubstituted by identical or different radicals from the group consisting of halogen, cyano, C 1 -C 3 -alkyl and C 1 -C 3 -alkoxy,

or

R 3 represents C 1 -C 6 -alkoxy, where

C 1 -C 6 -alkoxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkoxy,

or represents C 3 -C 6 -cycloalkyl, heterocycloalkyl or C 5 -C 11 -spirocycloalkyl, where

cycloalkyl, heterocycloalkyl and spirocycloalkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)R a , C(═O)OH, C(═O)OR a , C 1 -C 6 -alkyl and C 1 -C 4 -alkoxy;

or represents aryl or 5- to 10-membered heteroaryl, where

aryl and heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, hydroxy, cyano, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, NO 2 , NH 2 , NHR a , N(R a )R b , N(H)C(═O)R a , C 3 -C 8 -cycloalkyl, C 1 -C 3 -alkoxy and C 1 -C 3 -alkyl, where

C 1 -C 3 -alkyl may optionally be mono- or polysubstituted by identical or different halogen radicals;

R 4 represents halogen, hydroxy, cyano or C 1 -C 6 -alkyl, where C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, C 1 -C 6 -alkoxy, where C 1 -C 6 -alkoxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 10 -cycloalkyl, 3- to 10-membered heterocycloalkyl and aryl, where aryl may optionally be mono- or polysubstituted by identical or different radicals R,

or

R 4 represents aryl or heteroaryl which may optionally be mono- or polysubstituted by identical or different radicals R,

or

R 4 represents C(═O)R a , C(═O)NH 2 , C(═O)N(H)R a , C(═O)N(R a )R b , C(═O)OR a , NH 2 , NHR a , N(R a )R b , N(H)C(═O)R a , N(R a )C(═O)R a , N(H)C(═O)NH 2 , N(H)C(═O)NHR a , N(H)C(═O)N(R a )R b , N(R a )C(═O)NH 2 , N(R a )C(═O)NHR a , N(R a )C(═O)N(R a )R b , N(H)C(═O)OR a , N(R a )C(═O)OR a , NO 2 , N(H)S(═O)R a , N(R a )S(═O)R a , N(H)S(═O) 2 R a , N(R a )S(═O) 2 R a , N═S(═O)(R a )R b , OC(═O)R a , OC(═O)NH 2 , OC(═O)NHR a , OC(═O)N(R a )R b , SH, SR a , S(═O)R a , S(═O) 2 R a , S(═O) 2 NH 2 , S(═O) 2 NHR a , S(═O) 2 N(R a )R b or S(═O)(═N—R a )R b ;

R represents halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 10 -cycloalkyl, 3- to 10-membered heterocycloalkyl, aryl, heteroaryl, C(═O)R a , C(═O)NH 2 , C(═O)N(H)R a , C(═O)N(R a )R b , C(═O)OR a , NH 2 , NHR a , N(R a )R b , N(H)C(═O)R a , N(R a )C(═O)R a , N(H)C(═O)NH 2 , N(H)C(═O)NHR a , N(H)C(═O)N(R a )R b , N(R a )C(═O)NH 2 , N(R a )C(═O)NHR a , N(R a )C(═O)N(R a )R b , N(H)C(═O)OR a , N(R a )C(═O)OR a , NO 2 , N(H)S(═O)R a , N(R a )S(═O)R a , N(H)S(═O) 2 R a , N(R a )S(═O) 2 R a , N═S(═O)(R a )R b , OH, C 1 -C 6 -alkoxy, OC(═O)R a , OC(═O)NH 2 , OC(═O)NHR a , OC(═O)N(R a )R b , SH, SR a , S(═O)R a , S(═O) 2 R a , S(═O) 2 NH 2 , S(═O) 2 NHR a , S(═O) 2 N(R a )R b or S(═O)(═NR a )R b ;

n represents 0 or 1;

Y represents a group selected from:

where * represents the point of attachment of the group to the remainder of the molecule;

