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

Patent metadata

Field	Value
Publication number	US-9951086-B2
Application number	US-201415106073-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Dec 19, 2013
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

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.

First claim

The invention claimed is:

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

Assignees

• Bayer Pharma AG

Inventors

• Bothe Ulrich
• Siebeneicher Holger
• Schmidt Nicole
• Rotgeri Andrea
• Bömer Ulf
• Ring Sven
• Irlbacher Horst
• Günther Judith
• Steuber Holger
• Lange Martin
• Schäfer Martina

Classifications

• A61P37/02

  Immunomodulators · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P37/00

  Drugs for immunological or allergic disorders · CPC title