R 5 represents hydrogen, C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy and C 3 -C 8 -cycloalkyl;

R 6 represents hydrogen or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C 3 -C 10 -cycloalkyl, C(═O)R a , C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy and C 3 -C 8 -cycloalkoxy,

or represents C 3 -C 10 -cycloalkyl, where

C 3 -C 10 -cycloalkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be substituted by hydroxy,

or represents heterocycloalkyl, where

heterocycloalkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, cyano, C 1 -C 3 -alkyl and C 1 -C 3 -alkoxy,

or represents aryl or 5- or 6-membered heteroaryl, where

aryl and 5- or 6-membered heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, cyano, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, S(═O) 2 NH 2 , S(═O) 2 NHR a and S(═O) 2 N(R a )R b ;

R 7a represents hydrogen, halogen, N(R a )R b , C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

R 7b represents hydrogen, halogen or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

or R 7a and R 7b together with the carbon atom form C 3 -C 6 -cycloalkyl which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl,

or R 7a and R 7b together represent an oxo group;

R 7c represents hydrogen, halogen, N(R a )R b , C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

R 7d represents hydrogen, halogen or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

or R 7c and R 7d together with the carbon atom form C 3 -C 6 -cycloalkyl which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl,

or R 7c and R 7d together represent an oxo group;

R 8a represents hydrogen, halogen, N(R a )R b , C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

R 8b represents hydrogen, halogen or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

or R 8a and R 8b together with the carbon atom form C 3 -C 6 -cycloalkyl which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl,

R 8c represents hydrogen, halogen, N(R a )R b , C 1 -C 6 -alkyl or C 3 -C 10 -cycloalkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

R 8d represents hydrogen, halogen or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl and heterocycloalkyl;

or R 8c and R 8d together with the carbon atom form C 3 -C 6 -cycloalkyl which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano and C 1 -C 6 -alkyl,

or R 8c and R 8d together represent an oxo group;

o represents 0, 1 or 2,

p represents 0, 1 or 2,

q represents 0, 1 or 2,

r represents 0, 1 or 2,

s represents 0, 1 or 2,

where o, p, q, r and s do not simultaneously represent 0;

Z represents a group selected from C(═O), CR 9 R 10 , NR 11 , O, S, S(═O) and S(═O) 2 ;

R 9 represents hydrogen or C 1 -C 6 -alkyl,

R 10 represents hydrogen, halogen, cyano, C(═O)R a , C(═O)OH, C(═O)OR a , C(═O)NH 2 , C(═O)N(H)R a , C(═O)N(R a )R b , N(H)C(═O)R a , N(R b )C(═O)R a , S(═O) 2 R a , hydroxy, N(R a )R b and C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)R a , C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 1 -C 4 -alkoxy and C 3 -C 8 -cycloalkoxy,

or represents C 1 -C 6 -alkoxy, where

C 1 -C 6 -alkoxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkoxy, heterocycloalkyl, aryl and 5- or 6-membered heteroaryl, where

aryl and 5- or 6-membered heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, cyano, C 1 -C 3 -alkyl and C 1 -C 3 -alkoxy,

or represents aryloxy or 5- or 6-membered heteroaryloxy in which

aryloxy and 5- or 6-membered heteroaryloxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)OH, C(═O)OR a , C 1 -C 3 -alkyl and C 1 -C 3 -alkoxy,

or represents C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, heterocycloalkyl or heterocycloalkyl-C 1 -C 4 -alkyl, which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)R a , C(═O)OH, C(═O)OR a , C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy, where

C 1 -C 6 -alkoxy may optionally be mono- or polysubstituted by identical or different halogen radicals or an oxo group;

or represents C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl,

or represents aryl, 5- to 10-membered heteroaryl, aryl-C 1 -C 4 -alkyl or 5- or 6-membered heteroaryl-C 1 -C 4 -alkyl, where

aryl and heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, hydroxy, cyano, C(═O)OH, C(═O)OR a , NHR a , N(R a )R b , C 1 -C 3 -alkyl, C 3 -C 8 -cycloalkyl and C 1 -C 3 -alkoxy;

or R 9 and R 10 together with the carbon atom form C 3 -C 8 -cycloalkyl or a 4- to 6-membered heterocycle, where

the C 3 -C 8 -cycloalkyl radical or the 4- to 6-membered heterocycle may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C 1 -C 6 -alkyl, C(═O)R a and an oxo group;

R 11 represents hydrogen, C(═O)R a , C(═O)OR a , C(═O)NH 2 , C(═O)N(H)R a , C(═O)N(R a )R b , S(═O) 2 R a , S(═O) 2 N(R a )R b or C 1 -C 6 -alkyl, where

C 1 -C 6 -alkyl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C(═O)R a , C(═O)OR a , C(═O)NH 2 , C(═O)N(H)R a , C(═O)N(R a )R b , S(═O) 2 —C 1 -C 6 -alkyl, N(R a )R b , C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy and C 3 -C 8 -cycloalkoxy, where

C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy and C 3 -C 8 -cycloalkoxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy and halogen;

or represents C 3 -C 8 -cycloalkyl, heterocycloalkyl or heterocycloalkyl-C 1 -C 4 -alkyl which may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of hydroxy, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, where alkyl and alkoxy may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen and an oxo group,

or represents C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl,

or represents aryl, 5- to 10-membered heteroaryl, aryl-C 1 -C 4 -alkyl or 5- or 6-membered heteroaryl-C 1 -C 4 -alkyl, where

aryl and heteroaryl may optionally be mono- or polysubstituted by identical or different radicals from the group consisting of halogen, hydroxy, cyano, C(═O)OH, C(═O)OR a , C 1 -C 3 -alkyl, C 3 -C 8 -cycloalkyl and C 1 -C 3 -alkoxy;

and their diastereomers, enantiomers, their metabolites, their salts, their solvates or the solvates of their salts.

2. The compound of claim 1 in which R 1 represents hydrogen, halogen, hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 5 -alkyl substituted by hydroxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy substituted by C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy substituted by up to three fluorine atoms, C 1 -C 6 -alkoxy substituted by aryl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c or represents 5- or 6-membered heteroaryl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c .

3. The compound of claim 1 in which W represents a group selected from formulae (III) to (IX):

in which

R 12 represents hydrogen, halogen, C 1 -C 6 -alkyl which is optionally mono- or polysubstituted by identical or different halogen radicals, C 3 -C 6 -cycloalkyl which is optionally mono- or polysubstituted by identical or different halogen radicals, aryl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c or 5- or 6-membered heteroaryl which is optionally mono- or polysubstituted by identical or different radicals from the group consisting of R c or represents NHR a ;

m represents 0, 1, 2 or 3 and

R 3 and R 4 have the meanings given above and

* represents the point of attachment of the group to the remainder of the molecule.

4. The compound of claim 1 in which W represents a group of the general formula (X)

and R 3 and R 4 have the meaning given in claim 1 .

5. The compound of claim 1 in which Y is formula (II) where R 7a , R 7b , R 7c , R 7d , R 8a , R 8b , R 8c and R 8d are as defined in claim 1 :

6. The compound of claim 1 in which Y is a radical NR 5 R 6 where R 5 and R 6 are as defined in claim 1 .

7. The compound of claim 1 in which W represents a group of the general formula (IX)

in which

m represents 0 and R 2 , R 0 and R 13 all represent hydrogen and R 3 represents trifluoromethyl, ethyl, methyl, cyclopropyl, 2,2,2-trifluoro-1-hydroxyethyl or 1-hydroxyethyl; Y represents 4-methylpiperazin-1-yl, 4-ethylpiperazin-1-yl or morpholin-4-yl, n represents 0 and R 1 represents cyclopropylmethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, chlorine, ethoxy, methoxy, 2-hydroxypropan-2-yl or 3-hydroxypentan-3-yl.

8. The compound of claim 7 in which R 1 represents cyclopropylmethoxy, methoxy, ethoxy or 2-hydroxypropan-2-yl.

9. The compound of claim 7 in which R 3 is a trifluoromethyl or a cyclopropyl radical.

10. The compound of claim 1 , wherein the compound is selected from the group consisting of:

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-methyl-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

6-ethyl-N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

5-fluoro-N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

N-(2-{2-[4-(3-hydroxy-2,2-dimethylpropanoyl)piperazin-1-yl]-2-oxoethyl}-6-methyl-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(methoxyacetyl)piperazin-1-yl]-2-oxoethyl}-6-methyl-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-methylpyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylmethyl)piperazin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylmethyl)piperazin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-methylpyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-methoxy-2H-indazol-5-yl}-6-cyclopropylpyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-methoxy-2H-indazol-5-yl}-6-(1-hydroxyethyl)pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(trifluoromethoxy)-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

6-methyl-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(trifluoromethoxy)-2H-indazol-5-yl}pyridine-2-carboxamide;

tert-butyl 3-{[4-({2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(trifluoromethoxy)-2H-indazol-5-yl}carbamoyl)-1,3-thiazol-2-yl]amino}azetidine-1-carboxylate;

N-{6-bromo-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-bromo-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-{6-bromo-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-cyclopropyl-1,3-oxazole-4-carboxamide;

tert-butyl 3-{[4-({6-bromo-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}carbamoyl)-1,3-thiazol-2-yl]amino}azetidine-1-carboxylate;

2-(azetidin-3-ylamino)-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(trifluoromethoxy)-2H-indazol-5-yl}-1,3-thiazole-4-carboxamide;

N-{6-cyano-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

6′-methyl-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,3′-bipyridine-6-carboxamide;

5′-methyl-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,3′-bipyridine-6-carboxamide;

4′-methyl-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,3′-bipyridine-6-carboxamide;

6′-methoxy-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,3′-bipyridine-6-carboxamide;

6′-acetamido-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,3′-bipyridine-6-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6′-nitro-2,3′-bipyridine-6-carboxamide;

6′-amino-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,3′-bipyridine-6-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-fluoro-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-fluoro-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-fluoro-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-fluoro-2H-indazol-5-yl)-6-methylpyridine-2-carboxamide;

N-{6-fluoro-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-fluoro-2H-indazol-5-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-fluoro-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{6-fluoro-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-fluoro-2H-indazol-5-yl}-5-fluoro-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-fluoro-2H-indazol-5-yl)-5-fluoro-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-fluoro-2H-indazol-5-yl}-6-(morpholin-4-yl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-fluoro-2H-indazol-5-yl)-6-(morpholin-4-yl)pyridine-2-carboxamide;

N-{6-fluoro-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(morpholin-4-yl)pyridine-2-carboxamide;

N-{6-(benzyloxy)-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-isobutoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-isobutoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-isobutoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[(cyclopropylmethyl)(methyl)amino]-2-oxoethyl}-6-isobutoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(cyclopropylmethoxy)-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(cyclopropylmethoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[6-(cyclopropylmethoxy)-2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[6-(cyclopropylmethoxy)-2-{2-[(cyclopropylmethyl)(methyl)amino]-2-oxoethyl}-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(pyridin-2-ylmethoxy)-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(morpholin-4-yl)-2-oxoethyl]-6-(pyridin-2-ylmethoxy)-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1l-yl]-2-oxoethyl}-6-(pyridin-2-ylmethoxy)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-{2-[(cyclopropylmethyl)(methyl)amino]-2-oxoethyl}-6-(pyridin-2-ylmethoxy)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-chloro-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-chloro-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

ethyl 4-{[6-chloro-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-2-yl]acetyl}piperazine-1-carboxylate;

N-(6-chloro-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-[4-(3-hydroxy-2,2-dimethylpropanoyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-[3-(dimethylamino)azetidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-oxo-2-[3-(piperidin-1-yl)azetidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-[4-(2-hydroxy-2-methylpropyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-chloro-2-[2-(4-hydroxy-1,4′-bipiperidin-1′-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(dimethylamino)piperidin-1-yl]-2-oxoethyl}-6-ethoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-ethoxy-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-ethoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-ethoxy-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-ethoxy-2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-ethoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-3-methyl-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[3-(4-benzoylpiperazin-1-yl)-3-oxopropyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-2-(pyridin-3-yl)-1,3-thiazole-4-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-2-(pyridin-4-yl)-1,3-thiazole-4-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

6-(azetidin-3-ylamino)-N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-(pyridin-3-yl)-1,3-thiazole-4-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1H-pyrazol-4-yl)pyridine-2-carboxamide;

6-(1,3-dimethyl-1H-pyrazol-4-yl)-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-[3-(trifluoromethyl)-1H-pyrazol-4-yl]pyridine-2-carboxamide;

6-ethyl-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-(1-methyl-1H-pyrazol-4-yl)-N-(2-{2-oxo-2-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-ethyl-3-oxopiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(morpholin-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-(pyridin-4-yl)-1,3-thiazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-chloropyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-methyl-1,3-oxazole-5-carboxamide;

6-amino-N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-methyl-1,3-oxazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methoxypyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-cyclopropyl-1,3-oxazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(4H-1,2,4-triazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-phenyl-2H-1,2,3-triazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-5-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-(trifluoromethyl)-1,3-thiazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1H-pyrazol-1-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-1-ethyl-1H-pyrazole-3-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(4-chloro-1H-pyrazol-1-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-4-(trifluoromethyl)-1,3-thiazole-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1,3-dimethyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2,4′-bipyridine-6-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-5-fluoro-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(3-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1H-1,2,4-triazol-1-yl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-[3-(trifluoromethyl)-1H-pyrazol-4-yl]pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-ethoxypyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(cyclopropylmethoxy)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-ethylpyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-(4-methoxyphenyl)-1,3-thiazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-bromo-1,3-thiazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-(4-fluorophenyl)-1,3-thiazole-4-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-fluoropyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-bromopyridine-2-carboxamide;

N-(2-{2-[4-(4-fluorobenzoyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyridin-2-yl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(methoxyacetyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-cyclopentyl-3-oxopiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-oxo-2-(3-oxo-4-phenylpiperazin-1-yl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2,2-dimethylpropanoyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylmethyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-oxo-2-(pyridazin-4-ylamino)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(1-phenyl ethyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyridin-3-ylcarbonyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-isonicotinoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(morpholin-4-ylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[2-(methylamino)-2-oxoethyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyrazin-2-yl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(1-hydroxyethyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(2-methyl-2,8-diazaspiro[4.5]dec-8-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(6-acetyl-2,6-diazaspiro[3.3]hept-2-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-oxo-2-(3-oxo-2,8-diazaspiro[4.5]dec-8-yl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(6-methyl-2,6-diazaspiro[3.5]non-2-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(7-oxa-2-azaspiro[3.5]non-2-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(1,4′-bipiperidin-1′-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[2-(hydroxymethyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[3-(hydroxymethyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-carbamoylpiperidin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[3-(dimethylamino)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[3-(morpholin-4-ylmethyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(cyclopropylcarbonyl)amino]piperidin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]piperidin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyrrolidin-1-ylcarbonyl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[2-(morpholin-4-yl)ethyl]piperidin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]piperidin-1l-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[3-(pyrrolidin-1-ylmethyl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{[3-(dimethylsulphamoyl)phenyl]amino}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(1,2-oxazol-4-ylamino)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(methylsulphonyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-oxo-2-{4-[2-oxo-2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}ethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(phenylsulphonyl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[(3-sulphamoylphenyl)amino]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[isonicotinoyl(methyl)amino]piperidin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[2-(isopropylamino)-2-oxoethyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(1,1-dioxidotetrahydrothiophen-3-yl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(methoxyacetyl)(methyl)amino]piperidin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

ethyl 4-{[5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-2-yl]acetyl}piperazine-1-carboxylate;

N-(2-{2-[4-(cyclohexylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[2-(cyclopropylamino)-2-oxoethyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[2-(2-hydroxyethyl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(1H-pyrrol-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(3-hydroxypropyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

4-{[5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-2-yl]acetyl}piperazine-1-carboxamide;

N-(2-{2-oxo-2-[4-(2-oxopyrrolidin-1l-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-amino-2-oxoethyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(1,1-dioxidothiomorpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-isopropylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(2-thienylcarbonyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-cyclopropyl-2-oxoethyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(1-methyl-1H-pyrazol-4-yl)methyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(1,5-dimethyl-1H-pyrazol-3-yl)carbonyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N,N-diethyl-4-{[5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-2-yl]acetyl}piperazine-1-carboxamide;

N-{2-[2-oxo-2-(thiomorpholin-4-yl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-furylmethyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(3-thienylmethyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4′-methyl-1,4′-bipiperidin-1′-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(6-methyl-2,6-diazaspiro[3.3]hept-2-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-cyclopentylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyridin-4-ylmethyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(dimethylsulphamoyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyridin-4-yl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(methylsulphonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

formic acid N-[2-(2-{4-[2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide (1:1);

N-(2-{2-[4-(diethylsulphamoyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(pyridin-3-yl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-oxo-2-[4-(piperidin-1-ylsulphonyl)piperazin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[(1,5-dimethyl-1H-pyrazol-4-yl)sulphonyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylmethyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

6-(1-methyl-1H-pyrazol-4-yl)-N-(2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

N-{2-[2-(4-ethylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-(2-{2-[4-(dimethylamino)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide;

N-(2-{2-[(cyclopropylmethyl)(methyl)amino]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-methylpyridine-2-carboxamide;

N-(2-{2-[(cyclopropylmethyl)(methyl)amino]-2-oxoethyl}-6-ethoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[(cyclopropylmethyl)(methyl)amino]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

6-cyclopropyl-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)pyridine-2-carboxamide;

6-(1-hydroxyethyl)-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)pyridine-2-carboxamide;

6-(azetidin-3-ylamino)-N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-[(azetidin-2-ylmethyl)amino]-N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(3-hydroxyazetidin-1-yl)pyridine-2-carboxamide;

6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

N-[2-(2-{4-methyl-4-[(4-methylpiperazin-1-yl)carbonyl]piperidin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-oxo-2-[(3R)-piperidin-3-ylamino]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-isopropoxy-2H-indazol-5-yl)-6-methylpyridine-2-carboxamide;

N-(2-{2-[4-(cyclopropylcarbonyl)piperazin-1-yl]-2-oxoethyl}-6-isopropoxy-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-isopropoxy-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-6-isopropoxy-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-isopropoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-isopropoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-(2-{2-[4-(cyclobutylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(2-{2-[4-(cyclopentylcarbonyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[3-(methylsulphonyl)benzoyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[2-(2-{4-[2-methoxy-5-(methylsulphonyl)benzoyl]piperazin-1-yl}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

6-bromo-N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)pyridine-2-carboxamide;

2-(4-methoxyphenyl)-N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-1,3-thiazole-4-carboxamide;

2-(4-fluorophenyl)-N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-1,3-thiazole-4-carboxamide;

N-(6-methyl-2-{2-oxo-2-[4-(pyrrolidin-1-yl)piperidin-1-yl]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

6-bromo-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-bromo-N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(trifluoromethoxy)-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-(trifluoromethoxy)-2H-indazol-5-yl}-6-(4H-1,2,4-triazol-4-yl)pyridine-2-carboxamide;

2-bromo-N-{6-bromo-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-1,3-thiazole-4-carboxamide;

N-{6-hydroxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[6-(benzyloxy)-2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-2H-indazol-5-yl]-6-methylpyridine-2-carboxamide;

6-bromo-N-{6-bromo-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{6-(benzyloxy)-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

2-(azetidin-3-ylamino)-N-{2-[2-(4-benzoylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-1,3-thiazole-4-carboxamide;

6-acetamido-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-(dimethylamino)-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)pyridine-2-carboxamide;

6-(dimethylamino)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-acetamido-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)pyridine-2-carboxamide;

6-(dimethylamino)-N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-[3-(methylsulphonyl)phenyl]pyridine-2-carboxamide;

N-{2-[1-(4-benzoylpiperazin-1-yl)-1-oxopropan-2-yl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-[6-chloro-2-(2-{[trans-4-(2-hydroxypropan-2-yl)cyclohexyl]amino}-2-oxoethyl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide;

6-(2-hydroxypropan-2-yl)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{6-chloro-2-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-chloro-2-[2-oxo-2-(pyrrolidin-1-yl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-chloro-2-[2-(2-oxa-7-azaspiro[3.5]non-7-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-(6-chloro-2-{2-[4-(2-hydroxy-2-methylpropyl)piperazin-1-yl]-2-oxoethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-methoxy-2-[2-oxo-2-(pyrrolidin-1-yl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethyl]-6-methoxy-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

6-(difluoromethyl)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{2-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethyl]-6-methoxy-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-methylpyridine-2-carboxamide;

N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carboxamide;

N-{2-[2-(1,1-dioxido-1-thia-6-azaspiro[3.3]hept-6-yl)-2-oxoethyl]-6-methoxy-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(2-oxa-6-azaspiro[3.3]hept-6-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(3-hydroxy-2,2-dimethylpropoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

6-ethyl-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-isobutyl-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

methyl 2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazole-6-carboxylate;

methyl 5-{[(6-methylpyridin-2-yl)carbonyl]amino}-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazole-6-carboxylate;

N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(pyrrolidin-1-yl)pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(morpholin-4-yl)pyridine-2-carboxamide;

6-(cyclopropylamino)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-(butylamino)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(propylamino)pyridine-2-carboxamide;

6-(isobutylamino)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

R—N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(2,2,2-trifluoro-1-hydroxyethyl)pyridine-2-carboxamide;

S—N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(2,2,2-trifluoro-1-hydroxyethyl)pyridine-2-carboxamide;

6-(1-hydroxyethyl)-N-{6-methoxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-(cyclopropylamino)-N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(propylamino)pyridine-2-carboxamide;

6-(isobutylamino)-N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

6-(1-hydroxyethyl)-N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}pyridine-2-carboxamide;

N-{6-methoxy-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-4-methyl-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(benzyloxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

6-(cyclopropylamino)-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)pyridine-2-carboxamide;

6-(butylamino)-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-[(2-methoxyethyl)amino]pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1l-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-(propylamino)pyridine-2-carboxamide;

N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-(isobutylamino)pyridine-2-carboxamide;

5-fluoro-N-(2-{2-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]-2-oxoethyl}-6-methoxy-2H-indazol-5-yl)-6-methylpyridine-2-carboxamide;

N-{6-hydroxy-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(3-cyanopropoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(morpholin-4-yl)-2-oxoethyl]-6-(2,2,2-trifluoroethoxy)-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(cyclohexylmethoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(2,2-dimethylpropoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(morpholin-4-yl)-2-oxoethyl]-6-(tetrahydrofuran-2-ylmethoxy)-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(cyclopentyloxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(cyanomethoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

({2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-6-yl}oxy)acetic acid;

N-{6-(cyclobutylmethoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(morpholin-4-yl)-2-oxoethyl]-6-[2-(pyrrolidin-1-yl)ethoxy]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-[2-(morpholin-4-yl)ethoxy]-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{2-[2-(morpholin-4-yl)-2-oxoethyl]-6-[2-(piperidin-1-yl)ethoxy]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(3-hydroxypropoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(2-hydroxypropoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(2-hydroxyethoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-(2-methoxyethoxy)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

ethyl ({2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-6-yl}oxy)acetate;

methyl 4-({2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-6-yl}oxy)butanoate;

ethyl 2-({2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-6-yl)}oxy)propanoate;

ethyl 3-methyl-2-({2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-6-yl)}oxy)butanoate 2-({2-[2-(morpholin-4-yl)-2-oxoethyl]-5-({[6-(trifluoromethyl)pyridin-2-yl]carbonyl}amino)-2H-indazol-6-yl}oxy)propanoic acid;

N-{6-(2-hydroxypropan-2-yl)-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide;

N-{6-chloro-2-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(difluoromethyl)pyridine-2-carboxamide; and

N-{6-chloro-2-[2-(morpholin-4-yl)-2-oxoethyl]-2H-indazol-5-yl}-6-(difluoromethyl)pyridine-2-carboxamide.

11. A method of treating a disease that is mediated by IRAK4 selected from the group consisting of lymphomas, macular degeneration, endometriosis, psoriasis, lupus erythematosus, multiple sclerosis, COPD, and rheumatoid arthritis comprising administering an effective amount of the compound of claim 1 .

12. A method of inhibiting IRAK4 in a patient in need thereof comprising administering an effective amount of the compound of claim 1 to said patient.

13. A method of treating lymphomas, macular degeneration, endometriosis, psoriasis, lupus erythematosus, multiple sclerosis, COPD, or rheumatoid arthritis comprising administering an effective amount of the compound of claim 1 .

14. A method of making a medicament for the treatment of tumor disorders, dermatological disorders, gynaecological disorders, cardiovascular disorders, pulmonary disorders, ophthalmological disorders, neurological disorders, metabolic disorders, inflammatory disorders, autoimmune disorders, or pain comprising combining the compound of claim 1 with an inert, non-toxic, pharmaceutically suitable excipient.

15. A method of making a medicament for the treatment of lymphomas, macular degeneration, endometriosis, psoriasis, lupus erythematosus, multiple sclerosis, chronic obstructive pulmonary disease (COPD), or rheumatoid arthritis comprising combining the compound of claim 1 with an inert, non-toxic, pharmaceutically suitable excipient.

16. A medicament comprising the compound of claim 1 in combination with an inert, non-toxic, pharmaceutically suitable excipient.

17. A method of making a compound of formula (III) from a compound of formula (II)

in which R 14 is either a methyl or an ethyl radical by Grignard reaction with methyl- or ethylmagnesium bromide.

18. A compound of the formula (III)

in which R 14 is either a methyl or an ethyl radical.

19. A method of treating IL-1 receptor mediated diseases, MyD88 associated diseases, and TLR-associated diseases with the exception of TLR3 comprising administering an effective amount of the compound of claim 1 , wherein the disease is selected from the group consisting of lymphomas, macular degeneration, endometriosis, psoriasis, lupus erythematosus, multiple sclerosis, COPD, and rheumatoid arthritis.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2016
From: BOTHE, ULRICH, DR.; SIEBENEICHER, HOLGER, DR.; SCHMIDT, NICOLE, DR.; ROTGERI, ANDREA, DR.; BÖMER, ULF, DR.; RING, SVEN; IRLBACHER, HORST, DR.; GÜNTHER, JUDITH, DR.; STEUBER, HOLGER, DR.; LANGE, MARTIN, DR.; SCHÄFER, MARTINA, DR.
To: BAYER PHARMA AKTIENGESELLSCHAFT
Reel/Frame 038993/0993 →
Priority Claims (2)
EP 13198463 · Dec 19, 2013 · regional
EP 14189216 · Oct 16, 2014 · regional
Continuity (1)
Related Publication 20160311833A1 · Oct 27, 2016